diff --git a/.github/workflows/labrinth-build.yml b/.github/workflows/labrinth-build.yml
index 5fdc1ce080..7dfcffce83 100644
--- a/.github/workflows/labrinth-build.yml
+++ b/.github/workflows/labrinth-build.yml
@@ -8,6 +8,9 @@ on:
     paths:
       - .github/workflows/labrinth-build.yml
       - 'apps/labrinth/**'
+      - 'packages/**'
+      - '!packages/api-client/**'
+      - '!packages/app-lib/**'
       - Cargo.toml
       - Cargo.lock
   pull_request:
@@ -15,6 +18,9 @@ on:
     paths:
       - .github/workflows/labrinth-build.yml
       - 'apps/labrinth/**'
+      - 'packages/**'
+      - '!packages/api-client/**'
+      - '!packages/app-lib/**'
       - Cargo.toml
       - Cargo.lock
   merge_group:
diff --git a/Cargo.lock b/Cargo.lock
index db6f7b0ae2..6a53ac4b9b 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2331,15 +2331,6 @@ version = "0.4.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6245d59a3e82a7fc217c5828a6692dbc6dfb63a0c8c90495621f7b9d79704a0e"
 
-[[package]]
-name = "convert_case"
-version = "0.8.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "baaaa0ecca5b51987b9423ccdc971514dd8b0bb7b4060b983d3664dad3f1f89f"
-dependencies = [
- "unicode-segmentation",
-]
-
 [[package]]
 name = "convert_case"
 version = "0.10.0"
@@ -5217,15 +5208,6 @@ version = "1.70.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "7943c866cc5cd64cbc25b2e01621d07fa8eb2a1a23160ee81ce38704e97b8ecf"
 
-[[package]]
-name = "iso8601"
-version = "0.6.3"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e1082f0c48f143442a1ac6122f67e360ceee130b967af4d50996e5154a45df46"
-dependencies = [
- "nom 8.0.0",
-]
-
 [[package]]
 name = "itertools"
 version = "0.12.1"
@@ -5385,19 +5367,6 @@ dependencies = [
  "serde_json",
 ]
 
-[[package]]
-name = "jsonwebtoken"
-version = "9.3.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5a87cc7a48537badeae96744432de36f4be2b4a34a05a5ef32e9dd8a1c169dde"
-dependencies = [
- "base64 0.22.1",
- "js-sys",
- "ring",
- "serde",
- "serde_json",
-]
-
 [[package]]
 name = "keyboard-types"
 version = "0.7.0"
@@ -5491,7 +5460,6 @@ dependencies = [
  "json-patch 4.1.0",
  "labrinth",
  "lettre",
- "meilisearch-sdk",
  "modrinth-content-management",
  "modrinth-util",
  "muralpay",
@@ -5955,49 +5923,6 @@ version = "0.8.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "ae960838283323069879657ca3de837e9f7bbb4c7bf6ea7f1b290d5e9476d2e0"
 
-[[package]]
-name = "meilisearch-index-setting-macro"
-version = "0.30.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e36e5cad3754ed329feb201c24f26c0694442bef50a90dbcff0ba6d12b5ca133"
-dependencies = [
- "convert_case 0.8.0",
- "proc-macro2",
- "quote",
- "structmeta",
- "syn 2.0.106",
-]
-
-[[package]]
-name = "meilisearch-sdk"
-version = "0.30.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f620c9ed9b790cf292b66c8dab16f0e4aafb377583ec0e589da7c3ee81ff2038"
-dependencies = [
- "async-trait",
- "bytes",
- "either",
- "futures-channel",
- "futures-core",
- "futures-io",
- "futures-util",
- "iso8601",
- "jsonwebtoken",
- "log",
- "meilisearch-index-setting-macro",
- "pin-project-lite",
- "reqwest 0.12.24",
- "serde",
- "serde_json",
- "thiserror 2.0.17",
- "time",
- "tokio",
- "uuid 1.23.3",
- "wasm-bindgen-futures",
- "web-sys",
- "yaup",
-]
-
 [[package]]
 name = "memchr"
 version = "2.7.6"
@@ -13499,17 +13424,6 @@ dependencies = [
  "xml-rs",
 ]
 
-[[package]]
-name = "yaup"
-version = "0.3.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b0144f1a16a199846cb21024da74edd930b43443463292f536b7110b4855b5c6"
-dependencies = [
- "form_urlencoded",
- "serde",
- "thiserror 1.0.69",
-]
-
 [[package]]
 name = "yoke"
 version = "0.8.0"
diff --git a/Cargo.toml b/Cargo.toml
index 01c9a1af38..6670a240af 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -131,7 +131,6 @@ lz4_flex = { version = "0.11.5", default-features = false, features = [
   "std",
 ] }
 maxminddb = "0.26.0"
-meilisearch-sdk = { version = "0.30.0", default-features = false }
 modrinth-content-management = { path = "packages/modrinth-content-management" }
 modrinth-log = { path = "packages/modrinth-log" }
 modrinth-util = { path = "packages/modrinth-util" }
diff --git a/README.md b/README.md
index 7b4f90ef20..0def9bf509 100644
--- a/README.md
+++ b/README.md
@@ -9,7 +9,7 @@
 
 ## Modrinth Monorepo
 
-Welcome to the Modrinth Monorepo, the primary codebase for the Modrinth web interface and app. It contains ![Lines of Code](https://img.shields.io/endpoint?url=https://loctopus.creeperkatze.dev/github/modrinth/code/badge%3Fformat%3Dhuman&logoColor=white&color=black&label=) lines of code and has ![Contributors](https://img.shields.io/github/contributors/Modrinth/code?color=black&label=) contributors!
+Welcome to the Modrinth Monorepo, the primary codebase for the Modrinth web interface and app. It contains ![Lines of code](https://img.shields.io/endpoint?url=https://loctopus.creeperkatze.dev/github/modrinth/code/badge%3Fformat%3Dhuman&logoColor=white&color=black&label=) lines of code and has ![Contributors](https://img.shields.io/github/contributors/Modrinth/code?color=black&label=) contributors!
 
 If you're not a developer and you've stumbled upon this repository, you can access the web interface on the [Modrinth website](https://modrinth.com) and download the latest release of the app [here](https://modrinth.com/app).
 
diff --git a/apps/app-frontend/src/components/ui/modal/ModrinthAccountRequiredModal.vue b/apps/app-frontend/src/components/ui/modal/ModrinthAccountRequiredModal.vue
index 18b832278d..ad413f1ab8 100644
--- a/apps/app-frontend/src/components/ui/modal/ModrinthAccountRequiredModal.vue
+++ b/apps/app-frontend/src/components/ui/modal/ModrinthAccountRequiredModal.vue
@@ -73,7 +73,7 @@
 				<div class="grid grid-cols-1 gap-2 sm:grid-cols-2">
 					<Button type="outlined" class="w-full" native-type="button" @click="modal?.hide()">
 						<XIcon aria-hidden="true" />
-						{{ formatMessage(messages.cancelButton) }}
+						{{ formatMessage(commonMessages.cancelButton) }}
 					</Button>
 					<Button
 						class="w-full"
@@ -106,7 +106,14 @@
 
 <script setup lang="ts">
 import { LogInIcon, RefreshCwIcon, SpinnerIcon, UserPlusIcon, XIcon } from '@modrinth/assets'
-import { Button, defineMessages, IntlFormatted, NewModal, useVIntl } from '@modrinth/ui'
+import {
+	Button,
+	commonMessages,
+	defineMessages,
+	IntlFormatted,
+	NewModal,
+	useVIntl,
+} from '@modrinth/ui'
 import { openUrl } from '@tauri-apps/plugin-opener'
 import { ref } from 'vue'
 
@@ -245,10 +252,6 @@ const messages = defineMessages({
 		id: 'modal.modrinth-account-required.waiting-for-browser',
 		defaultMessage: 'Waiting for browser confirmation...',
 	},
-	cancelButton: {
-		id: 'modal.modrinth-account-required.cancel-button',
-		defaultMessage: 'Cancel',
-	},
 	openBrowserAgainButton: {
 		id: 'modal.modrinth-account-required.open-browser-again-button',
 		defaultMessage: 'Open browser again',
diff --git a/apps/app-frontend/src/locales/da-DK/index.json b/apps/app-frontend/src/locales/da-DK/index.json
index 249cb7b464..c0aa6b0e50 100644
--- a/apps/app-frontend/src/locales/da-DK/index.json
+++ b/apps/app-frontend/src/locales/da-DK/index.json
@@ -1112,9 +1112,6 @@
   "minecraft-required.sign-in": {
     "message": "Log ind på Microsoft"
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Annuller"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Fortsæt i din browser"
   },
diff --git a/apps/app-frontend/src/locales/de-CH/index.json b/apps/app-frontend/src/locales/de-CH/index.json
index 485ddb3f38..c74ea4c9f9 100644
--- a/apps/app-frontend/src/locales/de-CH/index.json
+++ b/apps/app-frontend/src/locales/de-CH/index.json
@@ -1853,9 +1853,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "Ein neuer Tab zum Anmelden wurde geöffnet. Schließe die Anmeldung dort ab und kehren anschließend zur App zurück."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Abbrechen"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Im Browser fortfahren"
   },
diff --git a/apps/app-frontend/src/locales/de-DE/index.json b/apps/app-frontend/src/locales/de-DE/index.json
index 3be909f0f0..aec68c7665 100644
--- a/apps/app-frontend/src/locales/de-DE/index.json
+++ b/apps/app-frontend/src/locales/de-DE/index.json
@@ -1853,9 +1853,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "Ein neuer Tab zum Anmelden wurde geöffnet. Schließe die Anmeldung dort ab und kehren anschließend zur App zurück."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Abbrechen"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Im Browser fortfahren"
   },
diff --git a/apps/app-frontend/src/locales/en-US/index.json b/apps/app-frontend/src/locales/en-US/index.json
index 884e06f247..9b5a674d18 100644
--- a/apps/app-frontend/src/locales/en-US/index.json
+++ b/apps/app-frontend/src/locales/en-US/index.json
@@ -1880,9 +1880,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "A new tab opened to sign in. Complete the sign in there, then return to the app."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Cancel"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Continue in your browser"
   },
diff --git a/apps/app-frontend/src/locales/es-419/index.json b/apps/app-frontend/src/locales/es-419/index.json
index caf734abfe..967688bdfb 100644
--- a/apps/app-frontend/src/locales/es-419/index.json
+++ b/apps/app-frontend/src/locales/es-419/index.json
@@ -1481,9 +1481,6 @@
   "minecraft-required.sign-in": {
     "message": "Iniciar sesión con Microsoft"
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Cancelar"
-  },
   "modal.modrinth-account-required.header": {
     "message": "Cuenta requerida"
   },
diff --git a/apps/app-frontend/src/locales/fr-FR/index.json b/apps/app-frontend/src/locales/fr-FR/index.json
index 246380a6b4..3fdb65f6f0 100644
--- a/apps/app-frontend/src/locales/fr-FR/index.json
+++ b/apps/app-frontend/src/locales/fr-FR/index.json
@@ -1754,9 +1754,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "A nouvel onglet a été ouvert pour vous connecter. Finissez la connexion, puis retournez dans l'application."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Annuler"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Continuer dans votre navigateur"
   },
diff --git a/apps/app-frontend/src/locales/hu-HU/index.json b/apps/app-frontend/src/locales/hu-HU/index.json
index 04455bc7a8..77f9bffdb4 100644
--- a/apps/app-frontend/src/locales/hu-HU/index.json
+++ b/apps/app-frontend/src/locales/hu-HU/index.json
@@ -1856,9 +1856,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "Megnyílt egy új lap a bejelentkezéshez. Végezd el ott a bejelentkezést, majd térj vissza az alkalmazásba."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Mégse"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Folytatás a böngészőben"
   },
diff --git a/apps/app-frontend/src/locales/it-IT/index.json b/apps/app-frontend/src/locales/it-IT/index.json
index 34de8b2a76..16587ed018 100644
--- a/apps/app-frontend/src/locales/it-IT/index.json
+++ b/apps/app-frontend/src/locales/it-IT/index.json
@@ -1853,9 +1853,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "Si è aperta una nuova scheda per effettuare l'accesso. Poi torna all'app."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Annulla"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Continua nel browser"
   },
diff --git a/apps/app-frontend/src/locales/ja-JP/index.json b/apps/app-frontend/src/locales/ja-JP/index.json
index 38db7d4b16..6bd7ff8194 100644
--- a/apps/app-frontend/src/locales/ja-JP/index.json
+++ b/apps/app-frontend/src/locales/ja-JP/index.json
@@ -1853,9 +1853,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "サインイン用のタブが開きました。そちらでサインインを完了してから、アプリに戻ってください。"
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "キャンセル"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "ブラウザで続行"
   },
diff --git a/apps/app-frontend/src/locales/ko-KR/index.json b/apps/app-frontend/src/locales/ko-KR/index.json
index 207a662b3c..1be3efe362 100644
--- a/apps/app-frontend/src/locales/ko-KR/index.json
+++ b/apps/app-frontend/src/locales/ko-KR/index.json
@@ -1853,9 +1853,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "로그인을 위한 새 탭이 열렸습니다. 해당 탭에서 로그인을 완료한 후 앱 돌아오세요."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "취소"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "브라우저에서 계속 진행"
   },
diff --git a/apps/app-frontend/src/locales/nl-NL/index.json b/apps/app-frontend/src/locales/nl-NL/index.json
index ea8bd2cdd3..10af52cfdb 100644
--- a/apps/app-frontend/src/locales/nl-NL/index.json
+++ b/apps/app-frontend/src/locales/nl-NL/index.json
@@ -1763,9 +1763,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "Er is een nieuw tabblad geopend om je aan te melden. Log daar in en ga vervolgens terug naar de app."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Annuleren"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Doorgaan in je browser"
   },
diff --git a/apps/app-frontend/src/locales/pl-PL/index.json b/apps/app-frontend/src/locales/pl-PL/index.json
index 1fc56093d7..5fb45c66c8 100644
--- a/apps/app-frontend/src/locales/pl-PL/index.json
+++ b/apps/app-frontend/src/locales/pl-PL/index.json
@@ -1619,9 +1619,6 @@
   "minecraft-required.sign-in": {
     "message": "Zaloguj się do Microsoft"
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Anuluj"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Kontynuuj w przeglądarce"
   },
diff --git a/apps/app-frontend/src/locales/pt-BR/index.json b/apps/app-frontend/src/locales/pt-BR/index.json
index 06aa6d9c18..f46b9bbab6 100644
--- a/apps/app-frontend/src/locales/pt-BR/index.json
+++ b/apps/app-frontend/src/locales/pt-BR/index.json
@@ -1856,9 +1856,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "Uma nova aba foi aberta para iniciar sessão. Conclua lá, então volte ao aplicativo."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Cancelar"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Continuar em seu navegador"
   },
diff --git a/apps/app-frontend/src/locales/ru-RU/index.json b/apps/app-frontend/src/locales/ru-RU/index.json
index 9588318155..76ad5b2c8e 100644
--- a/apps/app-frontend/src/locales/ru-RU/index.json
+++ b/apps/app-frontend/src/locales/ru-RU/index.json
@@ -1844,9 +1844,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "Открылась вкладка для входа. Завершение вход и вернитесь в приложение."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Отмена"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Продолжите в браузере"
   },
diff --git a/apps/app-frontend/src/locales/sv-SE/index.json b/apps/app-frontend/src/locales/sv-SE/index.json
index 9fafae441c..a6eb17552c 100644
--- a/apps/app-frontend/src/locales/sv-SE/index.json
+++ b/apps/app-frontend/src/locales/sv-SE/index.json
@@ -1640,9 +1640,6 @@
   "minecraft-required.sign-in": {
     "message": "Logga in på Microsoft"
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Avbryt"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Fortsätt i din webbläsare"
   },
diff --git a/apps/app-frontend/src/locales/tr-TR/index.json b/apps/app-frontend/src/locales/tr-TR/index.json
index 0df2fb9deb..9fe9fd9359 100644
--- a/apps/app-frontend/src/locales/tr-TR/index.json
+++ b/apps/app-frontend/src/locales/tr-TR/index.json
@@ -1457,9 +1457,6 @@
   "minecraft-required.sign-in": {
     "message": "Microsoft'a giriş yap"
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "İptal"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Tarayıcında devam et"
   },
diff --git a/apps/app-frontend/src/locales/uk-UA/index.json b/apps/app-frontend/src/locales/uk-UA/index.json
index b3b9cd20f6..1666af7c26 100644
--- a/apps/app-frontend/src/locales/uk-UA/index.json
+++ b/apps/app-frontend/src/locales/uk-UA/index.json
@@ -1853,9 +1853,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "Відкрилася нова вкладка, де ви зможете ввійти. Увійдіть, тоді поверніться до застосунку."
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "Скасувати"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "Продовжити у браузері"
   },
diff --git a/apps/app-frontend/src/locales/zh-CN/index.json b/apps/app-frontend/src/locales/zh-CN/index.json
index c6f14d0b9b..0d6ebfc67c 100644
--- a/apps/app-frontend/src/locales/zh-CN/index.json
+++ b/apps/app-frontend/src/locales/zh-CN/index.json
@@ -1856,9 +1856,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "一个新的标签页已打开，你需要在那里完成登录，然后回到Modrinth app。"
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "取消"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "请在你的浏览器中继续"
   },
diff --git a/apps/app-frontend/src/locales/zh-TW/index.json b/apps/app-frontend/src/locales/zh-TW/index.json
index cce0b1e88b..c87fdb7f28 100644
--- a/apps/app-frontend/src/locales/zh-TW/index.json
+++ b/apps/app-frontend/src/locales/zh-TW/index.json
@@ -1856,9 +1856,6 @@
   "modal.modrinth-account-required.browser-description": {
     "message": "一個新分頁已開啟供你登入。請在該分頁完成登入，然後返回應用程式。"
   },
-  "modal.modrinth-account-required.cancel-button": {
-    "message": "取消"
-  },
   "modal.modrinth-account-required.continue-in-browser-heading": {
     "message": "在瀏覽器中繼續"
   },
diff --git a/apps/app-frontend/src/pages/User.vue b/apps/app-frontend/src/pages/User.vue
index e04c0da3fa..daf79890c2 100644
--- a/apps/app-frontend/src/pages/User.vue
+++ b/apps/app-frontend/src/pages/User.vue
@@ -52,6 +52,8 @@ import { onBeforeRouteUpdate, useRoute, useRouter } from 'vue-router'
 
 import {
 	block_user,
+	change_user_avatar,
+	delete_user_avatar,
 	get_blocked_users,
 	get_user_collections,
 	get_user_organizations,
@@ -119,6 +121,10 @@ const userProfile = provideUserProfile({
 	getOrganizations: get_user_organizations,
 	getCollections: get_user_collections,
 	patchUser: patch_user,
+	changeAvatar: async (userId, file, extension) => {
+		await change_user_avatar(userId, new Uint8Array(await file.arrayBuffer()), extension)
+	},
+	deleteAvatar: delete_user_avatar,
 	getBlockedUsers: get_blocked_users,
 	blockUser: block_user,
 	unblockUser: unblock_user,
diff --git a/apps/app-frontend/src/pages/instance/components/page-header/index.vue b/apps/app-frontend/src/pages/instance/components/page-header/index.vue
index 50c0f4e4fe..507b03bd63 100644
--- a/apps/app-frontend/src/pages/instance/components/page-header/index.vue
+++ b/apps/app-frontend/src/pages/instance/components/page-header/index.vue
@@ -55,8 +55,8 @@
 				</PageHeaderMetadataItem>
 				<PageHeaderMetadataItem
 					v-if="sharedInstanceManager?.type !== 'user'"
-					:icon="ServerLoaderIcon"
-					:icon-props="{ loader: loaderDisplayName }"
+					:icon="TagIcon"
+					:icon-props="{ tag: loaderDisplayName, enforceType: 'loader' }"
 					tooltip="Mod loader"
 				>
 					{{ loaderLabel }}
@@ -205,7 +205,6 @@ import {
 	commonMessages,
 	defineMessages,
 	formatLoaderLabel,
-	LoaderIcon as ServerLoaderIcon,
 	type OverflowMenuOption,
 	PageHeader,
 	PageHeaderActions,
@@ -213,6 +212,7 @@ import {
 	PageHeaderMetadata,
 	PageHeaderMetadataItem,
 	type ServerLoader,
+	TagIcon,
 	useVIntl,
 } from '@modrinth/ui'
 import { computed } from 'vue'
diff --git a/apps/app-frontend/src/pages/instance/share/shared-instance-members-table.vue b/apps/app-frontend/src/pages/instance/share/shared-instance-members-table.vue
index 756f9b0430..fb35a9457a 100644
--- a/apps/app-frontend/src/pages/instance/share/shared-instance-members-table.vue
+++ b/apps/app-frontend/src/pages/instance/share/shared-instance-members-table.vue
@@ -283,7 +283,7 @@ function filterClass(active: boolean) {
 	return [
 		'cursor-pointer rounded-full border border-solid px-3 py-1.5 text-base font-semibold leading-5 transition-all duration-100 active:scale-[0.97]',
 		active
-			? 'border-green bg-brand-highlight text-brand'
+			? 'border-brand bg-brand-highlight text-brand'
 			: 'border-surface-5 bg-surface-4 text-primary hover:bg-surface-5',
 	]
 }
diff --git a/apps/app-frontend/src/pages/instance/worlds/index.vue b/apps/app-frontend/src/pages/instance/worlds/index.vue
index 1d9adca70d..10f9118401 100644
--- a/apps/app-frontend/src/pages/instance/worlds/index.vue
+++ b/apps/app-frontend/src/pages/instance/worlds/index.vue
@@ -263,7 +263,7 @@ function filterPillClass(isActive: boolean) {
 	return [
 		'cursor-pointer rounded-full border border-solid px-3 py-1.5 text-base font-semibold leading-5 transition-all duration-100 active:scale-[0.97]',
 		isActive
-			? 'border-green bg-brand-highlight text-brand'
+			? 'border-brand bg-brand-highlight text-brand'
 			: 'border-surface-5 bg-surface-4 text-primary hover:bg-surface-5',
 	]
 }
diff --git a/apps/frontend/src/assets/styles/layout.scss b/apps/frontend/src/assets/styles/layout.scss
index 83debb8ff8..d633ed8df9 100644
--- a/apps/frontend/src/assets/styles/layout.scss
+++ b/apps/frontend/src/assets/styles/layout.scss
@@ -111,6 +111,18 @@
 				max-width: 100%;
 			}
 		}
+
+		&.align-x {
+			margin: 0 auto;
+		}
+
+		&.align-l {
+			margin: 0 0 0 auto;
+		}
+
+		&.align-r {
+			margin: 0 auto 0 0;
+		}
 	}
 
 	.normal-page__sidebar {
@@ -140,6 +152,18 @@
 		'sidebar'
 		/ 100%;
 
+	&.align-x {
+		margin: 0 auto;
+	}
+
+	&.align-l {
+		margin: 0 0 0 auto;
+	}
+
+	&.align-r {
+		margin: 0 auto 0 0;
+	}
+
 	@media screen and (min-width: 1024px) {
 		&.sidebar {
 			grid-template:
diff --git a/apps/frontend/src/components/analytics-dashboard/stat-cards/StatCard.vue b/apps/frontend/src/components/analytics-dashboard/stat-cards/StatCard.vue
index 071e2eb584..9585972b1f 100644
--- a/apps/frontend/src/components/analytics-dashboard/stat-cards/StatCard.vue
+++ b/apps/frontend/src/components/analytics-dashboard/stat-cards/StatCard.vue
@@ -5,7 +5,7 @@
 		class="flex h-full appearance-none flex-col gap-2.5 rounded-2xl border border-solid p-5 px-4 text-left transition-colors sm:gap-4"
 		:class="{
 			'cursor-not-allowed border-surface-5 bg-surface-2 opacity-60': disabled,
-			'cursor-default border-brand bg-highlight-green': !disabled && active,
+			'cursor-default border-brand bg-brand-highlight': !disabled && active,
 			'border-surface-5 bg-surface-3 hover:bg-surface-4 active:scale-95': !disabled && !active,
 		}"
 		:disabled="disabled"
diff --git a/apps/frontend/src/components/ui/ProjectDownloadModal/DownloadProject.vue b/apps/frontend/src/components/ui/ProjectDownloadModal/DownloadProject.vue
index 976b2a681f..e267253398 100644
--- a/apps/frontend/src/components/ui/ProjectDownloadModal/DownloadProject.vue
+++ b/apps/frontend/src/components/ui/ProjectDownloadModal/DownloadProject.vue
@@ -82,10 +82,8 @@
 
 	<div
 		v-if="selectedVersion && downloadDataLoaded"
-		:role="compatibleVersions.length > 1 ? 'radiogroup' : undefined"
-		:aria-label="
-			compatibleVersions.length > 1 ? formatMessage(messages.compatibleVersionTitle) : undefined
-		"
+		:role="showVersionSelector ? 'radiogroup' : undefined"
+		:aria-label="showVersionSelector ? formatMessage(messages.compatibleVersionTitle) : undefined"
 		class="flex flex-col gap-2.5"
 	>
 		<h3
@@ -102,26 +100,12 @@
 			:download-reason="downloadReason"
 			:current-game-version="currentGameVersion"
 			:current-platform="currentPlatform"
-			:selectable="compatibleVersions.length > 1"
+			:selectable="showVersionSelector"
 			:selected="compatibleVersion.id === selectedVersion.id"
-			:show-download="
-				compatibleVersions.length === 1 || compatibleVersion.id === selectedVersion.id
-			"
-			:color="
-				compatibleVersion.id === selectedVersion.id &&
-				compatibleVersions.length === 1 &&
-				!hasAdditionalDownloads
-					? 'brand'
-					: 'standard'
-			"
-			:type="
-				compatibleVersion.id === selectedVersion.id &&
-				compatibleVersions.length === 1 &&
-				!hasAdditionalDownloads
-					? 'standard'
-					: 'transparent'
-			"
-			:circular="hasAdditionalDownloads || compatibleVersions.length > 1"
+			:show-download="!showVersionSelector || compatibleVersion.id === selectedVersion.id"
+			:color="isPrimaryDownloadVersion(compatibleVersion) ? 'brand' : 'standard'"
+			:type="isPrimaryDownloadVersion(compatibleVersion) ? 'standard' : 'transparent'"
+			:circular="!isPrimaryDownloadVersion(compatibleVersion)"
 			@select="selectCompatibleVersion(compatibleVersion)"
 			@download="emit('download')"
 		/>
@@ -494,6 +478,10 @@ const hasAdditionalDownloads = computed(() => {
 	return hrefs.size > 1
 })
 
+const showVersionSelector = computed(
+	() => hasAdditionalDownloads.value && compatibleVersions.value.length > 1,
+)
+
 watch(
 	[currentGameVersion, currentPlatform, selectedVersion, selectedPrimaryFile],
 	() => {
@@ -539,6 +527,10 @@ function selectCompatibleVersion(version: Labrinth.Versions.v3.Version) {
 	userSelectedCompatibleVersionId.value = version.id
 }
 
+function isPrimaryDownloadVersion(version: Labrinth.Versions.v3.Version) {
+	return !hasAdditionalDownloads.value && version.id === defaultSelectedVersion.value?.id
+}
+
 function latestVersionByType(type: Labrinth.Versions.v3.VersionChannel) {
 	return filteredVersions.value
 		.filter((version) => version.version_type === type)
diff --git a/apps/frontend/src/components/ui/create-project-version/components/LoaderPicker.vue b/apps/frontend/src/components/ui/create-project-version/components/LoaderPicker.vue
index 4c0ed3356f..1496ee3c4d 100644
--- a/apps/frontend/src/components/ui/create-project-version/components/LoaderPicker.vue
+++ b/apps/frontend/src/components/ui/create-project-version/components/LoaderPicker.vue
@@ -22,7 +22,7 @@
 						class="border !border-solid !transition-all hover:bg-button-bgHover hover:no-underline"
 						:class="
 							selectedLoaders.includes(loader.name)
-								? 'border-brand bg-highlight-green text-brand'
+								? 'border-brand bg-brand-highlight text-brand'
 								: 'border-surface-5'
 						"
 						:style="`--_color: var(--color-platform-${loader.name})`"
diff --git a/apps/frontend/src/components/ui/dashboard/CreatorTaxFormModal.vue b/apps/frontend/src/components/ui/dashboard/CreatorTaxFormModal.vue
index 83ca57653d..3999e22cb1 100644
--- a/apps/frontend/src/components/ui/dashboard/CreatorTaxFormModal.vue
+++ b/apps/frontend/src/components/ui/dashboard/CreatorTaxFormModal.vue
@@ -133,7 +133,7 @@
 				</div>
 				<div class="flex w-full flex-row justify-stretch gap-2">
 					<Button class="w-full text-contrast" @click="handleClose">
-						{{ props.closeButtonText ?? formatMessage(messages.closeButton) }}
+						{{ props.closeButtonText ?? formatMessage(commonMessages.closeButton) }}
 					</Button>
 					<Button
 						type="colored"
@@ -267,10 +267,6 @@ const messages = defineMessages({
 		id: 'dashboard.creator-tax-form-modal.confirmation.download-button',
 		defaultMessage: 'Download {formType}',
 	},
-	closeButton: {
-		id: 'dashboard.creator-tax-form-modal.close-button',
-		defaultMessage: 'Close',
-	},
 	incompleteTitle: {
 		id: 'dashboard.creator-tax-form-modal.incomplete.title',
 		defaultMessage: 'Tax form incomplete',
diff --git a/apps/frontend/src/components/ui/moderation/ModerationTechRevCard.vue b/apps/frontend/src/components/ui/moderation/ModerationTechRevCard.vue
index 0baa5864a0..e6f5b3f9a4 100644
--- a/apps/frontend/src/components/ui/moderation/ModerationTechRevCard.vue
+++ b/apps/frontend/src/components/ui/moderation/ModerationTechRevCard.vue
@@ -856,6 +856,10 @@ async function updateDetailStatus(
 
 	updatingDetails.add(detailId)
 
+	const previousMarkedCount = selectedFile.value
+		? getFileMarkedCount(selectedFile.value)
+		: undefined
+
 	try {
 		await updateIssueDetails([{ detail_id: detailId, verdict }])
 
@@ -880,7 +884,7 @@ async function updateDetailStatus(
 		if (verdict !== 'pending' && selectedFile.value) {
 			const markedCount = getFileMarkedCount(selectedFile.value)
 			const totalCount = getFileDetailCount(selectedFile.value)
-			if (markedCount === totalCount) {
+			if (previousMarkedCount != markedCount && markedCount === totalCount) {
 				backToFileList()
 			}
 		}
@@ -938,6 +942,10 @@ async function updateGlobalDetailStatus(
 
 	updatingGlobalDetailKeys.add(detail.key)
 
+	const previousMarkedCount = selectedFile.value
+		? getFileMarkedCount(selectedFile.value)
+		: undefined
+
 	try {
 		await updateGlobalIssueDetail(detail.key, verdict)
 
@@ -958,7 +966,7 @@ async function updateGlobalDetailStatus(
 		if (verdict !== 'pending' && selectedFile.value) {
 			const markedCount = getFileMarkedCount(selectedFile.value)
 			const totalCount = getFileDetailCount(selectedFile.value)
-			if (markedCount === totalCount) {
+			if (previousMarkedCount != markedCount && markedCount === totalCount) {
 				backToFileList()
 			}
 		}
@@ -1355,8 +1363,10 @@ const canSubmitReview = computed(() => {
 	if (totalIssues === 0) return true
 	return allIssuesResolved.value
 })
+const hasSubmittedPassReview = ref(false)
 
 async function handleSubmitReview(verdict: 'safe' | 'unsafe') {
+	hasSubmittedPassReview.value = verdict === 'safe'
 	const editorContent = threadViewRef.value?.getReplyContent() || ''
 
 	let message: string | undefined
@@ -1523,13 +1533,39 @@ function copyId() {
 
 			<div class="h-px w-full bg-surface-5"></div>
 
-			<NavTabs
-				mode="local"
-				:links="navTabsLinks"
-				:active-index="activeTabIndex"
-				class="bg-surface-3! shadow-none!"
-				@tab-click="handleTabClick"
-			/>
+			<div class="flex flex-row justify-between">
+				<NavTabs
+					mode="local"
+					:links="navTabsLinks"
+					:active-index="activeTabIndex"
+					class="bg-surface-3! shadow-none!"
+					@tab-click="handleTabClick"
+				/>
+
+				<div v-if="selectedFile" class="flex flex-row items-end gap-2">
+					<ButtonLink
+						v-tooltip="`Download`"
+						type="outlined"
+						target="_blank"
+						:href="selectedFile.download_url"
+						:download="selectedFile.file_name"
+						class="!bg-surface-2"
+						aria-label="Download"
+					>
+						<DownloadIcon aria-hidden="true" />
+					</ButtonLink>
+					<ButtonLink
+						v-tooltip="`Open in Slicer`"
+						type="outlined"
+						target="_blank"
+						:href="`https://slicer.run/?url=${encodeURIComponent(selectedFile.download_url)}`"
+						class="!bg-surface-2"
+						aria-label="Open in Slicer"
+					>
+						<ExternalIcon aria-hidden="true" /> Open
+					</ButtonLink>
+				</div>
+			</div>
 		</div>
 
 		<div class="border-t border-surface-3 bg-surface-2">
@@ -1552,10 +1588,16 @@ function copyId() {
 						>
 							<template #additionalActions>
 								<Button
-									v-tooltip="!canSubmitReview ? 'There are still pending flags!' : undefined"
+									v-tooltip="
+										!canSubmitReview
+											? 'There are still pending flags!'
+											: hasSubmittedPassReview
+												? 'Project already passed!'
+												: undefined
+									"
 									type="colored"
 									color="brand"
-									:disabled="!canSubmitReview"
+									:disabled="!canSubmitReview || hasSubmittedPassReview"
 									@click="handleSubmitReview('safe')"
 								>
 									<ShieldCheckIcon /> Pass
@@ -1683,7 +1725,16 @@ function copyId() {
 							:download="file.file_name"
 							tabindex="0"
 						>
-							<DownloadIcon /> Download
+							<DownloadIcon />
+						</ButtonLink>
+						<ButtonLink
+							v-tooltip="`Open in Slicer`"
+							type="outlined"
+							target="_blank"
+							:href="`https://slicer.run/?url=${encodeURIComponent(file.download_url)}`"
+							aria-label="Open in Slicer"
+						>
+							<ExternalIcon aria-hidden="true" /> Open
 						</ButtonLink>
 					</div>
 				</div>
@@ -2063,7 +2114,7 @@ function copyId() {
 										v-tooltip="`Copy code`"
 										type="quiet"
 										:label="`Copy code`"
-										class="absolute right-2 top-2 border-[1px]"
+										class="!absolute right-2 top-2 border-[1px]"
 										@click="copyToClipboard(getClassDecompiledSource(classItem)!, classItem.key)"
 									>
 										<CopyIcon v-if="!showCopyFeedback.get(classItem.key)" />
diff --git a/apps/frontend/src/components/ui/moderation/ModpackScanModal.vue b/apps/frontend/src/components/ui/moderation/ModpackScanModal.vue
index 41c0888f81..c3057c955c 100644
--- a/apps/frontend/src/components/ui/moderation/ModpackScanModal.vue
+++ b/apps/frontend/src/components/ui/moderation/ModpackScanModal.vue
@@ -11,6 +11,7 @@ import { Button, IconButton } from '@modrinth/ui'
 import {
 	Combobox,
 	type ComboboxOption,
+	commonMessages,
 	ConfirmModal,
 	defineMessages,
 	injectModrinthClient,
@@ -61,10 +62,6 @@ const messages = defineMessages({
 		id: 'modpack-scan-modal.scanning',
 		defaultMessage: 'Scanning...',
 	},
-	success: {
-		id: 'modpack-scan-modal.success',
-		defaultMessage: 'Success',
-	},
 	failed: {
 		id: 'modpack-scan-modal.failed',
 		defaultMessage: 'Failed',
@@ -102,10 +99,6 @@ const messages = defineMessages({
 		defaultMessage:
 			'This will permanently delete all attribution groups for this project and all files inside them. This action cannot be undone.',
 	},
-	deleteAllGroupsConfirmationProceed: {
-		id: 'modpack-scan-modal.delete-all-groups.proceed',
-		defaultMessage: 'Clear',
-	},
 	deleteAllGroupsSuccess: {
 		id: 'modpack-scan-modal.delete-all-groups.success',
 		defaultMessage: 'All groups cleared successfully.',
@@ -344,7 +337,7 @@ async function clearAllGroups() {
 	if (!failed) {
 		addNotification({
 			type: 'success',
-			title: formatMessage(messages.success),
+			title: formatMessage(commonMessages.successLabel),
 			text: formatMessage(messages.deleteAllGroupsSuccess),
 		})
 	}
@@ -369,7 +362,7 @@ defineExpose({ show, hide })
 		ref="clearModalRef"
 		:title="formatMessage(messages.deleteAllGroupsConfirmationTitle)"
 		:description="formatMessage(messages.deleteAllGroupsConfirmationDescription)"
-		:proceed-label="formatMessage(messages.deleteAllGroupsConfirmationProceed)"
+		:proceed-label="formatMessage(commonMessages.clearButton)"
 		@proceed="clearAllGroups"
 	/>
 
diff --git a/apps/frontend/src/components/ui/moderation/settings/ModerationKeybind.vue b/apps/frontend/src/components/ui/moderation/settings/ModerationKeybind.vue
index b9dd7a5320..377c658252 100644
--- a/apps/frontend/src/components/ui/moderation/settings/ModerationKeybind.vue
+++ b/apps/frontend/src/components/ui/moderation/settings/ModerationKeybind.vue
@@ -2,9 +2,13 @@
 	<div>
 		<span class="flex flex-row items-center gap-2 text-sm text-secondary">
 			<GlobeIcon
-				v-if="props.global"
+				v-if="props.scope === 'project'"
 				v-tooltip="'Can be used without the checklist open if setting enabled.'"
 			/>
+			<ShieldCheckIcon
+				v-if="props.scope === 'tech-review'"
+				v-tooltip="'Used within the tech review pages'"
+			/>
 			{{ props.title }}
 			<IconButton
 				type="quiet"
@@ -45,14 +49,14 @@
 </template>
 
 <script setup lang="ts">
-import { GlobeIcon, RotateCounterClockwiseIcon } from '@modrinth/assets'
+import { GlobeIcon, RotateCounterClockwiseIcon, ShieldCheckIcon } from '@modrinth/assets'
 import { type KeybindDefinition, toKeybindDefinition } from '@modrinth/moderation'
 import { IconButton } from '@modrinth/ui'
 import { onUnmounted } from 'vue'
 
 const props = defineProps<{
 	title: string
-	global: boolean
+	scope: string
 	definitions: KeybindDefinition[]
 	default: KeybindDefinition[]
 	onChange: (definitions: KeybindDefinition[]) => void
diff --git a/apps/frontend/src/components/ui/moderation/settings/ModerationKeybinds.vue b/apps/frontend/src/components/ui/moderation/settings/ModerationKeybinds.vue
index 35ae3a472c..2ef3e51d83 100644
--- a/apps/frontend/src/components/ui/moderation/settings/ModerationKeybinds.vue
+++ b/apps/frontend/src/components/ui/moderation/settings/ModerationKeybinds.vue
@@ -12,7 +12,7 @@ const keybinds = useModerationKeybinds()
 				v-for="[id, keybind] in keybinds"
 				:key="id"
 				:title="keybind.description"
-				:global="keybind.scope === 'project'"
+				:scope="keybind.scope"
 				:definitions="keybind.keybind"
 				:default="keybind.defaultKeybind"
 				:on-change="
diff --git a/apps/frontend/src/components/ui/servers/marketing/ServerPlanSelector.vue b/apps/frontend/src/components/ui/servers/marketing/ServerPlanSelector.vue
index c36537d79c..9e0bffc6e7 100644
--- a/apps/frontend/src/components/ui/servers/marketing/ServerPlanSelector.vue
+++ b/apps/frontend/src/components/ui/servers/marketing/ServerPlanSelector.vue
@@ -42,8 +42,7 @@ const plans: Record<
 	Plan,
 	{
 		buttonColor: 'blue' | 'green' | 'purple'
-		accentText: string
-		accentBg: string
+		buttonClasses: string
 		name: MessageDescriptor
 		description: MessageDescriptor
 		mostPopular: boolean
@@ -51,8 +50,7 @@ const plans: Record<
 > = {
 	small: {
 		buttonColor: 'blue',
-		accentText: 'text-blue',
-		accentBg: 'bg-bg-blue',
+		buttonClasses: '!bg-highlight-blue !text-blue',
 		name: commonMessages.planSmallLabel,
 		description: defineMessage({
 			id: 'servers.plan.small.description',
@@ -62,8 +60,7 @@ const plans: Record<
 	},
 	medium: {
 		buttonColor: 'green',
-		accentText: 'text-green',
-		accentBg: 'bg-bg-green',
+		buttonClasses: '',
 		name: commonMessages.planMediumLabel,
 		description: defineMessage({
 			id: 'servers.plan.medium.description',
@@ -73,8 +70,7 @@ const plans: Record<
 	},
 	large: {
 		buttonColor: 'purple',
-		accentText: 'text-purple',
-		accentBg: 'bg-bg-purple',
+		buttonClasses: '!bg-highlight-purple !text-purple',
 		name: commonMessages.planLargeLabel,
 		description: defineMessage({
 			id: 'servers.plan.large.description',
@@ -150,16 +146,20 @@ const billingMonths = computed(() => {
 				v-if="outOfStock"
 				disabled
 				size="xl"
-				:type="plans[plan].mostPopular ? 'colored' : 'base'"
-				:color="plans[plan].mostPopular ? plans[plan].buttonColor : undefined"
+				:type="plans[plan].mostPopular ? 'colored' : 'quiet'"
+				:color="plans[plan].buttonColor"
+				:interaction="plans[plan].mostPopular ? undefined : 'none'"
+				:class="plans[plan].buttonClasses"
 			>
 				{{ formatMessage(messages.outOfStock) }}
 			</Button>
 			<Button
 				v-else
 				size="xl"
-				:type="plans[plan].mostPopular ? 'colored' : 'base'"
-				:color="plans[plan].mostPopular ? plans[plan].buttonColor : undefined"
+				:type="plans[plan].mostPopular ? 'colored' : 'quiet'"
+				:color="plans[plan].buttonColor"
+				:interaction="plans[plan].mostPopular ? undefined : 'none'"
+				:class="plans[plan].buttonClasses"
 				@click="() => emit('select')"
 			>
 				{{ formatMessage(messages.selectPlanButton) }}
diff --git a/apps/frontend/src/layouts/default.vue b/apps/frontend/src/layouts/default.vue
index bf09d69e04..6ebd410f11 100644
--- a/apps/frontend/src/layouts/default.vue
+++ b/apps/frontend/src/layouts/default.vue
@@ -138,22 +138,6 @@
 						<BracesIcon aria-hidden="true" />
 						{{ formatMessage(commonProjectTypeCategoryMessages.datapack) }}
 					</ButtonLink>
-					<ButtonLink
-						type="quiet"
-						to="/discover/modpacks"
-						:class="
-							route.name === 'discover-modpacks' || route.path.startsWith('/modpack/')
-								? (route.name === 'discover-modpacks'
-										? 'main-nav-primary'
-										: 'main-nav-secondary') === 'main-nav-primary'
-									? '!bg-[var(--color-button-bg-selected)] !text-[var(--color-button-text-selected)] [&>svg]:!text-[var(--color-button-text-selected)]'
-									: '!bg-[var(--color-button-bg)] !text-contrast'
-								: ''
-						"
-					>
-						<PackageOpenIcon aria-hidden="true" />
-						{{ formatMessage(commonProjectTypeCategoryMessages.modpack) }}
-					</ButtonLink>
 					<ButtonLink
 						type="quiet"
 						to="/discover/shaders"
@@ -170,6 +154,22 @@
 						<GlassesIcon aria-hidden="true" />
 						{{ formatMessage(commonProjectTypeCategoryMessages.shader) }}
 					</ButtonLink>
+					<ButtonLink
+						type="quiet"
+						to="/discover/modpacks"
+						:class="
+							route.name === 'discover-modpacks' || route.path.startsWith('/modpack/')
+								? (route.name === 'discover-modpacks'
+										? 'main-nav-primary'
+										: 'main-nav-secondary') === 'main-nav-primary'
+									? '!bg-[var(--color-button-bg-selected)] !text-[var(--color-button-text-selected)] [&>svg]:!text-[var(--color-button-text-selected)]'
+									: '!bg-[var(--color-button-bg)] !text-contrast'
+								: ''
+						"
+					>
+						<PackageOpenIcon aria-hidden="true" />
+						{{ formatMessage(commonProjectTypeCategoryMessages.modpack) }}
+					</ButtonLink>
 					<ButtonLink
 						type="quiet"
 						to="/discover/plugins"
@@ -1215,8 +1215,8 @@ const navRoutes = computed(() => [
 		href: '/discover/mods',
 	},
 	{
-		label: formatMessage(getProjectTypeMessage('plugin', true)),
-		href: '/discover/plugins',
+		label: formatMessage(getProjectTypeMessage('resourcepack', true)),
+		href: '/discover/resourcepacks',
 	},
 	{
 		label: formatMessage(getProjectTypeMessage('datapack', true)),
@@ -1226,14 +1226,14 @@ const navRoutes = computed(() => [
 		label: formatMessage(getProjectTypeMessage('shader', true)),
 		href: '/discover/shaders',
 	},
-	{
-		label: formatMessage(getProjectTypeMessage('resourcepack', true)),
-		href: '/discover/resourcepacks',
-	},
 	{
 		label: formatMessage(getProjectTypeMessage('modpack', true)),
 		href: '/discover/modpacks',
 	},
+	{
+		label: formatMessage(getProjectTypeMessage('plugin', true)),
+		href: '/discover/plugins',
+	},
 	{
 		label: formatMessage(getProjectTypeMessage('server', true)),
 		href: '/discover/servers',
diff --git a/apps/frontend/src/locales/de-CH/index.json b/apps/frontend/src/locales/de-CH/index.json
index f597a9b449..44905b92fb 100644
--- a/apps/frontend/src/locales/de-CH/index.json
+++ b/apps/frontend/src/locales/de-CH/index.json
@@ -1481,9 +1481,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Kürzlich aktualisiert"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Schließen"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "{formType} herunterladen"
   },
@@ -2984,9 +2981,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Fehler beim Löschen aller Gruppen: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Löschen"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "Alle Gruppen wurden gelöscht."
   },
@@ -3026,9 +3020,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Wird gescannt..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Erfolg"
-  },
   "modpack-scan-modal.title": {
     "message": "Modpack-Scan ({scanned}/{total} Dateien)"
   },
@@ -3938,9 +3929,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Hervorgehobene Tags"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Du kannst bis zu 3 deiner relevantesten Tags als hervorheben. Andere Tags werden möglicherweise hervorgehoben, falls du nicht alle 3 auswählst."
-  },
   "project.settings.tags.features-description": {
     "message": "Wähle alle Funktionen aus, die dein {type} nutzt."
   },
@@ -3956,9 +3944,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Wähle mindestens eine Kategorie aus, um eine Kategorie hervorzuheben."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "Genaue Tags sind wichtig, damit Nutzer dein {type} leichter finden können. Achte darauf, alle zutreffenden Tags auszuwählen."
-  },
   "project.settings.tags.title": {
     "message": "Tags"
   },
diff --git a/apps/frontend/src/locales/de-DE/index.json b/apps/frontend/src/locales/de-DE/index.json
index e8cf4ad437..325ab58933 100644
--- a/apps/frontend/src/locales/de-DE/index.json
+++ b/apps/frontend/src/locales/de-DE/index.json
@@ -1481,9 +1481,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Kürzlich aktualisiert"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Schließen"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Lade {formType} herunter"
   },
@@ -2984,9 +2981,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Fehler beim Löschen aller Gruppen: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Löschen"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "Alle Gruppen wurden gelöscht."
   },
@@ -3026,9 +3020,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Wird gescannt..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Erfolg"
-  },
   "modpack-scan-modal.title": {
     "message": "Modpack-Scan ({scanned}/{total} Dateien)"
   },
@@ -3938,9 +3929,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Hervorgehobene Tags"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Du kannst bis zu 3 deiner relevantesten Tags als hervorheben. Andere Tags werden möglicherweise hervorgehoben, falls du nicht alle 3 auswählst."
-  },
   "project.settings.tags.features-description": {
     "message": "Wähle alle Funktionen aus, die dein {type} nutzt."
   },
@@ -3956,9 +3944,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Wähle mindestens eine Kategorie aus, um eine Kategorie hervorzuheben."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "Genaue Tags sind wichtig, damit Nutzer dein {type} leichter finden können. Achte darauf, alle zutreffenden Tags auszuwählen."
-  },
   "project.settings.tags.title": {
     "message": "Tags"
   },
diff --git a/apps/frontend/src/locales/en-US/index.json b/apps/frontend/src/locales/en-US/index.json
index 098f68d084..4ff5fc1241 100644
--- a/apps/frontend/src/locales/en-US/index.json
+++ b/apps/frontend/src/locales/en-US/index.json
@@ -1481,9 +1481,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Recently Updated"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Close"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Download {formType}"
   },
@@ -2984,9 +2981,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Failed to clear all groups: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Clear"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "All groups cleared successfully."
   },
@@ -3026,9 +3020,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Scanning..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Success"
-  },
   "modpack-scan-modal.title": {
     "message": "Modpack Scan ({scanned}/{total} Files)"
   },
@@ -4169,12 +4160,27 @@
   "project.settings.tags.featured-tags": {
     "message": "Featured tags"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "You can feature up to 3 of your most relevant tags. Other tags may be promoted to featured if you do not select all 3."
+  "project.settings.tags.featured-tags-required": {
+    "message": "You must have at least one featured tag."
+  },
+  "project.settings.tags.featured-tags-select-description": {
+    "message": "Select your most relevant tags. These are displayed before the rest of your tags."
   },
   "project.settings.tags.features-description": {
     "message": "Select all of the features that your {type} makes use of."
   },
+  "project.settings.tags.group-title.categories": {
+    "message": "{showType, select, yes {{types} categories} other {Categories}}"
+  },
+  "project.settings.tags.group-title.features": {
+    "message": "{showType, select, yes {{types} features} other {Features}}"
+  },
+  "project.settings.tags.group-title.performance-impact": {
+    "message": "{showType, select, yes {{types} performance impact} other {Performance impact}}"
+  },
+  "project.settings.tags.group-title.resolutions": {
+    "message": "{showType, select, yes {{types} resolutions} other {Resolutions}}"
+  },
   "project.settings.tags.multiple-resolution-tags-warning": {
     "message": "You've selected {count} resolution tags ({tags}). Resource packs should typically only have one resolution tag."
   },
@@ -4187,9 +4193,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Select at least one category in order to feature a category."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "Accurate tagging is important to help people find your {type}. Make sure to select all tags that apply."
-  },
   "project.settings.tags.title": {
     "message": "Tags"
   },
diff --git a/apps/frontend/src/locales/es-419/index.json b/apps/frontend/src/locales/es-419/index.json
index 7f1e7e5fa3..8bd587e734 100644
--- a/apps/frontend/src/locales/es-419/index.json
+++ b/apps/frontend/src/locales/es-419/index.json
@@ -1481,9 +1481,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Actualizado recientemente"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Cerrar"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Descargar {formType}"
   },
@@ -2984,9 +2981,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Error al borrar todos los grupos: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Borrar"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "Todos los grupos fueron borrados exitosamente."
   },
@@ -3026,9 +3020,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Escaneando..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Éxito"
-  },
   "modpack-scan-modal.title": {
     "message": "Análisis del modpack ({scanned}/{total} archivos)"
   },
@@ -3938,9 +3929,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Etiquetas destacadas"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Puedes destacar hasta 3 de tus etiquetas más relevantes. Otras etiquetas pueden ser promovidas a destacadas si no seleccionas las 3 completas."
-  },
   "project.settings.tags.features-description": {
     "message": "Selecciona todas las características que tu {type} usa."
   },
@@ -3956,9 +3944,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Selecciona al menos una categoría para destacar una categoría."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "Seleccionar etiquetas relevantes es importante para ayudar a la gente a encontrar tu {type}. Asegúrate de seleccionar todas las etiquetas que apliquen."
-  },
   "project.settings.tags.title": {
     "message": "Etiquetas"
   },
diff --git a/apps/frontend/src/locales/fr-FR/index.json b/apps/frontend/src/locales/fr-FR/index.json
index af7438269d..3917c02f11 100644
--- a/apps/frontend/src/locales/fr-FR/index.json
+++ b/apps/frontend/src/locales/fr-FR/index.json
@@ -1481,9 +1481,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Mis à jour récemment"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Fermer"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Télécharger {formType}"
   },
@@ -2984,9 +2981,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Le nettoyage des groupes a échoué : {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Effacer"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "Tous les groupes ont été nettoyés avec succès."
   },
@@ -3026,9 +3020,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Scan en cours..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Succès"
-  },
   "modpack-scan-modal.title": {
     "message": "Scan du modpack ({scanned}/{total} fichiers)"
   },
@@ -3938,9 +3929,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Tags mis en avant"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Vous pouvez mettre en avant jusqu'à 3 de vos tags les plus pertinents. D'autres tags peuvent être mis en avant si vous ne sélectionnez pas les 3."
-  },
   "project.settings.tags.features-description": {
     "message": "Sélectionnez toutes les fonctionnalités que votre {type} utilise."
   },
@@ -3956,9 +3944,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Sélectionnez au moins une catégorie afin de pouvoir mettre en avant une catégorie."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "Un étiquetage correct est important pour aider les gens à trouver votre {type}. Faites en sorte de sélectionner tous les tags qui s'appliquent."
-  },
   "project.settings.tags.title": {
     "message": "Tags"
   },
diff --git a/apps/frontend/src/locales/hu-HU/index.json b/apps/frontend/src/locales/hu-HU/index.json
index 9f73377c32..5e34c8243e 100644
--- a/apps/frontend/src/locales/hu-HU/index.json
+++ b/apps/frontend/src/locales/hu-HU/index.json
@@ -1415,9 +1415,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Nemrég frissített"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Bezárás"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Letöltés {formType}"
   },
@@ -3644,9 +3641,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Kiemelt címkék"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Legfeljebb 3 legrelevánsabb címkét jelölhetsz ki kiemeltként. Ha nem választod ki mind a 3-at, akkor a többi címke is kiemeltként jelenhet meg."
-  },
   "project.settings.tags.features-description": {
     "message": "Jelöld ki az összes olyan funkciót, amelyet a {type} használ."
   },
@@ -3662,9 +3656,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Válassz ki legalább egy kategóriát ahhoz, hogy kiemelj egy kategóriát."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "A pontos címkézés fontos ahhoz, hogy a {type} könnyebben me. Feltétlenül válaszd ki az összes releváns címkét."
-  },
   "project.settings.tags.title": {
     "message": "Címkék"
   },
diff --git a/apps/frontend/src/locales/it-IT/index.json b/apps/frontend/src/locales/it-IT/index.json
index 5f13f93ef8..50d33e8924 100644
--- a/apps/frontend/src/locales/it-IT/index.json
+++ b/apps/frontend/src/locales/it-IT/index.json
@@ -1475,9 +1475,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Ultima modifica"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Chiudi"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Scarica {formType}"
   },
@@ -2975,9 +2972,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Errore nell'eliminazione dei gruppi: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Procedi"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "Tutti i gruppi eliminati con successo."
   },
@@ -3017,9 +3011,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Scansione..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Successo"
-  },
   "modpack-scan-modal.title": {
     "message": "Scansione del pacchetto ({scanned}/{total} file)"
   },
@@ -3926,9 +3917,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Tag in evidenza"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Puoi mettere in evidenza fino a 3 tag. Altri tag potrebbero aggiungersi se non bastassero."
-  },
   "project.settings.tags.multiple-resolution-tags-warning": {
     "message": "Hai selezionato {count} tag di risoluzione ({tags}). I pacchetti di risorse dovrebbero averne solo uno."
   },
diff --git a/apps/frontend/src/locales/ja-JP/index.json b/apps/frontend/src/locales/ja-JP/index.json
index 7828035588..36175a8ce1 100644
--- a/apps/frontend/src/locales/ja-JP/index.json
+++ b/apps/frontend/src/locales/ja-JP/index.json
@@ -1109,9 +1109,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "更新順(新しい順)"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "閉じる"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "{formType} をダウンロード"
   },
diff --git a/apps/frontend/src/locales/ko-KR/index.json b/apps/frontend/src/locales/ko-KR/index.json
index ef7a66bdcf..6b9294a863 100644
--- a/apps/frontend/src/locales/ko-KR/index.json
+++ b/apps/frontend/src/locales/ko-KR/index.json
@@ -1481,9 +1481,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "최근 업데이트"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "닫기"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "{formType} 다운로드"
   },
@@ -2984,9 +2981,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "모든 그룹 삭제 실패: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "삭제"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "모든 그룹 삭제 완료."
   },
@@ -3026,9 +3020,6 @@
   "modpack-scan-modal.scanning": {
     "message": "스캔중..."
   },
-  "modpack-scan-modal.success": {
-    "message": "성공"
-  },
   "modpack-scan-modal.title": {
     "message": "모드팩 스캔 ({scanned}/{total} 파일)"
   },
@@ -3938,9 +3929,6 @@
   "project.settings.tags.featured-tags": {
     "message": "추천 태그"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "가장 적합한 태그를 최대 3개까지 지정할 수 있습니다. 3개를 모두 선택하지 않으면 다른 태그가 추천 태그로 표시될 수 있습니다."
-  },
   "project.settings.tags.features-description": {
     "message": " {type}에서 사용하는 모든 기능을 선택하세요."
   },
@@ -3956,9 +3944,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "추천 카테고리를 지정하려면 적어도 하나의 카테고리를 선택해야 합니다."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "정확한 태그 선택은 {type}을 쉽게 찾을 수 있도록 돕습니다. 관련된 모든 태그를 선택해 주세요."
-  },
   "project.settings.tags.title": {
     "message": "태그"
   },
diff --git a/apps/frontend/src/locales/ms-MY/index.json b/apps/frontend/src/locales/ms-MY/index.json
index 5e7baf7018..431014669d 100644
--- a/apps/frontend/src/locales/ms-MY/index.json
+++ b/apps/frontend/src/locales/ms-MY/index.json
@@ -1112,9 +1112,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Dikemas Kini Baru-baru Ini"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Tutup"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Muat turun {formType}"
   },
@@ -2423,9 +2420,6 @@
   "moderation.page.technicalReview": {
     "message": "Semakan teknikal"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Kosongkan"
-  },
   "modpack-scan-modal.failed": {
     "message": "Gagal"
   },
diff --git a/apps/frontend/src/locales/nl-NL/index.json b/apps/frontend/src/locales/nl-NL/index.json
index 3389ec38b2..ca68efa4fd 100644
--- a/apps/frontend/src/locales/nl-NL/index.json
+++ b/apps/frontend/src/locales/nl-NL/index.json
@@ -1478,9 +1478,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Recentelijk geüpdate"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Sluiten"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Download {formType}"
   },
@@ -2981,9 +2978,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Niet gelukt om alle groepen te wissen: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Wissen"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "Alle groepen zijn succesvol gewist."
   },
@@ -3023,9 +3017,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Scannen..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Gelukt"
-  },
   "modpack-scan-modal.title": {
     "message": "Modpack-scan ({scanned}/{total} bestanden)"
   },
@@ -3935,9 +3926,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Uitgelichte tags"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Je kunt maximaal 3 van je meest relevante tags als uitgelichte tags selecteren. Als je niet alle 3 selecteert, kunnen andere tags als uitgelichte tags worden weergegeven."
-  },
   "project.settings.tags.features-description": {
     "message": "Selecteer alle functies waarvan je {type} gebruikmaakt."
   },
@@ -3953,9 +3941,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Selecteer minstens één categorie om een categorie uit te lichten."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "Nauwkeurige tags zijn belangrijk om mensen te helpen je {type} te vinden. Zorg ervoor dat je alle relevante tags selecteert."
-  },
   "project.settings.tags.title": {
     "message": "Tags"
   },
diff --git a/apps/frontend/src/locales/pl-PL/index.json b/apps/frontend/src/locales/pl-PL/index.json
index 5dce4e6a1b..e3eeb8c07d 100644
--- a/apps/frontend/src/locales/pl-PL/index.json
+++ b/apps/frontend/src/locales/pl-PL/index.json
@@ -1478,9 +1478,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Ostatnio zaktualizowane"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Zamknij"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Pobierz {formType}"
   },
@@ -2975,9 +2972,6 @@
   "modpack-scan-modal.delete-all-groups-confirmation.description": {
     "message": "Trwale usunie to wszystkie grupy atrybucji i wszystkie zawarte w nich pliki. Tej akcji nie można cofnąć."
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Wyczyść"
-  },
   "modpack-scan-modal.failed": {
     "message": "Błąd"
   },
@@ -3014,9 +3008,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Skanowanie..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Sukces"
-  },
   "modpack-scan-modal.title": {
     "message": "Skanowanie paczki modów ({scanned}/{total} plików)"
   },
@@ -3884,9 +3875,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Wyróżnione tagi"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Możesz wyróżnić 3 z najlepiej pasujących do Twojego projektu tagów. Inne tagi mogą zostać pokazane jako wyróżnione, jeżeli nie wybierzesz wszystkich trzech."
-  },
   "project.settings.tags.features-description": {
     "message": "Wszystkie funkcjonalności, których używa {type}"
   },
diff --git a/apps/frontend/src/locales/pt-BR/index.json b/apps/frontend/src/locales/pt-BR/index.json
index 92c5499117..1b9202b017 100644
--- a/apps/frontend/src/locales/pt-BR/index.json
+++ b/apps/frontend/src/locales/pt-BR/index.json
@@ -1481,9 +1481,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Atualizado recentemente"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Fechar"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Baixar {formType}"
   },
@@ -2984,9 +2981,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Falhou ao excluir todos os grupos: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Excluir"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "Todos os grupos excluídos com sucesso."
   },
@@ -3026,9 +3020,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Verificando..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Sucesso"
-  },
   "modpack-scan-modal.title": {
     "message": "Verificação do pacote de mods ({scanned}/{total} Arquivos)"
   },
@@ -3938,9 +3929,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Etiquetas em destaque"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Você pode destacar até 3 das suas etiquetas mais relevantes. Outras etiquetas poderão ser promovidas a destaque caso você não selecione todas as 3."
-  },
   "project.settings.tags.features-description": {
     "message": "Selecione todas as funcionalidades que o seu {type} utiliza."
   },
@@ -3956,9 +3944,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Selecione pelo menos uma categoria para ela ser destacada."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "Etiquetar corretamente é importante para ajudar as pessoas a encontrarem seu {type}. Certifique-se de selecionar todas as etiquetas aplicáveis."
-  },
   "project.settings.tags.title": {
     "message": "Etiquetas"
   },
diff --git a/apps/frontend/src/locales/ru-RU/index.json b/apps/frontend/src/locales/ru-RU/index.json
index 195a9b8374..e86b7b8f66 100644
--- a/apps/frontend/src/locales/ru-RU/index.json
+++ b/apps/frontend/src/locales/ru-RU/index.json
@@ -1475,9 +1475,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Дата обновления"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Закрыть"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Скачать {formType}"
   },
@@ -2978,9 +2975,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Не удалось удалить все группы: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Удалить"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "Все группы успешно удалены."
   },
@@ -3020,9 +3014,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Сканирование..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Готово"
-  },
   "muralpay.account-type.checking": {
     "message": "Расчётный"
   },
@@ -3929,9 +3920,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Ключевые теги"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Можно выбрать до 3 ключевых тегов. Если не выбрать все 3, то другие теги могут стать ключевыми."
-  },
   "project.settings.tags.features-description": {
     "message": "Выберите все особенности, которые использует ваш {type}"
   },
@@ -3944,9 +3932,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Выберите хотя бы одну категорию, чтобы отобразить ее."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "Аккуратная маркировка важна, чтобы помочь людям найти ваш {type}"
-  },
   "project.settings.tags.title": {
     "message": "Теги"
   },
diff --git a/apps/frontend/src/locales/sv-SE/index.json b/apps/frontend/src/locales/sv-SE/index.json
index a0352c9d20..28164802e8 100644
--- a/apps/frontend/src/locales/sv-SE/index.json
+++ b/apps/frontend/src/locales/sv-SE/index.json
@@ -1313,9 +1313,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Nyligen uppdaterade"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Stäng"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Ladda ner {formType}"
   },
@@ -2645,9 +2642,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Misslyckades att tömma alla grupper: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Töm"
-  },
   "modpack-scan-modal.failed": {
     "message": "Misslyckades"
   },
diff --git a/apps/frontend/src/locales/tr-TR/index.json b/apps/frontend/src/locales/tr-TR/index.json
index 25590be2f7..f03248b4ca 100644
--- a/apps/frontend/src/locales/tr-TR/index.json
+++ b/apps/frontend/src/locales/tr-TR/index.json
@@ -1358,9 +1358,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Son Güncellenen"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Kapat"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "{formType} İndirin"
   },
@@ -2774,9 +2771,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Taranıyor..."
   },
-  "modpack-scan-modal.success": {
-    "message": "Başarılı"
-  },
   "modpack-scan-modal.title": {
     "message": "Mod paketi taraması ({scanned}/{total} Dosyalar)"
   },
diff --git a/apps/frontend/src/locales/uk-UA/index.json b/apps/frontend/src/locales/uk-UA/index.json
index 89002f292d..c8c4479a28 100644
--- a/apps/frontend/src/locales/uk-UA/index.json
+++ b/apps/frontend/src/locales/uk-UA/index.json
@@ -1478,9 +1478,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "Нещодавно оновлені"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "Закрити"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "Завантажити {formType}"
   },
@@ -2981,9 +2978,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "Не вдалося очистити всі групи: {error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "Очистити"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "Усі групи успішно очищено."
   },
@@ -3023,9 +3017,6 @@
   "modpack-scan-modal.scanning": {
     "message": "Скануємо…"
   },
-  "modpack-scan-modal.success": {
-    "message": "Успіх"
-  },
   "modpack-scan-modal.title": {
     "message": "Сканування збірки ({scanned}/{total} файлів)"
   },
@@ -3935,9 +3926,6 @@
   "project.settings.tags.featured-tags": {
     "message": "Основні теґи"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "Ви можете обрати основними до 3 найбільш описових теґів. Інші теґи можуть стати основними, якщо не оберете всі 3."
-  },
   "project.settings.tags.features-description": {
     "message": "Оберіть увесь функціонал, який присутній у {type}."
   },
@@ -3953,9 +3941,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "Виберіть хоча б одну категорію, щоб рекомендувати її."
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "Указання правильних теґів необхідне, щоб люди могли легше знайти ваш {type}. Переконайтеся, що ви обрали підхожі теґи."
-  },
   "project.settings.tags.title": {
     "message": "Теґи"
   },
diff --git a/apps/frontend/src/locales/zh-CN/index.json b/apps/frontend/src/locales/zh-CN/index.json
index 8e3ebae881..e6a09849fa 100644
--- a/apps/frontend/src/locales/zh-CN/index.json
+++ b/apps/frontend/src/locales/zh-CN/index.json
@@ -1481,9 +1481,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "最近更新"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "关闭"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "下载{formType}"
   },
@@ -2984,9 +2981,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "未能清除所有组:{error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "清除"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "所有组均已成功清除。"
   },
@@ -3026,9 +3020,6 @@
   "modpack-scan-modal.scanning": {
     "message": "扫描中……"
   },
-  "modpack-scan-modal.success": {
-    "message": "成功"
-  },
   "modpack-scan-modal.title": {
     "message": "模组包扫描 ({scanned}/{total} 个文件)"
   },
@@ -3938,9 +3929,6 @@
   "project.settings.tags.featured-tags": {
     "message": "精选标签"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "你可以设置最多 3 个精选标签，标示出最相关的特点。如果没有选完 3 个标签，其他标签也可能提升为精选标签。"
-  },
   "project.settings.tags.features-description": {
     "message": "选择你的{type}作用于哪类特性。"
   },
@@ -3956,9 +3944,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "请先至少选择一个分类，再设置精选分类。"
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "准确选好标签，能极大帮助别人找到你的{type}。请确保选择所有合适的标签。"
-  },
   "project.settings.tags.title": {
     "message": "标签"
   },
diff --git a/apps/frontend/src/locales/zh-TW/index.json b/apps/frontend/src/locales/zh-TW/index.json
index 999a28b3b6..8a1f1bae28 100644
--- a/apps/frontend/src/locales/zh-TW/index.json
+++ b/apps/frontend/src/locales/zh-TW/index.json
@@ -1481,9 +1481,6 @@
   "dashboard.collections.sort.recently-updated": {
     "message": "最近更新"
   },
-  "dashboard.creator-tax-form-modal.close-button": {
-    "message": "關閉"
-  },
   "dashboard.creator-tax-form-modal.confirmation.download-button": {
     "message": "下載 {formType}"
   },
@@ -2984,9 +2981,6 @@
   "modpack-scan-modal.delete-all-groups.error": {
     "message": "無法清除所有群組：{error}"
   },
-  "modpack-scan-modal.delete-all-groups.proceed": {
-    "message": "清除"
-  },
   "modpack-scan-modal.delete-all-groups.success": {
     "message": "已成功清除所有群組。"
   },
@@ -3026,9 +3020,6 @@
   "modpack-scan-modal.scanning": {
     "message": "正在掃描..."
   },
-  "modpack-scan-modal.success": {
-    "message": "成功"
-  },
   "modpack-scan-modal.title": {
     "message": "模組包掃描（{scanned}/{total} 個檔案）"
   },
@@ -3938,9 +3929,6 @@
   "project.settings.tags.featured-tags": {
     "message": "精選標籤"
   },
-  "project.settings.tags.featured-tags-description": {
-    "message": "你可以選擇最多 3 個最相關的標籤作為精選標籤。如果沒有選完 3 個標籤，系統可能會自動將其他標籤選為精選標籤。"
-  },
   "project.settings.tags.features-description": {
     "message": "請選擇你的{type}包含的功能。"
   },
@@ -3956,9 +3944,6 @@
   "project.settings.tags.select-at-least-one-category": {
     "message": "請選擇至少一個類別再選擇精選標籤。"
   },
-  "project.settings.tags.tagging-importance-description": {
-    "message": "精確的標籤對於協助使用者找到你的{type}非常重要。請務必選擇所有合適的標籤。"
-  },
   "project.settings.tags.title": {
     "message": "標籤"
   },
diff --git a/apps/frontend/src/pages/[type]/[project].vue b/apps/frontend/src/pages/[type]/[project].vue
index f14dbc4393..058e611977 100644
--- a/apps/frontend/src/pages/[type]/[project].vue
+++ b/apps/frontend/src/pages/[type]/[project].vue
@@ -4,7 +4,7 @@
 			<ProjectBackgroundGradient :project="project" />
 		</Teleport>
 		<template v-if="isSettings">
-			<div v-if="canAccessSettings" class="normal-page no-sidebar">
+			<div v-if="canAccessSettings" class="normal-page no-sidebar" :class="`align-${marginTarget}`">
 				<div class="normal-page__header mb-6">
 					<PageHeader :title="project.title" :row-class="'items-center'">
 						<template #leading>
@@ -115,17 +115,20 @@
 			/>
 			<div
 				class="new-page sidebar"
-				:class="{
-					'alt-layout': cosmetics.leftContentLayout,
-					'checklist-open':
-						showModerationChecklist &&
-						!collapsedModerationChecklist &&
-						!flags.alwaysShowChecklistAsPopup,
-					'checklist-collapsed':
-						showModerationChecklist &&
-						collapsedModerationChecklist &&
-						!flags.alwaysShowChecklistAsPopup,
-				}"
+				:class="[
+					{
+						'alt-layout': cosmetics.leftContentLayout,
+						'checklist-open':
+							showModerationChecklist &&
+							!collapsedModerationChecklist &&
+							!flags.alwaysShowChecklistAsPopup,
+						'checklist-collapsed':
+							showModerationChecklist &&
+							collapsedModerationChecklist &&
+							!flags.alwaysShowChecklistAsPopup,
+					},
+					`align-${marginTarget}`,
+				]"
 			>
 				<div
 					class="normal-page__header relative mb-4"
@@ -453,7 +456,8 @@
 
 				<div class="normal-page__sidebar">
 					<ProjectSidebarServerInfo
-						v-if="isServerProject && serverDataLoaded"
+						v-if="isServerProject"
+						:loading="!serverDataLoaded"
 						:project-v3="projectV3"
 						:tags="tags"
 						:required-content="serverRequiredContent"
@@ -483,6 +487,7 @@
 					<ProjectSidebarCreators
 						:organization="organization"
 						:members="members"
+						:loading="creatorsLoading"
 						:org-link="(slug) => `/organization/${slug}`"
 						:user-link="(username) => `/user/${username}`"
 						class="card flex-card"
@@ -490,6 +495,7 @@
 					<ProjectSidebarDetails
 						:project="project"
 						:link-target="$external()"
+						:hide-license="isServerProject"
 						:show-followers="isServerProject"
 						class="card flex-card"
 					/>
@@ -535,7 +541,7 @@ import {
 	SettingsIcon,
 	XIcon,
 } from '@modrinth/assets'
-import { moderationSettings } from '@modrinth/moderation'
+import { getMarginTarget, moderationSettings } from '@modrinth/moderation'
 import {
 	Admonition,
 	ArchivedProjectBanner,
@@ -612,6 +618,7 @@ const config = useRuntimeConfig()
 const moderationQueue = useModerationQueue()
 const keybinds = useModerationKeybinds()
 const modSettings = useModerationSettings()
+const marginTarget = computed(() => getMarginTarget(modSettings.value))
 const notifications = injectNotificationManager()
 const { addNotification } = notifications
 
@@ -1091,7 +1098,11 @@ watch(serverModpackVersionId, (versionId) => {
 })
 
 // Members
-const { data: allMembersRaw, error: _membersError } = useQuery({
+const {
+	data: allMembersRaw,
+	error: _membersError,
+	isPending: membersPending,
+} = useQuery({
 	queryKey: computed(() => ['project', projectId.value, 'members']),
 	queryFn: () => client.labrinth.projects_v3.getMembers(projectId.value),
 	staleTime: STALE_TIME,
@@ -1142,7 +1153,7 @@ const {
 
 // Organization
 // Only fetch organization if project belongs to one
-const { data: organizationRaw } = useQuery({
+const { data: organizationRaw, isPending: organizationPending } = useQuery({
 	queryKey: computed(() => ['project', projectId.value, 'organization']),
 	queryFn: () => client.labrinth.projects_v3.getOrganization(projectId.value),
 	staleTime: STALE_TIME,
@@ -1166,6 +1177,13 @@ const archivedDisclosure = computed(() =>
 )
 const isArchived = computed(() => !!archivedDisclosure.value)
 
+const creatorsLoading = computed(
+	() =>
+		!projectRaw.value ||
+		membersPending.value ||
+		(!!projectRaw.value.organization && organizationPending.value),
+)
+
 const { data: thread } = useQuery({
 	queryKey: computed(() => ['thread', projectRaw.value?.thread_id]),
 	queryFn: () => client.labrinth.threads_v3.getThread(projectRaw.value.thread_id),
@@ -2318,7 +2336,7 @@ provideProjectPageContext({
 
 .servers-popup {
 	box-shadow:
-		0 0 12px 1px rgba(0, 175, 92, 0.6),
+		0 0 12px 1px color-mix(in srgb, var(--color-brand) 60%, transparent),
 		var(--shadow-floating);
 
 	&::before {
diff --git a/apps/frontend/src/pages/[type]/[project]/settings/tags.vue b/apps/frontend/src/pages/[type]/[project]/settings/tags.vue
index 7aaaf62f79..ce00b0852d 100644
--- a/apps/frontend/src/pages/[type]/[project]/settings/tags.vue
+++ b/apps/frontend/src/pages/[type]/[project]/settings/tags.vue
@@ -1,174 +1,23 @@
-<template>
-	<div>
-		<ConfirmLeaveModal ref="confirmLeaveModal" />
-		<section class="universal-card">
-			<div class="label">
-				<h3>
-					<span class="label__title size-card-header">{{ formatMessage(messages.tagsTitle) }}</span>
-				</h3>
-			</div>
-
-			<div
-				v-if="tooManyTagsWarning && !allTagsSelectedWarning"
-				class="my-2 flex items-center gap-1.5 text-orange"
-			>
-				<TriangleAlertIcon class="my-auto" />
-				{{ tooManyTagsWarning }}
-			</div>
-
-			<div v-if="multipleResolutionTagsWarning" class="my-2 flex items-center gap-1.5 text-orange">
-				<TriangleAlertIcon class="my-auto" />
-				{{ multipleResolutionTagsWarning }}
-			</div>
-
-			<div v-if="allTagsSelectedWarning" class="my-2 flex items-center gap-1.5 text-red">
-				<TriangleAlertIcon class="my-auto" />
-				<span>{{ allTagsSelectedWarning }}</span>
-			</div>
-
-			<p>
-				{{
-					formatMessage(messages.taggingImportanceDescription, {
-						type: formatProjectType(project.project_type).toLowerCase(),
-					})
-				}}
-			</p>
-
-			<p
-				v-if="project.versions.length === 0 && projectV3?.minecraft_server == null"
-				class="known-errors"
-			>
-				{{ formatMessage(messages.uploadVersionFirst) }}
-			</p>
-			<template v-else>
-				<template v-for="header in Object.keys(categoryLists)" :key="`categories-${header}`">
-					<div class="label mb-3">
-						<h4>
-							<span class="label__title">{{ formatCategoryHeader(formatMessage, header) }}</span>
-						</h4>
-						<span class="label__description">
-							<template v-if="header === 'categories'">
-								{{
-									formatMessage(messages.categoriesDescription, {
-										type: formatProjectType(project.project_type).toLowerCase(),
-									})
-								}}
-							</template>
-							<template v-else-if="header === 'features'">
-								{{
-									formatMessage(messages.featuresDescription, {
-										type: formatProjectType(project.project_type).toLowerCase(),
-									})
-								}}
-							</template>
-							<template v-else-if="header === 'resolutions'">
-								{{
-									formatMessage(messages.resolutionsDescription, {
-										type: formatProjectType(project.project_type).toLowerCase(),
-									})
-								}}
-							</template>
-							<template v-else-if="header === 'performance impact'">
-								{{
-									formatMessage(messages.performanceImpactDescription, {
-										type: formatProjectType(project.project_type).toLowerCase(),
-									})
-								}}
-							</template>
-						</span>
-					</div>
-					<div class="category-list input-div">
-						<Checkbox
-							v-for="category in categoryLists[header]"
-							:key="`category-${header}-${category.name}`"
-							:model-value="current.selectedTags.includes(category)"
-							:description="formatCategory(formatMessage, category.name)"
-							class="category-selector"
-							@update:model-value="toggleCategory(category)"
-						>
-							<div class="category-selector__label">
-								<component
-									:is="getTagIcon(category.name)"
-									v-if="header !== 'resolutions' && getTagIcon(category.name)"
-									aria-hidden="true"
-									class="icon"
-								/>
-								<span aria-hidden="true">
-									<FormattedTag :tag="category.name" enforce-type="category" />
-								</span>
-							</div>
-						</Checkbox>
-					</div>
-				</template>
-				<div class="label">
-					<h4>
-						<span class="label__title"
-							><StarIcon /> {{ formatMessage(messages.featuredTags) }}</span
-						>
-					</h4>
-					<span class="label__description">{{
-						formatMessage(messages.featuredTagsDescription)
-					}}</span>
-				</div>
-				<p v-if="current.selectedTags.length < 1">
-					{{ formatMessage(messages.selectAtLeastOneCategory) }}
-				</p>
-				<div class="category-list input-div">
-					<Checkbox
-						v-for="category in current.selectedTags"
-						:key="`featured-category-${category.name}`"
-						class="category-selector"
-						:model-value="current.featuredTags.includes(category)"
-						:description="formatCategory(formatMessage, category.name)"
-						:disabled="current.featuredTags.length >= 3 && !current.featuredTags.includes(category)"
-						@update:model-value="toggleFeaturedCategory(category)"
-					>
-						<div class="category-selector__label">
-							<component
-								:is="getTagIcon(category.name)"
-								v-if="category.header !== 'resolutions' && getTagIcon(category.name)"
-								aria-hidden="true"
-								class="icon"
-							/>
-							<span aria-hidden="true">
-								<FormattedTag :tag="category.name" enforce-type="category" />
-							</span>
-						</div>
-					</Checkbox>
-				</div>
-			</template>
-		</section>
-		<UnsavedChangesPopup
-			:original="saved"
-			:modified="current"
-			:saving="saving"
-			@reset="reset"
-			@save="save"
-		/>
-	</div>
-</template>
-
 <script setup lang="ts">
 import {
-	getCategoryIcon,
-	SERVER_CATEGORY_ICON_MAP,
-	StarIcon,
-	TriangleAlertIcon,
-} from '@modrinth/assets'
-import {
+	Admonition,
 	Checkbox,
 	ConfirmLeaveModal,
 	defineMessages,
 	formatCategory,
 	formatCategoryHeader,
+	formatProjectTypeSentence,
 	FormattedTag,
 	injectProjectPageContext,
+	type MessageDescriptor,
+	sortProjectTypes,
+	TagItem,
 	UnsavedChangesPopup,
 	usePageLeaveSafety,
 	useSavable,
 	useVIntl,
 } from '@modrinth/ui'
-import { formatProjectType, sortedCategories } from '@modrinth/utils'
+import { capitalizeString, sortedCategories } from '@modrinth/utils'
 import { computed } from 'vue'
 
 interface Category {
@@ -178,19 +27,30 @@ interface Category {
 	project_type: string
 }
 
+interface CategoryGroup {
+	id: string
+	title: string
+	description?: string
+	categories: Category[]
+}
+
+const MAX_FEATURED_TAGS = 3
+
+const RESOLUTION_TAGS = ['8x-', '16x', '32x', '48x', '64x', '128x', '256x', '512x+']
+
+const SHARED_CATEGORY_PROJECT_TYPES: Record<string, string> = {
+	plugin: 'mod',
+	datapack: 'mod',
+}
+
 const tags = useGeneratedState()
 const { formatMessage, locale } = useVIntl()
 
 const messages = defineMessages({
-	tagsTitle: {
+	title: {
 		id: 'project.settings.tags.title',
 		defaultMessage: 'Tags',
 	},
-	taggingImportanceDescription: {
-		id: 'project.settings.tags.tagging-importance-description',
-		defaultMessage:
-			'Accurate tagging is important to help people find your {type}. Make sure to select all tags that apply.',
-	},
 	uploadVersionFirst: {
 		id: 'project.settings.tags.upload-version-first',
 		defaultMessage: 'Please upload a version first in order to select tags!',
@@ -217,14 +77,18 @@ const messages = defineMessages({
 		defaultMessage: 'Featured tags',
 	},
 	featuredTagsDescription: {
-		id: 'project.settings.tags.featured-tags-description',
+		id: 'project.settings.tags.featured-tags-select-description',
 		defaultMessage:
-			'You can feature up to 3 of your most relevant tags. Other tags may be promoted to featured if you do not select all 3.',
+			'Select your most relevant tags. These are displayed before the rest of your tags.',
 	},
 	selectAtLeastOneCategory: {
 		id: 'project.settings.tags.select-at-least-one-category',
 		defaultMessage: 'Select at least one category in order to feature a category.',
 	},
+	featuredTagsRequired: {
+		id: 'project.settings.tags.featured-tags-required',
+		defaultMessage: 'You must have at least one featured tag.',
+	},
 	tooManyTagsServerHardWarning: {
 		id: 'project.settings.tags.too-many-tags-server-hard-warning',
 		defaultMessage:
@@ -252,74 +116,185 @@ const messages = defineMessages({
 	},
 })
 
+const groupTitleMessages: Record<string, MessageDescriptor> = defineMessages({
+	categories: {
+		id: 'project.settings.tags.group-title.categories',
+		defaultMessage: '{showType, select, yes {{types} categories} other {Categories}}',
+	},
+	features: {
+		id: 'project.settings.tags.group-title.features',
+		defaultMessage: '{showType, select, yes {{types} features} other {Features}}',
+	},
+	resolutions: {
+		id: 'project.settings.tags.group-title.resolutions',
+		defaultMessage: '{showType, select, yes {{types} resolutions} other {Resolutions}}',
+	},
+	'performance impact': {
+		id: 'project.settings.tags.group-title.performance-impact',
+		defaultMessage:
+			'{showType, select, yes {{types} performance impact} other {Performance impact}}',
+	},
+})
+
+const groupDescriptionMessages: Record<string, MessageDescriptor> = {
+	categories: messages.categoriesDescription,
+	features: messages.featuresDescription,
+	resolutions: messages.resolutionsDescription,
+	'performance impact': messages.performanceImpactDescription,
+}
+
 const { projectV2: project, projectV3, patchProject } = injectProjectPageContext()
 
 useProjectSettingsHeadTitle(messages.tagsTitle)
 
-const formatCategoryName = (categoryName: string) => {
-	return formatCategory(formatMessage, categoryName)
-}
+const formatCategoryName = (categoryName: string) => formatCategory(formatMessage, categoryName)
 
 const isServerProject = computed(() => projectV3.value?.minecraft_server != null)
 
-const getTagIcon = (categoryName: string) => {
-	const iconName = isServerProject.value
-		? (SERVER_CATEGORY_ICON_MAP[categoryName] ?? categoryName)
-		: categoryName
-	return getCategoryIcon(iconName)
+const canSelectTags = computed(() => project.value.versions.length > 0 || isServerProject.value)
+
+const projectTypes = computed(() => {
+	if (isServerProject.value) {
+		return ['minecraft_java_server']
+	}
+
+	const types = projectV3.value?.project_types?.length
+		? projectV3.value.project_types
+		: [project.value.actualProjectType]
+
+	return sortProjectTypes(new Set(types))
+})
+
+const allCategories = computed(
+	() => sortedCategories(tags.value, formatCategoryName, locale.value) as Category[],
+)
+
+const projectTypesByCategoryList = computed(() => {
+	const lists = new Map<string, string[]>()
+	for (const projectType of projectTypes.value) {
+		const source = SHARED_CATEGORY_PROJECT_TYPES[projectType] ?? projectType
+		lists.set(source, [...(lists.get(source) ?? []), projectType])
+	}
+	return lists
+})
+
+const projectTypeListFormatter = computed(
+	() => new Intl.ListFormat(locale.value, { style: 'long', type: 'conjunction' }),
+)
+
+function formatProjectTypeName(type: string) {
+	return formatProjectTypeSentence(
+		formatMessage,
+		type === 'minecraft_java_server' ? 'server' : type,
+	)
 }
 
-const matchesProjectType = (x: Category) => {
-	if (isServerProject.value) {
-		return x.project_type === 'minecraft_java_server'
-	} else {
-		return x.project_type === project.value.actualProjectType
+function formatGroupTitle(header: string, types: string[]) {
+	const message = groupTitleMessages[header]
+	if (!message) {
+		return formatCategoryHeader(formatMessage, header)
 	}
+
+	const showType = projectTypes.value.length > 1
+	return formatMessage(message, {
+		showType: showType ? 'yes' : 'other',
+		types: showType
+			? capitalizeString(projectTypeListFormatter.value.format(types.map(formatProjectTypeName)))
+			: '',
+	})
+}
+
+function formatGroupDescription(header: string, types: string[]) {
+	const message = groupDescriptionMessages[header]
+	if (!message) {
+		return undefined
+	}
+
+	// listing out every type gets unwieldy, fallback to the generic term when there's more than one
+	return formatMessage(message, {
+		type: formatProjectTypeName(types.length > 1 ? 'project' : types[0]),
+	})
+}
+
+const categorySections = computed(() => {
+	const sections: {
+		categoryList: string
+		header: string
+		types: string[]
+		categories: Category[]
+	}[] = []
+
+	for (const [categoryList, types] of projectTypesByCategoryList.value) {
+		const byHeader = new Map<string, Category[]>()
+		for (const category of allCategories.value) {
+			if (category.project_type !== categoryList) continue
+			byHeader.set(category.header, [...(byHeader.get(category.header) ?? []), category])
+		}
+
+		for (const [header, categories] of byHeader) {
+			sections.push({
+				categoryList,
+				header,
+				types,
+				categories:
+					header === 'minecraft_server_features' ? withPokemonFirst(categories) : categories,
+			})
+		}
+	}
+
+	return sections
+})
+
+const categoryGroups = computed<CategoryGroup[]>(() =>
+	categorySections.value.map((section) => ({
+		id: `${section.categoryList}-${section.header}`,
+		title: formatGroupTitle(section.header, section.types),
+		description: formatGroupDescription(section.header, section.types),
+		categories: section.categories,
+	})),
+)
+
+function withPokemonFirst(categories: Category[]) {
+	return categories.slice().sort((a, b) => {
+		if (a.name === 'pokemon') return -1
+		if (b.name === 'pokemon') return 1
+		return 0
+	})
+}
+
+const availableTags = computed(() => [
+	...new Set(categorySections.value.flatMap((section) => section.categories.map((x) => x.name))),
+])
+
+function hasSameTags(a: string[], b: string[]) {
+	return a.length === b.length && a.every((tag) => b.includes(tag))
 }
 
 const { saved, current, saving, hasChanges, reset, save } = useSavable(
 	() => ({
-		selectedTags: sortedCategories(tags.value, formatCategoryName, locale.value).filter(
-			(x: Category) =>
-				matchesProjectType(x) &&
-				(project.value.categories.includes(x.name) ||
-					project.value.additional_categories.includes(x.name)),
-		) as Category[],
-		featuredTags: sortedCategories(tags.value, formatCategoryName, locale.value).filter(
-			(x: Category) => matchesProjectType(x) && project.value.categories.includes(x.name),
-		) as Category[],
+		selectedTags: availableTags.value.filter(
+			(tag) =>
+				project.value.categories.includes(tag) || project.value.additional_categories.includes(tag),
+		),
+		featuredTags: availableTags.value.filter((tag) => project.value.categories.includes(tag)),
 	}),
 	async () => {
-		// Promote selected categories to featured if there are less than 3 featured
-		const newFeaturedTags = current.value.featuredTags.slice()
-		if (newFeaturedTags.length < 1 && current.value.selectedTags.length > newFeaturedTags.length) {
-			const nonFeaturedCategories = current.value.selectedTags.filter(
-				(x) => !newFeaturedTags.includes(x),
-			)
-			nonFeaturedCategories
-				.slice(0, Math.min(nonFeaturedCategories.length, 3 - newFeaturedTags.length))
-				.forEach((x) => newFeaturedTags.push(x))
+		if (!canSave.value) {
+			throw new Error('At least one tag must be featured')
 		}
 
-		// Convert selected and featured categories to backend-usable arrays
-		const categories = newFeaturedTags.map((x) => x.name)
-		const additionalCategories = current.value.selectedTags
-			.filter((x) => !newFeaturedTags.includes(x))
-			.map((x) => x.name)
+		const featuredTags = current.value.featuredTags
+		const additionalCategories = current.value.selectedTags.filter(
+			(tag) => !featuredTags.includes(tag),
+		)
 
 		const data: Record<string, string[]> = {}
 
-		if (
-			categories.length !== project.value.categories.length ||
-			categories.some((value) => !project.value.categories.includes(value))
-		) {
-			data.categories = categories
+		if (!hasSameTags(featuredTags, project.value.categories)) {
+			data.categories = featuredTags
 		}
 
-		if (
-			additionalCategories.length !== project.value.additional_categories.length ||
-			additionalCategories.some((value) => !project.value.additional_categories.includes(value))
-		) {
+		if (!hasSameTags(additionalCategories, project.value.additional_categories)) {
 			data.additional_categories = additionalCategories
 		}
 
@@ -329,31 +304,15 @@ const { saved, current, saving, hasChanges, reset, save } = useSavable(
 
 const { confirmLeaveModal } = usePageLeaveSafety(hasChanges)
 
-const categoryLists = computed(() => {
-	const lists: Record<string, Category[]> = {}
-	sortedCategories(tags.value, formatCategoryName, locale.value).forEach((x: Category) => {
-		if (matchesProjectType(x)) {
-			const header = x.header
-			if (!lists[header]) {
-				lists[header] = []
-			}
-			lists[header].push(x)
-		}
-	})
-	const featuresKey = 'minecraft_server_features'
-	if (lists[featuresKey]) {
-		lists[featuresKey].sort((a, b) => {
-			if (a.name === 'pokemon') return -1
-			if (b.name === 'pokemon') return 1
-			return 0
-		})
-	}
-	return lists
-})
+const isFeaturedLimitReached = computed(
+	() => current.value.featuredTags.length >= MAX_FEATURED_TAGS,
+)
+
+const canSave = computed(() => current.value.featuredTags.length > 0)
 
 const tooManyTagsWarning = computed(() => {
 	const tagCount = current.value.selectedTags.length
-	if (projectV3?.value?.minecraft_server != null) {
+	if (isServerProject.value) {
 		if (tagCount > 18) {
 			return formatMessage(messages.tooManyTagsServerHardWarning, { count: tagCount })
 		} else if (tagCount > 12) {
@@ -366,122 +325,140 @@ const tooManyTagsWarning = computed(() => {
 })
 
 const multipleResolutionTagsWarning = computed(() => {
-	if (project.value.actualProjectType !== 'resourcepack') return null
+	if (!projectTypes.value.includes('resourcepack')) return null
 
-	const resolutionTags = current.value.selectedTags.filter((tag) =>
-		['8x-', '16x', '32x', '48x', '64x', '128x', '256x', '512x+'].includes(tag.name),
-	)
+	const resolutionTags = current.value.selectedTags.filter((tag) => RESOLUTION_TAGS.includes(tag))
+	if (resolutionTags.length < 2) return null
 
-	if (resolutionTags.length > 1) {
-		const tagsList = resolutionTags
-			.map((t) => t.name)
+	return formatMessage(messages.multipleResolutionTagsWarning, {
+		count: resolutionTags.length,
+		tags: resolutionTags
 			.join(', ')
 			.replace('8x-', '8x or lower')
-			.replace('512x+', '512x or higher')
-		return formatMessage(messages.multipleResolutionTagsWarning, {
-			count: resolutionTags.length,
-			tags: tagsList,
-		})
-	}
-	return null
+			.replace('512x+', '512x or higher'),
+	})
 })
 
 const allTagsSelectedWarning = computed(() => {
-	const categoriesForProjectType = sortedCategories(
-		tags.value,
-		formatCategoryName,
-		locale.value,
-	).filter((x: Category) => x.project_type === project.value.actualProjectType)
-	const totalSelectedTags = current.value.selectedTags.length
-
 	if (
-		totalSelectedTags === categoriesForProjectType.length &&
-		categoriesForProjectType.length > 0
+		availableTags.value.length < 1 ||
+		availableTags.value.length < 1 ||
+		current.value.selectedTags.length !== availableTags.value.length
 	) {
-		return formatMessage(messages.allTagsSelectedWarning, {
-			count: categoriesForProjectType.length,
-		})
+		return null
 	}
-	return null
+
+	return formatMessage(messages.allTagsSelectedWarning, { count: availableTags.value.length })
 })
 
-const toggleCategory = (category: Category) => {
-	if (current.value.selectedTags.includes(category)) {
-		current.value.selectedTags = current.value.selectedTags.filter((x) => x !== category)
-		if (current.value.featuredTags.includes(category)) {
-			current.value.featuredTags = current.value.featuredTags.filter((x) => x !== category)
-		}
-	} else {
-		current.value.selectedTags = [...current.value.selectedTags, category]
+function toggleTagRaw(selection: string[], tag: string) {
+	if (selection.includes(tag)) {
+		return selection.filter((x) => x !== tag)
+	}
+	return availableTags.value.filter((x) => x === tag || selection.includes(x))
+}
+
+const toggleTag = (tag: string) => {
+	current.value.selectedTags = toggleTagRaw(current.value.selectedTags, tag)
+	if (!current.value.selectedTags.includes(tag)) {
+		current.value.featuredTags = current.value.featuredTags.filter((x) => x !== tag)
 	}
 }
 
-const toggleFeaturedCategory = (category: Category) => {
-	if (current.value.featuredTags.includes(category)) {
-		current.value.featuredTags = current.value.featuredTags.filter((x) => x !== category)
-	} else {
-		current.value.featuredTags = [...current.value.featuredTags, category]
-	}
+const toggleFeatured = (tag: string) => {
+	current.value.featuredTags = toggleTagRaw(current.value.featuredTags, tag)
 }
 </script>
+<template>
+	<div>
+		<ConfirmLeaveModal ref="confirmLeaveModal" />
+		<h2 class="mb-4 mt-0 text-2xl font-semibold">
+			{{ formatMessage(messages.title) }}
+		</h2>
+		<p v-if="!canSelectTags" class="known-errors">
+			{{ formatMessage(messages.uploadVersionFirst) }}
+		</p>
+		<div v-else class="flex flex-col gap-4">
+			<Admonition v-if="allTagsSelectedWarning" type="critical" :body="allTagsSelectedWarning" />
+			<Admonition v-else-if="tooManyTagsWarning" type="warning" :body="tooManyTagsWarning" />
+			<Admonition
+				v-if="multipleResolutionTagsWarning"
+				type="warning"
+				:body="multipleResolutionTagsWarning"
+			/>
 
-<style lang="scss" scoped>
-.label__title {
-	display: flex;
-	align-items: center;
-	gap: var(--spacing-card-xs);
-	margin-top: var(--spacing-card-bg);
+			<div
+				v-for="group in categoryGroups"
+				:key="group.id"
+				class="rounded-2xl border border-solid border-surface-4 bg-surface-3 p-4"
+			>
+				<h3 class="mb-1 mt-0 text-base font-semibold text-contrast">
+					{{ group.title }}
+				</h3>
+				<p v-if="group.description" class="mb-3 mt-0 text-sm">
+					{{ group.description }}
+				</p>
+				<div class="grid grid-cols-2 gap-x-4 gap-y-2 sm:grid-cols-4">
+					<Checkbox
+						v-for="category in group.categories"
+						:key="`${group.id}-${category.name}`"
+						:model-value="current.selectedTags.includes(category.name)"
+						:description="formatCategoryName(category.name)"
+						@update:model-value="toggleTag(category.name)"
+					>
+						<span aria-hidden="true">
+							<FormattedTag :tag="category.name" enforce-type="category" />
+						</span>
+					</Checkbox>
+				</div>
+			</div>
 
-	svg {
-		vertical-align: top;
-	}
-}
-.category-list {
-	column-count: 4;
-	column-gap: var(--spacing-card-lg);
-	margin-bottom: var(--spacing-card-md);
-
-	:deep(.category-selector) {
-		margin-bottom: 0.75rem;
-
-		.category-selector__label {
-			display: flex;
-			align-items: center;
-			text-align: left;
-
-			.icon {
-				height: 1rem;
-				width: 1rem;
-				margin-right: 0.25rem;
-				display: flex;
-				align-items: center;
-
-				svg {
-					width: 1rem;
-					height: 1rem;
-				}
-			}
-		}
-
-		span {
-			user-select: none;
-		}
-	}
-
-	@media only screen and (max-width: 1250px) {
-		column-count: 3;
-	}
-	@media only screen and (max-width: 1024px) {
-		column-count: 4;
-	}
-	@media only screen and (max-width: 960px) {
-		column-count: 3;
-	}
-	@media only screen and (max-width: 750px) {
-		column-count: 2;
-	}
-	@media only screen and (max-width: 530px) {
-		column-count: 1;
-	}
-}
-</style>
+			<div class="rounded-2xl border border-solid border-surface-4 bg-surface-3 p-4">
+				<div class="mb-1 flex items-center gap-2">
+					<h3 class="m-0 text-base font-semibold text-contrast">
+						{{ formatMessage(messages.featuredTags) }}
+					</h3>
+					<TagItem
+						v-tooltip="
+							current.featuredTags.length === 0
+								? formatMessage(messages.featuredTagsRequired)
+								: undefined
+						"
+						:style="canSave ? undefined : { '--_color': 'var(--color-red)' }"
+					>
+						{{ current.featuredTags.length }}/{{ MAX_FEATURED_TAGS }}
+					</TagItem>
+				</div>
+				<p class="mb-3 mt-0 text-sm">
+					{{ formatMessage(messages.featuredTagsDescription) }}
+				</p>
+				<p v-if="current.selectedTags.length < 1" class="m-0 text-sm text-secondary">
+					{{ formatMessage(messages.selectAtLeastOneCategory) }}
+				</p>
+				<div v-else class="grid grid-cols-2 gap-x-4 gap-y-2 sm:grid-cols-4">
+					<Checkbox
+						v-for="name in current.selectedTags"
+						:key="`featured-${name}`"
+						:model-value="current.featuredTags.includes(name)"
+						:description="formatCategoryName(name)"
+						:disabled="isFeaturedLimitReached && !current.featuredTags.includes(name)"
+						@update:model-value="toggleFeatured(name)"
+					>
+						<span aria-hidden="true">
+							<FormattedTag :tag="name" enforce-type="category" />
+						</span>
+					</Checkbox>
+				</div>
+			</div>
+		</div>
+		<UnsavedChangesPopup
+			:original="saved"
+			:modified="current"
+			:saving="saving"
+			:can-save="canSave"
+			:save-disabled-reason="messages.featuredTagsRequired"
+			@reset="reset"
+			@save="save"
+		/>
+	</div>
+</template>
diff --git a/apps/frontend/src/pages/[type]/[project]/version/[version].vue b/apps/frontend/src/pages/[type]/[project]/version/[version].vue
index 25fd9b2851..193aeb89f7 100644
--- a/apps/frontend/src/pages/[type]/[project]/version/[version].vue
+++ b/apps/frontend/src/pages/[type]/[project]/version/[version].vue
@@ -144,6 +144,22 @@
 							<DownloadIcon aria-hidden="true" />
 							{{ formatMessage(commonMessages.downloadButton) }}
 						</ButtonLink>
+						<ButtonLink
+							v-if="
+								!!primaryFile?.url &&
+								isStaff(auth.user) &&
+								modSettings.get(moderationSettings.General.SlicerButtonInVersions)
+							"
+							v-tooltip="`Open in Slicer`"
+							type="quiet"
+							target="_blank"
+							:href="`https://slicer.run/?url=${encodeURIComponent(primaryFile?.url)}`"
+							class="!bg-button-bg"
+							aria-label="Open in Slicer"
+						>
+							<ExternalIcon aria-hidden="true" />
+							Open
+						</ButtonLink>
 						<ButtonLink
 							v-for="file in promotedFiles.filter(
 								(x) =>
@@ -502,6 +518,7 @@ import {
 	TrashIcon,
 	XIcon,
 } from '@modrinth/assets'
+import { moderationSettings } from '@modrinth/moderation'
 import {
 	Admonition,
 	Button,
@@ -545,6 +562,7 @@ const emit = defineEmits<{
 const data = useNuxtApp()
 const route = useNativeRoute()
 const router = useRouter()
+const modSettings = useModerationSettings()
 const auth = await useAuth()
 const tags = useGeneratedState()
 const client = injectModrinthClient()
diff --git a/apps/frontend/src/pages/[type]/[project]/versions.vue b/apps/frontend/src/pages/[type]/[project]/versions.vue
index 48bec39fc7..adefb0711f 100644
--- a/apps/frontend/src/pages/[type]/[project]/versions.vue
+++ b/apps/frontend/src/pages/[type]/[project]/versions.vue
@@ -53,6 +53,21 @@
 					>
 						<DownloadIcon aria-hidden="true" />
 					</ButtonLink>
+					<ButtonLink
+						v-if="
+							!!getPrimaryFile(version) &&
+							isStaff(auth.user) &&
+							modSettings.get(moderationSettings.General.SlicerButtonInVersions)
+						"
+						v-tooltip="`Open in Slicer`"
+						type="quiet"
+						target="_blank"
+						:href="`https://slicer.run/?url=${encodeURIComponent(createDownloadUrl(version))}`"
+						class="!w-9 !rounded-full !px-0 hover:!bg-button-bg"
+						aria-label="Open in Slicer"
+					>
+						<ExternalIcon aria-hidden="true" />
+					</ButtonLink>
 					<TeleportOverflowMenu
 						v-if="currentMember"
 						type="quiet"
@@ -268,6 +283,7 @@ import {
 	SpinnerIcon,
 	TrashIcon,
 } from '@modrinth/assets'
+import { moderationSettings } from '@modrinth/moderation'
 import {
 	ButtonLink,
 	ConfirmModal,
@@ -277,6 +293,7 @@ import {
 	ProjectPageVersions,
 	TeleportOverflowMenu,
 } from '@modrinth/ui'
+import { isStaff } from '@modrinth/utils'
 import { onMounted, useTemplateRef, watch } from 'vue'
 
 import CreateProjectVersionModal from '~/components/ui/create-project-version/CreateProjectVersionModal.vue'
@@ -289,6 +306,7 @@ const { createProjectDownloadUrl, updateVersionsFilterContext } = useCdnDownload
 
 const tags = useGeneratedState()
 const flags = useFeatureFlags()
+const modSettings = useModerationSettings()
 const auth = await useAuth()
 
 const client = injectModrinthClient()
diff --git a/apps/frontend/src/pages/app.vue b/apps/frontend/src/pages/app.vue
index 4f94a7ac1a..e7fd582636 100644
--- a/apps/frontend/src/pages/app.vue
+++ b/apps/frontend/src/pages/app.vue
@@ -533,7 +533,7 @@ useSeoMeta({
 	<div>
 		<div class="landing-hero">
 			<div
-				class="relative mt-4 h-fit w-fit rounded-full bg-highlight-green px-3 py-1 text-sm font-bold text-brand backdrop-blur-lg"
+				class="relative mt-4 h-fit w-fit rounded-full bg-brand-highlight px-3 py-1 text-sm font-bold text-brand backdrop-blur-lg"
 			>
 				{{ formatMessage(commonMessages.betaRelease) }}
 			</div>
diff --git a/apps/frontend/src/pages/collection/[collection].vue b/apps/frontend/src/pages/collection/[collection].vue
index 167ce44566..355c6abc24 100644
--- a/apps/frontend/src/pages/collection/[collection].vue
+++ b/apps/frontend/src/pages/collection/[collection].vue
@@ -425,6 +425,7 @@ import {
 	ProjectCardList,
 	RadioButtons,
 	SidebarCard,
+	sortProjectTypes,
 	StyledInput,
 	TeleportOverflowMenu,
 	useCompactNumber,
@@ -769,7 +770,7 @@ const projectTypes = computed(() => {
 		projects.value?.map((project) => project?.project_type).filter((x) => x !== undefined) || [],
 	)
 	projectSet.delete('project')
-	return Array.from(projectSet)
+	return sortProjectTypes(projectSet)
 })
 
 function getProjectTypeSentenceMessage(type) {
diff --git a/apps/frontend/src/pages/dashboard/revenue/index.vue b/apps/frontend/src/pages/dashboard/revenue/index.vue
index 60b503a931..82f4c48756 100644
--- a/apps/frontend/src/pages/dashboard/revenue/index.vue
+++ b/apps/frontend/src/pages/dashboard/revenue/index.vue
@@ -159,22 +159,22 @@
 							fill-rule="evenodd"
 							clip-rule="evenodd"
 							d="M319.052 54.2233C319.058 37.6952 315.689 21.3441 309.156 6.19864C302.624 -8.94682 293.07 -22.559 281.094 -33.7816C269.119 -45.0042 254.982 -53.5944 239.573 -59.012C224.164 -64.4295 207.815 -66.5571 191.556 -65.2609C175.297 -63.9648 159.479 -59.2729 145.097 -51.4805C130.715 -43.688 118.08 -32.9636 107.987 -19.9818C97.8942 -6.99995 90.5617 7.95837 86.4509 23.9523C82.3401 39.9462 81.5398 56.6297 84.1004 72.9533L103.415 67.7101C100.452 45.7823 104.805 23.4811 115.783 4.35031C126.761 -14.7805 143.734 -29.6435 164.005 -37.8768C184.275 -46.1102 206.681 -47.2415 227.661 -41.0911C248.641 -34.9407 266.991 -21.8613 279.797 -3.93146L262.376 6.25239C255.476 -2.83248 246.698 -10.2779 236.659 -15.5617C226.619 -20.8455 215.561 -23.8398 204.26 -24.3345L206.032 -3.60929C217.266 -2.58081 227.949 1.79213 236.737 8.95915C245.524 16.1262 252.024 25.767 255.418 36.6684C258.812 47.5697 258.949 59.2444 255.81 70.223C252.672 81.2017 246.398 90.9937 237.78 98.3668L248.048 116.384C261.575 105.867 271.303 91.124 275.725 74.437C280.146 57.7501 279.016 40.0505 272.507 24.079L289.873 13.9453C295.192 26.0533 298.028 39.1299 298.209 52.3816L319.052 54.2233Z"
-							fill="#1BD96A"
+							fill="var(--color-brand)"
 							fill-opacity="0.16"
 						/>
 						<path
 							d="M145.331 -51.0364C159.653 -58.796 175.404 -63.4691 191.595 -64.7598C207.786 -66.0504 224.065 -63.9308 239.41 -58.5361C254.754 -53.1414 268.832 -44.5878 280.757 -33.4124C292.682 -22.2369 302.196 -8.68194 308.702 6.39988C315.134 21.3138 318.483 37.4019 318.551 53.6733L298.696 51.919C298.455 38.7552 295.611 25.7724 290.326 13.7409L290.103 13.2307L289.625 13.5089L272.26 23.6428L271.882 23.8634L272.048 24.2711C278.514 40.1402 279.638 57.7262 275.245 74.3061C270.901 90.7012 261.401 105.207 248.194 115.632L238.415 98.4753C246.945 91.0702 253.16 81.3016 256.287 70.3626C259.453 59.2887 259.315 47.5128 255.892 36.5169C252.469 25.5209 245.912 15.7962 237.048 8.56694C228.292 1.42595 217.67 -2.9636 206.491 -4.06957L204.803 -23.8035C215.835 -23.2382 226.622 -20.2771 236.429 -15.1154L236.43 -15.1156C246.405 -9.8657 255.126 -2.46736 261.982 6.5593L262.247 6.9086L262.624 6.68831L280.046 -3.49542L280.522 -3.7744L280.2 -4.2262C267.329 -22.247 248.885 -35.3926 227.798 -41.5743C206.712 -47.7558 184.193 -46.6194 163.82 -38.3444C143.447 -30.0694 126.388 -15.1307 115.354 4.09694C104.394 23.1968 100.004 45.441 102.865 67.338L84.5078 72.3214C82.0618 56.2426 82.8841 39.8252 86.9313 24.0789C91.0248 8.15219 98.3266 -6.74338 108.377 -19.6706C118.427 -32.5979 131.01 -43.2767 145.331 -51.0364Z"
-							stroke="#1BD96A"
+							stroke="var(--color-brand)"
 							stroke-opacity="0.12"
 						/>
 						<path
 							d="M260.003 157.491C244.923 166.318 228.106 171.665 210.752 173.15C193.397 174.636 175.935 172.223 159.61 166.084C143.286 159.945 128.503 150.231 116.318 137.637C104.132 125.042 94.8439 109.878 89.1171 93.226L108.448 87.9782C110.395 93.3018 112.784 98.4486 115.59 103.363C118.525 108.52 121.913 113.398 125.713 117.939L140.152 102.814C131.996 92.3742 126.591 80.0086 124.444 66.8751C122.296 53.7416 123.476 40.2699 127.873 27.7219C132.27 15.1739 139.74 3.96017 149.584 -4.86882C159.427 -13.6978 171.322 -19.8532 184.154 -22.7584L185.891 -2.02536C177.437 0.311457 169.624 4.57902 163.052 10.4495C156.48 16.3201 151.323 23.6373 147.979 31.8393C144.634 40.0412 143.191 48.9096 143.759 57.7633C144.327 66.6169 146.892 75.2202 151.257 82.9123C152.243 84.6198 153.258 86.3022 154.382 87.7452L172.854 68.4135L161.573 52.4568L176.638 25.2047L201.398 12.3472L211.468 19.805L202.636 35.5055L192.974 41.7298L187.498 51.6422L193.955 61.0422C193.955 61.0422 203.56 67.0702 203.576 67.0659L213.41 61.3547L218.72 50.9454L233.753 41.2004L241.537 51.0445L230.214 76.6512L204.201 93.4501L187.642 82.5445L169.003 102.096C176.464 107.133 184.988 110.331 193.89 111.432C202.792 112.534 211.826 111.509 220.268 108.44L230.553 126.503C218.179 131.679 204.694 133.531 191.407 131.879C178.121 130.227 165.481 125.128 154.715 117.075L140.327 132.134C153.557 142.488 169.184 149.244 185.722 151.759C202.26 154.274 219.16 152.465 234.815 146.503C250.471 140.542 264.362 130.626 275.169 117.699C285.976 104.771 293.339 89.2611 296.56 72.6427L317.419 74.4794C314.438 91.7283 307.75 108.104 297.828 122.449C287.906 136.794 274.993 148.756 260.003 157.491Z"
-							fill="#1BD96A"
+							fill="var(--color-brand)"
 							fill-opacity="0.16"
 						/>
 						<path
 							d="M149.913 -4.49238C159.551 -13.1371 171.169 -19.2006 183.706 -22.1377L185.36 -2.39778C176.987 -0.0177107 169.248 4.24324 162.723 10.0719C156.094 15.9933 150.893 23.3739 147.519 31.6468C144.146 39.9199 142.69 48.8658 143.263 57.7963C143.837 66.7266 146.424 75.4045 150.826 83.1632L150.828 83.1668C151.816 84.8756 152.845 86.5845 153.993 88.0571L154.344 88.5081L154.739 88.0956L173.211 68.7634L173.5 68.4621L173.258 68.1208L162.16 52.4243L176.998 25.5829L201.351 12.9363L210.816 19.9464L202.265 35.1485L192.707 41.3047L192.602 41.373L192.541 41.4842L187.064 51.3967L186.912 51.6708L187.09 51.9298L193.547 61.3299L193.606 61.4157L193.693 61.4702L193.7 61.4744C193.705 61.4773 193.712 61.4815 193.721 61.4871C193.739 61.4985 193.766 61.5158 193.801 61.5377C193.871 61.5819 193.975 61.6461 194.106 61.7285C194.369 61.8933 194.744 62.1297 195.194 62.4122C196.095 62.9772 197.296 63.7303 198.498 64.4836C199.7 65.2368 200.903 65.9902 201.806 66.5549C202.257 66.8371 202.634 67.0726 202.898 67.2372C203.03 67.3195 203.136 67.3844 203.208 67.4289C203.244 67.4509 203.273 67.4687 203.293 67.4811C203.303 67.487 203.312 67.4932 203.321 67.498C203.324 67.5001 203.332 67.5044 203.341 67.5089C203.344 67.5108 203.354 67.516 203.367 67.522C203.375 67.5257 203.397 67.5353 203.411 67.5406C203.444 67.5507 203.59 67.5693 203.705 67.5525L203.767 67.5355L203.823 67.5021L213.656 61.7911L213.783 61.7179L213.851 61.5856L219.099 51.2968L233.644 41.8683L240.959 51.1188L229.821 76.3076L204.202 92.8511L187.912 82.1225L187.569 81.8961L187.285 82.1952L168.646 101.746L168.233 102.18L168.728 102.515C176.254 107.596 184.85 110.821 193.829 111.932C202.671 113.026 211.64 112.038 220.043 109.052L229.836 126.252C217.685 131.229 204.482 132.997 191.468 131.379C178.266 129.738 165.708 124.671 155.01 116.67L154.66 116.409L154.358 116.725L139.97 131.784L139.584 132.189L140.024 132.532C153.321 142.939 169.026 149.729 185.648 152.257C202.269 154.785 219.255 152.966 234.99 146.974C250.724 140.983 264.686 131.017 275.548 118.024C286.313 105.146 293.676 89.7174 296.957 73.1823L316.833 74.9331C313.819 91.9106 307.198 108.026 297.421 122.16C287.541 136.444 274.683 148.357 259.755 157.055L259.754 157.055C244.738 165.845 227.991 171.169 210.71 172.648C193.429 174.128 176.039 171.725 159.783 165.612C143.528 159.499 128.806 149.826 116.672 137.284C104.662 124.872 95.4819 109.951 89.7657 93.5707L108.141 88.5822C109.945 93.4461 112.116 98.1617 114.637 102.686L115.16 103.615C118.11 108.797 121.515 113.7 125.333 118.264L125.689 118.688L126.07 118.289L140.509 103.163L140.811 102.847L140.541 102.501C132.438 92.1288 127.067 79.8422 124.933 66.7929C122.799 53.7434 123.973 40.3579 128.341 27.8902C132.71 15.4225 140.132 4.28013 149.913 -4.49238Z"
-							stroke="#1BD96A"
+							stroke="var(--color-brand)"
 							stroke-opacity="0.12"
 						/>
 					</svg>
diff --git a/apps/frontend/src/pages/discover.vue b/apps/frontend/src/pages/discover.vue
index 7b0f537acb..74f3699db8 100644
--- a/apps/frontend/src/pages/discover.vue
+++ b/apps/frontend/src/pages/discover.vue
@@ -1,12 +1,15 @@
 <script setup lang="ts">
+import { getMarginTarget } from '@modrinth/moderation'
 import { commonProjectTypeCategoryMessages, NavTabs, useVIntl } from '@modrinth/ui'
 
 const { formatMessage } = useVIntl()
 
 const flags = useFeatureFlags()
 const route = useRoute()
+const modSettings = useModerationSettings()
 
 const allowTabChanging = computed(() => !route.query.sid)
+const marginTarget = computed(() => getMarginTarget(modSettings.value))
 
 const selectableProjectTypes = [
 	{
@@ -47,7 +50,10 @@ const selectableProjectTypes = [
 ]
 </script>
 <template>
-	<div class="mx-auto box-border flex w-full max-w-[1280px] flex-col gap-4 px-6 pb-6">
+	<div
+		class="box-border flex w-full max-w-[1280px] flex-col gap-4 px-6 pb-6"
+		:class="`m${marginTarget}-auto`"
+	>
 		<NavTabs
 			v-if="!flags.projectTypesPrimaryNav && allowTabChanging"
 			:links="selectableProjectTypes"
diff --git a/apps/frontend/src/pages/hosting/index.vue b/apps/frontend/src/pages/hosting/index.vue
index 5ea21cbd6d..827298042b 100644
--- a/apps/frontend/src/pages/hosting/index.vue
+++ b/apps/frontend/src/pages/hosting/index.vue
@@ -33,7 +33,7 @@
 			<div class="z-[5] flex w-full flex-col gap-8">
 				<div class="flex flex-col gap-4">
 					<div
-						class="relative h-fit w-fit rounded-full bg-highlight-green px-3 py-1 text-sm font-bold text-brand backdrop-blur-lg"
+						class="relative h-fit w-fit rounded-full bg-brand-highlight px-3 py-1 text-sm font-bold text-brand backdrop-blur-lg"
 					>
 						{{ formatMessage(commonMessages.betaRelease) }}
 					</div>
@@ -110,7 +110,7 @@
 			<div class="faded-brand-line absolute left-0 top-0 h-[1px] w-full"></div>
 			<div class="relative mx-auto flex w-full max-w-7xl flex-col gap-8">
 				<div
-					class="relative w-fit rounded-full bg-highlight-green px-3 py-1 text-sm font-bold text-brand backdrop-blur-lg"
+					class="relative w-fit rounded-full bg-brand-highlight px-3 py-1 text-sm font-bold text-brand backdrop-blur-lg"
 				>
 					{{ formatMessage(messages.whyModrinthHosting) }}
 				</div>
@@ -154,7 +154,7 @@
 					</div>
 
 					<div class="relative flex flex-col gap-4 rounded-2xl bg-bg p-6 text-left md:p-12">
-						<LoaderIcon loader="fabric" class="size-8 text-brand" />
+						<TagIcon tag="fabric" enforce-type="loader" class="size-8 text-brand" />
 						<h2 class="m-0 text-lg font-bold">{{ formatMessage(messages.yourFavoriteMods) }}</h2>
 						<h3 class="m-0 text-base font-normal text-secondary">
 							{{ formatMessage(messages.yourFavoriteModsDescription) }}
@@ -238,7 +238,7 @@
 			<div class="faded-brand-line absolute left-0 top-0 h-[1px] w-full"></div>
 			<div class="relative mx-auto flex w-full max-w-7xl flex-col gap-8">
 				<div
-					class="relative w-fit rounded-full bg-highlight-green px-3 py-1 text-sm font-bold text-brand backdrop-blur-lg"
+					class="relative w-fit rounded-full bg-brand-highlight px-3 py-1 text-sm font-bold text-brand backdrop-blur-lg"
 				>
 					{{ formatMessage(messages.includedWithYourServer) }}
 				</div>
@@ -641,9 +641,9 @@ import {
 	injectModrinthClient,
 	injectNotificationManager,
 	IntlFormatted,
-	LoaderIcon,
 	ModrinthServersPurchaseModal,
 	OptionGroup,
+	TagIcon,
 	useFormatPrice,
 	useVIntl,
 } from '@modrinth/ui'
diff --git a/apps/frontend/src/pages/moderation.vue b/apps/frontend/src/pages/moderation.vue
index 9352acabba..4334b52079 100644
--- a/apps/frontend/src/pages/moderation.vue
+++ b/apps/frontend/src/pages/moderation.vue
@@ -1,5 +1,8 @@
 <template>
-	<div class="relative mx-auto mb-6 flex min-h-screen w-full max-w-[1280px] flex-col px-6">
+	<div
+		class="relativemb-6 flex min-h-screen w-full max-w-[1280px] flex-col px-6"
+		:class="`m${marginTarget}-auto`"
+	>
 		<h1>Moderation</h1>
 		<NavTabs :links="moderationLinks" class="mb-4 hidden sm:flex" />
 		<div class="mb-4 sm:hidden">
@@ -16,6 +19,7 @@
 
 <script setup lang="ts">
 import { FolderIcon, GlobeIcon, HashIcon, ReportIcon, ShieldCheckIcon } from '@modrinth/assets'
+import { getMarginTarget } from '@modrinth/moderation'
 import { Chips, defineMessages, NavTabs, useVIntl } from '@modrinth/ui'
 
 definePageMeta({
@@ -30,6 +34,9 @@ const { formatMessage } = useVIntl()
 const route = useRoute()
 const router = useRouter()
 
+const modSettings = useModerationSettings()
+const marginTarget = computed(() => getMarginTarget(modSettings.value))
+
 const messages = defineMessages({
 	projectsTitle: {
 		id: 'moderation.page.projects',
diff --git a/apps/frontend/src/pages/moderation/technical-review/[project].vue b/apps/frontend/src/pages/moderation/technical-review/[project].vue
index 6f04ae4823..e3f413c26b 100644
--- a/apps/frontend/src/pages/moderation/technical-review/[project].vue
+++ b/apps/frontend/src/pages/moderation/technical-review/[project].vue
@@ -12,6 +12,7 @@ import ModerationTechRevCard from '~/components/ui/moderation/ModerationTechRevC
 const client = injectModrinthClient()
 const queryClient = useQueryClient()
 const route = useRoute()
+const keybinds = useModerationKeybinds()
 
 const projectId = String(useRouteId('project'))
 
@@ -269,6 +270,34 @@ function handleShowMaliciousSummary(unsafeFiles: UnsafeFile[]) {
 function refetch() {
 	queryClient.invalidateQueries({ queryKey: ['tech-review-project-report', projectId] })
 }
+
+function handleKeybinds(event: KeyboardEvent) {
+	keybinds.value.handle(event, {
+		scope: 'tech-review',
+		actions: {
+			goToTop: () => {
+				window.scrollTo({
+					top: 0,
+					behavior: 'smooth',
+				})
+			},
+			goToBottom: () => {
+				window.scrollTo({
+					top: document.body.scrollHeight,
+					behavior: 'smooth',
+				})
+			},
+		},
+	})
+}
+
+onMounted(() => {
+	window.addEventListener('keydown', handleKeybinds)
+})
+
+onUnmounted(() => {
+	window.removeEventListener('keydown', handleKeybinds)
+})
 </script>
 
 <template>
diff --git a/apps/frontend/src/pages/moderation/technical-review/index.vue b/apps/frontend/src/pages/moderation/technical-review/index.vue
index 23877ace6b..b46ed59776 100644
--- a/apps/frontend/src/pages/moderation/technical-review/index.vue
+++ b/apps/frontend/src/pages/moderation/technical-review/index.vue
@@ -32,6 +32,7 @@ useHead({ title: 'Tech review queue - Modrinth' })
 
 const client = injectModrinthClient()
 const queryClient = useQueryClient()
+const keybinds = useModerationKeybinds()
 
 const currentPage = ref(1)
 const API_PAGE_SIZE = 50
@@ -571,6 +572,50 @@ watch(totalPages, (pages) => {
 // 		complete: 20,
 // 	}
 // })
+
+const CARD_BOTTOM_OFFSET = 210
+
+function handleKeybinds(event: KeyboardEvent) {
+	keybinds.value.handle(event, {
+		scope: 'tech-review',
+		actions: {
+			goToTop: () => {
+				Array.from(cardRefs.values())
+					.filter((card) => card.getBoundingClientRect().top <= 0)
+					.reduce((prev, curr) =>
+						curr.getBoundingClientRect().top > prev.getBoundingClientRect().top ? curr : prev,
+					)
+					?.scrollIntoView({ behavior: 'smooth', block: 'start' })
+			},
+			goToBottom: () => {
+				const nearestCard = Array.from(cardRefs.values())
+					.filter((card) => card.getBoundingClientRect().bottom >= window.innerHeight)
+					.reduce((prev, curr) =>
+						curr.getBoundingClientRect().top < prev.getBoundingClientRect().top ? curr : prev,
+					)
+
+				if (nearestCard) {
+					window.scrollTo({
+						behavior: 'smooth',
+						top:
+							nearestCard.getBoundingClientRect().bottom +
+							window.scrollY -
+							window.innerHeight +
+							CARD_BOTTOM_OFFSET,
+					})
+				}
+			},
+		},
+	})
+}
+
+onMounted(() => {
+	window.addEventListener('keydown', handleKeybinds)
+})
+
+onUnmounted(() => {
+	window.removeEventListener('keydown', handleKeybinds)
+})
 </script>
 
 <template>
diff --git a/apps/frontend/src/pages/organization/[organization].vue b/apps/frontend/src/pages/organization/[organization].vue
index 15a805eeff..609d3c8e4c 100644
--- a/apps/frontend/src/pages/organization/[organization].vue
+++ b/apps/frontend/src/pages/organization/[organization].vue
@@ -236,6 +236,7 @@ import {
 	ProjectCard,
 	ProjectCardList,
 	SidebarCard,
+	sortProjectTypes,
 	useCompactNumber,
 	useVIntl,
 } from '@modrinth/ui'
@@ -386,15 +387,14 @@ const isInvited = computed(() => {
 })
 
 const projectTypes = computed(() => {
-	const obj: Record<string, boolean> = {}
+	const types = new Set<string>()
 
 	for (const project of projects.value ?? []) {
-		obj[project.project_types[0] ?? 'project'] = true
+		const type = project.project_types[0] ?? 'project'
+		if (type !== 'project') types.add(type)
 	}
 
-	delete obj.project
-
-	return Object.keys(obj)
+	return sortProjectTypes(types)
 })
 function isProjectServer(project: ProjectV3): boolean {
 	return project.minecraft_server != null
@@ -504,15 +504,12 @@ const navLinks = computed(() => [
 		label: formatMessage(commonMessages.allProjectType),
 		href: `/organization/${organization.value?.slug}`,
 	},
-	...projectTypes.value
-		.map((x) => {
-			return {
-				label: formatMessage(getProjectTypeMessage(x as ProjectType, true)),
-				href: `/organization/${organization.value?.slug}/${x}s`,
-			}
-		})
-		.slice()
-		.sort((a, b) => a.label.localeCompare(b.label)),
+	...projectTypes.value.map((x) => {
+		return {
+			label: formatMessage(getProjectTypeMessage(x as ProjectType, true)),
+			href: `/organization/${organization.value?.slug}/${x}s`,
+		}
+	}),
 ])
 
 async function copyId() {
diff --git a/apps/frontend/src/pages/user/[user].vue b/apps/frontend/src/pages/user/[user].vue
index 7f3921f4fe..c7f3ec27ed 100644
--- a/apps/frontend/src/pages/user/[user].vue
+++ b/apps/frontend/src/pages/user/[user].vue
@@ -35,6 +35,9 @@ const userProfile = provideUserProfile({
 	getOrganizations: (userId) => client.labrinth.users_v2.getOrganizations(userId),
 	getCollections: (userId) => client.labrinth.users_v2.getCollections(userId),
 	patchUser: (userId, patch) => client.labrinth.users_v2.patch(userId, patch),
+	changeAvatar: (userId, file, extension) =>
+		client.labrinth.users_v2.changeIcon(userId, file, extension),
+	deleteAvatar: (userId) => client.labrinth.users_v2.deleteIcon(userId),
 	getBlockedUsers: () => client.labrinth.blocked_users_v3.list(),
 	blockUser: (userId) => client.labrinth.blocked_users_v3.block(userId),
 	unblockUser: (userId) => client.labrinth.blocked_users_v3.unblock(userId),
diff --git a/apps/labrinth/.sqlx/query-6ebb0cffc875f50ebe95b91e4735f1c520155d65a5c51021224ab4461c688db8.json b/apps/labrinth/.sqlx/query-6ebb0cffc875f50ebe95b91e4735f1c520155d65a5c51021224ab4461c688db8.json
deleted file mode 100644
index 6d00c56a9f..0000000000
--- a/apps/labrinth/.sqlx/query-6ebb0cffc875f50ebe95b91e4735f1c520155d65a5c51021224ab4461c688db8.json
+++ /dev/null
@@ -1,22 +0,0 @@
-{
-  "db_name": "PostgreSQL",
-  "query": "\n        SELECT id FROM mods\n        WHERE id = ANY($1)\n            AND components ? 'minecraft_server'\n        ",
-  "describe": {
-    "columns": [
-      {
-        "ordinal": 0,
-        "name": "id",
-        "type_info": "Int8"
-      }
-    ],
-    "parameters": {
-      "Left": [
-        "Int8Array"
-      ]
-    },
-    "nullable": [
-      false
-    ]
-  },
-  "hash": "6ebb0cffc875f50ebe95b91e4735f1c520155d65a5c51021224ab4461c688db8"
-}
diff --git a/apps/labrinth/.sqlx/query-93b19a49ae305ab760792d22c5b955a75323663880b47aa9ed42c9f33cd65f16.json b/apps/labrinth/.sqlx/query-93b19a49ae305ab760792d22c5b955a75323663880b47aa9ed42c9f33cd65f16.json
new file mode 100644
index 0000000000..3e0b89ec2e
--- /dev/null
+++ b/apps/labrinth/.sqlx/query-93b19a49ae305ab760792d22c5b955a75323663880b47aa9ed42c9f33cd65f16.json
@@ -0,0 +1,28 @@
+{
+  "db_name": "PostgreSQL",
+  "query": "\n        SELECT v.id, v.mod_id\n        FROM versions v\n        INNER JOIN mods m ON m.id = v.mod_id\n        WHERE\n            v.id = ANY($1)\n            AND jsonb_typeof(m.components -> 'minecraft_server') IS DISTINCT FROM 'object'\n        ",
+  "describe": {
+    "columns": [
+      {
+        "ordinal": 0,
+        "name": "id",
+        "type_info": "Int8"
+      },
+      {
+        "ordinal": 1,
+        "name": "mod_id",
+        "type_info": "Int8"
+      }
+    ],
+    "parameters": {
+      "Left": [
+        "Int8Array"
+      ]
+    },
+    "nullable": [
+      false,
+      false
+    ]
+  },
+  "hash": "93b19a49ae305ab760792d22c5b955a75323663880b47aa9ed42c9f33cd65f16"
+}
diff --git a/apps/labrinth/Cargo.toml b/apps/labrinth/Cargo.toml
index fccb039a12..fbfe31b0bf 100644
--- a/apps/labrinth/Cargo.toml
+++ b/apps/labrinth/Cargo.toml
@@ -73,7 +73,6 @@ image = { workspace = true, features = [
 itertools = { workspace = true }
 json-patch = { workspace = true }
 lettre = { workspace = true }
-meilisearch-sdk = { workspace = true, features = ["reqwest"] }
 modrinth-content-management = { workspace = true }
 modrinth-util = { workspace = true, features = ["decimal", "sentry", "utoipa"] }
 muralpay = { workspace = true, features = ["client", "mock", "utoipa"] }
diff --git a/apps/labrinth/src/auth/checks.rs b/apps/labrinth/src/auth/checks.rs
index ea3d1e259b..daf9d35d00 100644
--- a/apps/labrinth/src/auth/checks.rs
+++ b/apps/labrinth/src/auth/checks.rs
@@ -11,6 +11,8 @@ use crate::models::projects::{
 use crate::models::users::User;
 use crate::queue::file_scan::get_files_missing_attribution;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use futures::TryStreamExt;
 use itertools::Itertools;
 use xredis::RedisPool;
@@ -91,7 +93,8 @@ pub async fn filter_visible_projects(
         pool,
         hide_unlisted,
     )
-    .await?;
+    .await
+    .wrap_api_err("filtering visible project ids")?;
     projects.retain(|x| filtered_project_ids.contains(&x.inner.id));
     Ok(projects.into_iter().map(|x| x.into()).collect())
 }
@@ -128,7 +131,8 @@ pub async fn filter_visible_project_ids(
     if !check_projects.is_empty() {
         return_projects.extend(
             filter_enlisted_projects_ids(check_projects, user_option, pool)
-                .await?,
+                .await
+                .wrap_api_err("filtering enlisted projects ids")?,
         );
     }
 
@@ -178,7 +182,8 @@ pub async fn filter_enlisted_projects_ids(
             }
         })
         .try_collect::<Vec<()>>()
-        .await?;
+        .await
+        .wrap_internal_err("fetching query results from database")?;
     }
     Ok(return_projects)
 }
@@ -218,7 +223,8 @@ pub async fn filter_visible_versions(
         pool,
         redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("filtering visible version ids")?;
     versions.retain(|x| filtered_version_ids.contains(&x.inner.id));
 
     let version_ids: Vec<_> = versions.iter().map(|v| v.inner.id).collect();
@@ -265,10 +271,9 @@ impl ValidateAuthorized for models::DBOAuthClient {
             return if user.role.is_mod() || user.id == self.created_by.into() {
                 Ok(())
             } else {
-                Err(ApiError::CustomAuthentication(
-                    "You don't have sufficient permissions to interact with this OAuth application"
-                        .to_string(),
-                ))
+                Err(ApiError::Auth(eyre::eyre!(
+                    "You don't have sufficient permissions to interact with this OAuth application",
+                )))
             };
         }
 
@@ -292,7 +297,8 @@ pub async fn filter_visible_version_ids(
     // Get visible projects- ones we are allowed to see public versions for.
     let visible_project_ids = filter_visible_project_ids(
         DBProject::get_many_ids(&project_ids, pool, redis)
-            .await?
+            .await
+            .wrap_api_err("fetching projects for visibility filtering")?
             .iter()
             .map(|x| &x.inner)
             .collect(),
@@ -300,12 +306,14 @@ pub async fn filter_visible_version_ids(
         pool,
         false,
     )
-    .await?;
+    .await
+    .wrap_api_err("filtering visible project IDs")?;
 
     // Then, get enlisted versions (Versions that are a part of a project we are a member of)
     let enlisted_version_ids =
         filter_enlisted_version_ids(versions.clone(), user_option, pool, redis)
-            .await?;
+            .await
+            .wrap_api_err("filtering enlisted version ids")?;
 
     let version_ids: Vec<_> = versions.iter().map(|v| v.id).collect();
     let withheld_versions = get_files_missing_attribution(pool, &version_ids)
@@ -346,14 +354,16 @@ pub async fn filter_enlisted_version_ids(
     // Get enlisted projects- ones we are allowed to see hidden versions for.
     let authorized_project_ids = filter_enlisted_projects_ids(
         DBProject::get_many_ids(&project_ids, pool, redis)
-            .await?
+            .await
+            .wrap_api_err("fetching projects for membership filtering")?
             .iter()
             .map(|x| &x.inner)
             .collect(),
         user_option,
         pool,
     )
-    .await?;
+    .await
+    .wrap_api_err("filtering projects by membership")?;
 
     for version in versions {
         if user_option.as_ref().is_some_and(|x| x.role.is_mod())
@@ -428,7 +438,8 @@ pub async fn is_visible_organization(
 ) -> Result<bool, ApiError> {
     let members =
         DBTeamMember::get_from_team_full(organization.team_id, pool, redis)
-            .await?;
+            .await
+            .wrap_internal_err("fetching team members from database")?;
 
     // This is meant to match the same projects as the `Project::is_searchable` method, but we're not using
     // it here because that'd entail pulling in all projects for the organization
@@ -437,7 +448,7 @@ pub async fn is_visible_organization(
         organization.id as database::models::ids::DBOrganizationId
     )
     .fetch_optional(pool)
-    .await?
+    .await.wrap_internal_err("checking organization for searchable projects")?
     .flatten()
     .unwrap_or(false);
 
diff --git a/apps/labrinth/src/clickhouse/fetch.rs b/apps/labrinth/src/clickhouse/fetch.rs
index b0245075b8..73d9be0e52 100644
--- a/apps/labrinth/src/clickhouse/fetch.rs
+++ b/apps/labrinth/src/clickhouse/fetch.rs
@@ -1,3 +1,4 @@
+use crate::util::error::Context as _;
 use std::sync::Arc;
 
 use crate::{models::ids::ProjectId, routes::ApiError};
@@ -47,7 +48,10 @@ pub async fn fetch_playtimes(
         .bind(end_date.timestamp())
         .bind(projects.iter().map(|x| x.0).collect::<Vec<_>>());
 
-    Ok(query.fetch_all().await?)
+    query
+        .fetch_all()
+        .await
+        .wrap_internal_err("querying database for `fetch_playtimes`")
 }
 
 // Fetches views as a Vec of ReturnViews
@@ -77,7 +81,10 @@ pub async fn fetch_views(
         .bind(end_date.timestamp())
         .bind(projects.iter().map(|x| x.0).collect::<Vec<_>>());
 
-    Ok(query.fetch_all().await?)
+    query
+        .fetch_all()
+        .await
+        .wrap_internal_err("querying database for `fetch_views`")
 }
 
 // Fetches downloads as a Vec of ReturnDownloads
@@ -106,7 +113,10 @@ pub async fn fetch_downloads(
         .bind(end_date.timestamp())
         .bind(projects.iter().map(|x| x.0).collect::<Vec<_>>());
 
-    Ok(query.fetch_all().await?)
+    query
+        .fetch_all()
+        .await
+        .wrap_internal_err("querying database for `fetch_downloads`")
 }
 
 pub async fn fetch_countries_downloads(
@@ -133,7 +143,10 @@ pub async fn fetch_countries_downloads(
         .bind(end_date.timestamp())
         .bind(projects.iter().map(|x| x.0).collect::<Vec<_>>());
 
-    Ok(query.fetch_all().await?)
+    query
+        .fetch_all()
+        .await
+        .wrap_internal_err("querying database for `fetch_countries_downloads`")
 }
 
 pub async fn fetch_countries_views(
@@ -160,5 +173,8 @@ pub async fn fetch_countries_views(
         .bind(end_date.timestamp())
         .bind(projects.iter().map(|x| x.0).collect::<Vec<_>>());
 
-    Ok(query.fetch_all().await?)
+    query
+        .fetch_all()
+        .await
+        .wrap_internal_err("querying database for `fetch_countries_views`")
 }
diff --git a/apps/labrinth/src/database/models/notifications_template_item.rs b/apps/labrinth/src/database/models/notifications_template_item.rs
index dbe908e39e..3c9ef97f70 100644
--- a/apps/labrinth/src/database/models/notifications_template_item.rs
+++ b/apps/labrinth/src/database/models/notifications_template_item.rs
@@ -1,7 +1,8 @@
 use crate::database::models::DatabaseError;
 use crate::models::v3::notifications::{NotificationChannel, NotificationType};
 use crate::routes::ApiError;
-use crate::util::error::Context;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use serde::{Deserialize, Serialize};
 use xredis::RedisPool;
 
@@ -140,7 +141,11 @@ where
 
     drop(redis_conn);
 
-    let cached = HtmlBody { html: get().await? };
+    let cached = HtmlBody {
+        html: get()
+            .await
+            .wrap_api_err("generating notification template HTML")?,
+    };
     let mut redis_conn = redis.connect().await.wrap_internal_err(
         "connecting to redis for dynamic notification html",
     )?;
diff --git a/apps/labrinth/src/database/models/products_tax_identifier_item.rs b/apps/labrinth/src/database/models/products_tax_identifier_item.rs
index 506a82ce2e..0a8a5a85e5 100644
--- a/apps/labrinth/src/database/models/products_tax_identifier_item.rs
+++ b/apps/labrinth/src/database/models/products_tax_identifier_item.rs
@@ -1,6 +1,7 @@
 use crate::database::models::ids::{DBProductId, DBProductPriceId};
 use crate::models::billing::ProductMetadata;
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 
 pub struct DBProductsTaxIdentifier {
     pub id: i32,
@@ -18,7 +19,8 @@ impl DBProductsTaxIdentifier {
             product_id.0,
         )
         .fetch_optional(exec)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `get_product`")?;
 
         Ok(maybe_row.map(|row| DBProductsTaxIdentifier {
             id: row.id,
@@ -41,7 +43,8 @@ impl DBProductsTaxIdentifier {
             price_id.0,
         )
         .fetch_optional(exec)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `get_price`")?;
 
         Ok(maybe_row.map(|row| DBProductsTaxIdentifier {
             id: row.id,
@@ -73,7 +76,7 @@ pub async fn product_info_by_product_price_id(
         product_price_id.0 as i64,
     )
     .fetch_optional(exec)
-    .await?;
+    .await.wrap_internal_err("querying database for `product_info_by_product_price_id`")?;
 
     match maybe_row {
         None => Ok(None),
@@ -83,7 +86,8 @@ pub async fn product_info_by_product_price_id(
                 tax_processor_id: row.tax_processor_id,
                 product_id: DBProductId(row.product_id),
             },
-            product_metadata: serde_json::from_value(row.product_metadata)?,
+            product_metadata: serde_json::from_value(row.product_metadata)
+                .wrap_request_err("deserializing JSON data")?,
         })),
     }
 }
diff --git a/apps/labrinth/src/lib.rs b/apps/labrinth/src/lib.rs
index e3ffe16b75..382dd9fc66 100644
--- a/apps/labrinth/src/lib.rs
+++ b/apps/labrinth/src/lib.rs
@@ -328,16 +328,16 @@ pub fn app_data_config(
     labrinth_config: LabrinthConfig,
 ) {
     cfg.app_data(web::FormConfig::default().error_handler(|err, _req| {
-        routes::ApiError::Validation(err.to_string()).into()
+        routes::ApiError::Request(eyre::eyre!("{err}")).into()
     }))
     .app_data(web::PathConfig::default().error_handler(|err, _req| {
-        routes::ApiError::Validation(err.to_string()).into()
+        routes::ApiError::Request(eyre::eyre!("{err}")).into()
     }))
     .app_data(web::QueryConfig::default().error_handler(|err, _req| {
-        routes::ApiError::Validation(err.to_string()).into()
+        routes::ApiError::Request(eyre::eyre!("{err}")).into()
     }))
     .app_data(web::JsonConfig::default().error_handler(|err, _req| {
-        routes::ApiError::Validation(err.to_string()).into()
+        routes::ApiError::Request(eyre::eyre!("{err}")).into()
     }))
     .app_data(web::Data::new(labrinth_config.redis_pool.clone()))
     .app_data(web::Data::new(labrinth_config.pool.clone()))
diff --git a/apps/labrinth/src/models/v3/moderation_notes.rs b/apps/labrinth/src/models/v3/moderation_notes.rs
index b6621dc8ea..5488ec0ddf 100644
--- a/apps/labrinth/src/models/v3/moderation_notes.rs
+++ b/apps/labrinth/src/models/v3/moderation_notes.rs
@@ -4,6 +4,7 @@ use chrono::{DateTime, Utc};
 use serde::{Deserialize, Serialize};
 
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 
 #[derive(Debug, Clone, Serialize, Deserialize, utoipa::ToSchema)]
 pub struct ModerationNote {
@@ -37,9 +38,9 @@ pub struct PatchModerationNote {
 impl PatchModerationNote {
     pub fn validate_not_empty(&self) -> Result<(), ApiError> {
         if self.notes.is_none() && self.user_rating.is_none() {
-            return Err(ApiError::InvalidInput(
-                "must specify `notes` or `user_rating`".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "must specify `notes` or `user_rating`",
+            )));
         }
 
         Ok(())
@@ -53,16 +54,14 @@ pub fn parse_if_match_header(
         return Ok(None);
     };
 
-    let value = value.to_str().map_err(|_| {
-        ApiError::InvalidInput(
-            "`if-match` header must be a valid integer".to_string(),
-        )
-    })?;
+    let value = value.to_str().wrap_request_err(
+        "`if-match` header must be a valid integer".to_string(),
+    )?;
 
     Some(value.parse::<i32>().map_err(|_| {
-        ApiError::InvalidInput(
-            "`if-match` header must be a valid integer".to_string(),
-        )
+        ApiError::Request(eyre::eyre!(
+            "`if-match` header must be a valid integer",
+        ))
     }))
     .transpose()
 }
diff --git a/apps/labrinth/src/models/v3/notifications.rs b/apps/labrinth/src/models/v3/notifications.rs
index 12598e7fed..2b9cb26dee 100644
--- a/apps/labrinth/src/models/v3/notifications.rs
+++ b/apps/labrinth/src/models/v3/notifications.rs
@@ -767,8 +767,8 @@ impl NotificationDeliveryStatus {
             NotificationDeliveryStatus::Delivered => Ok(()),
             NotificationDeliveryStatus::SkippedPreferences |
             NotificationDeliveryStatus::SkippedDefault |
-            NotificationDeliveryStatus::Pending => Err(ApiError::InvalidInput("An error occurred while sending an email to your email address. Please try again later.".to_owned())),
-            NotificationDeliveryStatus::PermanentlyFailed => Err(ApiError::InvalidInput("This email address doesn't exist! Please try another one.".to_owned())),
+            NotificationDeliveryStatus::Pending => Err(ApiError::Request(eyre::eyre!("An error occurred while sending an email to your email address. Please try again later.".to_owned()))),
+            NotificationDeliveryStatus::PermanentlyFailed => Err(ApiError::Request(eyre::eyre!("This email address doesn't exist! Please try another one.".to_owned()))),
         }
     }
 
diff --git a/apps/labrinth/src/queue/analytics/mod.rs b/apps/labrinth/src/queue/analytics/mod.rs
index 91c3f553d2..f1be710b4b 100644
--- a/apps/labrinth/src/queue/analytics/mod.rs
+++ b/apps/labrinth/src/queue/analytics/mod.rs
@@ -4,7 +4,7 @@ use crate::models::analytics::{
 };
 use crate::routes::ApiError;
 use crate::routes::analytics::MINECRAFT_SERVER_PLAYS;
-use crate::util::error::Context;
+use crate::util::error::Context as _;
 use dashmap::{DashMap, DashSet};
 use std::collections::HashMap;
 use tracing::trace;
@@ -100,25 +100,39 @@ impl AnalyticsQueue {
         if !affiliate_code_clicks_queue.is_empty() {
             let mut insert_clicks = client
                 .insert::<AffiliateCodeClick>("affiliate_code_clicks")
-                .await?;
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
 
             for (_, click_vec) in affiliate_code_clicks_queue {
                 for click in click_vec {
-                    insert_clicks.write(&click).await?;
+                    insert_clicks.write(&click).await.wrap_internal_err(
+                        "writing analytics data to ClickHouse",
+                    )?;
                 }
             }
 
-            insert_clicks.end().await?;
+            insert_clicks
+                .end()
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
         }
 
         if !playtime_queue.is_empty() {
-            let mut playtimes = client.insert::<Playtime>("playtime").await?;
+            let mut playtimes = client
+                .insert::<Playtime>("playtime")
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
 
             for playtime in playtime_queue {
-                playtimes.write(&playtime).await?;
+                playtimes.write(&playtime).await.wrap_internal_err(
+                    "writing analytics data to ClickHouse",
+                )?;
             }
 
-            playtimes.end().await?;
+            playtimes
+                .end()
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
         }
 
         if !minecraft_server_plays_queue.is_empty() {
@@ -176,13 +190,19 @@ impl AnalyticsQueue {
 
             let mut plays = client
                 .insert::<MinecraftServerPlay>(MINECRAFT_SERVER_PLAYS)
-                .await?;
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
 
             for (_, play) in raw_plays {
-                plays.write(&play).await?;
+                plays.write(&play).await.wrap_internal_err(
+                    "writing analytics data to ClickHouse",
+                )?;
             }
 
-            plays.end().await?;
+            plays
+                .end()
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
         }
 
         if !views_queue.is_empty() {
@@ -242,7 +262,10 @@ impl AnalyticsQueue {
                     .wrap_internal_err("writing view count to redis")?;
             }
 
-            let mut views = client.insert::<PageView>("views").await?;
+            let mut views = client
+                .insert::<PageView>("views")
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
 
             for (all_views, monetized) in raw_views {
                 for (idx, mut view) in all_views.into_iter().enumerate() {
@@ -250,11 +273,16 @@ impl AnalyticsQueue {
                         view.monetized = false;
                     }
 
-                    views.write(&view).await?;
+                    views.write(&view).await.wrap_internal_err(
+                        "writing analytics data to ClickHouse",
+                    )?;
                 }
             }
 
-            views.end().await?;
+            views
+                .end()
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
         }
 
         if !downloads_queue.is_empty() {
@@ -308,8 +336,14 @@ impl AnalyticsQueue {
                     .wrap_internal_err("writing download count to redis")?;
             }
 
-            let mut transaction = pool.begin().await?;
-            let mut downloads = client.insert::<Download>("downloads").await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
+            let mut downloads = client
+                .insert::<Download>("downloads")
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
 
             let mut version_downloads: HashMap<i64, i32> = HashMap::new();
             let mut project_downloads: HashMap<i64, i32> = HashMap::new();
@@ -329,7 +363,9 @@ impl AnalyticsQueue {
 
                 trace!("writing download {download:?}");
 
-                downloads.write(&download).await?;
+                downloads.write(&download).await.wrap_internal_err(
+                    "writing analytics data to ClickHouse",
+                )?;
             }
 
             sqlx::query!(
@@ -343,7 +379,8 @@ impl AnalyticsQueue {
                 &version_downloads.values().copied().collect::<Vec<_>>(),
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("incrementing version download counts")?;
 
             sqlx::query!(
                 "
@@ -356,10 +393,17 @@ impl AnalyticsQueue {
                 &project_downloads.values().copied().collect::<Vec<_>>(),
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("incrementing project download counts")?;
 
-            transaction.commit().await?;
-            downloads.end().await?;
+            transaction
+                .commit()
+                .await
+                .wrap_internal_err("committing database transaction")?;
+            downloads
+                .end()
+                .await
+                .wrap_internal_err("writing analytics data to ClickHouse")?;
         }
 
         Ok(())
diff --git a/apps/labrinth/src/queue/billing.rs b/apps/labrinth/src/queue/billing.rs
index f982ce48f8..504720adb4 100644
--- a/apps/labrinth/src/queue/billing.rs
+++ b/apps/labrinth/src/queue/billing.rs
@@ -24,6 +24,7 @@ use crate::routes::internal::billing::payments::*;
 use crate::util::anrok;
 use crate::util::archon::ArchonClient;
 use crate::util::archon::{CreateServerRequest, Specs};
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use ariadne::ids::base62_impl::to_base62;
 use chrono::Utc;
@@ -48,9 +49,14 @@ async fn update_tax_amounts(
     let mut processed_charges = 0;
 
     loop {
-        let mut txn = pg.begin().await?;
+        let mut txn = pg
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
-        let charges = DBCharge::get_updateable_lock(&mut txn, 5).await?;
+        let charges = DBCharge::get_updateable_lock(&mut txn, 5)
+            .await
+            .wrap_internal_err("fetching charges from database")?;
 
         if charges.is_empty() {
             info!("No more charges to process");
@@ -82,67 +88,70 @@ async fn update_tax_amounts(
                         charge.price_id,
                         &pg,
                     )
-                    .await?
+                    .await
+                    .wrap_api_err("fetching price")?
                     .ok_or_else(|| {
                         DatabaseError::Database(sqlx::Error::RowNotFound)
-                    })?;
+                    })
+                    .wrap_internal_err("querying database for `update_tax_amounts`")?;
 
-                    let product =
-                        DBProduct::get_price(charge.price_id, &pg)
-                            .await?
-                            .ok_or_else(|| {
-                            DatabaseError::Database(
-                                sqlx::Error::RowNotFound,
-                            )
-                        })?;
+                    let product = DBProduct::get_price(charge.price_id, &pg)
+                        .await
+                        .wrap_internal_err(
+                            "fetching product price from database",
+                        )?
+                        .ok_or_else(|| {
+                            DatabaseError::Database(sqlx::Error::RowNotFound)
+                        })
+                        .wrap_internal_err(
+                            "finding product price in database",
+                        )?;
 
                     let stripe_address = 'a: {
-                        let stripe_customer_id =
+                        let stripe_customer =
                             DBUser::get_id(charge.user_id, &pg, &redis)
-                                .await?
-                                .ok_or_else(|| {
-                                    ApiError::from(DatabaseError::Database(
-                                        sqlx::Error::RowNotFound,
-                                    ))
-                                })
-                                .and_then(|user| {
-                                    user.stripe_customer_id.ok_or_else(
-                                        || {
-                                            ApiError::InvalidInput(
-                                            "User has no Stripe customer ID"
-                                                .to_owned(),
-                                        )
-                                        },
-                                    )
-                                })?
-                                .parse()
-                                .map_err(|_| {
-                                    ApiError::InvalidInput(
-                                        "User Stripe customer ID was invalid".to_owned(),
-                                    )
-                                })?;
+                                .await
+                                .wrap_internal_err(
+                                    "fetching Stripe customer from database",
+                                )?
+                                .wrap_internal_err(
+                                    "finding Stripe customer in database",
+                                )?;
+                        let stripe_customer_id = stripe_customer
+                            .stripe_customer_id
+                            .wrap_request_err(
+                                "finding Stripe customer ID on user",
+                            )?
+                            .parse()
+                            .wrap_request_err(
+                                "parsing user Stripe customer ID",
+                            )?;
 
                         let customer = stripe::Customer::retrieve(
                             &stripe_client,
                             &stripe_customer_id,
                             &["invoice_settings.default_payment_method"],
                         )
-                        .await?;
+                        .await
+                        .wrap_failed_dependency_err(
+                            "communicating with payment provider",
+                        )?;
 
                         // A customer should have a default payment method if they have an active subscription.
 
                         let payment_method = customer
                             .invoice_settings
                             .and_then(|x| {
-                                x.default_payment_method.and_then(|x| x.into_object())
+                                x.default_payment_method
+                                    .and_then(|x| x.into_object())
                             })
-                            .ok_or_else(|| {
-                                ApiError::InvalidInput(
-                                    "Customer has no default payment method!".to_string(),
-                                )
+                            .wrap_request_err_with(|| {
+                                "customer has no default payment method!"
+                                    .to_string()
                             })?;
 
-                        let stripe_address = payment_method.billing_details.address;
+                        let stripe_address =
+                            payment_method.billing_details.address;
 
                         // Attempt the default payment method's address first, then the customer's address.
                         match stripe_address {
@@ -152,18 +161,14 @@ async fn update_tax_amounts(
                             }
                         };
 
-                        customer.address.ok_or_else(|| {
-                            ApiError::InvalidInput(
-                                "Couldn't get an address for the Stripe customer"
-                                    .to_owned(),
-                            )
+                        customer.address.wrap_request_err_with(|| {
+                            "couldn't get an address for the Stripe customer"
+                                .to_owned()
                         })?
                     };
 
                     let customer_address =
-                        anrok::Address::from_stripe_address(
-                            &stripe_address,
-                        );
+                        anrok::Address::from_stripe_address(&stripe_address);
 
                     let tax_amount = anrok_client
                         .create_ephemeral_txn(&anrok::TransactionFields {
@@ -179,17 +184,16 @@ async fn update_tax_amounts(
                             customer_id: None,
                             customer_name: None,
                         })
-                        .await?
+                        .await
+                        .wrap_internal_err("inserting database records for `update_tax_amounts`")?
                         .tax_amount_to_collect;
 
-                    Result::<ProcessedCharge, ApiError>::Ok(
-                        ProcessedCharge {
-                            new_tax_amount: tax_amount,
-                            product_name: product
-                                .name
-                                .unwrap_or_else(|| "Modrinth".to_owned()),
-                        },
-                    )
+                    Result::<ProcessedCharge, ApiError>::Ok(ProcessedCharge {
+                        new_tax_amount: tax_amount,
+                        product_name: product
+                            .name
+                            .unwrap_or_else(|| "Modrinth".to_owned()),
+                    })
                 };
 
                 op_fut.then(move |res| async move { (charge_clone, res) })
@@ -212,11 +216,9 @@ async fn update_tax_amounts(
                         // for this.
 
                         let subscription_id =
-                            charge.subscription_id.ok_or_else(|| {
-                                ApiError::InvalidInput(
-                                    "Charge has no subscription ID".to_owned(),
-                                )
-                            })?;
+                            charge.subscription_id.wrap_request_err_with(
+                                || "charge has no subscription ID".to_owned(),
+                            )?;
 
                         NotificationBuilder {
                             body: NotificationBody::TaxNotification {
@@ -234,7 +236,8 @@ async fn update_tax_amounts(
                             },
                         }
                         .insert(charge.user_id, &mut txn, redis)
-                        .await?;
+                        .await
+                        .wrap_internal_err("inserting database records for `update_tax_amounts`")?;
 
                         charge.tax_amount = new_tax_amount;
                     }
@@ -248,10 +251,15 @@ async fn update_tax_amounts(
             };
 
             charge.tax_last_updated = Some(Utc::now());
-            charge.upsert(&mut txn).await?;
+            charge
+                .upsert(&mut txn)
+                .await
+                .wrap_internal_err("updating subscription id in database")?;
         }
 
-        txn.commit().await?;
+        txn.commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         if processed_charges >= limit {
             break Ok(());
@@ -287,11 +295,9 @@ async fn update_anrok_transactions(
                     .payment_platform_id
                     .as_ref()
                     .and_then(|x| x.parse().ok())
-                    .ok_or_else(|| {
-                        ApiError::InvalidInput(
-                            "Refund charge has no or an invalid refund ID"
-                                .to_owned(),
-                        )
+                    .wrap_request_err_with(|| {
+                        "refund charge has no or an invalid refund ID"
+                            .to_owned()
                     })?;
 
                 let refund = stripe::Refund::retrieve(
@@ -299,15 +305,16 @@ async fn update_anrok_transactions(
                     &refund_id,
                     &["payment_intent.payment_method"],
                 )
-                .await?;
+                .await
+                .wrap_failed_dependency_err(
+                    "communicating with payment provider",
+                )?;
 
                 let pi = refund
                     .payment_intent
                     .and_then(|x| x.into_object())
-                    .ok_or_else(|| {
-                        ApiError::InvalidInput(
-                            "Refund charge has no payment intent".to_owned(),
-                        )
+                    .wrap_request_err_with(|| {
+                        "refund charge has no payment intent".to_owned()
                     })?;
 
                 (pi, anrok::transaction_id_stripe_pyr(&refund_id))
@@ -316,10 +323,8 @@ async fn update_anrok_transactions(
                     .payment_platform_id
                     .as_ref()
                     .and_then(|x| x.parse().ok())
-                    .ok_or_else(|| {
-                        ApiError::InvalidInput(
-                            "Charge has no payment platform ID".to_owned(),
-                        )
+                    .wrap_request_err_with(|| {
+                        "charge has no payment platform ID".to_owned()
                     })?;
 
                 // Attempt retrieving the address via the payment intent's payment method
@@ -329,7 +334,10 @@ async fn update_anrok_transactions(
                     &stripe_id,
                     &["payment_method"],
                 )
-                .await?;
+                .await
+                .wrap_failed_dependency_err(
+                    "communicating with payment provider",
+                )?;
 
                 let anrok_id = anrok::transaction_id_stripe_pi(&stripe_id);
 
@@ -341,27 +349,17 @@ async fn update_anrok_transactions(
                 .and_then(|x| x.into_object())
                 .and_then(|x| x.billing_details.address);
 
-            let stripe_customer_id =
-                DBUser::get_id(c.user_id, &mut *txn, redis)
-                    .await?
-                    .ok_or_else(|| {
-                        ApiError::from(DatabaseError::Database(
-                            sqlx::Error::RowNotFound,
-                        ))
-                    })
-                    .and_then(|user| {
-                        user.stripe_customer_id.ok_or_else(|| {
-                            ApiError::InvalidInput(
-                                "User has no Stripe customer ID".to_owned(),
-                            )
-                        })
-                    })?;
+            let stripe_customer = DBUser::get_id(c.user_id, &mut *txn, redis)
+                .await
+                .wrap_internal_err("fetching Stripe customer from database")?
+                .wrap_internal_err("finding Stripe customer in database")?;
+            let stripe_customer_id = stripe_customer
+                .stripe_customer_id
+                .wrap_request_err("finding Stripe customer ID on user")?;
 
-            let customer_id = stripe_customer_id.parse().map_err(|e| {
-                ApiError::InvalidInput(format!(
-                    "Charge's Stripe customer ID was invalid ({e})"
-                ))
-            })?;
+            let customer_id = stripe_customer_id
+                .parse()
+                .wrap_request_err("parsing request value")?;
 
             match pi_stripe_address {
                 Some(address) => {
@@ -377,7 +375,10 @@ async fn update_anrok_transactions(
 
             let customer =
                 stripe::Customer::retrieve(stripe_client, &customer_id, &[])
-                    .await?;
+                    .await
+                    .wrap_failed_dependency_err(
+                        "communicating with payment provider",
+                    )?;
 
             let Some(address) = customer.address else {
                 // We won't really be able to do anything about this.
@@ -388,7 +389,9 @@ async fn update_anrok_transactions(
                 );
 
                 c.tax_platform_id = Some("unresolved".to_owned());
-                c.upsert(txn).await?;
+                c.upsert(txn)
+                    .await
+                    .wrap_internal_err("updating customer in database")?;
 
                 return Ok(());
             };
@@ -397,8 +400,12 @@ async fn update_anrok_transactions(
         };
 
         let tax_id = DBProductsTaxIdentifier::get_price(c.price_id, &mut *txn)
-            .await?
-            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))?;
+            .await
+            .wrap_api_err("fetching price")?
+            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))
+            .wrap_internal_err(
+                "fetching products tax identifier from database",
+            )?;
 
         // Note: if the tax amount that was charged to the customer is *different* than
         // what it *should* be NOW, we will take on a loss here.
@@ -427,18 +434,18 @@ async fn update_anrok_transactions(
 
         match result {
             Ok(response) => {
-                let version = response.version.ok_or_else(|| {
-                    ApiError::InvalidInput(
-                        "Anrok response is missing tax transaction version"
-                            .to_owned(),
-                    )
+                let version = response.version.wrap_request_err_with(|| {
+                    "anrok response is missing tax transaction version"
+                        .to_owned()
                 })?;
 
                 c.tax_drift_loss = Some(response.tax_amount_to_collect);
                 c.tax_platform_id = Some(tax_platform_id);
                 c.tax_transaction_version = Some(version);
                 c.tax_platform_accounting_time = Some(c.due);
-                c.upsert(txn).await?;
+                c.upsert(txn)
+                    .await
+                    .wrap_internal_err("updating version in database")?;
 
                 Ok(())
             }
@@ -449,11 +456,15 @@ async fn update_anrok_transactions(
                     .is_conflict_and(|x| x == "customerAddressCouldNotResolve")
                 {
                     c.tax_platform_id = Some("unresolved".to_owned());
-                    c.upsert(txn).await?;
+                    c.upsert(txn)
+                        .await
+                        .wrap_internal_err("updating version in database")?;
 
                     Ok(())
                 } else {
-                    Err(error.into())
+                    Err(ApiError::Internal(eyre::eyre!(
+                        "calculating tax with Anrok: {error}"
+                    )))
                 }
             }
         }
@@ -464,11 +475,15 @@ async fn update_anrok_transactions(
     let mut offset = 0;
 
     loop {
-        let mut txn = pg.begin().await?;
+        let mut txn = pg
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         let mut charges =
             DBCharge::get_missing_tax_identifier_lock(&mut txn, offset, 1)
-                .await?;
+                .await
+                .wrap_internal_err("fetching charges from database")?;
 
         let Some(c) = charges.pop() else {
             info!("No more charges to process");
@@ -492,7 +507,9 @@ async fn update_anrok_transactions(
             offset += 1;
         }
 
-        txn.commit().await?;
+        txn.commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         if processed_charges >= limit {
             break Ok(());
@@ -512,7 +529,10 @@ pub async fn try_process_user_redeemal(
     user_redeemal.last_attempt = Some(Utc::now());
     user_redeemal.n_attempts += 1;
     user_redeemal.status = users_redeemals::Status::Processing;
-    let updated = user_redeemal.update_status_if_pending(pool).await?;
+    let updated = user_redeemal
+        .update_status_if_pending(pool)
+        .await
+        .wrap_internal_err("updating updated in database")?;
 
     if !updated {
         return Ok(());
@@ -526,7 +546,8 @@ pub async fn try_process_user_redeemal(
         product_item::QueryProductWithPrices::list_by_product_type(
             pool, "medal",
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching query product with prices from Redis")?;
 
     let Some(product_item::QueryProductWithPrices {
         id: _product_id,
@@ -536,9 +557,9 @@ pub async fn try_process_user_redeemal(
         name: _,
     }) = medal_products.pop()
     else {
-        return Err(ApiError::Conflict(
+        return Err(ApiError::Conflict(eyre::eyre!(
             "Missing Medal subscription product".to_owned(),
-        ));
+        )));
     };
 
     let ProductMetadata::Medal {
@@ -549,31 +570,31 @@ pub async fn try_process_user_redeemal(
         region,
     } = metadata
     else {
-        return Err(ApiError::Conflict(
+        return Err(ApiError::Conflict(eyre::eyre!(
             "Missing or incorrect metadata for Medal subscription".to_owned(),
-        ));
+        )));
     };
 
     let Some(medal_price) = prices.pop() else {
-        return Err(ApiError::Conflict(
+        return Err(ApiError::Conflict(eyre::eyre!(
             "Missing price for Medal subscription".to_owned(),
-        ));
+        )));
     };
 
     let (price_duration, price_amount) = match medal_price.prices {
         Price::OneTime { price: _ } => {
-            return Err(ApiError::Conflict(
+            return Err(ApiError::Conflict(eyre::eyre!(
                 "Unexpected metadata for Medal subscription price".to_owned(),
-            ));
+            )));
         }
 
         Price::Recurring { intervals } => {
             let Some((price_duration, price_amount)) =
                 intervals.into_iter().next()
             else {
-                return Err(ApiError::Conflict(
+                return Err(ApiError::Conflict(eyre::eyre!(
                     "Missing price interval for Medal subscription".to_owned(),
-                ));
+                )));
             };
 
             (price_duration, price_amount)
@@ -585,13 +606,15 @@ pub async fn try_process_user_redeemal(
     // Get the user's username
 
     let user = DBUser::get_id(user_id, pool, redis)
-        .await?
-        .ok_or(ApiError::NotFound)?;
+        .await
+        .wrap_internal_err("fetching user from database")?
+        .wrap_not_found_err("resource not found")?;
 
     // Send the provision request to Archon. On failure, the redeemal will be "stuck" processing,
     // and moved back to pending by `index_subscriptions`.
 
-    let archon_client = ArchonClient::from_env()?;
+    let archon_client = ArchonClient::from_env()
+        .wrap_api_err("executing `ArchonClient::from_env`")?;
     let server_id = archon_client
         .create_server(&CreateServerRequest {
             user_id: to_base62(user_id.0 as u64),
@@ -606,13 +629,21 @@ pub async fn try_process_user_redeemal(
             region,
             tags: vec!["medal".to_owned()],
         })
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `try_process_user_redeemal`",
+        )?;
 
-    let mut txn = pool.begin().await?;
+    let mut txn = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     // Build a subscription using this price ID.
     let subscription = DBUserSubscription {
-        id: generate_user_subscription_id(&mut txn).await?,
+        id: generate_user_subscription_id(&mut txn)
+            .await
+            .wrap_internal_err("generating user subscription ID")?,
         user_id,
         price_id,
         interval: PriceDuration::FiveDays,
@@ -623,12 +654,17 @@ pub async fn try_process_user_redeemal(
         }),
     };
 
-    subscription.upsert(&mut txn).await?;
+    subscription
+        .upsert(&mut txn)
+        .await
+        .wrap_internal_err("generating user subscription ID")?;
 
     // Insert an expiring charge, `index_subscriptions` will unprovision the
     // subscription when expired.
     DBCharge {
-        id: generate_charge_id(&mut txn).await?,
+        id: generate_charge_id(&mut txn)
+            .await
+            .wrap_internal_err("generating redeemal charge ID")?,
         user_id,
         price_id,
         amount: price_amount.into(),
@@ -651,26 +687,42 @@ pub async fn try_process_user_redeemal(
         tax_platform_accounting_time: None,
     }
     .upsert(&mut txn)
-    .await?;
+    .await
+    .wrap_internal_err("upserting redeemal charge")?;
 
     // Update `users_redeemal`, mark subscription as redeemed.
     user_redeemal.status = users_redeemals::Status::Processed;
-    user_redeemal.update(&mut txn).await?;
+    user_redeemal.update(&mut txn).await.wrap_internal_err(
+        "updating database records for `try_process_user_redeemal`",
+    )?;
 
-    txn.commit().await?;
+    txn.commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(())
 }
 
 pub async fn cancel_failing_charges(pool: &PgPool) -> Result<(), ApiError> {
-    let charges_to_cancel = DBCharge::get_cancellable(pool).await?;
+    let charges_to_cancel = DBCharge::get_cancellable(pool)
+        .await
+        .wrap_internal_err("fetching charge from database")?;
 
     for mut charge in charges_to_cancel {
         charge.status = ChargeStatus::Cancelled;
 
-        let mut transaction = pool.begin().await?;
-        charge.upsert(&mut transaction).await?;
-        transaction.commit().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
+        charge
+            .upsert(&mut transaction)
+            .await
+            .wrap_internal_err("updating transaction in database")?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
     }
 
     Ok(())
@@ -682,7 +734,9 @@ pub async fn process_chargeable_charges(
     stripe_client: &stripe::Client,
     anrok_client: &anrok::Client,
 ) -> Result<(), ApiError> {
-    let charges_to_do = DBCharge::get_chargeable(pool).await?;
+    let charges_to_do = DBCharge::get_chargeable(pool)
+        .await
+        .wrap_internal_err("fetching charge from database")?;
 
     let prices = product_item::DBProductPrice::get_many(
         &charges_to_do
@@ -693,7 +747,8 @@ pub async fn process_chargeable_charges(
             .collect::<Vec<_>>(),
         pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching product prices from database")?;
 
     let users = crate::database::models::DBUser::get_many_ids(
         &charges_to_do
@@ -705,7 +760,8 @@ pub async fn process_chargeable_charges(
         pool,
         redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching users from database")?;
 
     for mut charge in charges_to_do {
         let Some(product_price) =
@@ -784,9 +840,18 @@ pub async fn process_chargeable_charges(
             charge.status = ChargeStatus::Failed;
         }
 
-        let mut transaction = pool.begin().await?;
-        charge.upsert(&mut transaction).await?;
-        transaction.commit().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
+        charge
+            .upsert(&mut transaction)
+            .await
+            .wrap_internal_err("updating transaction in database")?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
     }
 
     Ok(())
@@ -798,7 +863,10 @@ async fn unprovision_subscriptions(
 ) -> Result<(), ApiError> {
     info!("Gathering charges to unprovision");
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
     let mut clear_cache_users = Vec::new();
 
     // If an active subscription has:
@@ -806,7 +874,9 @@ async fn unprovision_subscriptions(
     // - An expiring charge due now
     // - A failed charge more than two days ago
     // It should be unprovisioned
-    let all_charges = DBCharge::get_unprovision(pool).await?;
+    let all_charges = DBCharge::get_unprovision(pool)
+        .await
+        .wrap_internal_err("fetching charges from database")?;
 
     let mut all_subscriptions =
         user_subscription_item::DBUserSubscription::get_many(
@@ -818,7 +888,8 @@ async fn unprovision_subscriptions(
                 .collect::<Vec<_>>(),
             pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching user subscriptions from database")?;
     let subscription_prices = product_item::DBProductPrice::get_many(
         &all_subscriptions
             .iter()
@@ -828,7 +899,8 @@ async fn unprovision_subscriptions(
             .collect::<Vec<_>>(),
         pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching product prices from database")?;
     let subscription_products = product_item::DBProduct::get_many(
         &subscription_prices
             .iter()
@@ -838,7 +910,8 @@ async fn unprovision_subscriptions(
             .collect::<Vec<_>>(),
         pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching products from database")?;
     let users = DBUser::get_many_ids(
         &all_subscriptions
             .iter()
@@ -849,7 +922,8 @@ async fn unprovision_subscriptions(
         pool,
         redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching users from database")?;
 
     for charge in all_charges {
         debug!("Unprovisioning charge '{}'", to_base62(charge.id.0 as u64));
@@ -898,7 +972,10 @@ async fn unprovision_subscriptions(
                     user.id as DBUserId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `unprovision_subscriptions`",
+                )?;
 
                 true
             }
@@ -939,7 +1016,10 @@ async fn unprovision_subscriptions(
 
         if unprovisioned {
             subscription.status = SubscriptionStatus::Unprovisioned;
-            subscription.upsert(&mut transaction).await?;
+            subscription
+                .upsert(&mut transaction)
+                .await
+                .wrap_internal_err("updating err in database")?;
 
             DBUsersSubscriptionsAffiliations::deactivate(
                 subscription.id,
@@ -961,8 +1041,12 @@ async fn unprovision_subscriptions(
             .collect::<Vec<_>>(),
         redis,
     )
-    .await?;
-    transaction.commit().await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(())
 }
@@ -972,11 +1056,17 @@ async fn process_redeemals(
     redis: &RedisPool,
 ) -> Result<(), ApiError> {
     // If an offer redeemal has been processing for over 5 minutes, it should be set pending.
-    UserRedeemal::update_stuck_5_minutes(pool).await?;
+    UserRedeemal::update_stuck_5_minutes(pool)
+        .await
+        .wrap_internal_err(
+            "updating database records for `process_redeemals`",
+        )?;
 
     // If an offer redeemal is pending, try processing it.
     // Try processing it.
-    let pending_redeemals = UserRedeemal::get_pending(pool, 100).await?;
+    let pending_redeemals = UserRedeemal::get_pending(pool, 100)
+        .await
+        .wrap_internal_err("fetching user redeemal from Redis")?;
     for redeemal in pending_redeemals {
         if let Err(error) =
             try_process_user_redeemal(pool, redis, redeemal).await
diff --git a/apps/labrinth/src/queue/email.rs b/apps/labrinth/src/queue/email.rs
index ff1b9cfb7b..5ee5374b17 100644
--- a/apps/labrinth/src/queue/email.rs
+++ b/apps/labrinth/src/queue/email.rs
@@ -10,6 +10,8 @@ use crate::models::v3::notifications::{
     NotificationChannel, NotificationDeliveryStatus,
 };
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use chrono::Utc;
 use futures::stream::{FuturesUnordered, StreamExt};
 use lettre::message::Mailbox;
@@ -150,7 +152,13 @@ impl EmailQueue {
     /// Returns `Ok(false)` if no emails were processed, `Ok(true)` if some were processed.
     #[instrument(name = "EmailQueue::index", skip_all)]
     pub async fn index(&self, limit: i64) -> Result<bool, ApiError> {
-        let transport = self.mailer.lock().await.to_transport().await?;
+        let transport = self
+            .mailer
+            .lock()
+            .await
+            .to_transport()
+            .await
+            .wrap_internal_err("creating email transport")?;
 
         let begin = std::time::Instant::now();
 
@@ -159,7 +167,8 @@ impl EmailQueue {
             limit,
             &self.pg,
         )
-        .await?;
+        .await
+        .wrap_internal_err("creating email transport")?;
 
         if deliveries.is_empty() {
             return Ok(false);
@@ -171,7 +180,9 @@ impl EmailQueue {
         // ballooning the error rate.
         for d in deliveries.iter_mut().filter(|d| d.attempt_count >= 3) {
             d.status = NotificationDeliveryStatus::PermanentlyFailed;
-            d.update(&self.pg).await?;
+            d.update(&self.pg).await.wrap_internal_err(
+                "marking exhausted email delivery as failed",
+            )?;
         }
 
         // We hold a FOR UPDATE lock on the rows here, so no other workers are accessing them
@@ -183,7 +194,9 @@ impl EmailQueue {
             .map(|d| d.notification_id)
             .collect::<Vec<_>>();
         let notifications =
-            DBNotification::get_many(&notification_ids, &self.pg).await?;
+            DBNotification::get_many(&notification_ids, &self.pg)
+                .await
+                .wrap_internal_err("fetching notifications from database")?;
 
         // For all notifications we collected, fill out the template
         // and send it via SMTP in parallel.
@@ -201,11 +214,16 @@ impl EmailQueue {
             let seq = Arc::clone(&sequential_processing);
 
             futures.push(async move {
-                let mut txn = this.pg.begin().await?;
+                let mut txn = this
+                    .pg
+                    .begin()
+                    .await
+                    .wrap_internal_err("starting database transaction")?;
 
                 let maybe_user =
                     DBUser::get_id(notification.user_id, &mut txn, &this.redis)
-                        .await?;
+                        .await
+                        .wrap_internal_err("fetching user from database")?;
 
                 let Some(mailbox) = maybe_user
                     .and_then(|user| user.email)
@@ -268,7 +286,9 @@ impl EmailQueue {
                         };
 
                         delivery.attempt_count += 1;
-                        delivery.update(&self.pg).await?;
+                        delivery.update(&self.pg).await.wrap_internal_err(
+                            "updating processed email delivery",
+                        )?;
                     }
                 }
 
@@ -283,7 +303,10 @@ impl EmailQueue {
             delivery.next_attempt = Utc::now()
                 + chrono::Duration::seconds(EMAIL_RETRY_DELAY_SECONDS);
 
-            delivery.update(&self.pg).await?;
+            delivery
+                .update(&self.pg)
+                .await
+                .wrap_internal_err("scheduling email delivery retry")?;
         }
 
         info!(
@@ -302,7 +325,13 @@ impl EmailQueue {
         user_id: DBUserId,
         address: Mailbox,
     ) -> Result<NotificationDeliveryStatus, ApiError> {
-        let transport = self.mailer.lock().await.to_transport().await?;
+        let transport = self
+            .mailer
+            .lock()
+            .await
+            .to_transport()
+            .await
+            .wrap_internal_err("creating email transport")?;
         self.send_one_with_transport(
             txn,
             transport,
@@ -329,7 +358,8 @@ impl EmailQueue {
             &mut *txn,
             &self.redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("creating email transport")?
         .into_iter()
         .find(|t| t.notification_type == notification.notification_type()) else {
             return Ok(NotificationDeliveryStatus::SkippedDefault);
@@ -345,7 +375,8 @@ impl EmailQueue {
             self.identity.clone(),
             address,
         )
-        .await?;
+        .await
+        .wrap_api_err("executing `templates::build_email`")?;
 
         let send_result = transport.send(message).await;
 
diff --git a/apps/labrinth/src/queue/email/templates.rs b/apps/labrinth/src/queue/email/templates.rs
index 1ef37e77fe..1ba595cdae 100644
--- a/apps/labrinth/src/queue/email/templates.rs
+++ b/apps/labrinth/src/queue/email/templates.rs
@@ -11,6 +11,7 @@ use crate::database::models::{
 use crate::env::ENV;
 use crate::models::v3::notifications::NotificationBody;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use crate::util::http::HTTP_CLIENT;
 use ariadne::ids::base62_impl::to_base62;
@@ -135,7 +136,11 @@ pub async fn build_email(
 ) -> Result<Message, ApiError> {
     let get_html_body = async {
         let result: Result<Result<String, reqwest::Error>, ApiError> =
-            match template.get_cached_html_data(redis).await? {
+            match template
+                .get_cached_html_data(redis)
+                .await
+                .wrap_internal_err("fetching email template HTML from Redis")?
+            {
                 Some(html_body) => Ok(Ok(html_body)),
                 None => {
                     let result = client
@@ -149,7 +154,10 @@ pub async fn build_email(
                     if let Ok(ref body) = result {
                         template
                             .set_cached_html_data(body.clone(), redis)
-                            .await?;
+                            .await
+                            .wrap_internal_err(
+                                "updating database records for `build_email`",
+                            )?;
                     }
 
                     Ok(result)
@@ -167,8 +175,10 @@ pub async fn build_email(
     } = from;
 
     let db_user = DBUser::get_id(user_id, &mut *exec, redis)
-        .await?
-        .ok_or(DatabaseError::Database(sqlx::Error::RowNotFound))?;
+        .await
+        .wrap_internal_err("fetching user from database")?
+        .ok_or(DatabaseError::Database(sqlx::Error::RowNotFound))
+        .wrap_internal_err("fetching user from database")?;
 
     let map = [
         (USER_NAME, db_user.username),
@@ -180,17 +190,24 @@ pub async fn build_email(
     let (html_body_result, either) = futures::try_join!(
         get_html_body,
         collect_template_variables(exec, redis, user_id, body, map)
-    )?;
+    )
+    .wrap_api_err("executing `collect_template_variables`")?;
 
     let mut message_builder = Message::builder().from(Mailbox::new(
         Some(from_name),
-        from_address.parse().map_err(MailError::from)?,
+        from_address
+            .parse()
+            .map_err(MailError::from)
+            .wrap_internal_err("reading HTTP response body")?,
     ));
 
     if let Some((name, address)) = reply_name.zip(reply_address) {
         message_builder = message_builder.reply_to(Mailbox::new(
             Some(name),
-            address.parse().map_err(MailError::from)?,
+            address
+                .parse()
+                .map_err(MailError::from)
+                .wrap_internal_err("reading HTTP response body")?,
         ));
     }
 
@@ -244,21 +261,26 @@ pub async fn build_email(
             html: Some(html),
         } => message_builder
             .multipart(MultiPart::alternative_plain_html(plaintext, html))
-            .map_err(MailError::from)?,
+            .map_err(MailError::from)
+            .wrap_internal_err(
+                "executing `MultiPart::alternative_plain_html`",
+            )?,
 
         Body {
             plaintext: Some(plaintext),
             html: None,
         } => message_builder
             .singlepart(SinglePart::plain(plaintext))
-            .map_err(MailError::from)?,
+            .map_err(MailError::from)
+            .wrap_internal_err("executing `SinglePart::plain`")?,
 
         Body {
             plaintext: None,
             html: Some(html),
         } => message_builder
             .singlepart(SinglePart::html(html))
-            .map_err(MailError::from)?,
+            .map_err(MailError::from)
+            .wrap_internal_err("executing `SinglePart::html`")?,
 
         Body {
             plaintext: None,
@@ -329,7 +351,10 @@ async fn resolve_report_title(
         return Ok(title);
     }
 
-    let Some(report) = DBReport::get(report_id, &mut *exec).await? else {
+    let Some(report) = DBReport::get(report_id, &mut *exec)
+        .await
+        .wrap_internal_err("fetching report from database")?
+    else {
         return Ok(title);
     };
     let Some(shared_instance_id) = report.shared_instance_id else {
@@ -398,8 +423,10 @@ async fn collect_template_variables(
                 exec,
                 redis,
             )
-            .await?
-            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))?
+            .await
+            .wrap_api_err("fetching email project")?
+            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))
+            .wrap_internal_err("fetching project from database")?
             .inner;
 
             map.insert(PROJECT_ID, to_base62(project_id.0));
@@ -423,7 +450,7 @@ async fn collect_template_variables(
                 report_id.0 as i64
             )
             .fetch_one(&mut *exec)
-            .await?;
+            .await.wrap_internal_err("querying database for `collect_template_variables`")?;
 
             map.insert(REPORT_ID, to_base62(report_id.0));
             map.insert(
@@ -433,7 +460,8 @@ async fn collect_template_variables(
                     DBReportId(report_id.0 as i64),
                     result.title,
                 )
-                .await?,
+                .await
+                .wrap_api_err("executing `resolve_report_title`")?,
             );
             map.insert(REPORT_DATE, date_human_readable(result.created));
             Ok(EmailTemplate::Static(map))
@@ -453,7 +481,7 @@ async fn collect_template_variables(
                 report_id.0 as i64
             )
             .fetch_one(&mut *exec)
-            .await?;
+            .await.wrap_internal_err("querying database for `collect_template_variables`")?;
 
             map.insert(
                 REPORT_TITLE,
@@ -462,7 +490,8 @@ async fn collect_template_variables(
                     DBReportId(report_id.0 as i64),
                     result.title,
                 )
-                .await?,
+                .await
+                .wrap_api_err("executing `resolve_report_title`")?,
             );
             map.insert(NEWREPORT_ID, to_base62(report_id.0));
             Ok(EmailTemplate::Static(map))
@@ -476,7 +505,10 @@ async fn collect_template_variables(
                 project_id.0 as i64
             )
             .fetch_one(&mut *exec)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "querying database for `collect_template_variables`",
+            )?;
 
             map.insert(PROJECT_ID, to_base62(project_id.0));
             map.insert(PROJECT_NAME, result.name);
@@ -494,8 +526,10 @@ async fn collect_template_variables(
                 exec,
                 redis,
             )
-            .await?
-            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))?
+            .await
+            .wrap_api_err("fetching email project")?
+            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))
+            .wrap_internal_err("fetching project from database")?
             .inner;
 
             map.insert(PROJECT_ID, to_base62(project_id.0));
@@ -516,8 +550,10 @@ async fn collect_template_variables(
                 &mut *exec,
                 redis,
             )
-            .await?
-            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))?
+            .await
+            .wrap_api_err("fetching email project")?
+            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))
+            .wrap_internal_err("fetching project from database")?
             .inner;
 
             map.insert(PROJECT_ID, to_base62(project_id.0));
@@ -530,10 +566,14 @@ async fn collect_template_variables(
                     &mut *exec,
                     redis,
                 )
-                .await?
+                .await
+                .wrap_internal_err("fetching user from database")?
                 .ok_or_else(|| {
                     DatabaseError::Database(sqlx::Error::RowNotFound)
-                })?;
+                })
+                .wrap_internal_err(
+                    "querying database for `collect_template_variables`",
+                )?;
 
                 map.insert(NEWOWNER_TYPE, "user".to_string());
                 map.insert(NEWOWNER_TYPE_CAPITALIZED, "User".to_string());
@@ -546,10 +586,14 @@ async fn collect_template_variables(
                     &mut *exec,
                     redis,
                 )
-                .await?
+                .await
+                .wrap_internal_err("fetching organization from database")?
                 .ok_or_else(|| {
                     DatabaseError::Database(sqlx::Error::RowNotFound)
-                })?;
+                })
+                .wrap_internal_err(
+                    "querying database for `collect_template_variables`",
+                )?;
 
                 map.insert(NEWOWNER_TYPE, "organization".to_string());
                 map.insert(
@@ -584,7 +628,10 @@ async fn collect_template_variables(
                 user_id.0 as i64
             )
             .fetch_one(&mut *exec)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "querying database for `collect_template_variables`",
+            )?;
 
             map.insert(TEAMINVITE_INVITER_NAME, result.inviter_name);
             map.insert(TEAMINVITE_PROJECT_NAME, result.project_name);
@@ -616,7 +663,10 @@ async fn collect_template_variables(
                 user_id.0 as i64
             )
             .fetch_one(&mut *exec)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "querying database for `collect_template_variables`",
+            )?;
 
             map.insert(ORGINVITE_INVITER_NAME, result.inviter_name);
             map.insert(ORGINVITE_ORG_NAME, result.organization_name);
@@ -644,7 +694,10 @@ async fn collect_template_variables(
                 user_id.0 as i64,
             )
             .fetch_one(&mut *exec)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "querying database for `collect_template_variables`",
+            )?;
 
             map.insert(STATUSCHANGE_PROJECT_NAME, result.project_name);
             map.insert(STATUSCHANGE_OLD_STATUS, old_status.as_str().to_owned());
@@ -829,7 +882,9 @@ async fn collect_template_variables(
             key,
         } => Ok(EmailTemplate::Dynamic {
             variables: map,
-            body: dynamic_email_body(redis, title, body_md, key).await?,
+            body: dynamic_email_body(redis, title, body_md, key)
+                .await
+                .wrap_api_err("executing `dynamic_email_body`")?,
             title: title.to_string(),
         }),
 
@@ -844,8 +899,10 @@ async fn collect_template_variables(
                 &mut *exec,
                 redis,
             )
-            .await?
-            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))?;
+            .await
+            .wrap_internal_err("fetching user from database")?
+            .ok_or_else(|| DatabaseError::Database(sqlx::Error::RowNotFound))
+            .wrap_internal_err("fetching user from database")?;
 
             map.insert(SERVERINVITE_INVITER_NAME, inviter.username);
             map.insert(SERVERINVITE_SERVER_NAME, server_name.clone());
@@ -883,9 +940,11 @@ async fn dynamic_email_body(
                 }))
                 .send()
                 .await
-                .and_then(|res| res.error_for_status())?
+                .and_then(|res| res.error_for_status())
+                .wrap_internal_err("deserializing HTTP response")?
                 .bytes()
-                .await?
+                .await
+                .wrap_internal_err("deserializing HTTP response")?
                 .as_ref(),
         )
         .wrap_internal_err("email body is not valid UTF-8")
diff --git a/apps/labrinth/src/queue/payouts/flow/mod.rs b/apps/labrinth/src/queue/payouts/flow/mod.rs
index 08c8d7776a..240b525acf 100644
--- a/apps/labrinth/src/queue/payouts/flow/mod.rs
+++ b/apps/labrinth/src/queue/payouts/flow/mod.rs
@@ -1,6 +1,7 @@
 //! Centralized place where payout rails are defined - their fees, minimum and
 //! maximum withdraw amounts, and execution logic.
 
+use crate::util::error::ApiContext as _;
 use eyre::eyre;
 use modrinth_util::decimal::Decimal2dp;
 use rust_decimal::Decimal;
@@ -59,7 +60,9 @@ impl PayoutsQueue {
                     self,
                     withdrawal.amount,
                     method_details,
-                    &get_method.await?,
+                    &get_method
+                        .await
+                        .wrap_api_err("executing `tremendous::create`")?,
                 )
                 .await
             }
diff --git a/apps/labrinth/src/queue/payouts/flow/mural.rs b/apps/labrinth/src/queue/payouts/flow/mural.rs
index 15ff290e80..6cf2dad6f3 100644
--- a/apps/labrinth/src/queue/payouts/flow/mural.rs
+++ b/apps/labrinth/src/queue/payouts/flow/mural.rs
@@ -19,7 +19,7 @@ use crate::{
         mural::MuralPayoutRequest,
     },
     routes::ApiError,
-    util::error::Context,
+    util::error::{ApiContext as _, Context},
 };
 
 pub const PLATFORM_FEE: PayoutMethodFee = PayoutMethodFee {
@@ -67,7 +67,7 @@ pub(super) async fn create(
     let mural = queue.muralpay.load();
     let mural = mural
         .as_ref()
-        .wrap_internal_err("Mural client not available")?;
+        .wrap_internal_err("required Mural client is not available")?;
 
     let method_fee_usd;
     let forex_usd_to_currency;
@@ -158,14 +158,15 @@ pub(super) async fn execute(
         recipient_info,
     }: MuralFlow,
 ) -> Result<(), ApiError> {
-    let user_email = get_verified_email(user)?;
+    let user_email = get_verified_email(user)
+        .wrap_api_err("fetching verified user email")?;
     let sent_to_method_usd = net_usd + method_fee_usd;
     let total_fee_usd = method_fee_usd + platform_fee_usd;
 
     let mural = queue.muralpay.load();
     let mural = mural
         .as_ref()
-        .wrap_internal_err("Mural client not available")?;
+        .wrap_internal_err("required Mural client is not available")?;
 
     let payment_statement_doc = queue
         .create_mural_payment_statement_doc(
@@ -175,7 +176,8 @@ pub(super) async fn execute(
             &recipient_info,
             gotenberg,
         )
-        .await?;
+        .await
+        .wrap_api_err("creating Mural payment statement document")?;
 
     let user_id = UserId::from(user.id);
     let method_id = match &payout_details {
@@ -235,13 +237,18 @@ pub(super) async fn execute(
             Some(format!("User {user_id}")),
             &[payout],
         )
-        .await
-        .map_err(|err| match err {
-            muralpay::MuralError::Api(err) => ApiError::Mural(Box::new(err)),
-            err => ApiError::Internal(
+        .await;
+    let payout_request = match payout_request {
+        Ok(payout_request) => payout_request,
+        Err(muralpay::MuralError::Api(err)) => {
+            return Err(ApiError::Request(eyre::eyre!(Box::new(err))));
+        }
+        Err(err) => {
+            return Err(ApiError::Internal(
                 eyre!(err).wrap_err("failed to create payout request"),
-            ),
-        })?;
+            ));
+        }
+    };
 
     // Once the Mural payout request has been created successfully,
     // then we *must* commit *a* payout row into the DB, to link the Mural
diff --git a/apps/labrinth/src/queue/payouts/flow/paypal.rs b/apps/labrinth/src/queue/payouts/flow/paypal.rs
index c8e20e279a..de4b158f34 100644
--- a/apps/labrinth/src/queue/payouts/flow/paypal.rs
+++ b/apps/labrinth/src/queue/payouts/flow/paypal.rs
@@ -102,21 +102,20 @@ pub(super) async fn execute(
         if let Some(venmo) = &user.venmo_handle {
             ("Venmo", "user_handle", venmo.clone(), venmo)
         } else {
-            return Err(ApiError::InvalidInput(
-                "Venmo address has not been set for account!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "Venmo address has not been set for account!",
+            )));
         }
     } else if let Some(paypal_id) = &user.paypal_id {
         if let Some(paypal_country) = &user.paypal_country {
             if paypal_country == "US" && method_id != "paypal_us" {
-                return Err(ApiError::InvalidInput(
-                    "Please use the US PayPal transfer option!".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "Please use the US PayPal transfer option!",
+                )));
             } else if paypal_country != "US" && method_id == "paypal_us" {
-                return Err(ApiError::InvalidInput(
-                    "Please use the International PayPal transfer option!"
-                        .to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "Please use the International PayPal transfer option!",
+                )));
             }
 
             (
@@ -126,14 +125,14 @@ pub(super) async fn execute(
                 user.paypal_email.as_ref().unwrap_or(paypal_id),
             )
         } else {
-            return Err(ApiError::InvalidInput(
-                "Please re-link your PayPal account!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "Please re-link your PayPal account!",
+            )));
         }
     } else {
-        return Err(ApiError::InvalidInput(
-            "You have not linked a PayPal account!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "You have not linked a PayPal account!",
+        )));
     };
 
     let payout_req = json!({
diff --git a/apps/labrinth/src/queue/payouts/flow/tremendous.rs b/apps/labrinth/src/queue/payouts/flow/tremendous.rs
index 21f6b7100e..19b00bba95 100644
--- a/apps/labrinth/src/queue/payouts/flow/tremendous.rs
+++ b/apps/labrinth/src/queue/payouts/flow/tremendous.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use chrono::Utc;
 use eyre::eyre;
 use modrinth_util::decimal::Decimal2dp;
@@ -64,7 +65,8 @@ pub(super) async fn create(
         "paypal" | "venmo" => {
             let currency = details.currency.unwrap_or(TremendousCurrency::Usd);
             let currency_code = currency.to_string();
-            let usd_to_currency = usd_to_currency_for(&currency_code)?;
+            let usd_to_currency = usd_to_currency_for(&currency_code)
+                .wrap_api_err("executing `usd_to_currency_for`")?;
 
             let fee = PayoutMethodFee {
                 // If a user withdraws $10:
@@ -127,7 +129,8 @@ pub(super) async fn create(
                 } else {
                     TremendousCurrency::Usd.to_string()
                 };
-            let usd_to_currency = usd_to_currency_for(&currency_code)?;
+            let usd_to_currency = usd_to_currency_for(&currency_code)
+                .wrap_api_err("executing `usd_to_currency_for`")?;
             let currency_to_usd = dec!(1) / usd_to_currency;
 
             // no fees
@@ -190,7 +193,8 @@ pub(super) async fn execute(
         pub order: Order,
     }
 
-    let user_email = get_verified_email(user)?;
+    let user_email = get_verified_email(user)
+        .wrap_api_err("fetching verified user email")?;
 
     let order_req = json!({
         "payment": {
diff --git a/apps/labrinth/src/queue/payouts/mod.rs b/apps/labrinth/src/queue/payouts/mod.rs
index c237f6d624..cdc5b34cdd 100644
--- a/apps/labrinth/src/queue/payouts/mod.rs
+++ b/apps/labrinth/src/queue/payouts/mod.rs
@@ -8,6 +8,7 @@ use crate::models::payouts::{
 };
 use crate::models::projects::MonetizationStatus;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use crate::util::webhook::{
     PayoutSourceAlertType, send_slack_payout_source_alert_webhook,
@@ -207,19 +208,17 @@ impl PayoutsQueue {
             .form(&form)
             .send()
             .await
-            .map_err(|_| {
-                ApiError::Payments(
-                    "Error while authenticating with PayPal".to_string(),
-                )
-            })?
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_failed_dependency_err(
+                "error while authenticating with PayPal".to_string(),
+            )?
             .json()
             .await
-            .map_err(|_| {
-                ApiError::Payments(
-                    "Error while authenticating with PayPal (deser error)"
-                        .to_string(),
-                )
-            })?;
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_failed_dependency_err(
+                "error while authenticating with PayPal (deser error)"
+                    .to_string(),
+            )?;
 
         let new_creds = PayPalCredentials {
             access_token: credential.access_token,
@@ -244,21 +243,23 @@ impl PayoutsQueue {
         let credentials = if let Some(credentials) = read.as_ref() {
             if credentials.expires < Utc::now() {
                 drop(read);
-                self.refresh_token().await.map_err(|_| {
-                    ApiError::Payments(
-                        "Error while authenticating with PayPal".to_string(),
-                    )
-                })?
+                self.refresh_token()
+                    .await
+                    .map_err(|err| eyre::eyre!(err))
+                    .wrap_failed_dependency_err(
+                        "error while authenticating with PayPal".to_string(),
+                    )?
             } else {
                 credentials.clone()
             }
         } else {
             drop(read);
-            self.refresh_token().await.map_err(|_| {
-                ApiError::Payments(
-                    "Error while authenticating with PayPal".to_string(),
-                )
-            })?
+            self.refresh_token()
+                .await
+                .map_err(|err| eyre::eyre!(err))
+                .wrap_failed_dependency_err(
+                    "error while authenticating with PayPal".to_string(),
+                )?
         };
 
         let client = reqwest::Client::new();
@@ -287,17 +288,23 @@ impl PayoutsQueue {
                 .body(body);
         }
 
-        let resp = request.send().await.map_err(|_| {
-            ApiError::Payments("could not communicate with PayPal".to_string())
-        })?;
+        let resp = request
+            .send()
+            .await
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_failed_dependency_err(
+                "could not communicate with PayPal".to_string(),
+            )?;
 
         let status = resp.status();
 
-        let value = resp.json::<Value>().await.map_err(|_| {
-            ApiError::Payments(
+        let value = resp
+            .json::<Value>()
+            .await
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_failed_dependency_err(
                 "could not retrieve PayPal response body".to_string(),
-            )
-        })?;
+            )?;
 
         if !status.is_success() {
             #[derive(Deserialize)]
@@ -318,27 +325,28 @@ impl PayoutsQueue {
                 if error.name == "INSUFFICIENT_FUNDS" {
                     error.message = "We're currently transferring funds to our PayPal account. Please try again in a couple days.".to_string();
                 }
-                return Err(ApiError::Payments(format!(
+                return Err(ApiError::FailedDependency(eyre::eyre!(format!(
                     "error name: {}, message: {}",
                     error.name, error.message
-                )));
+                ))));
             }
 
             if let Ok(error) =
                 serde_json::from_value::<PayPalIdentityError>(value)
             {
-                return Err(ApiError::Payments(format!(
+                return Err(ApiError::FailedDependency(eyre::eyre!(format!(
                     "error name: {}, message: {}",
                     error.error, error.error_description
-                )));
+                ))));
             }
 
-            return Err(ApiError::Payments(
-                "could not retrieve PayPal error body".to_string(),
-            ));
+            return Err(ApiError::FailedDependency(eyre::eyre!(
+                "could not retrieve PayPal error body",
+            )));
         }
 
-        Ok(serde_json::from_value(value)?)
+        serde_json::from_value(value)
+            .wrap_request_err("deserializing JSON data")
     }
 
     pub async fn make_tremendous_request<T: Serialize, X: DeserializeOwned>(
@@ -359,19 +367,23 @@ impl PayoutsQueue {
             request = request.json(&body);
         }
 
-        let resp = request.send().await.map_err(|_| {
-            ApiError::Payments(
+        let resp = request
+            .send()
+            .await
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_failed_dependency_err(
                 "could not communicate with Tremendous".to_string(),
-            )
-        })?;
+            )?;
 
         let status = resp.status();
 
-        let value = resp.json::<Value>().await.map_err(|_| {
-            ApiError::Payments(
+        let value = resp
+            .json::<Value>()
+            .await
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_failed_dependency_err(
                 "could not retrieve Tremendous response body".to_string(),
-            )
-        })?;
+            )?;
 
         if !status.is_success()
             && let Some(obj) = value.as_object()
@@ -385,25 +397,25 @@ impl PayoutsQueue {
 
                 let err =
                     serde_json::from_value::<TremendousError>(array.clone())
-                        .map_err(|_| {
-                            ApiError::Payments(
-                                "could not retrieve Tremendous error json body"
-                                    .to_string(),
-                            )
-                        })?;
+                        .map_err(|err| eyre::eyre!(err))
+                        .wrap_failed_dependency_err(
+                            "could not retrieve Tremendous error json body"
+                                .to_string(),
+                        )?;
 
-                return Err(ApiError::Payments(format!(
+                return Err(ApiError::FailedDependency(eyre::eyre!(format!(
                     "Tremendous error: {} ({:?})",
                     err.message, err.payload
-                )));
+                ))));
             }
 
-            return Err(ApiError::Payments(
-                "could not retrieve Tremendous error body".to_string(),
-            ));
+            return Err(ApiError::FailedDependency(eyre::eyre!(
+                "could not retrieve Tremendous error body",
+            )));
         }
 
-        Ok(serde_json::from_value(value)?)
+        serde_json::from_value(value)
+            .wrap_request_err("deserializing JSON data")
     }
 
     pub async fn get_payout_methods(
@@ -469,13 +481,17 @@ impl PayoutsQueue {
         let options = if let Some(options) = read.as_ref() {
             if options.expires < Utc::now() {
                 drop(read);
-                refresh_payout_methods(self).await?
+                refresh_payout_methods(self)
+                    .await
+                    .wrap_api_err("executing `refresh_payout_methods`")?
             } else {
                 options.clone()
             }
         } else {
             drop(read);
-            refresh_payout_methods(self).await?
+            refresh_payout_methods(self)
+                .await
+                .wrap_api_err("executing `refresh_payout_methods`")?
         };
 
         Ok(options.options)
@@ -876,12 +892,18 @@ pub async fn make_aditude_request(
             "interval": interval
         }))
         .send()
-        .await?
-        .error_for_status()?;
+        .await
+        .wrap_internal_err("deserializing HTTP response")?
+        .error_for_status()
+        .wrap_internal_err("deserializing HTTP response")?;
 
-    let text = request.text().await?;
+    let text = request
+        .text()
+        .await
+        .wrap_internal_err("reading HTTP response body")?;
 
-    let json: Vec<AditudePoints> = serde_json::from_str(&text)?;
+    let json: Vec<AditudePoints> = serde_json::from_str(&text)
+        .wrap_request_err("deserializing JSON data")?;
 
     Ok(json)
 }
@@ -900,7 +922,8 @@ pub async fn process_payout(
         crate::models::payouts::PayoutStatus::InTransit.as_str(),
     )
     .execute(pool)
-    .await?;
+    .await
+    .wrap_internal_err("writing analytics data to ClickHouse")?;
 
     let start: DateTime<Utc> = DateTime::from_naive_utc_and_offset(
         (Utc::now() - Duration::days(1))
@@ -915,7 +938,8 @@ pub async fn process_payout(
         start,
     )
     .fetch_one(pool)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `process_payout`")?;
 
     if results.exists.unwrap_or(false) {
         return Ok(());
@@ -966,9 +990,12 @@ pub async fn process_payout(
             .bind(end.timestamp())
             .fetch_one::<u64>(),
     )
-        .await?;
+        .await.wrap_internal_err("querying database for `process_payout`")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     struct PayoutMultipliers {
         sum: u64,
@@ -1029,7 +1056,7 @@ pub async fn process_payout(
             .insert(r.user_id, r.payouts_split);
         async move { Ok(acc) }
     })
-    .await?;
+    .await.wrap_internal_err("inserting project org members into database")?;
 
     let project_team_members = sqlx::query!(
         "
@@ -1055,7 +1082,7 @@ pub async fn process_payout(
             async move { Ok(acc) }
         },
     )
-    .await?;
+    .await.wrap_internal_err("inserting project team members into database")?;
 
     for project_id in project_ids {
         let team_members: HashMap<i64, Decimal> = project_team_members
@@ -1098,7 +1125,8 @@ pub async fn process_payout(
         "Yesterday",
         "1d",
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `make_aditude_request`")?;
 
     let aditude_amount: Decimal = aditude_res
         .iter()
@@ -1193,9 +1221,12 @@ pub async fn process_payout(
         &insert_availables[..]
     )
     .execute(&mut transaction)
-    .await?;
+    .await.wrap_internal_err("inserting database records for `process_payout`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(())
 }
@@ -1230,14 +1261,18 @@ pub async fn index_payouts_notifications(
 ) -> Result<(), ApiError> {
     info!("Updating payout notifications");
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     payouts_values_notifications::synchronize_future_payout_values(
         &mut transaction,
         200,
     )
-    .await?;
-    let items = payouts_values_notifications::PayoutsValuesNotification::unnotified_users_with_available_payouts_with_limit(&mut transaction, 200).await?;
+    .await
+    .wrap_internal_err("executing `payouts_values_notifications::synchronize_future_payout_values`")?;
+    let items = payouts_values_notifications::PayoutsValuesNotification::unnotified_users_with_available_payouts_with_limit(&mut transaction, 200).await.wrap_internal_err("executing `PayoutsValuesNotification::unnotified_users_with_available_payouts_with_limit`")?;
 
     let payout_ref_ids = items.iter().map(|x| x.id).collect::<Vec<_>>();
     let dates_available =
@@ -1250,14 +1285,23 @@ pub async fn index_payouts_notifications(
         &mut transaction,
         redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err(
+        "inserting database records for `index_payouts_notifications`",
+    )?;
     payouts_values_notifications::PayoutsValuesNotification::set_notified_many(
         &payout_ref_ids,
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_internal_err(
+        "updating database records for `index_payouts_notifications`",
+    )?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(())
 }
diff --git a/apps/labrinth/src/routes/analytics.rs b/apps/labrinth/src/routes/analytics.rs
index 5319350e7b..7330f80d59 100644
--- a/apps/labrinth/src/routes/analytics.rs
+++ b/apps/labrinth/src/routes/analytics.rs
@@ -9,6 +9,7 @@ use crate::queue::analytics::AnalyticsQueue;
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
 use crate::util::date::get_current_tenths_of_ms;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use crate::util::http::HttpClient;
 use actix_web::{HttpRequest, HttpResponse};
@@ -84,11 +85,11 @@ pub async fn page_view_ingest(
     .ok();
     let conn_info = req.connection_info().peer_addr().map(|x| x.to_string());
 
-    let url = Url::parse(&url_input.url).map_err(|_| {
-        ApiError::InvalidInput("invalid page view URL specified!".to_string())
-    })?;
-    let domain = url.host_str().ok_or_else(|| {
-        ApiError::InvalidInput("invalid page view URL specified!".to_string())
+    let url = Url::parse(&url_input.url)
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("invalid page view URL specified!".to_string())?;
+    let domain = url.host_str().wrap_request_err_with(|| {
+        "invalid page view URL specified!".to_string()
     })?;
     let url_origin = url.origin().ascii_serialization();
 
@@ -98,9 +99,9 @@ pub async fn page_view_ingest(
         .any(|origin| origin == "*" || url_origin == *origin);
 
     if !is_valid_url_origin {
-        return Err(ApiError::InvalidInput(
-            "invalid page view URL specified!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "invalid page view URL specified!",
+        )));
     }
 
     let headers = req
@@ -158,7 +159,8 @@ pub async fn page_view_ingest(
                     &**pool,
                     &redis,
                 )
-                .await?;
+                .await
+                .wrap_api_err("fetching project from database")?;
 
                 if let Some(project) = project {
                     view.project_id = project.inner.id.0 as u64;
@@ -209,14 +211,15 @@ pub async fn playtime_ingest(
         &session_queue,
         Scopes::PERFORM_ANALYTICS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let playtimes = playtime_input.0;
 
     if playtimes.len() > 2000 {
-        return Err(ApiError::InvalidInput(
-            "Too much playtime entered for version!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Too much playtime entered for version!",
+        )));
     }
 
     let versions = crate::database::models::DBVersion::get_many(
@@ -224,7 +227,8 @@ pub async fn playtime_ingest(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching versions from database")?;
 
     let headers = req.headers();
 
@@ -300,8 +304,9 @@ pub async fn minecraft_server_play_ingest(
     let project_id = play_input.project_id;
 
     let project = DBProject::get(&project_id.to_string(), &**pool, &redis)
-        .await?
-        .ok_or(ApiError::NotFound)?;
+        .await
+        .wrap_api_err("fetching project from database")?
+        .wrap_not_found_err("resource not found")?;
 
     if project.components.minecraft_server.is_none() {
         return Err(ApiError::Request(eyre!(
diff --git a/apps/labrinth/src/routes/debug/pprof.rs b/apps/labrinth/src/routes/debug/pprof.rs
index cf338ee386..89845bb77c 100644
--- a/apps/labrinth/src/routes/debug/pprof.rs
+++ b/apps/labrinth/src/routes/debug/pprof.rs
@@ -1,7 +1,9 @@
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use crate::util::guards::admin_key_guard;
 use actix_web::{HttpResponse, get};
-use eyre::{Context, eyre};
+use eyre::eyre;
 use prometheus::{IntGauge, Registry};
 use std::time::Duration;
 
@@ -21,10 +23,12 @@ pub fn config(cfg: &mut actix_web::web::ServiceConfig) {
 #[get("/pprof/heap", guard = "admin_key_guard")]
 pub async fn heap() -> Result<HttpResponse, ApiError> {
     let mut prof_ctl = jemalloc_pprof::PROF_CTL.as_ref().unwrap().lock().await;
-    require_profiling_activated(&prof_ctl)?;
+    require_profiling_activated(&prof_ctl)
+        .wrap_api_err("executing `require_profiling_activated`")?;
     let pprof = prof_ctl
         .dump_pprof()
-        .map_err(|err| ApiError::InvalidInput(err.to_string()))?;
+        .map_err(|err| eyre::Report::msg(err.to_string()))
+        .wrap_request_err("processing request")?;
 
     Ok(HttpResponse::Ok()
         .content_type("application/octet-stream")
@@ -39,10 +43,12 @@ pub async fn heap() -> Result<HttpResponse, ApiError> {
 #[get("/pprof/heap/flamegraph", guard = "admin_key_guard")]
 pub async fn flame_graph() -> Result<HttpResponse, ApiError> {
     let mut prof_ctl = jemalloc_pprof::PROF_CTL.as_ref().unwrap().lock().await;
-    require_profiling_activated(&prof_ctl)?;
+    require_profiling_activated(&prof_ctl)
+        .wrap_api_err("executing `require_profiling_activated`")?;
     let svg = prof_ctl
         .dump_flamegraph()
-        .map_err(|err| ApiError::InvalidInput(err.to_string()))?;
+        .map_err(|err| eyre::Report::msg(err.to_string()))
+        .wrap_request_err("processing request")?;
 
     Ok(HttpResponse::Ok().content_type("image/svg+xml").body(svg))
 }
@@ -53,8 +59,8 @@ fn require_profiling_activated(
     if prof_ctl.activated() {
         Ok(())
     } else {
-        Err(ApiError::InvalidInput(
-            "Profiling is not activated".to_string(),
+        Err(ApiError::Request(
+            eyre::eyre!("Profiling is not activated",),
         ))
     }
 }
diff --git a/apps/labrinth/src/routes/internal/admin.rs b/apps/labrinth/src/routes/internal/admin.rs
index dcce8286c5..0fa0196156 100644
--- a/apps/labrinth/src/routes/internal/admin.rs
+++ b/apps/labrinth/src/routes/internal/admin.rs
@@ -9,6 +9,7 @@ use crate::routes::ApiError;
 use crate::search::SearchBackend;
 use crate::search::incremental::consume::reindex_project_document;
 use crate::util::date::get_current_tenths_of_ms;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use crate::util::guards::admin_key_guard;
 use crate::util::tags::valid_download_tags;
@@ -78,12 +79,11 @@ fn parse_download_meta_from_query(
     for (key, value) in url.query_pairs() {
         match key.as_ref() {
             "mr_download_reason" => {
-                meta.reason =
-                    Some(DownloadReason::from_str(&value).map_err(|_| {
-                        ApiError::Request(eyre!(
-                            "invalid download reason specified"
-                        ))
-                    })?);
+                meta.reason = Some(
+                    DownloadReason::from_str(&value)
+                        .map_err(|()| eyre::eyre!("invalid download reason"))
+                        .wrap_request_err("parsing download reason")?,
+                );
             }
             "mr_game_version" => {
                 meta.game_version = Some(value.into_owned());
@@ -92,8 +92,12 @@ fn parse_download_meta_from_query(
                 meta.loader = Some(value.into_owned());
             }
             "mr_dependent_on" => {
-                meta.dependent_on =
-                    Some(parse_download_meta_version(&value, "dependent_on")?);
+                meta.dependent_on = Some(
+                    parse_download_meta_version(&value, "dependent_on")
+                        .wrap_api_err(
+                            "executing `parse_download_meta_version`",
+                        )?,
+                );
             }
             _ => {}
         }
@@ -122,8 +126,8 @@ async fn resolve_download_attribution_version(
     crate::database::models::DBVersion::get(version_id, pool, redis)
         .await
         .wrap_internal_err("failed to fetch download attribution version")?
-        .ok_or_else(|| {
-            ApiError::Request(eyre!("invalid `{field}` version specified"))
+        .wrap_request_err_with(|| {
+            format!("invalid `{field}` version specified")
         })?;
 
     Ok(version_id.0 as u64)
@@ -185,7 +189,8 @@ pub async fn count_download(
         download_body.url,
     )
     .fetch_optional(pool.as_ref())
-    .await?
+    .await
+    .wrap_internal_err("fetching version from database")?
     {
         (version.id, version.mod_id)
     } else if let Some(version) = sqlx::query!(
@@ -198,18 +203,19 @@ pub async fn count_download(
         id_option
     )
     .fetch_optional(pool.as_ref())
-    .await?
+    .await
+    .wrap_internal_err("fetching version from database")?
     {
         (version.id, version.mod_id)
     } else {
-        return Err(ApiError::InvalidInput(
-            "Specified version does not exist!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Specified version does not exist!",
+        )));
     };
 
-    let url = url::Url::parse(&download_body.url).map_err(|_| {
-        ApiError::InvalidInput("invalid download URL specified!".to_string())
-    })?;
+    let url = url::Url::parse(&download_body.url)
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("invalid download URL specified!".to_string())?;
 
     let ip = crate::util::ip::convert_to_ip_v6(&download_body.ip)
         .unwrap_or_else(|_| Ipv4Addr::new(127, 0, 0, 1).to_ipv6_mapped());
@@ -220,7 +226,8 @@ pub async fn count_download(
                 .map(Some)
                 .wrap_request_err("invalid download meta")?
         } else {
-            parse_download_meta_from_query(&url)?
+            parse_download_meta_from_query(&url)
+                .wrap_api_err("parsing download metadata from URL")?
         };
 
     if let Some(meta) = &meta {
@@ -250,7 +257,8 @@ pub async fn count_download(
         meta.as_ref().and_then(|m| m.dependent_on),
         "dependent_on",
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `resolve_download_attribution_version`")?;
 
     let download = Download {
         recorded: get_current_tenths_of_ms(),
diff --git a/apps/labrinth/src/routes/internal/affiliate.rs b/apps/labrinth/src/routes/internal/affiliate.rs
index 85f6e9ae69..8716dffba1 100644
--- a/apps/labrinth/src/routes/internal/affiliate.rs
+++ b/apps/labrinth/src/routes/internal/affiliate.rs
@@ -66,8 +66,8 @@ pub async fn ingest_click(
     let conn_info = req.connection_info().peer_addr().map(|x| x.to_string());
 
     let url = ingest_click.url;
-    let domain = url.host_str().ok_or_else(|| {
-        ApiError::InvalidInput("invalid page view URL specified!".to_string())
+    let domain = url.host_str().wrap_request_err_with(|| {
+        "invalid page view URL specified!".to_string()
     })?;
     let url_origin = url.origin().ascii_serialization();
 
@@ -77,9 +77,9 @@ pub async fn ingest_click(
         .any(|origin| origin == "*" || url_origin == *origin);
 
     if !is_valid_url_origin {
-        return Err(ApiError::InvalidInput(
-            "invalid page view URL specified!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "invalid page view URL specified!",
+        )));
     }
 
     let exists = sqlx::query!(
@@ -159,7 +159,8 @@ pub async fn get_all(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     if user.role.is_admin() {
         let codes = DBAffiliateCode::get_all(&**pool)
@@ -181,9 +182,9 @@ pub async fn get_all(
             .collect::<Vec<_>>();
         Ok(web::Json(codes))
     } else {
-        Err(ApiError::CustomAuthentication(
-            "You do not have permission to view affiliate codes!".to_string(),
-        ))
+        Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to view affiliate codes!",
+        )))
     }
 }
 
@@ -214,16 +215,16 @@ pub async fn create(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let is_admin = creator.role.is_admin();
     let is_affiliate = creator.badges.contains(Badges::AFFILIATE);
 
     if !is_admin && !is_affiliate {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to create an affiliate code!"
-                .to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to create an affiliate code!",
+        )));
     }
 
     let creator_id = DBUserId::from(creator.id);
@@ -239,19 +240,25 @@ pub async fn create(
 
     if affiliate_id != creator_id {
         let Some(_affiliate_user) =
-            DBUser::get_id(affiliate_id, &**pool, &redis).await?
+            DBUser::get_id(affiliate_id, &**pool, &redis)
+                .await
+                .wrap_internal_err("fetching user from database")?
         else {
-            return Err(ApiError::CustomAuthentication(
-                "Affiliate user not found!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "Affiliate user not found!",
+            )));
         };
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let affiliate_code_id =
         crate::database::models::generate_affiliate_code_id(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("generating affiliate code ID")?;
 
     let code = DBAffiliateCode {
         id: affiliate_code_id,
@@ -293,13 +300,15 @@ pub async fn get(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let (affiliate_code_id,) = path.into_inner();
     let affiliate_code_id = DBAffiliateCodeId::from(affiliate_code_id);
 
-    if let Some(model) =
-        DBAffiliateCode::get_by_id(affiliate_code_id, &**pool).await?
+    if let Some(model) = DBAffiliateCode::get_by_id(affiliate_code_id, &**pool)
+        .await
+        .wrap_internal_err("fetching affiliate code from database")?
     {
         let is_admin = user.role.is_admin();
         let is_owner = model.affiliate == DBUserId::from(user.id);
@@ -307,10 +316,10 @@ pub async fn get(
         if is_admin || is_owner {
             Ok(web::Json(AffiliateCode::from(model, is_admin)))
         } else {
-            Err(ApiError::NotFound)
+            Err(ApiError::NotFound(eyre::eyre!("resource not found")))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -335,30 +344,33 @@ pub async fn delete(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let (affiliate_code_id,) = path.into_inner();
     let affiliate_code_id = DBAffiliateCodeId::from(affiliate_code_id);
 
-    if let Some(model) =
-        DBAffiliateCode::get_by_id(affiliate_code_id, &**pool).await?
+    if let Some(model) = DBAffiliateCode::get_by_id(affiliate_code_id, &**pool)
+        .await
+        .wrap_internal_err("fetching affiliate code from database")?
     {
         let is_admin = user.role.is_admin();
         let is_owner = model.affiliate == DBUserId::from(user.id);
 
         if is_admin || is_owner {
-            let result =
-                DBAffiliateCode::remove(affiliate_code_id, &**pool).await?;
+            let result = DBAffiliateCode::remove(affiliate_code_id, &**pool)
+                .await
+                .wrap_internal_err("deleting affiliate code from database")?;
             if result.is_some() {
                 Ok(())
             } else {
-                Err(ApiError::NotFound)
+                Err(ApiError::NotFound(eyre::eyre!("resource not found")))
             }
         } else {
-            Err(ApiError::NotFound)
+            Err(ApiError::NotFound(eyre::eyre!("resource not found")))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -389,26 +401,28 @@ pub async fn patch(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let (affiliate_code_id,) = path.into_inner();
     let affiliate_code_id = DBAffiliateCodeId::from(affiliate_code_id);
 
     let existing_code = DBAffiliateCode::get_by_id(affiliate_code_id, &**pool)
-        .await?
-        .ok_or(ApiError::NotFound)?;
+        .await
+        .wrap_internal_err("fetching affiliate code from database")?
+        .wrap_not_found_err("resource not found")?;
 
     let is_admin = user.role.is_admin();
     let is_owner = existing_code.affiliate == DBUserId::from(user.id);
 
     if !is_admin && !is_owner {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     if !is_admin && !user.badges.contains(Badges::AFFILIATE) {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to update affiliate codes!".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to update affiliate codes!",
+        )));
     }
 
     DBAffiliateCode::update_source_name(
diff --git a/apps/labrinth/src/routes/internal/analytics_event.rs b/apps/labrinth/src/routes/internal/analytics_event.rs
index a743703da3..5a6bec2b7e 100644
--- a/apps/labrinth/src/routes/internal/analytics_event.rs
+++ b/apps/labrinth/src/routes/internal/analytics_event.rs
@@ -56,7 +56,8 @@ pub async fn analytics_event_create(
         &session_queue,
         Scopes::empty(),
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if !user.role.is_admin() {
@@ -116,7 +117,8 @@ pub async fn analytics_event_edit(
         &session_queue,
         Scopes::empty(),
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if !user.role.is_admin() {
@@ -137,7 +139,7 @@ pub async fn analytics_event_edit(
         .await
         .wrap_internal_err("failed to update analytics event")?;
     if !updated {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
     DBAnalyticsEvent::clear_cache(&redis)
         .await
@@ -166,7 +168,8 @@ pub async fn analytics_event_delete(
         &session_queue,
         Scopes::empty(),
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if !user.role.is_admin() {
@@ -182,7 +185,7 @@ pub async fn analytics_event_delete(
     .await
     .wrap_internal_err("failed to delete analytics event")?;
     if !deleted {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
     DBAnalyticsEvent::clear_cache(&redis)
         .await
diff --git a/apps/labrinth/src/routes/internal/attribution.rs b/apps/labrinth/src/routes/internal/attribution.rs
index b12e7e931d..444065345c 100644
--- a/apps/labrinth/src/routes/internal/attribution.rs
+++ b/apps/labrinth/src/routes/internal/attribution.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use actix_web::{HttpRequest, delete, get, patch, post, web};
 use chrono::{DateTime, Utc};
 use eyre::eyre;
@@ -125,7 +126,8 @@ pub async fn scan(
         &session_queue,
         Scopes::VERSION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let mut version_ids: Vec<i64> = body
@@ -155,7 +157,7 @@ pub async fn scan(
     .wrap_internal_err("failed to fetch versions for attribution scan")?;
 
     if versions.len() != version_ids.len() {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     let mut project_ids: Vec<DBProjectId> =
@@ -170,7 +172,8 @@ pub async fn scan(
             &user,
             "you do not have permission to upload versions to this project",
         )
-        .await?;
+        .await
+        .wrap_api_err("validating can upload versions to project")?;
     }
 
     let project_ids = project_ids.iter().map(|id| id.0).collect::<Vec<_>>();
@@ -238,7 +241,8 @@ async fn force_scan_file(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let file_id: DBFileId = path.into_inner().into();
     let file = sqlx::query!(
@@ -256,7 +260,7 @@ async fn force_scan_file(
     .fetch_optional(pool.as_ref())
     .await
     .wrap_internal_err("failed to fetch attribution scan file")?
-    .ok_or(ApiError::NotFound)?;
+    .wrap_not_found_err("resource not found")?;
 
     let mut transaction = pool.begin().await.wrap_internal_err(
         "failed to begin attribution file scan transaction",
@@ -320,13 +324,15 @@ pub async fn list(
         &session_queue,
         Scopes::VERSION_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let requester_is_mod = user.role.is_mod();
 
     let project = DBProject::get_id(project_id, pool.as_ref(), redis.as_ref())
-        .await?
-        .ok_or(ApiError::NotFound)?;
+        .await
+        .wrap_api_err("fetching attribution project")?
+        .wrap_not_found_err("resource not found")?;
     let (team_member, organization_team_member) =
         DBTeamMember::get_for_project_permissions(
             &project.inner,
@@ -651,13 +657,17 @@ pub async fn update_group(
         &session_queue,
         Scopes::VERSION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    if !can_edit_attribution_group(pool.as_ref(), group_id, &user).await? {
-        return Err(ApiError::CustomAuthentication(
-            "This attribution group cannot be edited".to_string(),
-        ));
+    if !can_edit_attribution_group(pool.as_ref(), group_id, &user)
+        .await
+        .wrap_api_err("checking edit attribution group")?
+    {
+        return Err(ApiError::Auth(eyre::eyre!(
+            "This attribution group cannot be edited",
+        )));
     }
 
     if matches!(
@@ -665,15 +675,15 @@ pub async fn update_group(
         AttributionResolutionKind::GloballyAllowed { .. }
     ) && !user.role.is_mod()
     {
-        return Err(ApiError::CustomAuthentication(
-            "Only moderators can set globally allowed attributions".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "Only moderators can set globally allowed attributions",
+        )));
     }
 
     if body.attribution.moderation_status.is_some() && !user.role.is_mod() {
-        return Err(ApiError::CustomAuthentication(
-            "Only moderators can set attribution moderation status".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "Only moderators can set attribution moderation status",
+        )));
     }
 
     let mut attribution = body.attribution;
@@ -698,11 +708,12 @@ pub async fn update_group(
     .wrap_internal_err("failed to update attribution group")?;
 
     if result.rows_affected() == 0 {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     clear_group_version_cache(pool.as_ref(), redis.as_ref(), &[group_id])
-        .await?;
+        .await
+        .wrap_api_err("executing `clear_group_version_cache`")?;
 
     Ok(())
 }
@@ -734,7 +745,8 @@ pub async fn delete_groups(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("deleting database records for `delete_groups`")?;
 
     let group_ids = body
         .groups
@@ -772,7 +784,8 @@ pub async fn delete_all_groups(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("deleting database records for `delete_all_groups`")?;
 
     let project_id = DBProjectId::from(body.project_id).0;
     let group_ids = sqlx::query_scalar!(
@@ -849,7 +862,7 @@ async fn delete_attribution_groups(
     .wrap_internal_err("failed to delete attribution groups")?;
 
     if result.rows_affected() != group_ids.len() as u64 {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     txn.commit().await.wrap_internal_err(
@@ -891,14 +904,13 @@ pub async fn assign(
         &session_queue,
         Scopes::VERSION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let sha1 = body.sha1.trim().to_lowercase();
     if hex_to_bytes(&sha1).is_none() {
-        return Err(ApiError::InvalidInput(
-            "invalid sha1 hex string".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!("invalid sha1 hex string",)));
     }
     let sha1_bytes = sha1.as_bytes().to_vec();
     let project_id: DBProjectId = body.project_id.into();
@@ -916,7 +928,7 @@ pub async fn assign(
     .fetch_optional(pool.as_ref())
     .await
     .wrap_internal_err("failed to fetch source attribution group")?
-    .ok_or(ApiError::NotFound)?;
+    .wrap_not_found_err("resource not found")?;
 
     let target_group_exists = sqlx::query_scalar!(
         "
@@ -932,21 +944,23 @@ pub async fn assign(
     .wrap_internal_err("failed to check target attribution group")?;
 
     if !target_group_exists {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     if !can_edit_attribution_group(pool.as_ref(), source_group_id, &user)
-        .await?
+        .await
+        .wrap_api_err("checking edit attribution group")?
         || !can_edit_attribution_group(
             pool.as_ref(),
             body.target_group_id,
             &user,
         )
-        .await?
+        .await
+        .wrap_api_err("checking edit attribution group")?
     {
-        return Err(ApiError::CustomAuthentication(
-            "This attribution group cannot be edited".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "This attribution group cannot be edited",
+        )));
     }
 
     let mut txn = pool.begin().await.wrap_internal_err(
@@ -986,7 +1000,7 @@ pub async fn assign(
     .wrap_internal_err("failed to insert assigned attribution file")?;
 
     if result.rows_affected() == 0 {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     sqlx::query!(
@@ -1020,7 +1034,8 @@ pub async fn assign(
         project_id,
         &sha1_bytes,
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `clear_project_sha1_version_cache`")?;
 
     Ok(())
 }
@@ -1052,14 +1067,13 @@ pub async fn split(
         &session_queue,
         Scopes::VERSION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let sha1 = body.sha1.trim().to_lowercase();
     if hex_to_bytes(&sha1).is_none() {
-        return Err(ApiError::InvalidInput(
-            "invalid sha1 hex string".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!("invalid sha1 hex string",)));
     }
     let sha1_bytes = sha1.as_bytes().to_vec();
     let project_id: DBProjectId = body.project_id.into();
@@ -1078,15 +1092,16 @@ pub async fn split(
     .wrap_internal_err("failed to fetch attribution file to split")?;
 
     let Some(existing) = existing else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
     if !can_edit_attribution_group(pool.as_ref(), existing.group_id, &user)
-        .await?
+        .await
+        .wrap_api_err("checking edit attribution group")?
     {
-        return Err(ApiError::CustomAuthentication(
-            "This attribution group cannot be edited".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "This attribution group cannot be edited",
+        )));
     }
 
     let mut txn = pool
@@ -1138,7 +1153,8 @@ pub async fn split(
         project_id,
         &sha1_bytes,
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `clear_project_sha1_version_cache`")?;
 
     Ok(())
 }
@@ -1217,7 +1233,7 @@ async fn can_edit_attribution_group(
     .fetch_optional(pool)
     .await
     .wrap_internal_err("failed to fetch attribution group")?
-    .ok_or(ApiError::NotFound)?;
+    .wrap_not_found_err("resource not found")?;
 
     ensure_can_upload_versions_to_project(
         pool,
@@ -1225,7 +1241,8 @@ async fn can_edit_attribution_group(
         user,
         "you do not have permission to edit this attribution group",
     )
-    .await?;
+    .await
+    .wrap_api_err("validating can upload versions to project")?;
 
     let attribution: Option<AttributionResolution> = group
         .attribution
diff --git a/apps/labrinth/src/routes/internal/billing.rs b/apps/labrinth/src/routes/internal/billing.rs
index 82242dd145..5b4f971c96 100644
--- a/apps/labrinth/src/routes/internal/billing.rs
+++ b/apps/labrinth/src/routes/internal/billing.rs
@@ -25,6 +25,8 @@ use crate::models::users::Badges;
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
 use crate::util::anrok;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, post, web};
 use ariadne::ids::base62_impl::{parse_base62, to_base62};
 use chrono::{Duration, Utc};
@@ -79,7 +81,8 @@ pub async fn products(
     let products = product_item::QueryProductWithPrices::list_purchaseable(
         &**pool, &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching query product with prices from Redis")?;
 
     let products = products
         .into_iter()
@@ -137,7 +140,8 @@ pub async fn subscriptions(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let db_subscriptions =
@@ -146,23 +150,24 @@ pub async fn subscriptions(
                 if user.role.is_admin() {
                     user_id.into()
                 } else {
-                    return Err(ApiError::InvalidInput(
-                        "You cannot see the subscriptions of other users!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Request(eyre::eyre!(
+                        "You cannot see the subscriptions of other users!",
+                    )));
                 }
             } else {
                 user.id.into()
             },
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching user subscriptions from database")?;
 
     let mut subscriptions = Vec::with_capacity(db_subscriptions.len());
     for subscription in db_subscriptions {
         let next_charge_tax_amount =
             DBCharge::get_open_subscription(subscription.id, &**pool)
-                .await?
+                .await
+                .wrap_internal_err("fetching charge from database")?
                 .map(|charge| charge.tax_amount);
 
         subscriptions.push(UserSubscriptionWithNextChargeTaxAmount {
@@ -215,19 +220,25 @@ pub async fn refund_charge(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let (id,) = info.into_inner();
 
     if !user.role.is_admin() {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to refund a subscription!".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to refund a subscription!",
+        )));
     }
 
-    if let Some(charge) = DBCharge::get(id.into(), &**pool).await? {
-        let refunds = DBCharge::get_children(id.into(), &**pool).await?;
+    if let Some(charge) = DBCharge::get(id.into(), &**pool)
+        .await
+        .wrap_internal_err("fetching charge from database")?
+    {
+        let refunds = DBCharge::get_children(id.into(), &**pool)
+            .await
+            .wrap_internal_err("fetching charges from database")?;
         let refunds = -refunds
             .into_iter()
             .filter_map(|x| match x.status {
@@ -249,16 +260,15 @@ pub async fn refund_charge(
         };
 
         if charge.status != ChargeStatus::Succeeded {
-            return Err(ApiError::InvalidInput(
-                "This charge cannot be refunded!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "This charge cannot be refunded!",
+            )));
         }
 
         if (refundable - refund_amount) < 0 {
-            return Err(ApiError::InvalidInput(
-                "You cannot refund more than the amount of the charge!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You cannot refund more than the amount of the charge!",
+            )));
         }
 
         let (id, net, anrok_result) = if refund_amount == 0 {
@@ -287,29 +297,33 @@ pub async fn refund_charge(
                             &payment_platform_id,
                             &["payment_method"],
                         )
-                        .await?;
+                        .await
+                        .wrap_failed_dependency_err(
+                            "communicating with payment provider",
+                        )?;
 
                         let Some(billing_address) = pi
                             .payment_method
                             .and_then(|x| x.into_object())
                             .and_then(|x| x.billing_details.address)
                         else {
-                            return Err(ApiError::InvalidInput(
+                            return Err(ApiError::Request(eyre::eyre!(
                                 "Couldn't retrieve billing address for payment method!"
                                     .to_owned(),
-                            ));
+                            )));
                         };
 
                         let tax_id = product_info_by_product_price_id(
                             charge.price_id,
                             &**pool,
                         )
-                        .await?
-                        .ok_or_else(|| {
-                            ApiError::InvalidInput(
-                                "Could not find product tax info for price ID!"
-                                    .to_owned(),
-                            )
+                        .await
+                        .wrap_api_err(
+                            "executing `product_info_by_product_price_id`",
+                        )?
+                        .wrap_request_err_with(|| {
+                            "could not find product tax info for price ID!"
+                                .to_owned()
                         })?
                         .tax_identifier
                         .tax_processor_id;
@@ -326,10 +340,10 @@ pub async fn refund_charge(
                             .zip(charge.tax_transaction_version)
                             .zip(charge.tax_platform_accounting_time)
                         else {
-                            return Err(ApiError::InvalidInput(
+                            return Err(ApiError::Request(eyre::eyre!(
                                 "Charge is missing full tax information. Please wait for the original charge to be synchronized with the tax processor."
                                     .to_owned(),
-                            ));
+                            )));
                         };
 
                         let refund = stripe::Refund::create(
@@ -344,7 +358,10 @@ pub async fn refund_charge(
                                 ..Default::default()
                             },
                         )
-                        .await?;
+                        .await
+                        .wrap_failed_dependency_err(
+                            "communicating with payment provider",
+                        )?;
 
                         let anrok_txn_result = anrok_client.negate_or_create_partial_negation(
                             original_tax_platform_id,
@@ -373,24 +390,28 @@ pub async fn refund_charge(
                             Some(anrok_txn_result),
                         )
                     } else {
-                        return Err(ApiError::InvalidInput(
-                            "Charge does not have attached payment id!"
-                                .to_string(),
-                        ));
+                        return Err(ApiError::Request(eyre::eyre!(
+                            "Charge does not have attached payment id!",
+                        )));
                     }
                 }
                 PaymentPlatform::None => {
-                    return Err(ApiError::InvalidInput(
+                    return Err(ApiError::Request(eyre::eyre!(
                         "This charge was not processed via a payment platform."
                             .to_owned(),
-                    ));
+                    )));
                 }
             }
         };
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
-        let charge_id = generate_charge_id(&mut transaction).await?;
+        let charge_id = generate_charge_id(&mut transaction)
+            .await
+            .wrap_internal_err("generating charge ID")?;
         DBCharge {
             id: charge_id,
             user_id: charge.user_id,
@@ -419,39 +440,47 @@ pub async fn refund_charge(
             tax_platform_accounting_time: None,
         }
         .upsert(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("generating charge ID")?;
 
         if body.0.unprovision.unwrap_or(false)
             && let Some(subscription_id) = charge.subscription_id
         {
             let open_charge =
                 DBCharge::get_open_subscription(subscription_id, &**pool)
-                    .await?;
+                    .await
+                    .wrap_internal_err("fetching charge from database")?;
             if let Some(mut open_charge) = open_charge {
                 open_charge.status = ChargeStatus::Cancelled;
                 open_charge.due = Utc::now();
 
-                open_charge.upsert(&mut transaction).await?;
+                open_charge
+                    .upsert(&mut transaction)
+                    .await
+                    .wrap_internal_err("cancelling subscription charge")?;
             }
         }
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         if let Some(Err(error)) = anrok_result {
             if let anrok::AnrokError::Conflict(m) = &error
                 && m.contains("transactionExpectedVersionMismatch")
             {
-                return Err(ApiError::InvalidInput(
+                return Err(ApiError::Request(eyre::eyre!(
                     "This refund has been processed on Stripe's end, but not on the tax processor's end. The tax transaction has been modified externally since its creation. \
                     This is likely caused by a change in nexus for the customer's jurisdiction, which lead to a new tax amount paid by the seller being calculated on the transaction. \
                     Manual intervention is required to verify the tax transaction on the platform's end and update the refund's tax transaction record."
                         .to_owned(),
-                ));
+                )));
             } else {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "This refund has been processed on Stripe's end, but not on the tax processor's end. An unexpected error occurred, preventing the refund transaction from being processed \
                     on the tax platform's end. Error: {error}"
-                )));
+                ))));
             }
         }
     }
@@ -482,80 +511,86 @@ pub async fn reprocess_charge_tax(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let (id,) = info.into_inner();
 
     if !user.role.is_admin() {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to reprocess a tax transaction!"
-                .to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to reprocess a tax transaction!",
+        )));
     }
 
-    let mut txn = pool.begin().await?;
+    let mut txn = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let charge_refund = charge_item::DBCharge::get(id.into(), &mut txn)
-        .await?
-        .ok_or_else(|| ApiError::NotFound)?;
+        .await
+        .wrap_internal_err("fetching charge from database")?
+        .wrap_not_found_err_with(|| "resource not found")?;
 
     let Some(parent_charge_id) = charge_refund.parent_charge_id else {
-        return Err(ApiError::InvalidInput(
-            "This charge does not have a parent!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "This charge does not have a parent!",
+        )));
     };
 
     match charge_refund.tax_platform_id {
         Some(_) => {
-            return Err(ApiError::InvalidInput(
-                "Refund charge already has a tax transaction ID!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "Refund charge already has a tax transaction ID!",
+            )));
         }
         None => {
             let charge = charge_item::DBCharge::get(parent_charge_id, &mut txn)
-                .await?
-                .ok_or_else(|| ApiError::NotFound)?;
+                .await
+                .wrap_internal_err("fetching charge from database")?
+                .wrap_not_found_err_with(|| "resource not found")?;
 
             let payment_platform_id = charge
                 .payment_platform_id
-                .ok_or_else(|| {
-                    ApiError::Internal(eyre::eyre!(
-                        "parent charge is missing a payment platform ID"
-                    ))
-                })?
+                .wrap_internal_err_with(
+                    || "parent charge is missing a payment platform ID",
+                )?
                 .parse::<stripe::PaymentIntentId>()
-                .map_err(|_| {
-                    ApiError::Internal(eyre::eyre!(
-                        "parent charge has an invalid payment platform ID."
-                    ))
-                })?;
+                .map_err(|err| eyre::eyre!(err))
+                .wrap_internal_err(
+                    "parent charge has an invalid payment platform ID.",
+                )?;
 
             let pi = stripe::PaymentIntent::retrieve(
                 &stripe_client,
                 &payment_platform_id,
                 &["payment_method"],
             )
-            .await?;
+            .await
+            .wrap_failed_dependency_err(
+                "communicating with payment provider",
+            )?;
 
             let Some(billing_address) = pi
                 .payment_method
                 .and_then(|x| x.into_object())
                 .and_then(|x| x.billing_details.address)
             else {
-                return Err(ApiError::InvalidInput(
+                return Err(ApiError::Request(eyre::eyre!(
                     "Missing billing address for payment method.".to_owned(),
-                ));
+                )));
             };
 
             let tax_id =
                 product_info_by_product_price_id(charge.price_id, &mut txn)
-                    .await?
-                    .ok_or_else(|| {
-                        ApiError::InvalidInput(
-                            "Could not find product tax info for price ID!"
-                                .to_owned(),
-                        )
+                    .await
+                    .wrap_api_err(
+                        "executing `product_info_by_product_price_id`",
+                    )?
+                    .wrap_request_err_with(|| {
+                        "could not find product tax info for price ID!"
+                            .to_owned()
                     })?
                     .tax_identifier
                     .tax_processor_id;
@@ -569,22 +604,19 @@ pub async fn reprocess_charge_tax(
                 .zip(charge.tax_transaction_version)
                 .zip(charge.tax_platform_accounting_time)
             else {
-                return Err(ApiError::InvalidInput(
+                return Err(ApiError::Request(eyre::eyre!(
                     "Charge is missing full tax information. Please wait for the original charge to be synchronized with the tax processor."
                         .to_owned(),
-                ));
+                )));
             };
             let refund_id =
-                charge_refund.payment_platform_id.ok_or_else(|| {
-                    ApiError::Internal(eyre::eyre!(
-                        "Refund charge is missing a payment platform ID!"
-                    ))
-                })?;
+                charge_refund.payment_platform_id.wrap_internal_err_with(
+                    || "refund charge is missing a payment platform ID!",
+                )?;
 
-            let refund_id =
-                stripe::RefundId::from_str(&refund_id).map_err(|_| {
-                    ApiError::Internal(eyre::eyre!("Invalid refund ID!"))
-                })?;
+            let refund_id = stripe::RefundId::from_str(&refund_id)
+                .map_err(|err| eyre::eyre!(err))
+                .wrap_internal_err("invalid refund ID!")?;
 
             let anrok_txn_result = anrok_client
                 .negate_or_create_partial_negation(
@@ -621,14 +653,16 @@ pub async fn reprocess_charge_tax(
                 .await;
 
             if let Err(error) = anrok_txn_result {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "There was an error processing the tax transaction: {error}. Please make sure the version has been incremented in case of an external modification."
-                )));
+                ))));
             }
         }
     }
 
-    txn.commit().await?;
+    txn.commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::NoContent().finish())
 }
@@ -678,7 +712,8 @@ pub async fn edit_subscription(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     #[derive(Clone, Copy, PartialEq, Eq)]
@@ -699,21 +734,19 @@ pub async fn edit_subscription(
             new_product_price.product_id,
             &mut *txn,
         )
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "Could not link new product price to product.".to_owned(),
-            )
+        .await
+        .wrap_internal_err("fetching product from database")?
+        .wrap_request_err_with(|| {
+            "could not link new product price to product.".to_owned()
         })?;
         let current_product = product_item::DBProduct::get(
             current_product_price.product_id,
             &mut *txn,
         )
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "Could not link current product price to product.".to_owned(),
-            )
+        .await
+        .wrap_internal_err("fetching product from database")?
+        .wrap_request_err_with(|| {
+            "could not link current product price to product.".to_owned()
         })?;
 
         // Special case: for promoting a 'medal' subscription to 'pyro', compare the RAM. If pyro plan has:
@@ -765,11 +798,9 @@ pub async fn edit_subscription(
         let current_amount = match &current_price.prices {
             Price::OneTime { price } => *price,
             Price::Recurring { intervals } => {
-                *intervals.get(&duration).ok_or_else(|| {
-                    ApiError::InvalidInput(
-                        "Could not find a valid price for the user's duration"
-                            .to_owned(),
-                    )
+                *intervals.get(&duration).wrap_request_err_with(|| {
+                    "could not find a valid price for the user's duration"
+                        .to_owned()
                 })?
             }
         };
@@ -777,11 +808,9 @@ pub async fn edit_subscription(
         let amount = match &new_product_price.prices {
             Price::OneTime { price } => *price,
             Price::Recurring { intervals } => {
-                *intervals.get(&duration).ok_or_else(|| {
-                    ApiError::InvalidInput(
-                        "Could not find a valid price for the user's duration"
-                            .to_owned(),
-                    )
+                *intervals.get(&duration).wrap_request_err_with(|| {
+                    "could not find a valid price for the user's duration"
+                        .to_owned()
                 })?
             }
         };
@@ -791,10 +820,8 @@ pub async fn edit_subscription(
         let proration = (Decimal::from(amount - current_amount) * complete)
             .floor()
             .to_i32()
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "Could not convert proration to i32".to_owned(),
-                )
+            .wrap_request_err_with(|| {
+                "could not convert proration to i32".to_owned()
             })?;
 
         Ok((
@@ -815,35 +842,37 @@ pub async fn edit_subscription(
 
     let subscription =
         user_subscription_item::DBUserSubscription::get(id.into(), &**pool)
-            .await?
-            .ok_or_else(|| ApiError::NotFound)?;
+            .await
+            .wrap_internal_err("fetching user subscription from database")?
+            .wrap_not_found_err_with(|| "resource not found")?;
 
     if subscription.user_id != user.id.into() && !user.role.is_admin() {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let mut open_charge = charge_item::DBCharge::get_open_subscription(
         subscription.id,
         &mut transaction,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(
-            "Could not find open charge for this subscription".to_string(),
-        )
+    .await
+    .wrap_internal_err("fetching charge from database")?
+    .wrap_request_err_with(|| {
+        "could not find open charge for this subscription".to_string()
     })?;
 
     let current_price = product_item::DBProductPrice::get(
         subscription.price_id,
         &mut transaction,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(
-            "Could not find current product price".to_string(),
-        )
+    .await
+    .wrap_internal_err("fetching product price from database")?
+    .wrap_request_err_with(|| {
+        "could not find current product price".to_string()
     })?;
 
     let maybe_intent_metadata = match edit_subscription.into_inner() {
@@ -857,7 +886,10 @@ pub async fn edit_subscription(
                     subscription.id,
                     &mut transaction,
                 )
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "updating users subscriptions affiliations in database",
+                )?;
                 open_charge.status = ChargeStatus::Cancelled;
             } else {
                 // Forces another resubscription attempt
@@ -881,7 +913,10 @@ pub async fn edit_subscription(
                     subscription.id,
                     &mut transaction,
                 )
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "executing `DBUsersSubscriptionsAffiliations::deactivate`",
+                )?;
                 ChargeStatus::Cancelled
             } else {
                 ChargeStatus::Open
@@ -904,22 +939,21 @@ pub async fn edit_subscription(
                     product_id.into(),
                     &mut transaction,
                 )
-                .await?
+                .await
+                .wrap_internal_err("fetching product prices from database")?
                 .into_iter()
                 .find(|x| x.currency_code == current_price.currency_code)
-                .ok_or_else(|| {
-                    ApiError::InvalidInput(
-                        "Could not find a valid price for your currency code!"
-                            .to_owned(),
-                    )
+                .wrap_request_err_with(|| {
+                    "could not find a valid price for your currency code!"
+                        .to_owned()
                 })?;
 
             // The price is the same! The request likely asked to edit the product to what it already is.
             if new_product_price.id == current_price.id {
-                return Err(ApiError::InvalidInput(
+                return Err(ApiError::Request(eyre::eyre!(
                     "You cannot use the existing product when modifying a subscription! Modifications to only the billing interval aren't yet supported."
                         .to_owned(),
-                ));
+                )));
             }
 
             #[derive(Serialize)]
@@ -931,9 +965,8 @@ pub async fn edit_subscription(
             let currency = stripe::Currency::from_str(
                 &current_price.currency_code.to_lowercase(),
             )
-            .map_err(|_| {
-                ApiError::InvalidInput("Invalid currency code".to_string())
-            })?;
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_request_err("invalid currency code".to_string())?;
 
             // The next charge is an expiring charge, so we are promoting the subscription to a paid product.
             // Instead of doing a proration (since the product is likely free) we either:
@@ -944,15 +977,16 @@ pub async fn edit_subscription(
             //
             // ..depending on the special cases defined in `promotion_payment_requirement`.
             if open_charge.status == ChargeStatus::Expiring {
-                let new_region = region.ok_or_else(|| ApiError::InvalidInput("You need to specify a region when promoting an expiring charge.".to_owned()))?;
-                let new_interval = interval.ok_or_else(|| ApiError::InvalidInput("You need to specify an interval when promoting an expiring charge.".to_owned()))?;
+                let new_region = region.wrap_request_err_with(|| "you need to specify a region when promoting an expiring charge.".to_owned())?;
+                let new_interval = interval.wrap_request_err_with(|| "you need to specify an interval when promoting an expiring charge.".to_owned())?;
 
                 let req = promotion_payment_requirement(
                     &mut transaction,
                     &current_price,
                     &new_product_price,
                 )
-                .await?;
+                .await
+                .wrap_api_err("executing `promotion_payment_requirement`")?;
 
                 if dry {
                     // Note: we aren't committing the transaction here and it will be aborted.
@@ -966,10 +1000,8 @@ pub async fn edit_subscription(
 
                 let payment_request_type =
                     PaymentRequestType::from_stripe_id(payment_method)
-                        .ok_or_else(|| {
-                            ApiError::InvalidInput(
-                                "Invalid payment method ID".to_owned(),
-                            )
+                        .wrap_request_err_with(|| {
+                            "invalid payment method ID".to_owned()
                         })?;
 
                 if req == PaymentRequirement::RequiresPayment {
@@ -994,14 +1026,15 @@ pub async fn edit_subscription(
                             attach_payment_metadata: None,
                         },
                     )
-                    .await?;
+                    .await
+                    .wrap_api_err("creating subscription charge")?;
 
                     Some(results)
                 } else {
                     /*
                     open_charge.status = ChargeStatus::Open;
                     open_charge.payment_platform = PaymentPlatform::Stripe;
-                    open_charge.amount = new_product_price.prices.get_interval(new_interval).ok_or_else(|| ApiError::InvalidInput("Could not find a valid price for the user's duration".to_owned()))?;
+                    open_charge.amount = new_product_price.prices.get_interval(new_interval).wrap_request_err_with(|| "could not find a valid price for the user's duration".to_owned())?;
                     open_charge.currency_code = new_product_price.currency_code;
                     open_charge.subscription_interval = Some(new_interval);
                     open_charge.price_id = new_product_price.id;
@@ -1019,7 +1052,8 @@ pub async fn edit_subscription(
                     &subscription,
                     &current_price,
                     &new_product_price,
-                )?;
+                )
+                .wrap_api_err("executing `proration_amount`")?;
 
                 if dry {
                     // Note: we aren't committing the transaction here and it will be aborted.
@@ -1083,7 +1117,8 @@ pub async fn edit_subscription(
                                 attach_payment_metadata: None,
                             },
                         )
-                        .await?;
+                        .await
+                        .wrap_api_err("creating subscription charge")?;
 
                         Some(results)
                     }
@@ -1097,25 +1132,25 @@ pub async fn edit_subscription(
             interval,
             ..
         } if region.is_some() || interval.is_some() => {
-            return Err(ApiError::InvalidInput(
+            return Err(ApiError::Request(eyre::eyre!(
                 "It is not currently possible to only modify the region or interval of a subscription".to_owned(),
-            ));
+            )));
         }
 
         SubscriptionEdit {
             payment_method: None,
             ..
         } => {
-            return Err(ApiError::InvalidInput(
+            return Err(ApiError::Request(eyre::eyre!(
                 "A known payment method is required at this point to calculate tax information".to_owned(),
-            ));
+            )));
         }
 
         _ => {
-            return Err(ApiError::InvalidInput(
+            return Err(ApiError::Request(eyre::eyre!(
                 "Unexpected combination of fields in subscription PATCH request. Please either only specify `cancelled`, or specify `product` \
                 alongside optionally specifying a `region` and `interval`. In some cases, you may be required to provide `region` and `interval`.".to_owned(),
-            ));
+            )));
         }
     };
 
@@ -1125,8 +1160,14 @@ pub async fn edit_subscription(
         // At this point, if dry is true, we've already early-returned, except in
         // the `cancelled` branches.
 
-        open_charge.upsert(&mut transaction).await?;
-        transaction.commit().await?;
+        open_charge
+            .upsert(&mut transaction)
+            .await
+            .wrap_internal_err("committing database transaction")?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
     }
 
     if let Some(PaymentBootstrapResults {
@@ -1169,7 +1210,8 @@ pub async fn user_customer(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let customer_id = get_or_create_customer(
@@ -1180,9 +1222,14 @@ pub async fn user_customer(
         &pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching or creating Stripe customer")?;
     let customer =
-        stripe::Customer::retrieve(&stripe_client, &customer_id, &[]).await?;
+        stripe::Customer::retrieve(&stripe_client, &customer_id, &[])
+            .await
+            .wrap_failed_dependency_err(
+                "communicating with payment provider",
+            )?;
 
     Ok(HttpResponse::Ok().json(customer))
 }
@@ -1214,7 +1261,8 @@ pub async fn charges(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let charges =
@@ -1223,17 +1271,17 @@ pub async fn charges(
                 if user.role.is_admin() {
                     user_id.into()
                 } else {
-                    return Err(ApiError::InvalidInput(
-                        "You cannot see the subscriptions of other users!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Request(eyre::eyre!(
+                        "You cannot see the subscriptions of other users!",
+                    )));
                 }
             } else {
                 user.id.into()
             },
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching user charges from database")?;
 
     Ok(HttpResponse::Ok().json(
         charges
@@ -1279,7 +1327,8 @@ pub async fn add_payment_method_flow(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let customer = get_or_create_customer(
@@ -1290,7 +1339,8 @@ pub async fn add_payment_method_flow(
         &pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching or creating Stripe customer")?;
 
     let intent = SetupIntent::create(
         &stripe_client,
@@ -1305,7 +1355,7 @@ pub async fn add_payment_method_flow(
             ..Default::default()
         },
     )
-    .await?;
+    .await.wrap_failed_dependency_err("communicating with payment provider")?;
 
     Ok(HttpResponse::Ok().json(serde_json::json!({
         "client_secret": intent.client_secret
@@ -1339,13 +1389,14 @@ pub async fn edit_payment_method(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let (id,) = info.into_inner();
 
     let Ok(payment_method_id) = PaymentMethodId::from_str(&id) else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
     let customer = get_or_create_customer(
@@ -1356,14 +1407,16 @@ pub async fn edit_payment_method(
         &pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching or creating Stripe customer")?;
 
     let payment_method = stripe::PaymentMethod::retrieve(
         &stripe_client,
         &payment_method_id,
         &[],
     )
-    .await?;
+    .await
+    .wrap_failed_dependency_err("communicating with payment provider")?;
 
     if payment_method.customer.is_some_and(|x| x.id() == customer)
         || user.role.is_admin()
@@ -1379,11 +1432,12 @@ pub async fn edit_payment_method(
                 ..Default::default()
             },
         )
-        .await?;
+        .await
+        .wrap_failed_dependency_err("communicating with payment provider")?;
 
         Ok(HttpResponse::NoContent().finish())
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1409,13 +1463,14 @@ pub async fn remove_payment_method(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let (id,) = info.into_inner();
 
     let Ok(payment_method_id) = PaymentMethodId::from_str(&id) else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
     let customer = get_or_create_customer(
@@ -1426,28 +1481,35 @@ pub async fn remove_payment_method(
         &pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching or creating Stripe customer")?;
 
     let payment_method = stripe::PaymentMethod::retrieve(
         &stripe_client,
         &payment_method_id,
         &[],
     )
-    .await?;
+    .await
+    .wrap_failed_dependency_err("communicating with payment provider")?;
 
     let user_subscriptions =
         user_subscription_item::DBUserSubscription::get_all_user(
             user.id.into(),
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching user subscriptions from database")?;
 
     if user_subscriptions
         .iter()
         .any(|x| x.status != SubscriptionStatus::Unprovisioned)
     {
         let customer =
-            stripe::Customer::retrieve(&stripe_client, &customer, &[]).await?;
+            stripe::Customer::retrieve(&stripe_client, &customer, &[])
+                .await
+                .wrap_failed_dependency_err(
+                    "communicating with payment provider",
+                )?;
 
         if customer
             .invoice_settings
@@ -1457,10 +1519,9 @@ pub async fn remove_payment_method(
             })
             .unwrap_or(false)
         {
-            return Err(ApiError::InvalidInput(
-                "You may not remove the default payment method if you have active subscriptions!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You may not remove the default payment method if you have active subscriptions!",
+            )));
         }
     }
 
@@ -1468,11 +1529,14 @@ pub async fn remove_payment_method(
         || user.role.is_admin()
     {
         stripe::PaymentMethod::detach(&stripe_client, &payment_method_id)
-            .await?;
+            .await
+            .wrap_failed_dependency_err(
+                "communicating with payment provider",
+            )?;
 
         Ok(HttpResponse::NoContent().finish())
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1500,7 +1564,8 @@ pub async fn payment_methods(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if let Some(customer_id) = user
@@ -1516,7 +1581,8 @@ pub async fn payment_methods(
                 ..Default::default()
             },
         )
-        .await?;
+        .await
+        .wrap_failed_dependency_err("communicating with payment provider")?;
 
         Ok(HttpResponse::Ok().json(methods.data))
     } else {
@@ -1560,16 +1626,15 @@ pub async fn active_servers(
         .get("X-Master-Key")
         .is_none_or(|it| it.as_bytes() != master_key.as_bytes())
     {
-        return Err(ApiError::CustomAuthentication(
-            "Invalid master key".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!("Invalid master key",)));
     }
 
     let servers = user_subscription_item::DBUserSubscription::get_all_servers(
         query.subscription_status,
         &**pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching user subscriptions from database")?;
 
     let server_ids = servers
         .into_iter()
@@ -1676,7 +1741,8 @@ pub async fn initiate_payment(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let payment_request = payment_request.into_inner();
@@ -1696,12 +1762,16 @@ pub async fn initiate_payment(
                 &**pool,
                 payment_request.charge,
             )
-            .await?,
+            .await
+            .wrap_api_err(
+                "executing `AttachedCharge::from_charge_request_type`",
+            )?,
             currency: CurrencyMode::Infer,
             attach_payment_metadata: payment_request.metadata,
         },
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `AttachedCharge::from_charge_request_type`")?;
 
     match results.new_payment_intent {
         Some(payment_intent) => {
@@ -1785,7 +1855,8 @@ pub async fn stripe_webhook(
                     crate::database::models::user_item::DBUser::get_id(
                         user_id, pool, redis,
                     )
-                    .await?
+                    .await
+                    .wrap_internal_err("fetching user from database")?
                 else {
                     break 'metadata;
                 };
@@ -1826,13 +1897,17 @@ pub async fn stripe_webhook(
                         crate::database::models::charge_item::DBCharge::get(
                             charge_id, pool,
                         )
-                        .await?
+                        .await
+                        .wrap_internal_err("fetching charge from database")?
                     {
                         let Some(price) = product_item::DBProductPrice::get(
                             charge.price_id,
                             pool,
                         )
-                        .await?
+                        .await
+                        .wrap_internal_err(
+                            "fetching product price from database",
+                        )?
                         else {
                             break 'metadata;
                         };
@@ -1841,7 +1916,8 @@ pub async fn stripe_webhook(
                             price.product_id,
                             pool,
                         )
-                        .await?
+                        .await
+                        .wrap_internal_err("fetching product from database")?
                         else {
                             break 'metadata;
                         };
@@ -1852,7 +1928,9 @@ pub async fn stripe_webhook(
                             Some(payment_intent_id.to_string());
                         charge.tax_amount = tax_amount;
                         charge.tax_platform_id = None;
-                        charge.upsert(transaction).await?;
+                        charge.upsert(transaction).await.wrap_internal_err(
+                            "updating payment intent charge",
+                        )?;
 
                         if let Some(subscription_id) = charge.subscription_id {
                             let maybe_subscription =
@@ -1860,7 +1938,7 @@ pub async fn stripe_webhook(
                                 subscription_id,
                                 pool,
                             )
-                            .await?;
+                            .await.wrap_internal_err("fetching user subscription from database")?;
 
                             let Some(mut subscription) = maybe_subscription
                             else {
@@ -1880,14 +1958,18 @@ pub async fn stripe_webhook(
                                     subscription.price_id = charge.price_id;
                                 }
                                 ChargeType::Refund => {
-                                    return Err(ApiError::InvalidInput(
-                                        "Invalid charge type: Refund"
-                                            .to_string(),
+                                    return Err(ApiError::Request(
+                                        eyre::eyre!(
+                                            "Invalid charge type: Refund",
+                                        ),
                                     ));
                                 }
                             }
 
-                            subscription.upsert(transaction).await?;
+                            subscription
+                                .upsert(transaction)
+                                .await
+                                .wrap_internal_err("upserting subscription")?;
 
                             (
                                 charge,
@@ -1914,7 +1996,10 @@ pub async fn stripe_webhook(
 
                         let Some(price) =
                             product_item::DBProductPrice::get(price_id, pool)
-                                .await?
+                                .await
+                                .wrap_internal_err(
+                                    "fetching product price from database",
+                                )?
                         else {
                             break 'metadata;
                         };
@@ -1923,7 +2008,8 @@ pub async fn stripe_webhook(
                             price.product_id,
                             pool,
                         )
-                        .await?;
+                        .await
+                        .wrap_internal_err("fetching product from database")?;
 
                         let Some(product) = maybe_product else {
                             break 'metadata;
@@ -1949,7 +2035,7 @@ pub async fn stripe_webhook(
                                     break 'metadata;
                                 };
 
-                                    let subscription = if let Some(mut subscription) = user_subscription_item::DBUserSubscription::get(subscription_id, pool).await? {
+                                    let subscription = if let Some(mut subscription) = user_subscription_item::DBUserSubscription::get(subscription_id, pool).await.wrap_internal_err("fetching user subscription from database")? {
                                     subscription.status = SubscriptionStatus::Unprovisioned;
                                     subscription.price_id = price_id;
                                     subscription.interval = interval;
@@ -1970,7 +2056,10 @@ pub async fn stripe_webhook(
                                     if charge_status != ChargeStatus::Failed {
                                         subscription
                                             .upsert(&mut *transaction)
-                                            .await?;
+                                            .await
+                                            .wrap_internal_err(
+                                                "upserting subscription",
+                                            )?;
                                     }
 
                                     Some(subscription)
@@ -2011,7 +2100,10 @@ pub async fn stripe_webhook(
                         };
 
                         if charge_status != ChargeStatus::Failed {
-                            charge.upsert(&mut *transaction).await?;
+                            charge
+                                .upsert(&mut *transaction)
+                                .await
+                                .wrap_internal_err("upserting charge")?;
                         }
 
                         (charge, price, product, subscription, new_region)
@@ -2029,9 +2121,9 @@ pub async fn stripe_webhook(
                 });
             }
 
-            Err(ApiError::InvalidInput(
-                "Webhook missing required webhook metadata!".to_string(),
-            ))
+            Err(ApiError::Request(eyre::eyre!(
+                "Webhook missing required webhook metadata!",
+            )))
         }
 
         match event.type_ {
@@ -2039,7 +2131,10 @@ pub async fn stripe_webhook(
                 if let EventObject::PaymentIntent(payment_intent) =
                     event.data.object
                 {
-                    let mut transaction = pool.begin().await?;
+                    let mut transaction = pool
+                        .begin()
+                        .await
+                        .wrap_internal_err("starting database transaction")?;
 
                     let mut metadata = get_payment_intent_metadata(
                         payment_intent.id,
@@ -2051,7 +2146,8 @@ pub async fn stripe_webhook(
                         ChargeStatus::Succeeded,
                         &mut transaction,
                     )
-                    .await?;
+                    .await
+                    .wrap_api_err("fetching payment intent metadata")?;
 
                     if let Some(latest_charge) = payment_intent.latest_charge {
                         let charge = stripe::Charge::retrieve(
@@ -2059,7 +2155,10 @@ pub async fn stripe_webhook(
                             &latest_charge.id(),
                             &["balance_transaction"],
                         )
-                        .await?;
+                        .await
+                        .wrap_failed_dependency_err(
+                            "communicating with payment provider",
+                        )?;
 
                         if let Some(balance_transaction) = charge
                             .balance_transaction
@@ -2070,7 +2169,8 @@ pub async fn stripe_webhook(
                             metadata
                                 .charge_item
                                 .upsert(&mut transaction)
-                                .await?;
+                                .await
+                                .wrap_internal_err("upserting charge")?;
                         }
                     }
 
@@ -2098,7 +2198,8 @@ pub async fn stripe_webhook(
                                     as crate::database::models::ids::DBUserId,
                             )
                             .execute(&mut transaction)
-                            .await?;
+                            .await
+                            .wrap_internal_err("querying database for `get_payment_intent_metadata`")?;
                         }
                         ProductMetadata::Pyro {
                             ram,
@@ -2124,11 +2225,11 @@ pub async fn stripe_webhook(
                                             let region = metadata.new_region.clone();
 
                                             if region.is_none() {
-                                                return Err(ApiError::InvalidInput(
+                                                return Err(ApiError::Request(eyre::eyre!(
                                                     "We attempted to promote a subscription with type=medal, which requires specifying \
                                                     a new region to move the server to. However, no new region was present in the payment \
                                                     intent metadata.".to_owned()
-                                                ));
+                                                )));
                                             }
 
                                             region
@@ -2162,8 +2263,8 @@ pub async fn stripe_webhook(
                                         ))
                                         .header("X-Master-Key", &ENV.PYRO_API_KEY)
                                         .send()
-                                        .await?
-                                        .error_for_status()?;
+                                        .await.wrap_internal_err("sending HTTP request")?
+                                        .error_for_status().wrap_internal_err("sending HTTP request")?;
 
                                     client
                                         .post(format!(
@@ -2177,8 +2278,8 @@ pub async fn stripe_webhook(
                                         )
                                         .json(&body)
                                         .send()
-                                        .await?
-                                        .error_for_status()?;
+                                        .await.wrap_internal_err("deserializing HTTP response")?
+                                        .error_for_status().wrap_internal_err("deserializing HTTP response")?;
 
                                     // As the subscription has been promoted, this is now a Pyro subscription.
                                     // Ensure the metadata is properly updated.
@@ -2206,7 +2307,7 @@ pub async fn stripe_webhook(
                                                 None,
                                                 &**pool,
                                                 &redis,
-                                            ).await?;
+                                            ).await.wrap_internal_err("fetching minecraft versions from database")?;
 
                                             (
                                                 None,
@@ -2257,10 +2358,10 @@ pub async fn stripe_webhook(
                                             })
                                         }))
                                         .send()
-                                        .await?
-                                        .error_for_status()?
+                                        .await.wrap_internal_err("sending HTTP request")?
+                                        .error_for_status().wrap_internal_err("sending HTTP request")?
                                         .json::<PyroServerResponse>()
-                                        .await?;
+                                        .await.wrap_internal_err("deserializing HTTP response")?;
 
                                     if let Some(ref mut subscription) =
                                         metadata.user_subscription_item
@@ -2283,17 +2384,14 @@ pub async fn stripe_webhook(
                             subscription.id,
                             &mut transaction,
                         )
-                        .await?;
+                        .await
+                        .wrap_internal_err("fetching charge from database")?;
 
                         let new_price = match metadata.product_price_item.prices {
                             Price::OneTime { price } => price,
                             Price::Recurring { intervals } => {
-                                *intervals.get(&subscription.interval).ok_or_else(|| {
-                                    ApiError::InvalidInput(
-                                        "Could not find a valid price for the user's country"
-                                            .to_string(),
-                                    )
-                                })?
+                                *intervals.get(&subscription.interval).wrap_request_err_with(|| "could not find a valid price for the user's country"
+                                            .to_string())?
                             }
                         };
 
@@ -2333,12 +2431,19 @@ pub async fn stripe_webhook(
                                     metadata.product_price_item.id;
                                 charge.amount = new_price as i64;
                             }
-                            charge.upsert(&mut transaction).await?;
+                            charge
+                                .upsert(&mut transaction)
+                                .await
+                                .wrap_internal_err("upserting charge")?;
                         } else if metadata.charge_item.status
                             != ChargeStatus::Cancelled
                         {
                             let charge_id =
-                                generate_charge_id(&mut transaction).await?;
+                                generate_charge_id(&mut transaction)
+                                    .await
+                                    .wrap_internal_err(
+                                        "generating charge ID",
+                                    )?;
                             DBCharge {
                                 id: charge_id,
                                 user_id: metadata.user_item.id,
@@ -2375,7 +2480,10 @@ pub async fn stripe_webhook(
                                 tax_platform_accounting_time: None,
                             }
                             .upsert(&mut transaction)
-                            .await?;
+                            .await
+                            .wrap_internal_err(
+                                "upserting subscription charge",
+                            )?;
 
                             if let Some(affiliate_code) = metadata
                                 .payment_metadata
@@ -2390,27 +2498,42 @@ pub async fn stripe_webhook(
                                     deactivated_at: None,
                                 }
                                 .insert(&mut transaction)
-                                .await?;
+                                .await
+                                .wrap_internal_err(
+                                    "inserting subscription affiliation into database",
+                                )?;
                             }
                         };
 
                         subscription.status = SubscriptionStatus::Provisioned;
-                        subscription.upsert(&mut transaction).await?;
+                        subscription
+                            .upsert(&mut transaction)
+                            .await
+                            .wrap_internal_err(
+                                "updating affiliate code id in database",
+                            )?;
                     }
 
-                    transaction.commit().await?;
+                    transaction
+                        .commit()
+                        .await
+                        .wrap_internal_err("committing database transaction")?;
                     crate::database::models::user_item::DBUser::clear_caches(
                         &[(metadata.user_item.id, None)],
                         &redis,
                     )
-                    .await?;
+                    .await
+                    .wrap_internal_err("clearing cached data from Redis")?;
                 }
             }
             EventType::PaymentIntentProcessing => {
                 if let EventObject::PaymentIntent(payment_intent) =
                     event.data.object
                 {
-                    let mut transaction = pool.begin().await?;
+                    let mut transaction = pool
+                        .begin()
+                        .await
+                        .wrap_internal_err("starting database transaction")?;
                     get_payment_intent_metadata(
                         payment_intent.id,
                         payment_intent.amount,
@@ -2421,15 +2544,22 @@ pub async fn stripe_webhook(
                         ChargeStatus::Processing,
                         &mut transaction,
                     )
-                    .await?;
-                    transaction.commit().await?;
+                    .await
+                    .wrap_api_err("fetching payment intent metadata")?;
+                    transaction
+                        .commit()
+                        .await
+                        .wrap_internal_err("committing database transaction")?;
                 }
             }
             EventType::PaymentIntentPaymentFailed => {
                 if let EventObject::PaymentIntent(payment_intent) =
                     event.data.object
                 {
-                    let mut transaction = pool.begin().await?;
+                    let mut transaction = pool
+                        .begin()
+                        .await
+                        .wrap_internal_err("starting database transaction")?;
 
                     let metadata = get_payment_intent_metadata(
                         payment_intent.id,
@@ -2441,7 +2571,8 @@ pub async fn stripe_webhook(
                         ChargeStatus::Failed,
                         &mut transaction,
                     )
-                    .await?;
+                    .await
+                    .wrap_api_err("fetching payment intent metadata")?;
 
                     if metadata.user_item.email.is_some() {
                         let money = rusty_money::Money::from_minor(
@@ -2474,10 +2605,16 @@ pub async fn stripe_webhook(
                             },
                         }
                         .insert(metadata.user_item.id, &mut transaction, &redis)
-                        .await?;
+                        .await
+                        .wrap_internal_err(
+                            "inserting payment failure notification",
+                        )?;
                     }
 
-                    transaction.commit().await?;
+                    transaction
+                        .commit()
+                        .await
+                        .wrap_internal_err("committing database transaction")?;
                 }
             }
             EventType::PaymentMethodAttached => {
@@ -2491,7 +2628,10 @@ pub async fn stripe_webhook(
                         &customer_id,
                         &[],
                     )
-                    .await?;
+                    .await
+                    .wrap_failed_dependency_err(
+                        "communicating with payment provider",
+                    )?;
 
                     if customer
                         .invoice_settings
@@ -2512,16 +2652,19 @@ pub async fn stripe_webhook(
                                 ..Default::default()
                             },
                         )
-                        .await?;
+                        .await
+                        .wrap_failed_dependency_err(
+                            "communicating with payment provider",
+                        )?;
                     }
                 }
             }
             _ => {}
         }
     } else {
-        return Err(ApiError::InvalidInput(
-            "Webhook signature validation failed!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Webhook signature validation failed!",
+        )));
     }
 
     Ok(HttpResponse::Ok().finish())
@@ -2545,7 +2688,8 @@ async fn apply_credit_many(
         &subs_ids,
         &mut *transaction,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching user subscriptions from database")?;
 
     let provisioned_count = subs
         .iter()
@@ -2573,18 +2717,22 @@ async fn apply_credit_many(
             subscription.id,
             &mut *transaction,
         )
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(format!(
-                "Could not find open charge for subscription {}",
+        .await
+        .wrap_internal_err("fetching charge from database")?
+        .wrap_request_err_with(|| {
+            format!(
+                "could not find open charge for subscription `{}`",
                 to_base62(subscription.id.0 as u64)
-            ))
+            )
         })?;
 
         let previous_due = open_charge.due;
         open_charge.due = previous_due + Duration::days(days as i64);
         let next_due = open_charge.due;
-        open_charge.upsert(&mut *transaction).await?;
+        open_charge
+            .upsert(&mut *transaction)
+            .await
+            .wrap_internal_err("updating next due in database")?;
 
         credit_sub_ids.push(subscription.id);
         credit_user_ids.push(subscription.user_id);
@@ -2604,7 +2752,10 @@ async fn apply_credit_many(
                 },
             }
             .insert(subscription.user_id, &mut *transaction, redis)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "inserting database records for `apply_credit_many`",
+            )?;
         }
     }
 
@@ -2618,7 +2769,8 @@ async fn apply_credit_many(
         &credit_next_dues,
     )
     .await
-    .map_err(|e| ApiError::Internal(eyre::eyre!(e)))?;
+    .map_err(|err| eyre::eyre!(err))
+    .wrap_internal_err("inserting subscription credits into database")?;
 
     Ok(())
 }
@@ -2668,13 +2820,14 @@ pub async fn credit(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if !user.role.is_admin() {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to credit subscriptions!".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to credit subscriptions!",
+        )));
     }
 
     let CreditRequest {
@@ -2685,18 +2838,21 @@ pub async fn credit(
     } = body.into_inner();
 
     if days <= 0 {
-        return Err(ApiError::InvalidInput(
-            "Days must be greater than zero".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Days must be greater than zero",
+        )));
     }
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     match target {
         CreditTarget::Subscriptions { subscription_ids } => {
             if subscription_ids.is_empty() {
-                return Err(ApiError::InvalidInput(
-                    "You must specify at least one subscription id".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "You must specify at least one subscription id",
+                )));
             }
             apply_credit_many(
                 &mut transaction,
@@ -2707,18 +2863,23 @@ pub async fn credit(
                 send_email,
                 message,
             )
-            .await?;
+            .await
+            .wrap_api_err("crediting user subscriptions")?;
         }
         CreditTarget::Nodes { nodes } => {
             if nodes.is_empty() {
-                return Err(ApiError::InvalidInput(
-                    "You must specify at least one node hostname".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "You must specify at least one node hostname",
+                )));
             }
             let mut server_ids: Vec<String> = Vec::new();
             for hostname in nodes {
-                let ids =
-                    archon_client.get_servers_by_hostname(&hostname).await?;
+                let ids = archon_client
+                    .get_servers_by_hostname(&hostname)
+                    .await
+                    .wrap_internal_err(
+                        "fetching servers by hostname from Archon",
+                    )?;
                 server_ids.extend(ids.into_iter().map(|id| id.to_string()));
             }
             server_ids.dedup();
@@ -2726,11 +2887,11 @@ pub async fn credit(
                 &server_ids,
                 &mut transaction,
             )
-            .await?;
+            .await.wrap_internal_err("fetching user subscriptions from database")?;
             if subs.is_empty() {
-                return Err(ApiError::InvalidInput(
-                    "No subscriptions found for provided nodes".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "No subscriptions found for provided nodes",
+                )));
             }
             apply_credit_many(
                 &mut transaction,
@@ -2741,20 +2902,23 @@ pub async fn credit(
                 send_email,
                 message,
             )
-            .await?;
+            .await
+            .wrap_api_err("crediting server subscriptions")?;
         }
         CreditTarget::Region { region } => {
-            let servers =
-                archon_client.get_active_servers_by_region(&region).await?;
+            let servers = archon_client
+                .get_active_servers_by_region(&region)
+                .await
+                .wrap_internal_err("fetching servers from database")?;
             let subs = user_subscription_item::DBUserSubscription::get_many_by_server_ids(
                 &servers.into_iter().map(|id| id.to_string()).collect::<Vec<String>>(),
                 &mut transaction,
             )
-            .await?;
+            .await.wrap_internal_err("fetching user subscriptions from database")?;
             if subs.is_empty() {
-                return Err(ApiError::InvalidInput(
-                    "No subscriptions found for provided region".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "No subscriptions found for provided region",
+                )));
             }
             apply_credit_many(
                 &mut transaction,
@@ -2765,11 +2929,15 @@ pub async fn credit(
                 send_email,
                 message,
             )
-            .await?;
+            .await
+            .wrap_api_err("crediting region subscriptions")?;
         }
     }
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::NoContent().finish())
 }
diff --git a/apps/labrinth/src/routes/internal/billing/payments.rs b/apps/labrinth/src/routes/internal/billing/payments.rs
index 2e0f445243..e73bd778b5 100644
--- a/apps/labrinth/src/routes/internal/billing/payments.rs
+++ b/apps/labrinth/src/routes/internal/billing/payments.rs
@@ -8,6 +8,7 @@ use crate::models::v3::billing::SubscriptionStatus;
 use crate::models::v3::users::User;
 use crate::routes::ApiError;
 use crate::util::anrok;
+use crate::util::error::{ApiContext as _, Context as _};
 use xredis::RedisPool;
 
 use crate::database::PgPool;
@@ -97,13 +98,12 @@ impl AttachedCharge {
     ) -> Result<Self, ApiError> {
         Ok(match charge_request_type {
             ChargeRequestType::Existing { id } => AttachedCharge::UseExisting {
-                charge: DBCharge::get(id.into(), exec).await?.ok_or_else(
-                    || {
-                        ApiError::InvalidInput(
-                            "Could not find charge".to_string(),
-                        )
-                    },
-                )?,
+                charge: DBCharge::get(id.into(), exec)
+                    .await
+                    .wrap_internal_err("fetching charge from database")?
+                    .wrap_request_err_with(|| {
+                        "could not find charge".to_string()
+                    })?,
             },
             ChargeRequestType::New {
                 product_id,
@@ -212,7 +212,8 @@ pub async fn create_or_update_payment_intent(
         pg,
         redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching or creating Stripe customer")?;
 
     let mut intent_uses_confirmation_token = false;
 
@@ -220,15 +221,15 @@ pub async fn create_or_update_payment_intent(
         PaymentSession::Interactive {
             payment_request_type: PaymentRequestType::PaymentMethod { id },
         } => {
-            let payment_method_id =
-                PaymentMethodId::from_str(id).map_err(|_| {
-                    ApiError::InvalidInput(
-                        "Invalid payment method id".to_string(),
-                    )
-                })?;
+            let payment_method_id = PaymentMethodId::from_str(id)
+                .map_err(|err| eyre::eyre!(err))
+                .wrap_request_err("invalid payment method id".to_string())?;
 
             PaymentMethod::retrieve(stripe_client, &payment_method_id, &[])
-                .await?
+                .await
+                .wrap_failed_dependency_err(
+                    "communicating with payment provider",
+                )?
         }
         PaymentSession::Interactive {
             payment_request_type:
@@ -243,7 +244,10 @@ pub async fn create_or_update_payment_intent(
 
             let mut confirmation: serde_json::Value = stripe_client
                 .get(&format!("confirmation_tokens/{token}"))
-                .await?;
+                .await
+                .wrap_failed_dependency_err(
+                    "communicating with payment provider",
+                )?;
 
             // We patch the JSONs to support the PaymentMethod struct
             let p: json_patch::Patch = serde_json::from_value(serde_json::json!([
@@ -254,19 +258,20 @@ pub async fn create_or_update_payment_intent(
             json_patch::patch(&mut confirmation, &p).unwrap();
 
             let confirmation: ConfirmationToken =
-                serde_json::from_value(confirmation)?;
+                serde_json::from_value(confirmation)
+                    .wrap_request_err("deserializing JSON data")?;
 
-            confirmation.payment_method_preview.ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "Confirmation token is missing payment method!".to_string(),
-                )
-            })?
+            confirmation
+                .payment_method_preview
+                .wrap_request_err_with(|| {
+                    "confirmation token is missing payment method!".to_string()
+                })?
         }
         PaymentSession::AutomatedRenewal => {
             if attached_charge.as_charge().is_none() {
-                return Err(ApiError::InvalidInput(
-                    "Missing attached charge for automated renewal".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "Missing attached charge for automated renewal",
+                )));
             }
 
             let customer = stripe::Customer::retrieve(
@@ -274,17 +279,18 @@ pub async fn create_or_update_payment_intent(
                 &customer_id,
                 &["invoice_settings.default_payment_method"],
             )
-            .await?;
+            .await
+            .wrap_failed_dependency_err(
+                "communicating with payment provider",
+            )?;
 
             customer
                 .invoice_settings
                 .and_then(|x| {
                     x.default_payment_method.and_then(|x| x.into_object())
                 })
-                .ok_or_else(|| {
-                    ApiError::InvalidInput(
-                        "Customer has no default payment method!".to_string(),
-                    )
+                .wrap_request_err_with(|| {
+                    "customer has no default payment method!".to_string()
                 })?
         }
     };
@@ -301,9 +307,8 @@ pub async fn create_or_update_payment_intent(
         CurrencyMode::Infer => infer_currency_code(user_country)
             .to_lowercase()
             .parse::<Currency>()
-            .map_err(|_| {
-                ApiError::InvalidInput("Invalid currency code".to_string())
-            })?,
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_request_err("invalid currency code".to_string())?,
     };
 
     let charge_data = match attached_charge {
@@ -335,7 +340,8 @@ pub async fn create_or_update_payment_intent(
                 Some(next_interval),
                 inferred_stripe_currency,
             )
-            .await?;
+            .await
+            .wrap_api_err("deriving proration charge data")?;
 
             charge_data.amount = amount;
             charge_data.charge_type = ChargeType::Proration;
@@ -346,29 +352,27 @@ pub async fn create_or_update_payment_intent(
             interval,
             current_subscription: _,
             new_region: _,
-        } => {
-            derive_charge_data_from_product_selector(
-                pg,
-                user.id,
-                product_id,
-                Some(interval),
-                inferred_stripe_currency,
-            )
-            .await?
-        }
+        } => derive_charge_data_from_product_selector(
+            pg,
+            user.id,
+            product_id,
+            Some(interval),
+            inferred_stripe_currency,
+        )
+        .await
+        .wrap_api_err("deriving promotion charge data")?,
         AttachedCharge::BaseUpon {
             product_id,
             interval,
-        } => {
-            derive_charge_data_from_product_selector(
-                pg,
-                user.id,
-                product_id,
-                interval,
-                inferred_stripe_currency,
-            )
-            .await?
-        }
+        } => derive_charge_data_from_product_selector(
+            pg,
+            user.id,
+            product_id,
+            interval,
+            inferred_stripe_currency,
+        )
+        .await
+        .wrap_api_err("deriving base charge data")?,
     };
 
     // Create an ephemeral transaction to calculate the tax amount if needed
@@ -388,23 +392,18 @@ pub async fn create_or_update_payment_intent(
                 charge_data.price_id.into(),
                 pg,
             )
-            .await?
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "Missing product tax identifier for charge to continue"
-                        .to_owned(),
-                )
+            .await
+            .wrap_internal_err("fetching product tax identifier")?
+            .wrap_request_err_with(|| {
+                "missing product tax identifier for charge to continue"
+                    .to_owned()
             })?;
 
-        let address =
-            payment_method.billing_details.address.clone().ok_or_else(
-                || {
-                    ApiError::InvalidInput(
-						"Missing billing details from payment method to continue"
-							.to_owned(),
-					)
-                },
-            )?;
+        let address = payment_method
+            .billing_details
+            .address
+            .clone()
+            .wrap_request_err("finding billing details on payment method")?;
 
         let ephemeral_invoice = anrok_client
             .create_ephemeral_txn(&anrok::TransactionFields {
@@ -419,7 +418,8 @@ pub async fn create_or_update_payment_intent(
                 customer_id: None,
                 customer_name: None,
             })
-            .await?;
+            .await
+            .wrap_internal_err("inserting database records for `create_or_update_payment_intent`")?;
 
         ephemeral_invoice.tax_amount_to_collect
     };
@@ -436,7 +436,8 @@ pub async fn create_or_update_payment_intent(
     if let Some(payment_metadata) = attach_payment_metadata {
         metadata.insert(
             MODRINTH_PAYMENT_METADATA.to_owned(),
-            serde_json::to_string(&payment_metadata)?,
+            serde_json::to_string(&payment_metadata)
+                .wrap_request_err("inserting payment metadata into database")?,
         );
     }
 
@@ -459,8 +460,13 @@ pub async fn create_or_update_payment_intent(
         current_subscription,
     } = attached_charge
     {
-        let mut transaction = pg.begin().await?;
-        let charge_id = generate_charge_id(&mut transaction).await?;
+        let mut transaction = pg
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
+        let charge_id = generate_charge_id(&mut transaction)
+            .await
+            .wrap_internal_err("generating charge ID")?;
 
         metadata.insert(
             MODRINTH_CHARGE_ID.to_owned(),
@@ -486,8 +492,13 @@ pub async fn create_or_update_payment_intent(
         new_region,
     } = attached_charge
     {
-        let mut transaction = pg.begin().await?;
-        let charge_id = generate_charge_id(&mut transaction).await?;
+        let mut transaction = pg
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
+        let charge_id = generate_charge_id(&mut transaction)
+            .await
+            .wrap_internal_err("generating charge ID")?;
 
         metadata.insert(
             MODRINTH_CHARGE_ID.to_owned(),
@@ -508,10 +519,16 @@ pub async fn create_or_update_payment_intent(
         );
         metadata.insert(MODRINTH_NEW_REGION.to_owned(), new_region);
     } else {
-        let mut transaction = pg.begin().await?;
-        let charge_id = generate_charge_id(&mut transaction).await?;
-        let subscription_id =
-            generate_user_subscription_id(&mut transaction).await?;
+        let mut transaction = pg
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
+        let charge_id = generate_charge_id(&mut transaction)
+            .await
+            .wrap_internal_err("generating charge ID")?;
+        let subscription_id = generate_user_subscription_id(&mut transaction)
+            .await
+            .wrap_internal_err("generating charge ID")?;
 
         metadata.insert(
             MODRINTH_CHARGE_ID.to_owned(),
@@ -538,7 +555,11 @@ pub async fn create_or_update_payment_intent(
     if let Some(payment_intent_id) = existing_payment_intent {
         let mut update_payment_intent = stripe::UpdatePaymentIntent {
             amount: Some(charge_data.amount + tax_amount),
-            currency: Some(charge_data.stripe_currency_code()?),
+            currency: Some(
+                charge_data
+                    .stripe_currency_code()
+                    .wrap_api_err("converting charge currency for Stripe")?,
+            ),
             customer: Some(customer_id),
             metadata: Some(metadata),
             ..Default::default()
@@ -560,7 +581,10 @@ pub async fn create_or_update_payment_intent(
             &payment_intent_id,
             update_payment_intent,
         )
-        .await?;
+        .await
+        .wrap_failed_dependency_err(
+            "updating database records for `create_or_update_payment_intent`",
+        )?;
 
         Ok(PaymentBootstrapResults {
             new_payment_intent: None,
@@ -572,7 +596,9 @@ pub async fn create_or_update_payment_intent(
     } else {
         let mut intent = CreatePaymentIntent::new(
             charge_data.amount + tax_amount,
-            charge_data.stripe_currency_code()?,
+            charge_data
+                .stripe_currency_code()
+                .wrap_api_err("converting charge currency for Stripe")?,
         );
 
         intent.customer = Some(customer_id);
@@ -585,7 +611,11 @@ pub async fn create_or_update_payment_intent(
         payment_session.set_payment_intent_session_options(&mut intent);
 
         let payment_intent =
-            stripe::PaymentIntent::create(stripe_client, intent).await?;
+            stripe::PaymentIntent::create(stripe_client, intent)
+                .await
+                .wrap_failed_dependency_err(
+                    "communicating with payment provider",
+                )?;
 
         Ok(PaymentBootstrapResults {
             new_payment_intent: Some(payment_intent),
@@ -621,7 +651,8 @@ pub async fn get_or_create_customer(
                 ..Default::default()
             },
         )
-        .await?;
+        .await
+        .wrap_failed_dependency_err("communicating with payment provider")?;
 
         sqlx::query!(
             "
@@ -633,13 +664,15 @@ pub async fn get_or_create_customer(
             user_id.0 as i64
         )
         .execute(pool)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `get_or_create_customer`")?;
 
         crate::database::models::user_item::DBUser::clear_caches(
             &[(user_id.into(), None)],
             redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
         Ok(customer.id)
     }
@@ -720,9 +753,9 @@ impl ChargeData {
         self.currency_code
             .to_lowercase()
             .parse::<stripe::Currency>()
-            .map_err(|_| ApiError::InvalidInput(
+            .map_err(|_| ApiError::Request(eyre::eyre!(
                 format!("Invalid currency code '{}': could not convert to Stripe currency", &self.currency_code)
-            ))
+            )))
     }
 }
 
@@ -736,18 +769,18 @@ async fn derive_charge_data_from_product_selector(
     let recommended_currency_code = stripe_currency.to_string().to_uppercase();
 
     let product = product_item::DBProduct::get(product_id.into(), pool)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "Specified product could not be found!".to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching product from database")?
+        .wrap_request_err_with(|| {
+            "specified product could not be found!".to_string()
         })?;
 
     let mut product_prices =
         product_item::DBProductPrice::get_all_public_product_prices(
             product.id, pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching product prices from database")?;
 
     let price_item = if let Some(pos) = product_prices
         .iter()
@@ -759,26 +792,22 @@ async fn derive_charge_data_from_product_selector(
     {
         product_prices.remove(pos)
     } else {
-        return Err(ApiError::InvalidInput(
-            "Could not find a valid price for the user's country".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Could not find a valid price for the user's country",
+        )));
     };
 
     let price = match price_item.prices {
         Price::OneTime { price } => price,
         Price::Recurring { ref intervals } => {
-            let interval = interval.ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "Could not find a valid price for the user's country"
-                        .to_string(),
-                )
+            let interval = interval.wrap_request_err_with(|| {
+                "could not find a valid price for the user's country"
+                    .to_string()
             })?;
 
-            *intervals.get(&interval).ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "Could not find a valid price for the user's country"
-                        .to_string(),
-                )
+            *intervals.get(&interval).wrap_request_err_with(|| {
+                "could not find a valid price for the user's country"
+                    .to_string()
             })?
         }
     };
@@ -791,7 +820,8 @@ async fn derive_charge_data_from_product_selector(
                 user_id.into(),
                 pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching user subscriptions from database")?;
 
         let user_products = product_item::DBProductPrice::get_many(
             &user_subscriptions
@@ -801,15 +831,16 @@ async fn derive_charge_data_from_product_selector(
                 .collect::<Vec<_>>(),
             pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching product prices from database")?;
 
         if user_products
             .into_iter()
             .any(|x| x.product_id == product.id)
         {
-            return Err(ApiError::InvalidInput(
-                "You are already subscribed to this product!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You are already subscribed to this product!",
+            )));
         }
     }
 
diff --git a/apps/labrinth/src/routes/internal/billing/update_subscriptions.rs b/apps/labrinth/src/routes/internal/billing/update_subscriptions.rs
index cc003d4d22..592d11a00a 100644
--- a/apps/labrinth/src/routes/internal/billing/update_subscriptions.rs
+++ b/apps/labrinth/src/routes/internal/billing/update_subscriptions.rs
@@ -104,7 +104,10 @@ pub async fn update_many(
             *region = Some(new_region);
         }
 
-        subscription.upsert(&mut txn).await?;
+        subscription
+            .upsert(&mut txn)
+            .await
+            .wrap_internal_err("updating uuid in database")?;
     }
 
     txn.commit()
diff --git a/apps/labrinth/src/routes/internal/blocked_users.rs b/apps/labrinth/src/routes/internal/blocked_users.rs
index 67b305970d..acffff0475 100644
--- a/apps/labrinth/src/routes/internal/blocked_users.rs
+++ b/apps/labrinth/src/routes/internal/blocked_users.rs
@@ -2,6 +2,7 @@ use crate::database::PgPool;
 use crate::database::models::DBUserId;
 use crate::database::models::blocked_user_item::DBBlockedUser;
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 use crate::util::guards::admin_key_guard;
 use actix_web::{get, web};
 use ariadne::ids::base62_impl::parse_base62;
@@ -25,17 +26,20 @@ pub async fn block_status(
 ) -> Result<web::Json<BlockStatus>, ApiError> {
     let (user_id, target_id) = info.into_inner();
 
-    let user_id =
-        DBUserId(parse_base62(&user_id).map_err(|_| {
-            ApiError::InvalidInput("invalid user_id".to_string())
-        })? as i64);
-    let target_id =
-        DBUserId(parse_base62(&target_id).map_err(|_| {
-            ApiError::InvalidInput("invalid target_id".to_string())
-        })? as i64);
+    let user_id = DBUserId(
+        parse_base62(&user_id)
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_request_err("invalid user_id".to_string())? as i64,
+    );
+    let target_id = DBUserId(
+        parse_base62(&target_id)
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_request_err("invalid target_id".to_string())? as i64,
+    );
 
-    let blocked =
-        DBBlockedUser::is_blocked(user_id, target_id, &**pool).await?;
+    let blocked = DBBlockedUser::is_blocked(user_id, target_id, &**pool)
+        .await
+        .wrap_internal_err("checking whether user is blocked")?;
 
     Ok(web::Json(BlockStatus { blocked }))
 }
diff --git a/apps/labrinth/src/routes/internal/campaign.rs b/apps/labrinth/src/routes/internal/campaign.rs
index 5da7ebc414..4e317bfdbd 100644
--- a/apps/labrinth/src/routes/internal/campaign.rs
+++ b/apps/labrinth/src/routes/internal/campaign.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use actix_web::{HttpRequest, get, post, web};
 use base64::Engine;
 use chrono::{DateTime, Duration, Utc};
@@ -158,7 +159,8 @@ pub async fn tiltify_webhook(
     payouts_queue: web::Data<PayoutsQueue>,
     body: String,
 ) -> Result<(), ApiError> {
-    verify_tiltify_webhook_signature(&req, &body)?;
+    verify_tiltify_webhook_signature(&req, &body)
+        .wrap_api_err("executing `verify_tiltify_webhook_signature`")?;
 
     let raw_payload = serde_json::from_str::<serde_json::Value>(&body)
         .wrap_internal_err_with(|| eyre!("invalid Tiltify webhook JSON"))?;
@@ -181,7 +183,9 @@ pub async fn tiltify_webhook(
         .begin()
         .await
         .wrap_internal_err("beginning transaction")?;
-    let id = generate_campaign_donation_id(&mut transaction).await?;
+    let id = generate_campaign_donation_id(&mut transaction)
+        .await
+        .wrap_internal_err("generating campaign donation ID")?;
 
     let mut donation = CampaignDonation {
         id,
@@ -377,7 +381,8 @@ pub async fn pride_26(
             total_donations_usd: response.data.total_amount_raised.value,
             target_usd: response.data.goal.value,
             num_donators: num_donators(&http, &access_token, campaign_id)
-                .await?,
+                .await
+                .wrap_api_err("executing `num_donators`")?,
             cached_at: Utc::now(),
         };
 
diff --git a/apps/labrinth/src/routes/internal/delphi/mod.rs b/apps/labrinth/src/routes/internal/delphi/mod.rs
index 1a5d9e55fb..ef265171d2 100644
--- a/apps/labrinth/src/routes/internal/delphi/mod.rs
+++ b/apps/labrinth/src/routes/internal/delphi/mod.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use std::{collections::HashMap, fmt::Write, time::Instant};
 use xredis::RedisPool;
 
@@ -156,7 +157,7 @@ pub async fn ingest_report(
     let report = serde_json::from_value::<DelphiReport>(report.clone())
         .wrap_internal_err_with(|| {
             eyre!(
-                "Delphi sent a response which does not match our schema\n\n{}",
+                "received a Delphi response which does not match our schema\n\n{}",
                 serde_json::to_string_pretty(&report).unwrap()
             )
         })?;
@@ -251,7 +252,8 @@ async fn ingest_report_deserialized(
         tech_review_sync::TechReviewExitReason::Resolved,
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_api_err("synchronizing project technical-review state")?;
 
     transaction
         .commit()
@@ -278,7 +280,7 @@ pub async fn run(
         run_parameters.file_id.0 as i64
     )
     .fetch_one(exec)
-    .await?;
+    .await.wrap_internal_err("fetching file from database")?;
 
     tracing::debug!(
         "Running Delphi for project {}, version {}, file {}",
@@ -297,7 +299,7 @@ pub async fn run(
         .send()
         .await
         .and_then(|res| res.error_for_status())
-        .map_err(ApiError::delphi)?;
+        .wrap_internal_err("requesting a Delphi scan")?;
 
     Ok(HttpResponse::NoContent().finish())
 }
@@ -325,7 +327,8 @@ pub async fn _run(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     run(&**pool, run_parameters.into_inner(), &http).await
 }
@@ -350,12 +353,14 @@ pub async fn version(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     Ok(HttpResponse::Ok().json(
         sqlx::query_scalar!("SELECT MAX(delphi_version) FROM delphi_reports")
             .fetch_one(&**pool)
-            .await?,
+            .await
+            .wrap_internal_err("deserializing HTTP response")?,
     ))
 }
 
@@ -380,7 +385,8 @@ pub async fn issue_type_schema(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("deserializing HTTP response")?;
 
     // This route is expected to be called often by the frontend, and Delphi is not necessarily
     // built to scale beyond malware analysis, so cache the result of its quasi-constant-valued
@@ -401,10 +407,10 @@ pub async fn issue_type_schema(
                         .send()
                         .await
                         .and_then(|res| res.error_for_status())
-                        .map_err(ApiError::delphi)?
+                        .wrap_internal_err("fetching the Delphi schema")?
                         .json::<serde_json::Map<String, serde_json::Value>>()
                         .await
-                        .map_err(ApiError::delphi)?,
+                        .wrap_internal_err("deserializing the Delphi schema")?,
                     Instant::now(),
                 ))
                 .0,
diff --git a/apps/labrinth/src/routes/internal/delphi/tech_review_sync.rs b/apps/labrinth/src/routes/internal/delphi/tech_review_sync.rs
index e67c9e517e..ca80c6e9e9 100644
--- a/apps/labrinth/src/routes/internal/delphi/tech_review_sync.rs
+++ b/apps/labrinth/src/routes/internal/delphi/tech_review_sync.rs
@@ -38,6 +38,7 @@
 //! to act as a single chokepoint which (correctly) syncs all the state, instead
 //! of having each mutation run its own ad-hoc update logic.
 
+use crate::util::error::ApiContext as _;
 use itertools::Itertools;
 
 use crate::{
@@ -170,7 +171,9 @@ pub async fn sync_project_tech_review_state(
             last_tech_review_message_type: row.last_tech_review_message_type,
         };
 
-        sync_one_project_tech_review_state(state, exit_reason, txn).await?;
+        sync_one_project_tech_review_state(state, exit_reason, txn)
+            .await
+            .wrap_api_err("executing `sync_one_project_tech_review_state`")?;
     }
 
     Ok(())
@@ -245,7 +248,8 @@ pub async fn sync_deleted_project_tech_review_exit(
         && should_send_exit(row.last_tech_review_message_type.as_deref())
     {
         insert_exit_message(thread_id, TechReviewExitReason::FileDeleted, txn)
-            .await?;
+            .await
+            .wrap_api_err("executing `insert_exit_message`")?;
     }
 
     Ok(())
@@ -275,7 +279,9 @@ async fn sync_one_project_tech_review_state(
             // an append-only project tech review event table where the latest
             // enter/exit event is the current state. Until then, this dummy
             // issue detail acts as the pending queue blocker.
-            ensure_dummy_issue_detail(report_id, txn).await?;
+            ensure_dummy_issue_detail(report_id, txn)
+                .await
+                .wrap_api_err("validating dummy issue detail")?;
         }
 
         if let Some(thread_id) = state.thread_id
@@ -301,7 +307,9 @@ async fn sync_one_project_tech_review_state(
             == Some(MessageBody::TechReviewEntered.as_ref())
     {
         if let Some(report_id) = state.report_id {
-            ensure_dummy_issue_detail(report_id, txn).await?;
+            ensure_dummy_issue_detail(report_id, txn)
+                .await
+                .wrap_api_err("validating dummy issue detail")?;
         }
 
         return Ok(());
@@ -310,7 +318,9 @@ async fn sync_one_project_tech_review_state(
     if let Some(thread_id) = state.thread_id
         && should_send_exit(state.last_tech_review_message_type.as_deref())
     {
-        insert_exit_message(thread_id, exit_reason, txn).await?;
+        insert_exit_message(thread_id, exit_reason, txn)
+            .await
+            .wrap_api_err("executing `insert_exit_message`")?;
     }
 
     Ok(())
diff --git a/apps/labrinth/src/routes/internal/external_notifications.rs b/apps/labrinth/src/routes/internal/external_notifications.rs
index 122edfbf79..e43eae6c54 100644
--- a/apps/labrinth/src/routes/internal/external_notifications.rs
+++ b/apps/labrinth/src/routes/internal/external_notifications.rs
@@ -1,3 +1,5 @@
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use std::collections::HashMap;
 
 use crate::auth::get_user_from_headers;
@@ -152,16 +154,23 @@ async fn create_impl(
         .map(|x| DBUserId(*x))
         .collect::<Vec<_>>();
 
-    let mut txn = pool.begin().await?;
+    let mut txn = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
-    if !DBUser::exists_many(&user_ids, &mut txn).await? {
-        return Err(ApiError::InvalidInput(
+    if !DBUser::exists_many(&user_ids, &mut txn)
+        .await
+        .wrap_internal_err("fetching users from database")?
+    {
+        return Err(ApiError::Request(eyre::eyre!(
             "One of the specified users do not exist.".to_owned(),
-        ));
+        )));
     }
 
     // Skip users who already have an identical notification
-    let body_value = serde_json::value::to_value(&body)?;
+    let body_value = serde_json::value::to_value(&body)
+        .wrap_request_err("serializing external notification body")?;
     let already_notified = sqlx::query!(
         "
         SELECT DISTINCT user_id
@@ -172,7 +181,8 @@ async fn create_impl(
         body_value,
     )
     .fetch_all(&mut txn)
-    .await?
+    .await
+    .wrap_internal_err("fetching already notified from database")?
     .into_iter()
     .map(|row| DBUserId(row.user_id))
     .collect::<std::collections::HashSet<_>>();
@@ -188,7 +198,8 @@ async fn create_impl(
     let notification_ids = if email_strategy == EmailStrategy::Async {
         notification_builder
             .insert_many(notification_user_ids, &mut txn, &redis)
-            .await?
+            .await
+            .wrap_internal_err("inserting notification IDs into database")?
     } else {
         notification_builder
             .insert_many_without_delivery(
@@ -196,22 +207,31 @@ async fn create_impl(
                 &mut txn,
                 &redis,
             )
-            .await?
+            .await
+            .wrap_internal_err("inserting database records for `create_impl`")?
     };
 
     let notifications =
-        get_site_exposed_notifications(&notification_ids, &mut txn).await?;
+        get_site_exposed_notifications(&notification_ids, &mut txn)
+            .await
+            .wrap_api_err("fetching site exposed notifications")?;
 
-    txn.commit().await?;
+    txn.commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     broadcast_notifications(&redis, notifications).await;
 
     if email_strategy == EmailStrategy::Sync {
-        let mut email_txn = pool.begin().await?;
+        let mut email_txn = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         let mut failed = HashMap::new();
         let users = DBUser::get_many_ids(&user_ids, &mut email_txn, &redis)
-            .await?
+            .await
+            .wrap_internal_err("fetching users from database")?
             .into_iter()
             .map(|user| (user.id, user))
             .collect::<HashMap<_, _>>();
@@ -242,10 +262,7 @@ async fn create_impl(
                     }
                 }
                 Err(error) => {
-                    if matches!(
-                        error,
-                        ApiError::SqlxDatabase(_) | ApiError::Database(_)
-                    ) {
+                    if matches!(error, ApiError::Internal(_)) {
                         return Err(error);
                     };
                     failed.insert(user_id, error.into());
@@ -253,7 +270,10 @@ async fn create_impl(
             };
         }
 
-        email_txn.commit().await?;
+        email_txn
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         let status = if failed
             .values()
@@ -310,14 +330,20 @@ pub async fn remove(
         .map(|x| DBUserId(x.0 as i64))
         .collect::<Vec<_>>();
 
-    let mut txn = pool.begin().await?;
+    let mut txn = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     DBNotification::remove_many_matching_body(
         &filters, &user_ids, &mut txn, &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("deleting notifications from database")?;
 
-    txn.commit().await?;
+    txn.commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::NoContent().finish())
 }
@@ -350,13 +376,14 @@ pub async fn send_custom_email(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if user.role != Role::Admin {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to send custom emails!".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to send custom emails!",
+        )));
     }
 
     let SendEmail {
@@ -371,7 +398,10 @@ pub async fn send_custom_email(
         .map(|x| DBUserId(x.0 as i64))
         .collect::<Vec<_>>();
 
-    let mut txn = pool.begin().await?;
+    let mut txn = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     NotificationBuilder {
         body: NotificationBody::Custom {
@@ -381,9 +411,12 @@ pub async fn send_custom_email(
         },
     }
     .insert_many(users, &mut txn, &redis)
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `send_custom_email`")?;
 
-    txn.commit().await?;
+    txn.commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::Accepted().finish())
 }
@@ -404,13 +437,15 @@ async fn get_site_exposed_notifications(
         &raw_ids[..],
     )
     .fetch_all(&mut *txn)
-    .await?
+    .await
+    .wrap_internal_err("fetching exposed IDs from database")?
     .into_iter()
     .map(DBNotificationId)
     .collect::<Vec<_>>();
 
     Ok(DBNotification::get_many(&exposed_ids, txn)
-        .await?
+        .await
+        .wrap_internal_err("fetching notifications from database")?
         .into_iter()
         .map(Notification::from)
         .collect())
diff --git a/apps/labrinth/src/routes/internal/flows.rs b/apps/labrinth/src/routes/internal/flows.rs
index fd70c60c55..4bf40c8d20 100644
--- a/apps/labrinth/src/routes/internal/flows.rs
+++ b/apps/labrinth/src/routes/internal/flows.rs
@@ -20,6 +20,7 @@ use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
 use crate::routes::internal::session::issue_session;
 use crate::util::captcha::check_hcaptcha;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use crate::util::ext::get_image_ext;
 use crate::util::img::upload_image_optimized;
@@ -1477,14 +1478,21 @@ pub async fn create_oauth_account(
     redis: Data<RedisPool>,
     web::Json(new_account): web::Json<NewOAuthAccount>,
 ) -> Result<HttpResponse, ApiError> {
-    new_account.validate().map_err(|err| {
-        ApiError::InvalidInput(validation_errors_to_string(err, None))
-    })?;
+    new_account
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
-    validate_account_consent(new_account.account_consent)?;
+    validate_account_consent(new_account.account_consent)
+        .wrap_api_err("validating account consent")?;
 
-    if !check_hcaptcha(&req, &new_account.challenge).await? {
-        return Err(ApiError::Turnstile);
+    if !check_hcaptcha(&req, &new_account.challenge)
+        .await
+        .wrap_api_err("checking captcha response")?
+    {
+        return Err(ApiError::Request(eyre::eyre!(
+            "captcha validation failed"
+        )));
     }
 
     let flow = DBFlow::get(&new_account.state, &redis)
@@ -1502,7 +1510,8 @@ pub async fn create_oauth_account(
     };
 
     if let Some(email) = &user.email {
-        ensure_email_domain_is_allowed(email)?;
+        ensure_email_domain_is_allowed(email)
+            .wrap_api_err("validating email domain is allowed")?;
     }
 
     let mut txn = db
@@ -1520,11 +1529,16 @@ pub async fn create_oauth_account(
             new_account.username,
             new_account.sign_up_newsletter,
         )
-        .await?;
+        .await
+        .wrap_auth_err("inserting user ID into database")?;
 
-    let session = issue_session(req, user_id, &mut txn, &redis, None).await?;
+    let session = issue_session(req, user_id, &mut txn, &redis, None)
+        .await
+        .wrap_auth_err("authenticating API request")?;
     let res = crate::models::sessions::Session::from(session, true, None);
-    txn.commit().await?;
+    txn.commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::Ok().json(res))
 }
@@ -1585,7 +1599,8 @@ pub async fn discord_community_link(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let Some(discord_id) = db_user.discord_id else {
@@ -1656,23 +1671,30 @@ pub async fn delete_auth_provider(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if user.auth_providers.is_none_or(|x| x.len() <= 1)
         && !user.has_password.unwrap_or(false)
     {
-        return Err(ApiError::InvalidInput(
-            "You must have another authentication method added to this account!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "You must have another authentication method added to this account!",
+        )));
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     delete_provider
         .provider
         .update_user_id(user.id.into(), None, &mut transaction)
-        .await?;
+        .await
+        .wrap_auth_err(
+            "updating database records for `delete_auth_provider`",
+        )?;
 
     if delete_provider.provider != AuthProvider::PayPal {
         NotificationBuilder {
@@ -1681,15 +1703,22 @@ pub async fn delete_auth_provider(
             },
         }
         .insert(user.id.into(), &mut transaction, &redis)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `delete_auth_provider`",
+        )?;
     }
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     crate::database::models::DBUser::clear_caches(
         &[(user.id.into(), None)],
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::NoContent().finish())
 }
@@ -1779,6 +1808,18 @@ impl AccountRegisterValidateError {
             AccountRegisterValidateError::InvalidInput(_) => "invalid_input",
         }
     }
+
+    fn into_api_error(self) -> ApiError {
+        match &self {
+            Self::UsernameTaken => {
+                ApiError::Auth(eyre::eyre!(AuthenticationError::UsernameTaken))
+            }
+            Self::DuplicateEmail => {
+                ApiError::Auth(eyre::eyre!(AuthenticationError::DuplicateEmail))
+            }
+            _ => ApiError::Request(eyre::eyre!("{self}")),
+        }
+    }
 }
 
 impl actix_web::ResponseError for AccountRegisterValidateError {
@@ -1795,20 +1836,6 @@ impl actix_web::ResponseError for AccountRegisterValidateError {
     }
 }
 
-impl From<AccountRegisterValidateError> for ApiError {
-    fn from(value: AccountRegisterValidateError) -> Self {
-        match &value {
-            AccountRegisterValidateError::UsernameTaken => {
-                ApiError::Authentication(AuthenticationError::UsernameTaken)
-            }
-            AccountRegisterValidateError::DuplicateEmail => {
-                ApiError::Authentication(AuthenticationError::DuplicateEmail)
-            }
-            _ => ApiError::InvalidInput(value.to_string()),
-        }
-    }
-}
-
 impl From<NewAccount> for AccountRegisterFlow {
     fn from(account: NewAccount) -> Self {
         Self {
@@ -1862,9 +1889,12 @@ fn ensure_email_domain_is_allowed(email: &str) -> Result<(), ApiError> {
 }
 
 async fn ensure_email_is_usable(email: &str) -> Result<(), ApiError> {
-    ensure_email_domain_is_allowed(email)?;
+    ensure_email_domain_is_allowed(email)
+        .wrap_api_err("validating email domain is allowed")?;
 
-    let result = check_email(email).await.map_err(ApiError::Request)?;
+    let result = check_email(email)
+        .await
+        .wrap_request_err("checking email address")?;
 
     if matches!(
         result,
@@ -1941,16 +1971,18 @@ impl ReadyAccountRegisterFlow {
     ) -> Result<crate::models::sessions::Session, ApiError> {
         let register_flow = self.inner;
 
-        let user_id =
-            crate::database::models::generate_user_id(transaction).await?;
+        let user_id = crate::database::models::generate_user_id(transaction)
+            .await
+            .wrap_internal_err("generating user ID")?;
 
         let hasher = Argon2::default();
         let salt = SaltString::generate(&mut ChaCha20Rng::from_entropy());
         let password_hash = hasher
-            .hash_password(register_flow.password.as_bytes(), &salt)?
+            .hash_password(register_flow.password.as_bytes(), &salt)
+            .wrap_internal_err("hashing password")?
             .to_string();
 
-        crate::database::models::DBUser {
+        let insert_result = crate::database::models::DBUser {
             id: user_id,
             github_id: None,
             discord_id: None,
@@ -1980,41 +2012,51 @@ impl ReadyAccountRegisterFlow {
             eligibility_verified_at: Some(Utc::now()),
         }
         .insert(transaction)
-        .await
-        .map_err(|err| {
-            if let sqlx::Error::Database(database_error) = &err {
-                match database_error.constraint() {
-                    Some("username_unique" | "users_username_key") => {
-                        return ApiError::from(
-                            AccountRegisterValidateError::UsernameTaken,
-                        );
+        .await;
+        match insert_result {
+            Ok(()) => {}
+            Err(err) => {
+                if let sqlx::Error::Database(database_error) = &err {
+                    match database_error.constraint() {
+                        Some("username_unique" | "users_username_key") => {
+                            return Err(
+                                AccountRegisterValidateError::UsernameTaken
+                                    .into_api_error(),
+                            );
+                        }
+                        Some("email_unique" | "users_email_key") => {
+                            return Err(
+                                AccountRegisterValidateError::DuplicateEmail
+                                    .into_api_error(),
+                            );
+                        }
+                        _ => {}
                     }
-                    Some("email_unique" | "users_email_key") => {
-                        return ApiError::from(
-                            AccountRegisterValidateError::DuplicateEmail,
-                        );
-                    }
-                    _ => {}
                 }
+
+                return Err(ApiError::Internal(eyre::eyre!(
+                    "inserting registered user: {err}"
+                )));
             }
+        }
 
-            ApiError::from(err)
-        })?;
-
-        let session =
-            issue_session(req, user_id, transaction, redis, None).await?;
+        let session = issue_session(req, user_id, transaction, redis, None)
+            .await
+            .wrap_auth_err("authenticating API request")?;
         let res = crate::models::sessions::Session::from(session, true, None);
 
-        let mailbox: Mailbox = register_flow.email.parse().map_err(|_| {
-            ApiError::InvalidInput("Invalid email address!".to_string())
-        })?;
+        let mailbox: Mailbox = register_flow
+            .email
+            .parse()
+            .wrap_request_err("invalid email address!".to_string())?;
 
         let flow = DBFlow::ConfirmEmail {
             user_id,
             confirm_email: register_flow.email.clone(),
         }
         .insert(Duration::hours(24), redis)
-        .await?;
+        .await
+        .wrap_internal_err("storing email-verification flow in Redis")?;
 
         email_queue
             .send_one(
@@ -2023,8 +2065,10 @@ impl ReadyAccountRegisterFlow {
                 user_id,
                 mailbox,
             )
-            .await?
-            .as_user_error()?;
+            .await
+            .wrap_api_err("sending account email")?
+            .as_user_error()
+            .wrap_api_err("validating email delivery status")?;
 
         Ok(res)
     }
@@ -2079,26 +2123,40 @@ pub async fn create_account_with_password(
 ) -> Result<HttpResponse, ApiError> {
     let new_account = new_account.into_inner();
 
-    validate_account_consent(new_account.account_consent)?;
+    validate_account_consent(new_account.account_consent)
+        .wrap_api_err("validating account consent")?;
 
     if !check_hcaptcha(&req, new_account.challenge.as_deref().unwrap_or(""))
-        .await?
+        .await
+        .wrap_api_err("checking captcha response")?
     {
-        return Err(ApiError::Turnstile);
+        return Err(ApiError::Request(eyre::eyre!(
+            "captcha validation failed"
+        )));
     }
 
-    ensure_email_is_usable(&new_account.email).await?;
+    ensure_email_is_usable(&new_account.email)
+        .await
+        .wrap_api_err("validating email is usable")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let ready_flow = AccountRegisterFlow::from(new_account)
         .validate(&mut transaction, &redis)
-        .await?;
+        .await
+        .wrap_internal_err("validating ready flow")?;
 
     let res = ready_flow
         .execute(req, &mut transaction, &redis, &email)
-        .await?;
-    transaction.commit().await?;
+        .await
+        .wrap_api_err("executing `execute`")?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::Ok().json(res))
 }
@@ -2129,8 +2187,13 @@ pub async fn login_password(
     redis: Data<RedisPool>,
     login: web::Json<Login>,
 ) -> Result<HttpResponse, ApiError> {
-    if !check_hcaptcha(&req, &login.challenge).await? {
-        return Err(ApiError::Turnstile);
+    if !check_hcaptcha(&req, &login.challenge)
+        .await
+        .wrap_api_err("checking captcha response")?
+    {
+        return Err(ApiError::Request(eyre::eyre!(
+            "captcha validation failed"
+        )));
     }
 
     let user = if let Some(user) = crate::database::models::DBUser::get(
@@ -2138,7 +2201,8 @@ pub async fn login_password(
         &**pool,
         &redis,
     )
-    .await?
+    .await
+    .wrap_internal_err("fetching user from database")?
     {
         user
     } else {
@@ -2146,12 +2210,16 @@ pub async fn login_password(
             &login.username_or_email,
             &**pool,
         )
-        .await?
-        .ok_or_else(|| AuthenticationError::InvalidCredentials)?;
+        .await
+        .wrap_internal_err("fetching user from database")?
+        .ok_or_else(|| AuthenticationError::InvalidCredentials)
+        .wrap_auth_err("fetching user from database")?;
 
         crate::database::models::DBUser::get_id(user, &**pool, &redis)
-            .await?
-            .ok_or_else(|| AuthenticationError::InvalidCredentials)?
+            .await
+            .wrap_internal_err("fetching user from database")?
+            .ok_or_else(|| AuthenticationError::InvalidCredentials)
+            .wrap_auth_err("fetching user from database")?
     };
 
     let hasher = Argon2::default();
@@ -2161,15 +2229,19 @@ pub async fn login_password(
             &PasswordHash::new(
                 &user
                     .password
-                    .ok_or_else(|| AuthenticationError::InvalidCredentials)?,
-            )?,
+                    .ok_or_else(|| AuthenticationError::InvalidCredentials)
+                    .wrap_auth_err("authenticating API request")?,
+            )
+            .wrap_internal_err("validating data")?,
         )
-        .map_err(|_| AuthenticationError::InvalidCredentials)?;
+        .map_err(|_| AuthenticationError::InvalidCredentials)
+        .wrap_auth_err("authenticating API request")?;
 
     if user.totp_secret.is_some() {
         let flow = DBFlow::Login2FA { user_id: user.id }
             .insert(Duration::minutes(30), &redis)
-            .await?;
+            .await
+            .wrap_internal_err("inserting authentication flow into database")?;
 
         Ok(HttpResponse::Ok().json(serde_json::json!({
             "error": "2fa_required",
@@ -2177,11 +2249,19 @@ pub async fn login_password(
             "flow": flow,
         })))
     } else {
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
         let session =
-            issue_session(req, user.id, &mut transaction, &redis, None).await?;
+            issue_session(req, user.id, &mut transaction, &redis, None)
+                .await
+                .wrap_auth_err("authenticating API request")?;
         let res = crate::models::sessions::Session::from(session, true, None);
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::Ok().json(res))
     }
@@ -2285,44 +2365,60 @@ pub async fn login_2fa(
     login: web::Json<Login2FA>,
 ) -> Result<HttpResponse, ApiError> {
     let flow = DBFlow::get(&login.flow, &redis)
-        .await?
-        .ok_or_else(|| AuthenticationError::InvalidCredentials)?;
+        .await
+        .wrap_internal_err("fetching login flow from Redis")?
+        .ok_or_else(|| AuthenticationError::InvalidCredentials)
+        .wrap_auth_err("finding login flow")?;
 
     if let DBFlow::Login2FA { user_id } = flow {
         let user =
             crate::database::models::DBUser::get_id(user_id, &**pool, &redis)
-                .await?
-                .ok_or_else(|| AuthenticationError::InvalidCredentials)?;
+                .await
+                .wrap_internal_err("fetching user from database")?
+                .ok_or_else(|| AuthenticationError::InvalidCredentials)
+                .wrap_auth_err("fetching user from database")?;
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
         if !validate_2fa_code(
             login.code.clone(),
             user.totp_secret
-                .ok_or_else(|| AuthenticationError::InvalidCredentials)?,
+                .ok_or_else(|| AuthenticationError::InvalidCredentials)
+                .wrap_auth_err("authenticating API request")?,
             true,
             user.id,
             &redis,
             &pool,
             &mut transaction,
         )
-        .await?
+        .await
+        .wrap_auth_err("authenticating API request")?
         {
-            return Err(ApiError::Authentication(
+            return Err(ApiError::Auth(eyre::eyre!(
                 AuthenticationError::InvalidCredentials,
-            ));
+            )));
         }
-        DBFlow::remove(&login.flow, &redis).await?;
+        DBFlow::remove(&login.flow, &redis)
+            .await
+            .wrap_internal_err("removing authentication flow from Redis")?;
 
         let session =
-            issue_session(req, user_id, &mut transaction, &redis, None).await?;
+            issue_session(req, user_id, &mut transaction, &redis, None)
+                .await
+                .wrap_auth_err("authenticating API request")?;
         let res = crate::models::sessions::Session::from(session, true, None);
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::Ok().json(res))
     } else {
-        Err(ApiError::Authentication(
+        Err(ApiError::Auth(eyre::eyre!(
             AuthenticationError::InvalidCredentials,
-        ))
+        )))
     }
 }
 
@@ -2352,7 +2448,8 @@ pub async fn begin_2fa_flow(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if !user.has_totp.unwrap_or(false) {
@@ -2364,16 +2461,17 @@ pub async fn begin_2fa_flow(
             secret: encoded.to_string(),
         }
         .insert(Duration::minutes(30), &redis)
-        .await?;
+        .await
+        .wrap_internal_err("inserting database records for `begin_2fa_flow`")?;
 
         Ok(HttpResponse::Ok().json(serde_json::json!({
             "secret": encoded.to_string(),
             "flow": flow,
         })))
     } else {
-        Err(ApiError::InvalidInput(
-            "User already has 2FA enabled on their account!".to_string(),
-        ))
+        Err(ApiError::Request(eyre::eyre!(
+            "User already has 2FA enabled on their account!",
+        )))
     }
 }
 
@@ -2398,8 +2496,10 @@ pub async fn finish_2fa_flow(
     session_queue: Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
     let flow = DBFlow::get(&login.flow, &redis)
-        .await?
-        .ok_or_else(|| AuthenticationError::InvalidCredentials)?;
+        .await
+        .wrap_internal_err("fetching 2FA initialization flow from Redis")?
+        .ok_or_else(|| AuthenticationError::InvalidCredentials)
+        .wrap_auth_err("finding 2FA initialization flow")?;
 
     if let DBFlow::Initialize2FA { user_id, secret } = flow {
         let user = get_user_from_headers(
@@ -2409,16 +2509,20 @@ pub async fn finish_2fa_flow(
             &session_queue,
             Scopes::USER_AUTH_WRITE,
         )
-        .await?
+        .await
+        .wrap_auth_err("authenticating API request")?
         .1;
 
         if user.id != user_id.into() {
-            return Err(ApiError::Authentication(
+            return Err(ApiError::Auth(eyre::eyre!(
                 AuthenticationError::InvalidCredentials,
-            ));
+            )));
         }
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         if !validate_2fa_code(
             login.code.clone(),
@@ -2429,14 +2533,17 @@ pub async fn finish_2fa_flow(
             &pool,
             &mut transaction,
         )
-        .await?
+        .await
+        .wrap_auth_err("authenticating API request")?
         {
-            return Err(ApiError::Authentication(
+            return Err(ApiError::Auth(eyre::eyre!(
                 AuthenticationError::InvalidCredentials,
-            ));
+            )));
         }
 
-        DBFlow::remove(&login.flow, &redis).await?;
+        DBFlow::remove(&login.flow, &redis)
+            .await
+            .wrap_internal_err("removing authentication flow from Redis")?;
 
         sqlx::query!(
             "
@@ -2448,7 +2555,8 @@ pub async fn finish_2fa_flow(
             user_id as crate::database::models::ids::DBUserId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `finish_2fa_flow`")?;
 
         sqlx::query!(
             "
@@ -2458,7 +2566,8 @@ pub async fn finish_2fa_flow(
             user_id as crate::database::models::ids::DBUserId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `finish_2fa_flow`")?;
 
         let mut codes = Vec::new();
 
@@ -2479,7 +2588,8 @@ pub async fn finish_2fa_flow(
                 val as i64,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `finish_2fa_flow`")?;
 
             codes.push(to_base62(val));
         }
@@ -2488,22 +2598,29 @@ pub async fn finish_2fa_flow(
             body: NotificationBody::TwoFactorEnabled,
         }
         .insert(user.id.into(), &mut transaction, &redis)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `finish_2fa_flow`",
+        )?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         crate::database::models::DBUser::clear_caches(
             &[(user.id.into(), None)],
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
         Ok(HttpResponse::Ok().json(serde_json::json!({
             "backup_codes": codes,
         })))
     } else {
-        Err(ApiError::Authentication(
+        Err(ApiError::Auth(eyre::eyre!(
             AuthenticationError::InvalidCredentials,
-        ))
+        )))
     }
 }
 
@@ -2540,23 +2657,26 @@ pub async fn remove_2fa(
         &session_queue,
         false,
     )
-    .await?
-    .ok_or_else(|| AuthenticationError::InvalidCredentials)?;
+    .await
+    .wrap_auth_err("authenticating API request")?
+    .ok_or_else(|| AuthenticationError::InvalidCredentials)
+    .wrap_auth_err("authenticating API request")?;
 
     if !scopes.contains(Scopes::USER_AUTH_WRITE) {
-        return Err(ApiError::Authentication(
+        return Err(ApiError::Auth(eyre::eyre!(
             AuthenticationError::InvalidCredentials,
-        ));
+        )));
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     if !validate_2fa_code(
         login.code.clone(),
-        user.totp_secret.ok_or_else(|| {
-            ApiError::InvalidInput(
-                "User does not have 2FA enabled on the account!".to_string(),
-            )
+        user.totp_secret.wrap_request_err_with(|| {
+            "user does not have 2FA enabled on the account!".to_string()
         })?,
         true,
         user.id,
@@ -2564,11 +2684,12 @@ pub async fn remove_2fa(
         &pool,
         &mut transaction,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     {
-        return Err(ApiError::Authentication(
+        return Err(ApiError::Auth(eyre::eyre!(
             AuthenticationError::InvalidCredentials,
-        ));
+        )));
     }
 
     sqlx::query!(
@@ -2580,7 +2701,8 @@ pub async fn remove_2fa(
         user.id as crate::database::models::ids::DBUserId,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `remove_2fa`")?;
 
     sqlx::query!(
         "
@@ -2590,17 +2712,23 @@ pub async fn remove_2fa(
         user.id as crate::database::models::ids::DBUserId,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `remove_2fa`")?;
 
     NotificationBuilder {
         body: NotificationBody::TwoFactorRemoved,
     }
     .insert(user.id, &mut transaction, &redis)
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `remove_2fa`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     crate::database::models::DBUser::clear_caches(&[(user.id, None)], &redis)
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::NoContent().finish())
 }
@@ -2631,18 +2759,27 @@ pub async fn reset_password_begin(
     reset_password: web::Json<ResetPassword>,
     email: web::Data<EmailQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    if !check_hcaptcha(&req, &reset_password.challenge).await? {
-        return Err(ApiError::Turnstile);
+    if !check_hcaptcha(&req, &reset_password.challenge)
+        .await
+        .wrap_api_err("checking captcha response")?
+    {
+        return Err(ApiError::Request(eyre::eyre!(
+            "captcha validation failed"
+        )));
     }
 
-    let mut txn = pool.begin().await?;
+    let mut txn = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let user =
         match crate::database::models::DBUser::get_by_case_insensitive_email(
             &reset_password.username_or_email,
             &mut txn,
         )
-        .await?[..]
+        .await
+        .wrap_internal_err("fetching user from database")?[..]
         {
             [] => {
                 // Try finding by username or ID
@@ -2651,7 +2788,8 @@ pub async fn reset_password_begin(
                     &mut txn,
                     &redis,
                 )
-                .await?
+                .await
+                .wrap_internal_err("fetching user from database")?
             }
             [user_id] => {
                 // If there is only one user with the given email, ignoring case,
@@ -2659,7 +2797,8 @@ pub async fn reset_password_begin(
                 crate::database::models::DBUser::get_id(
                     user_id, &mut txn, &redis,
                 )
-                .await?
+                .await
+                .wrap_internal_err("fetching user from database")?
             }
             _ => {
                 // When several users use variations of the same email with
@@ -2671,12 +2810,16 @@ pub async fn reset_password_begin(
                         &reset_password.username_or_email,
                         &mut txn,
                     )
-                    .await?
+                    .await
+                    .wrap_internal_err(
+                        "fetching password-reset user by email",
+                    )?
                 {
                     crate::database::models::DBUser::get_id(
                         user_id, &mut txn, &redis,
                     )
-                    .await?
+                    .await
+                    .wrap_internal_err("fetching password-reset user by ID")?
                 } else {
                     None
                 }
@@ -2691,7 +2834,8 @@ pub async fn reset_password_begin(
     {
         let flow = DBFlow::ForgotPassword { user_id }
             .insert(Duration::hours(24), &redis)
-            .await?;
+            .await
+            .wrap_internal_err("inserting authentication flow into database")?;
 
         if let Ok(mailbox) = user_email.unwrap_or_default().parse() {
             email
@@ -2701,12 +2845,16 @@ pub async fn reset_password_begin(
                     user_id,
                     mailbox,
                 )
-                .await?
-                .as_user_error()?;
+                .await
+                .wrap_api_err("sending account email")?
+                .as_user_error()
+                .wrap_api_err("validating email delivery status")?;
         }
     }
 
-    txn.commit().await?;
+    txn.commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::Ok().finish())
 }
@@ -2740,20 +2888,24 @@ pub async fn change_password(
     session_queue: Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
     let user = if let Some(flow) = &change_password.flow {
-        let flow = DBFlow::get(flow, &redis).await?;
+        let flow = DBFlow::get(flow, &redis)
+            .await
+            .wrap_internal_err("fetching password-reset flow from Redis")?;
 
         if let Some(DBFlow::ForgotPassword { user_id }) = flow {
             let user = crate::database::models::DBUser::get_id(
                 user_id, &**pool, &redis,
             )
-            .await?
-            .ok_or_else(|| AuthenticationError::InvalidCredentials)?;
+            .await
+            .wrap_internal_err("fetching user from database")?
+            .ok_or_else(|| AuthenticationError::InvalidCredentials)
+            .wrap_auth_err("fetching user from database")?;
 
             Some(user)
         } else {
-            return Err(ApiError::CustomAuthentication(
-                "The password change flow code is invalid or has expired. Did you copy it promptly and correctly?".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "The password change flow code is invalid or has expired. Did you copy it promptly and correctly?",
+            )));
         }
     } else {
         None
@@ -2770,33 +2922,43 @@ pub async fn change_password(
             &session_queue,
             false,
         )
-        .await?
-        .ok_or_else(|| AuthenticationError::InvalidCredentials)?;
+        .await
+        .wrap_auth_err("authenticating API request")?
+        .ok_or_else(|| AuthenticationError::InvalidCredentials)
+        .wrap_auth_err("authenticating API request")?;
 
         if !scopes.contains(Scopes::USER_AUTH_WRITE) {
-            return Err(ApiError::Authentication(
+            return Err(ApiError::Auth(eyre::eyre!(
                 AuthenticationError::InvalidCredentials,
-            ));
+            )));
         }
 
         if let Some(pass) = user.password.as_ref() {
-            let old_password = change_password.old_password.as_ref().ok_or_else(|| {
-                ApiError::CustomAuthentication(
-                    "You must specify the old password to change your password!".to_string(),
-                )
-            })?;
+            let old_password = change_password
+                .old_password
+                .as_ref()
+                .wrap_auth_err_with(|| {
+                    "you must specify the old password to change your password!"
+                        .to_string()
+                })?;
 
             let hasher = Argon2::default();
-            hasher.verify_password(
-                old_password.as_bytes(),
-                &PasswordHash::new(pass)?,
-            )?;
+            hasher
+                .verify_password(
+                    old_password.as_bytes(),
+                    &PasswordHash::new(pass)
+                        .wrap_internal_err("validating data")?,
+                )
+                .wrap_internal_err("validating data")?;
         }
 
         user
     };
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let update_password = if let Some(new_password) =
         &change_password.new_password
@@ -2807,21 +2969,25 @@ pub async fn change_password(
         );
 
         if score.score() < Score::Three {
-            return Err(ApiError::InvalidInput(
-                if let Some(feedback) =
-                    score.feedback().and_then(|x| x.warning())
-                {
-                    format!("Password too weak: {feedback}")
-                } else {
-                    "Specified password is too weak! Please improve its strength.".to_string()
-                },
-            ));
+            let report = score
+                .feedback()
+                .and_then(|feedback| feedback.warning())
+                .map_or_else(
+                    || {
+                        eyre::eyre!(
+                            "Specified password is too weak! Please improve its strength."
+                        )
+                    },
+                    |feedback| eyre::eyre!("Password too weak: {feedback}"),
+                );
+            return Err(ApiError::Request(report));
         }
 
         let hasher = Argon2::default();
         let salt = SaltString::generate(&mut ChaCha20Rng::from_entropy());
         let password_hash = hasher
-            .hash_password(new_password.as_bytes(), &salt)?
+            .hash_password(new_password.as_bytes(), &salt)
+            .wrap_internal_err("hashing password")?
             .to_string();
 
         Some(password_hash)
@@ -2833,9 +2999,9 @@ pub async fn change_password(
             || user.steam_id.is_some()
             || user.discord_id.is_some())
         {
-            return Err(ApiError::InvalidInput(
-                "You must have another authentication method added to remove password authentication!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You must have another authentication method added to remove password authentication!",
+            )));
         }
 
         None
@@ -2851,10 +3017,13 @@ pub async fn change_password(
         user.id as crate::database::models::ids::DBUserId,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("updating database records for `change_password`")?;
 
     if let Some(flow) = &change_password.flow {
-        DBFlow::remove(flow, &redis).await?;
+        DBFlow::remove(flow, &redis)
+            .await
+            .wrap_internal_err("removing authentication flow from Redis")?;
     }
 
     if update_password.is_some() {
@@ -2862,18 +3031,28 @@ pub async fn change_password(
             body: NotificationBody::PasswordChanged,
         }
         .insert(user.id, &mut transaction, &redis)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `change_password`",
+        )?;
     } else {
         NotificationBuilder {
             body: NotificationBody::PasswordRemoved,
         }
         .insert(user.id, &mut transaction, &redis)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `change_password`",
+        )?;
     }
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     crate::database::models::DBUser::clear_caches(&[(user.id, None)], &redis)
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::Ok().finish())
 }
@@ -2907,13 +3086,15 @@ pub async fn set_email(
     session_queue: Data<AuthQueue>,
     stripe_client: Data<stripe::Client>,
 ) -> Result<HttpResponse, ApiError> {
-    email_address.0.validate().map_err(|err| {
-        ApiError::InvalidInput(validation_errors_to_string(err, None))
-    })?;
+    email_address
+        .0
+        .validate()
+        .wrap_request_err("validating request")?;
 
-    let mailbox: Mailbox = email_address.email.parse().map_err(|_| {
-        ApiError::InvalidInput("Invalid email address!".to_string())
-    })?;
+    let mailbox: Mailbox = email_address
+        .email
+        .parse()
+        .wrap_request_err("invalid email address!".to_string())?;
 
     let user = get_user_from_headers(
         &req,
@@ -2922,24 +3103,31 @@ pub async fn set_email(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if !crate::database::models::DBUser::get_by_case_insensitive_email(
         &email_address.email,
         &**pool,
     )
-    .await?
+    .await
+    .wrap_internal_err("fetching user from database")?
     .is_empty()
     {
-        return Err(ApiError::InvalidInput(
-            "Email is already registered on Modrinth! Try 'Forgot password' in incognito to access and delete your other account.".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Email is already registered on Modrinth! Try 'Forgot password' in incognito to access and delete your other account.",
+        )));
     }
 
-    ensure_email_is_usable(&email_address.email).await?;
+    ensure_email_is_usable(&email_address.email)
+        .await
+        .wrap_api_err("validating email is usable")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     sqlx::query!(
         "
@@ -2951,7 +3139,8 @@ pub async fn set_email(
         user.id.0 as i64,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `set_email`")?;
 
     if let Some(user_email) = user.email.clone() {
         NotificationBuilder {
@@ -2961,7 +3150,8 @@ pub async fn set_email(
             },
         }
         .insert(user.id.into(), &mut transaction, &redis)
-        .await?;
+        .await
+        .wrap_internal_err("inserting database records for `set_email`")?;
     }
 
     if let Some(customer_id) = user
@@ -2977,7 +3167,8 @@ pub async fn set_email(
                 ..Default::default()
             },
         )
-        .await?;
+        .await
+        .wrap_failed_dependency_err("communicating with payment provider")?;
     }
 
     let flow = DBFlow::ConfirmEmail {
@@ -2985,7 +3176,8 @@ pub async fn set_email(
         confirm_email: email_address.email.clone(),
     }
     .insert(Duration::hours(24), &redis)
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `set_email`")?;
 
     email
         .send_one(
@@ -2994,16 +3186,22 @@ pub async fn set_email(
             user.id.into(),
             mailbox,
         )
-        .await?
-        .as_user_error()?;
+        .await
+        .wrap_api_err("sending account email")?
+        .as_user_error()
+        .wrap_api_err("validating email delivery status")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     crate::database::models::DBUser::clear_caches(
         &[(user.id.into(), None)],
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::Ok().finish())
 }
@@ -3035,14 +3233,15 @@ pub async fn resend_verify_email(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if let Some(email_address) = user.email {
         if user.email_verified.unwrap_or(false) {
-            return Err(ApiError::InvalidInput(
-                "User email is already verified!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "User email is already verified!",
+            )));
         }
 
         let flow = DBFlow::ConfirmEmail {
@@ -3050,13 +3249,19 @@ pub async fn resend_verify_email(
             confirm_email: email_address.clone(),
         }
         .insert(Duration::hours(24), &redis)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `resend_verify_email`",
+        )?;
 
-        let mailbox: Mailbox = email_address.parse().map_err(|_| {
-            ApiError::InvalidInput("Invalid email address!".to_string())
-        })?;
+        let mailbox: Mailbox = email_address
+            .parse()
+            .wrap_request_err("invalid email address!".to_string())?;
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         email
             .send_one(
@@ -3065,16 +3270,21 @@ pub async fn resend_verify_email(
                 user.id.into(),
                 mailbox,
             )
-            .await?
-            .as_user_error()?;
+            .await
+            .wrap_api_err("sending account email")?
+            .as_user_error()
+            .wrap_api_err("validating email delivery status")?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::NoContent().finish())
     } else {
-        Err(ApiError::InvalidInput(
-            "User does not have an email.".to_string(),
-        ))
+        Err(ApiError::Request(eyre::eyre!(
+            "User does not have an email.",
+        )))
     }
 }
 
@@ -3100,7 +3310,9 @@ pub async fn verify_email(
     redis: Data<RedisPool>,
     email: web::Json<VerifyEmail>,
 ) -> Result<HttpResponse, ApiError> {
-    let flow = DBFlow::get(&email.flow, &redis).await?;
+    let flow = DBFlow::get(&email.flow, &redis)
+        .await
+        .wrap_internal_err("fetching email-verification flow from Redis")?;
 
     if let Some(DBFlow::ConfirmEmail {
         user_id,
@@ -3109,17 +3321,21 @@ pub async fn verify_email(
     {
         let user =
             crate::database::models::DBUser::get_id(user_id, &**pool, &redis)
-                .await?
-                .ok_or_else(|| AuthenticationError::InvalidCredentials)?;
+                .await
+                .wrap_internal_err("fetching user from database")?
+                .ok_or_else(|| AuthenticationError::InvalidCredentials)
+                .wrap_auth_err("fetching user from database")?;
 
         if user.email != Some(confirm_email) {
-            return Err(ApiError::InvalidInput(
-                "E-mail does not match verify email. Try re-requesting the verification link."
-                    .to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "E-mail does not match verify email. Try re-requesting the verification link.",
+            )));
         }
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         sqlx::query!(
             "
@@ -3130,22 +3346,28 @@ pub async fn verify_email(
             user.id as crate::database::models::ids::DBUserId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `verify_email`")?;
 
-        DBFlow::remove(&email.flow, &redis).await?;
-        transaction.commit().await?;
+        DBFlow::remove(&email.flow, &redis)
+            .await
+            .wrap_internal_err("removing authentication flow from Redis")?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         crate::database::models::DBUser::clear_caches(
             &[(user.id, None)],
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
         Ok(HttpResponse::NoContent().finish())
     } else {
-        Err(ApiError::InvalidInput(
-            "Flow does not exist. Try re-requesting the verification link."
-                .to_string(),
-        ))
+        Err(ApiError::Request(eyre::eyre!(
+            "Flow does not exist. Try re-requesting the verification link.",
+        )))
     }
 }
 
@@ -3175,7 +3397,8 @@ pub async fn subscribe_newsletter(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     sqlx::query!(
@@ -3187,13 +3410,15 @@ pub async fn subscribe_newsletter(
         user.id.0 as i64,
     )
     .execute(&**pool)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `subscribe_newsletter`")?;
 
     crate::database::models::DBUser::clear_caches(
         &[(user.id.into(), None)],
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::NoContent().finish())
 }
@@ -3224,12 +3449,15 @@ pub async fn get_newsletter_subscription_status(
         &session_queue,
         Scopes::USER_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let is_subscribed = user.is_subscribed_to_newsletter
         || if let Some(email) = user.email {
-            check_sendy_subscription(&email).await?
+            check_sendy_subscription(&email)
+                .await
+                .wrap_auth_err("authenticating API request")?
         } else {
             false
         };
@@ -3275,7 +3503,8 @@ pub async fn register_passkey_start(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     // Get currently registered credentials, so an authenticator knows not to register
@@ -3377,12 +3606,14 @@ pub async fn register_passkey_finish(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    response.validate().map_err(|err| {
-        ApiError::InvalidInput(validation_errors_to_string(err, None))
-    })?;
+    response
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let db_user_id: DBUserId = user.id.into();
     let flow = DBFlow::take_if(
@@ -3390,19 +3621,22 @@ pub async fn register_passkey_finish(
         |f| matches!(f, DBFlow::RegisterPasskey { user_id, .. } if *user_id == db_user_id),
         &redis,
     )
-    .await?;
+    .await.wrap_internal_err("executing `DBFlow::take_if`")?;
     if let Some(DBFlow::RegisterPasskey { user_id, state }) = flow {
         if user_id != db_user_id {
-            return Err(ApiError::Authentication(
+            return Err(ApiError::Auth(eyre::eyre!(
                 AuthenticationError::InvalidCredentials,
-            ));
+            )));
         }
 
         let result = webauthn
             .finish_passkey_registration(&response.credential, &state)
             .wrap_request_err("failed to finish passkey registration")?;
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         let existing_passkeys =
             DBPasskey::get_for_user(db_user_id, &mut transaction)
@@ -3431,9 +3665,12 @@ pub async fn register_passkey_finish(
         passkey
             .insert(&mut transaction)
             .await
-            .wrap_internal_err("Failed to create passkey object")?;
+            .wrap_internal_err("failed to create passkey object")?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         Ok((
             web::Json(PasskeyResponse {
                 id: passkey.id.into(),
@@ -3524,7 +3761,8 @@ pub async fn authenticate_passkey_finish(
         |f| matches!(f, DBFlow::AuthenticatePasskey { .. }),
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("executing `DBFlow::take_if`")?;
 
     if let Some(DBFlow::AuthenticatePasskey { state }) = flow {
         let credential_id = response.credential.get_credential_id();
@@ -3532,7 +3770,7 @@ pub async fn authenticate_passkey_finish(
             DBPasskey::get_by_credential_id(credential_id, &**pool)
                 .await
                 .wrap_internal_err("failed to fetch passkey")?
-                .ok_or_else(|| ApiError::Request(eyre!("passkey not found")))?;
+                .wrap_request_err_with(|| "passkey not found")?;
 
         let mut transaction = pool
             .begin()
@@ -3559,7 +3797,10 @@ pub async fn authenticate_passkey_finish(
                 )
                 .await
                 .wrap_internal_err("failed to invalidate user sessions")?;
-                transaction.commit().await?;
+                transaction
+                    .commit()
+                    .await
+                    .wrap_internal_err("committing database transaction")?;
                 DBSession::clear_cache(
                     sessions
                         .into_iter()
@@ -3605,10 +3846,14 @@ pub async fn authenticate_passkey_finish(
             &redis,
             None,
         )
-        .await?;
+        .await
+        .wrap_auth_err("authenticating API request")?;
         let res = crate::models::sessions::Session::from(session, true, None);
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         Ok(web::Json(res))
     } else {
         Err(ApiError::Request(eyre!(
@@ -3643,7 +3888,8 @@ pub async fn list_passkeys(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let passkeys = DBPasskey::get_for_user(user.id.into(), &**pool)
@@ -3696,29 +3942,36 @@ pub async fn rename_passkey(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    body.validate().map_err(|err| {
-        ApiError::InvalidInput(validation_errors_to_string(err, None))
-    })?;
+    body.validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let id = DBPasskeyId(
         parse_base62(&info.into_inner().0)
             .wrap_request_err("invalid passkey id")? as i64,
     );
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let found =
         DBPasskey::rename(id, user.id.into(), &body.name, &mut transaction)
             .await
             .wrap_internal_err("failed to rename passkey")?;
     if !found {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     Ok(HttpResponse::NoContent().finish())
 }
 
@@ -3749,7 +4002,8 @@ pub async fn delete_passkey(
         &session_queue,
         Scopes::USER_AUTH_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let id = DBPasskeyId(
@@ -3757,16 +4011,22 @@ pub async fn delete_passkey(
             .wrap_request_err("invalid passkey id")? as i64,
     );
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let found =
         DBPasskey::remove_for_user(id, user.id.into(), &mut transaction)
             .await
             .wrap_internal_err("failed to delete passkey")?;
     if !found {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     Ok(HttpResponse::NoContent().finish())
 }
diff --git a/apps/labrinth/src/routes/internal/gdpr.rs b/apps/labrinth/src/routes/internal/gdpr.rs
index de25c7746d..479209bd17 100644
--- a/apps/labrinth/src/routes/internal/gdpr.rs
+++ b/apps/labrinth/src/routes/internal/gdpr.rs
@@ -3,6 +3,7 @@ use crate::database::PgPool;
 use crate::models::pats::Scopes;
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 use actix_web::{HttpRequest, HttpResponse, post, web};
 use xredis::RedisPool;
 
@@ -30,46 +31,52 @@ pub async fn export(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let user_id = user.id.into();
 
     let collection_ids =
         crate::database::models::DBUser::get_collections(user_id, &**pool)
-            .await?;
+            .await
+            .wrap_internal_err("fetching users from database")?;
     let collections = crate::database::models::DBCollection::get_many(
         &collection_ids,
         &**pool,
         &redis,
     )
-    .await?
+    .await
+    .wrap_internal_err("fetching collections from database")?
     .into_iter()
     .map(crate::models::collections::Collection::from)
     .collect::<Vec<_>>();
 
     let follows =
         crate::database::models::DBUser::get_follows(user_id, &**pool)
-            .await?
+            .await
+            .wrap_internal_err("fetching users from database")?
             .into_iter()
             .map(crate::models::ids::ProjectId::from)
             .collect::<Vec<_>>();
 
     let projects =
         crate::database::models::DBUser::get_projects(user_id, &**pool, &redis)
-            .await?
+            .await
+            .wrap_internal_err("fetching users from database")?
             .into_iter()
             .map(crate::models::ids::ProjectId::from)
             .collect::<Vec<_>>();
 
     let org_ids =
         crate::database::models::DBUser::get_organizations(user_id, &**pool)
-            .await?;
+            .await
+            .wrap_internal_err("fetching users from database")?;
     let orgs =
         crate::database::models::organization_item::DBOrganization::get_many_ids(
             &org_ids, &**pool, &redis,
         )
-        .await?
+        .await.wrap_internal_err("fetching organizations from database")?
         .into_iter()
         // TODO: add team members
         .map(|x| crate::models::organizations::Organization::from(x, vec![]))
@@ -78,7 +85,7 @@ pub async fn export(
     let notifs = crate::database::models::notification_item::DBNotification::get_all_user(
         user_id, &**pool,
     )
-    .await?
+    .await.wrap_internal_err("fetching notifications from database")?
     .into_iter()
     .map(crate::models::notifications::Notification::from)
     .collect::<Vec<_>>();
@@ -86,7 +93,7 @@ pub async fn export(
     let notifs_deliveries = crate::database::models::notifications_deliveries_item::DBNotificationDelivery::get_all_user(
         user_id, &**pool,
     )
-    .await?
+    .await.wrap_internal_err("fetching notification deliveries from database")?
     .into_iter()
     .map(crate::models::notifications::NotificationDelivery::from)
     .collect::<Vec<_>>();
@@ -95,7 +102,7 @@ pub async fn export(
         crate::database::models::oauth_client_item::DBOAuthClient::get_all_user_clients(
             user_id, &**pool,
         )
-        .await?
+        .await.wrap_internal_err("fetching OAuth clients from database")?
         .into_iter()
         .map(crate::models::oauth_clients::OAuthClient::from)
         .collect::<Vec<_>>();
@@ -103,7 +110,7 @@ pub async fn export(
     let oauth_authorizations = crate::database::models::oauth_client_authorization_item::DBOAuthClientAuthorization::get_all_for_user(
         user_id, &**pool,
     )
-        .await?
+        .await.wrap_internal_err("fetching OAuth client authorizations from database")?
         .into_iter()
         .map(crate::models::oauth_clients::OAuthClientAuthorization::from)
         .collect::<Vec<_>>();
@@ -112,12 +119,13 @@ pub async fn export(
         crate::database::models::pat_item::DBPersonalAccessToken::get_user_pats(
             user_id, &**pool, &redis,
         )
-        .await?;
+        .await.wrap_internal_err("fetching personal access tokens from database")?;
     let pats =
         crate::database::models::pat_item::DBPersonalAccessToken::get_many_ids(
             &pat_ids, &**pool, &redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching personal access tokens from database")?
         .into_iter()
         .map(|x| crate::models::pats::PersonalAccessToken::from(x, false))
         .collect::<Vec<_>>();
@@ -126,13 +134,15 @@ pub async fn export(
         crate::database::models::payout_item::DBPayout::get_all_for_user(
             user_id, &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching payouts from database")?;
 
     let payouts = crate::database::models::payout_item::DBPayout::get_many(
         &payout_ids,
         &**pool,
     )
-    .await?
+    .await
+    .wrap_internal_err("fetching payouts from database")?
     .into_iter()
     .map(crate::models::payouts::Payout::from)
     .collect::<Vec<_>>();
@@ -140,12 +150,14 @@ pub async fn export(
     let report_ids = crate::database::models::user_item::DBUser::get_reports(
         user_id, &**pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching users from database")?;
     let reports = crate::database::models::report_item::DBReport::get_many(
         &report_ids,
         &**pool,
     )
-    .await?
+    .await
+    .wrap_internal_err("fetching reports from database")?
     .into_iter()
     .map(crate::models::reports::Report::from)
     .collect::<Vec<_>>();
@@ -157,7 +169,7 @@ pub async fn export(
         user_id.0
     )
     .fetch_all(pool.as_ref())
-    .await?
+    .await.wrap_internal_err("fetching message IDs from database")?
     .into_iter()
     .map(|x| crate::database::models::ids::DBThreadMessageId(x.id))
     .collect::<Vec<_>>();
@@ -167,7 +179,8 @@ pub async fn export(
             &message_ids,
             &**pool,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching thread messages from database")?
         .into_iter()
         .map(|x| crate::models::threads::ThreadMessage::from(x, &user))
         .collect::<Vec<_>>();
@@ -177,7 +190,8 @@ pub async fn export(
         user_id.0
     )
     .fetch_all(pool.as_ref())
-    .await?
+    .await
+    .wrap_internal_err("fetching uploaded images IDs from database")?
     .into_iter()
     .map(|x| crate::database::models::ids::DBImageId(x.id))
     .collect::<Vec<_>>();
@@ -188,7 +202,8 @@ pub async fn export(
             &**pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching images from database")?
         .into_iter()
         .map(crate::models::images::Image::from)
         .collect::<Vec<_>>();
@@ -197,7 +212,7 @@ pub async fn export(
         crate::database::models::user_subscription_item::DBUserSubscription::get_all_user(
             user_id, &**pool,
         )
-        .await?
+        .await.wrap_internal_err("fetching user subscriptions from database")?
         .into_iter()
         .map(crate::models::billing::UserSubscription::from)
         .collect::<Vec<_>>();
diff --git a/apps/labrinth/src/routes/internal/medal.rs b/apps/labrinth/src/routes/internal/medal.rs
index 67c8f637dc..c443e19e75 100644
--- a/apps/labrinth/src/routes/internal/medal.rs
+++ b/apps/labrinth/src/routes/internal/medal.rs
@@ -1,4 +1,5 @@
 use crate::database::PgPool;
+use crate::util::error::Context as _;
 use actix_web::{HttpResponse, post, web};
 use ariadne::ids::UserId;
 use chrono::Utc;
@@ -45,10 +46,11 @@ pub async fn verify(
             &username,
             Offer::Medal,
         )
-        .await?;
+        .await
+        .wrap_internal_err("executing `RedeemalLookupFields::redeemal_status_by_username_and_offer`")?;
 
     match maybe_fields {
-        None => Err(ApiError::NotFound),
+        None => Err(ApiError::NotFound(eyre::eyre!("resource not found"))),
         Some(fields) => Ok(HttpResponse::Ok().json(VerifyResponse {
             user_id: fields.user_id.into(),
             redeemed: fields.redeemal_status.is_some(),
@@ -71,7 +73,10 @@ pub async fn redeem(
     // Check the offer hasn't been redeemed yet, then insert into the table.
     // In a transaction to avoid double inserts.
 
-    let mut txn = pool.begin().await?;
+    let mut txn = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let maybe_fields =
         RedeemalLookupFields::redeemal_status_by_username_and_offer(
@@ -79,15 +84,18 @@ pub async fn redeem(
             &username,
             Offer::Medal,
         )
-        .await?;
+        .await
+        .wrap_internal_err("executing `RedeemalLookupFields::redeemal_status_by_username_and_offer`")?;
 
     let user_id = match maybe_fields {
-        None => return Err(ApiError::NotFound),
+        None => {
+            return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
+        }
         Some(fields) => {
             if fields.redeemal_status.is_some() {
-                return Err(ApiError::Conflict(
-                    "User already redeemed this offer".to_string(),
-                ));
+                return Err(ApiError::Conflict(eyre::eyre!(
+                    "User already redeemed this offer",
+                )));
             }
 
             fields.user_id
@@ -105,9 +113,14 @@ pub async fn redeem(
         n_attempts: 0,
     };
 
-    redeemal.insert(&mut txn).await?;
+    redeemal
+        .insert(&mut txn)
+        .await
+        .wrap_internal_err("inserting database records for `redeem`")?;
 
-    txn.commit().await?;
+    txn.commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     // Immediately try to process the redeemal
     if let Err(error) = try_process_user_redeemal(&pool, &redis, redeemal).await
diff --git a/apps/labrinth/src/routes/internal/moderation/external_license.rs b/apps/labrinth/src/routes/internal/moderation/external_license.rs
index 493a866b59..84ae825b04 100644
--- a/apps/labrinth/src/routes/internal/moderation/external_license.rs
+++ b/apps/labrinth/src/routes/internal/moderation/external_license.rs
@@ -1,3 +1,5 @@
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use std::collections::HashMap;
 
 use actix_web::{HttpRequest, get, patch, post, web};
@@ -99,9 +101,9 @@ impl LicenseId {
         match self {
             LicenseId::Number(id) => Ok(id),
             LicenseId::String(id) => id.parse().map_err(|_| {
-                ApiError::InvalidInput(
-                    "license_id must be a valid integer".to_string(),
-                )
+                ApiError::Request(eyre::eyre!(
+                    "license_id must be a valid integer",
+                ))
             }),
         }
     }
@@ -143,9 +145,9 @@ fn normalize_sha1_hashes(hashes: &[String]) -> Result<Vec<String>, ApiError> {
             let hash = hash.trim().to_lowercase();
             if hash.len() != 40 || !hash.chars().all(|c| c.is_ascii_hexdigit())
             {
-                return Err(ApiError::InvalidInput(
-                    "hash must be a valid SHA1 hex string".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "hash must be a valid SHA1 hex string",
+                )));
             }
 
             Ok(hash)
@@ -196,7 +198,8 @@ async fn fetch_linked_files(
         license_ids,
     )
     .fetch_all(pool)
-    .await?;
+    .await
+    .wrap_internal_err("fetching file rows from database")?;
 
     let mut map: HashMap<i64, Vec<LinkedFile>> = HashMap::new();
     for row in file_rows {
@@ -247,10 +250,12 @@ async fn fetch_by_hashes(
         &hash_bytes,
     )
     .fetch_all(pool)
-    .await?;
+    .await.wrap_internal_err("querying database for `fetch_by_hashes`")?;
 
     let license_ids = rows.iter().map(|row| row.id).collect::<Vec<_>>();
-    let files_map = fetch_linked_files(pool, &license_ids).await?;
+    let files_map = fetch_linked_files(pool, &license_ids)
+        .await
+        .wrap_api_err("fetching linked files")?;
 
     let mut results = HashMap::new();
     for row in rows {
@@ -309,10 +314,13 @@ async fn fetch_by_flame_ids(
         flame_ids,
     )
     .fetch_all(pool)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `fetch_by_flame_ids`")?;
 
     let license_ids = rows.iter().map(|row| row.id).collect::<Vec<_>>();
-    let files_map = fetch_linked_files(pool, &license_ids).await?;
+    let files_map = fetch_linked_files(pool, &license_ids)
+        .await
+        .wrap_api_err("fetching linked files")?;
 
     let mut results: HashMap<i32, Vec<ExternalProject>> = HashMap::new();
     for row in rows {
@@ -350,7 +358,8 @@ pub async fn search(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating external license search")?;
 
     let rows = sqlx::query_as!(
         LicenseRow,
@@ -381,10 +390,13 @@ pub async fn search(
         body.flame_ids.as_deref(),
     )
     .fetch_all(&**pool)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `search`")?;
 
     let license_ids: Vec<i64> = rows.iter().map(|r| r.id).collect();
-    let files_map = fetch_linked_files(&pool, &license_ids).await?;
+    let files_map = fetch_linked_files(&pool, &license_ids)
+        .await
+        .wrap_api_err("fetching linked files")?;
 
     let results = rows
         .into_iter()
@@ -419,12 +431,18 @@ pub async fn lookup(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let body = body.into_inner();
-    let hashes = normalize_sha1_hashes(&body.hashes)?;
-    let flame_ids = fetch_by_flame_ids(&pool, &body.flame_ids).await?;
-    let hashes = fetch_by_hashes(&pool, &hashes).await?;
+    let hashes = normalize_sha1_hashes(&body.hashes)
+        .wrap_api_err("executing `normalize_sha1_hashes`")?;
+    let flame_ids = fetch_by_flame_ids(&pool, &body.flame_ids)
+        .await
+        .wrap_api_err("fetching by flame ids")?;
+    let hashes = fetch_by_hashes(&pool, &hashes)
+        .await
+        .wrap_api_err("fetching by hashes")?;
 
     Ok(web::Json(ExternalLicenseLookupResponse {
         flame_ids,
@@ -453,12 +471,18 @@ pub async fn get_by_sha1(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    let hashes = normalize_sha1_hashes(&[path.into_inner().0])?;
-    let hash = hashes.first().ok_or(ApiError::NotFound)?;
-    let mut results = fetch_by_hashes(&pool, &hashes).await?;
-    let result = results.remove(hash).ok_or(ApiError::NotFound)?;
+    let hashes = normalize_sha1_hashes(&[path.into_inner().0])
+        .wrap_api_err("normalizing SHA-1 hash")?;
+    let hash = hashes.first().wrap_not_found_err("resource not found")?;
+    let mut results = fetch_by_hashes(&pool, &hashes)
+        .await
+        .wrap_api_err("fetching by hashes")?;
+    let result = results
+        .remove(hash)
+        .wrap_not_found_err("resource not found")?;
 
     Ok(web::Json(result))
 }
@@ -484,10 +508,14 @@ pub async fn get_by_sha1_bulk(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    let hashes = normalize_sha1_hashes(&body.hashes)?;
-    let results = fetch_by_hashes(&pool, &hashes).await?;
+    let hashes = normalize_sha1_hashes(&body.hashes)
+        .wrap_api_err("executing `normalize_sha1_hashes`")?;
+    let results = fetch_by_hashes(&pool, &hashes)
+        .await
+        .wrap_api_err("fetching by hashes")?;
 
     Ok(web::Json(results))
 }
@@ -540,16 +568,21 @@ async fn upsert_file_license(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let body = body.into_inner();
-    let license_id = body.license_id.parse()?;
+    let license_id = body
+        .license_id
+        .parse()
+        .wrap_api_err("parsing external license ID")?;
     if body.hashes.is_empty() {
-        return Err(ApiError::InvalidInput(
-            "hashes must contain at least one SHA1 hex string".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "hashes must contain at least one SHA1 hex string",
+        )));
     }
-    let hashes = normalize_sha1_hashes(&body.hashes)?;
+    let hashes = normalize_sha1_hashes(&body.hashes)
+        .wrap_api_err("executing `normalize_sha1_hashes`")?;
     let hash_bytes = hashes
         .iter()
         .map(|hash| hash.as_bytes().to_vec())
@@ -557,7 +590,10 @@ async fn upsert_file_license(
     let filenames = vec![None; hashes.len()];
     let license_ids = vec![license_id; hashes.len()];
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let license = sqlx::query!(
         r#"
@@ -579,8 +615,9 @@ async fn upsert_file_license(
         license_id,
     )
     .fetch_optional(&mut transaction)
-    .await?
-    .ok_or(ApiError::NotFound)?;
+    .await
+    .wrap_internal_err("fetching license from database")?
+    .wrap_not_found_err("resource not found")?;
 
     ExternalLicense::insert_files(
         &mut transaction,
@@ -589,11 +626,19 @@ async fn upsert_file_license(
         &license_ids,
         DBUserId(user.id.0 as i64),
     )
-    .await?;
+    .await
+    .wrap_internal_err(
+        "inserting database records for `upsert_file_license`",
+    )?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
-    let files_map = fetch_linked_files(&pool, &[license_id]).await?;
+    let files_map = fetch_linked_files(&pool, &[license_id])
+        .await
+        .wrap_api_err("fetching linked files")?;
     let linked_files = files_map.get(&license_id).cloned().unwrap_or_default();
 
     Ok(web::Json(
@@ -636,7 +681,8 @@ pub async fn update_license(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let id = path.into_inner().0;
 
@@ -666,10 +712,13 @@ pub async fn update_license(
         user.id.0 as i64,
     )
     .fetch_optional(&**pool)
-    .await?
-    .ok_or(ApiError::NotFound)?;
+    .await
+    .wrap_internal_err("querying database for `update_license`")?
+    .wrap_not_found_err("resource not found")?;
 
-    let files_map = fetch_linked_files(&pool, &[id]).await?;
+    let files_map = fetch_linked_files(&pool, &[id])
+        .await
+        .wrap_api_err("fetching linked files")?;
     let linked_files = files_map.get(&id).cloned().unwrap_or_default();
 
     Ok(web::Json(
diff --git a/apps/labrinth/src/routes/internal/moderation/mod.rs b/apps/labrinth/src/routes/internal/moderation/mod.rs
index aecce43cbb..b6d28c760a 100644
--- a/apps/labrinth/src/routes/internal/moderation/mod.rs
+++ b/apps/labrinth/src/routes/internal/moderation/mod.rs
@@ -8,6 +8,7 @@ use crate::models::ids::{OrganizationId, ProjectId};
 use crate::models::projects::{ProjectStatus, VersionStatus};
 use crate::queue::moderation::{ApprovalType, IdentifiedFile, MissingMetadata};
 use crate::queue::session::AuthQueue;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use crate::{
     auth::{check_is_moderator_from_headers, get_user_from_bearer_token},
@@ -254,7 +255,8 @@ pub async fn get_projects_internal(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let request_opts = request_opts.into_inner();
     let query = normalize_optional_string(request_opts.query.as_deref());
@@ -518,7 +520,9 @@ pub async fn get_projects_internal(
                 row.owner_icon_url,
                 row.project_types,
                 row.external_dependencies_count,
-            )? {
+            )
+            .wrap_api_err("executing `row_to_queue_project`")?
+            {
                 projects.push(project);
             }
         }
@@ -693,7 +697,9 @@ pub async fn get_projects_internal(
                 row.owner_icon_url,
                 row.project_types,
                 row.external_dependencies_count,
-            )? {
+            )
+            .wrap_api_err("executing `row_to_queue_project`")?
+            {
                 projects.push(project);
             }
         }
@@ -731,7 +737,8 @@ pub async fn get_project_ids(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let request_opts = request_opts.into_inner();
     let query = normalize_optional_string(request_opts.query.as_deref());
@@ -978,7 +985,8 @@ fn row_to_queue_project(
         owner_id,
         owner_name,
         owner_icon_url,
-    )?;
+    )
+    .wrap_api_err("executing `row_to_ownership`")?;
 
     Ok(Some(ModerationQueueProject {
         id: project_id,
@@ -1076,11 +1084,14 @@ pub async fn get_project_meta(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let project_id = info.into_inner().0;
     let project =
-        database::models::DBProject::get(&project_id, &**pool, &redis).await?;
+        database::models::DBProject::get(&project_id, &**pool, &redis)
+            .await
+            .wrap_api_err("fetching project from database")?;
 
     if let Some(project) = project {
         let rows = sqlx::query!(
@@ -1094,7 +1105,8 @@ pub async fn get_project_meta(
             project.inner.id.0
         )
         .fetch_all(&**pool)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `get_project_meta`")?;
 
         let mut merged = MissingMetadata {
             identified: HashMap::new(),
@@ -1134,7 +1146,7 @@ pub async fn get_project_meta(
                 .collect::<Vec<_>>()
         )
         .fetch_all(&**pool)
-        .await?;
+        .await.wrap_internal_err("querying database for `get_project_meta`")?;
 
         for row in rows {
             if let Some(sha1) = row.sha1 {
@@ -1169,7 +1181,8 @@ pub async fn get_project_meta(
             &check_flames,
         )
         .fetch_all(&**pool)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `get_project_meta`")?;
 
         for row in rows {
             if let Some(sha1) = merged
@@ -1192,7 +1205,7 @@ pub async fn get_project_meta(
 
         Ok(web::Json(merged))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1234,9 +1247,13 @@ pub async fn set_project_meta(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let mut licenses = Vec::new();
     let mut file_hashes = Vec::new();
@@ -1287,7 +1304,8 @@ pub async fn set_project_meta(
         &licenses,
         user_id,
     )
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `set_project_meta`")?;
 
     moderation_external_item::ExternalLicense::insert_files(
         &mut transaction,
@@ -1299,9 +1317,13 @@ pub async fn set_project_meta(
         &file_license_ids,
         user_id,
     )
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `set_project_meta`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(())
 }
@@ -1331,18 +1353,23 @@ pub async fn acquire_lock(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let project_id_str = path.into_inner().0;
     let project =
         database::models::DBProject::get(&project_id_str, &**pool, &redis)
-            .await?
-            .ok_or(ApiError::NotFound)?;
+            .await
+            .wrap_api_err("fetching project from database")?
+            .wrap_not_found_err("resource not found")?;
 
     let db_project_id = project.inner.id;
     let db_user_id = database::models::DBUserId::from(user.id);
 
-    match DBModerationLock::acquire(db_project_id, db_user_id, &pool).await? {
+    match DBModerationLock::acquire(db_project_id, db_user_id, &pool)
+        .await
+        .wrap_internal_err("executing `DBModerationLock::acquire`")?
+    {
         Ok(()) => Ok(web::Json(LockAcquireResponse {
             success: true,
             is_own_lock: true,
@@ -1390,18 +1417,22 @@ pub async fn override_lock(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let project_id_str = path.into_inner().0;
     let project =
         database::models::DBProject::get(&project_id_str, &**pool, &redis)
-            .await?
-            .ok_or(ApiError::NotFound)?;
+            .await
+            .wrap_api_err("fetching project from database")?
+            .wrap_not_found_err("resource not found")?;
 
     let db_project_id = project.inner.id;
     let db_user_id = database::models::DBUserId::from(user.id);
 
-    DBModerationLock::force_acquire(db_project_id, db_user_id, &pool).await?;
+    DBModerationLock::force_acquire(db_project_id, db_user_id, &pool)
+        .await
+        .wrap_internal_err("executing `DBModerationLock::force_acquire`")?;
 
     Ok(web::Json(LockAcquireResponse {
         success: true,
@@ -1437,18 +1468,23 @@ pub async fn get_lock_status(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let project_id_str = path.into_inner().0;
     let project =
         database::models::DBProject::get(&project_id_str, &**pool, &redis)
-            .await?
-            .ok_or(ApiError::NotFound)?;
+            .await
+            .wrap_api_err("fetching project from database")?
+            .wrap_not_found_err("resource not found")?;
 
     let db_project_id = project.inner.id;
     let db_user_id = database::models::DBUserId::from(user.id);
 
-    match DBModerationLock::get_with_user(db_project_id, &pool).await? {
+    match DBModerationLock::get_with_user(db_project_id, &pool)
+        .await
+        .wrap_internal_err("fetching moderation lock from database")?
+    {
         Some(lock) => {
             let is_own_lock = lock.moderator_id == db_user_id;
             Ok(web::Json(LockStatusResponse {
@@ -1499,19 +1535,22 @@ pub async fn release_lock(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let project_id_str = path.into_inner().0;
     let project =
         database::models::DBProject::get(&project_id_str, &**pool, &redis)
-            .await?
-            .ok_or(ApiError::NotFound)?;
+            .await
+            .wrap_api_err("fetching project from database")?
+            .wrap_not_found_err("resource not found")?;
 
     let db_project_id = project.inner.id;
     let db_user_id = database::models::DBUserId::from(user.id);
 
-    let released =
-        DBModerationLock::release(db_project_id, db_user_id, &pool).await?;
+    let released = DBModerationLock::release(db_project_id, db_user_id, &pool)
+        .await
+        .wrap_internal_err("executing `DBModerationLock::release`")?;
 
     let _ = DBModerationLock::cleanup_expired(&pool).await;
 
@@ -1547,9 +1586,9 @@ pub async fn release_lock_beacon(
 ) -> Result<web::Json<LockReleaseResponse>, ApiError> {
     let token = body.trim();
     if token.is_empty() {
-        return Err(ApiError::InvalidInput(
-            "missing token in request body".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "missing token in request body",
+        )));
     }
     let token = token.strip_prefix("Bearer ").unwrap_or(token).trim();
 
@@ -1561,30 +1600,33 @@ pub async fn release_lock_beacon(
         &session_queue,
         false,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     if !scopes.contains(Scopes::PROJECT_WRITE) {
-        return Err(ApiError::CustomAuthentication(
-            "token is missing required scopes".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "token is missing required scopes",
+        )));
     }
     if !user.role.is_mod() {
-        return Err(ApiError::CustomAuthentication(
-            "only moderators may release moderation locks".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "only moderators may release moderation locks",
+        )));
     }
 
     let project_id_str = path.into_inner().0;
     let project =
         database::models::DBProject::get(&project_id_str, &**pool, &redis)
-            .await?
-            .ok_or(ApiError::NotFound)?;
+            .await
+            .wrap_api_err("fetching project from database")?
+            .wrap_not_found_err("resource not found")?;
 
     let db_project_id = project.inner.id;
     let db_user_id = database::models::DBUserId::from(user.id);
 
-    let released =
-        DBModerationLock::release(db_project_id, db_user_id, &pool).await?;
+    let released = DBModerationLock::release(db_project_id, db_user_id, &pool)
+        .await
+        .wrap_internal_err("executing `DBModerationLock::release`")?;
 
     let _ = DBModerationLock::cleanup_expired(&pool).await;
 
@@ -1614,16 +1656,19 @@ pub async fn delete_all_locks(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if !user.role.is_admin() {
-        return Err(ApiError::CustomAuthentication(
-            "You must be an admin to delete all locks".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You must be an admin to delete all locks",
+        )));
     }
 
-    let deleted_count = DBModerationLock::delete_all(&pool).await?;
+    let deleted_count = DBModerationLock::delete_all(&pool)
+        .await
+        .wrap_internal_err("deleting moderation locks from database")?;
 
     Ok(web::Json(DeleteAllLocksResponse { deleted_count }))
 }
diff --git a/apps/labrinth/src/routes/internal/moderation/tech_review.rs b/apps/labrinth/src/routes/internal/moderation/tech_review.rs
index ea694627eb..c55d8fdbc7 100644
--- a/apps/labrinth/src/routes/internal/moderation/tech_review.rs
+++ b/apps/labrinth/src/routes/internal/moderation/tech_review.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use std::{collections::HashMap, fmt};
 use xredis::RedisPool;
 
@@ -225,7 +226,8 @@ pub async fn get_issue(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let (issue_id,) = path.into_inner();
     let row = sqlx::query!(
@@ -261,7 +263,7 @@ pub async fn get_issue(
     .fetch_optional(&**pool)
     .await
     .wrap_internal_err("failed to fetch issue from database")?
-    .ok_or(ApiError::NotFound)?;
+    .wrap_not_found_err("resource not found")?;
 
     Ok(web::Json(row.data.0))
 }
@@ -288,7 +290,8 @@ pub async fn get_report(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let (report_id,) = path.into_inner();
 
@@ -348,7 +351,7 @@ pub async fn get_report(
     .fetch_optional(&**pool)
     .await
     .wrap_internal_err("failed to fetch report from database")?
-    .ok_or(ApiError::NotFound)?;
+    .wrap_not_found_err("resource not found")?;
 
     Ok(web::Json(row.data.0))
 }
@@ -703,7 +706,8 @@ pub async fn search_projects(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let sort_by = search_req.sort_by.to_string();
     let limit = search_req.limit.max(50);
@@ -819,8 +823,9 @@ pub async fn search_projects(
         thread_ids.push(row.thread_id);
     }
 
-    let project_reports =
-        fetch_project_reports(&project_ids, &pool, &redis).await?;
+    let project_reports = fetch_project_reports(&project_ids, &pool, &redis)
+        .await
+        .wrap_api_err("fetching project reports")?;
 
     let projects = DBProject::get_many_ids(&project_ids, &**pool, &redis)
         .await
@@ -913,7 +918,8 @@ pub async fn get_project_report(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let (project_id,) = path.into_inner();
     let db_project_id = DBProjectId::from(project_id);
@@ -929,10 +935,12 @@ pub async fn get_project_report(
     .fetch_optional(&**pool)
     .await
     .wrap_internal_err("failed to fetch thread")?
-    .ok_or(ApiError::NotFound)?;
+    .wrap_not_found_err("resource not found")?;
 
     let project_reports =
-        fetch_project_reports(&[db_project_id], &pool, &redis).await?;
+        fetch_project_reports(&[db_project_id], &pool, &redis)
+            .await
+            .wrap_api_err("fetching project reports")?;
 
     let project_report = project_reports.into_iter().next();
 
@@ -966,7 +974,7 @@ pub async fn get_project_report(
     let thread = threads
         .get(&row.thread_id.into())
         .cloned()
-        .ok_or(ApiError::NotFound)?;
+        .wrap_not_found_err("resource not found")?;
 
     Ok(web::Json(ProjectReportResponse {
         project_report,
@@ -988,8 +996,8 @@ pub struct SubmitReport {
 ///
 /// Before this is called, all issues for this project's reports must have been
 /// marked as either safe or unsafe. Otherwise, this will error with
-/// [`ApiError::TechReviewIssuesWithNoVerdict`], providing the issue IDs which
-/// are still unmarked.
+/// A request error is returned with the issue detail IDs which are still
+/// unmarked.
 #[utoipa::path(
 	context_path = "/moderation/tech-review",
 	tag = "moderation",
@@ -1013,7 +1021,8 @@ pub async fn submit_report(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
     let (project_id,) = path.into_inner();
     let project_id = DBProjectId::from(project_id);
 
@@ -1045,14 +1054,13 @@ pub async fn submit_report(
     .wrap_internal_err("failed to fetch pending issues")?;
 
     if !pending_issue_details.is_empty() {
-        return Err(ApiError::TechReviewDetailsWithNoVerdict {
-            details: pending_issue_details
-                .into_iter()
-                .map(|record| {
-                    DelphiReportIssueDetailsId(record.issue_detail_id)
-                })
-                .collect(),
-        });
+        let details = pending_issue_details
+            .into_iter()
+            .map(|record| DelphiReportIssueDetailsId(record.issue_detail_id))
+            .collect_vec();
+        return Err(ApiError::Request(eyre::eyre!(
+            "report still has issue details with no verdict: {details:?}"
+        )));
     }
 
     sqlx::query!(
@@ -1171,7 +1179,10 @@ pub async fn submit_report(
             None,
             None,
         )
-        .await?;
+        .await
+        .wrap_api_err(
+            "executing `projects::clear_project_cache_and_queue_search`",
+        )?;
     }
 
     Ok(())
@@ -1224,7 +1235,8 @@ pub async fn update_issue_details(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?;
+    .await
+    .wrap_auth_err("updating database records for `update_issue_details`")?;
 
     let mut txn = pool
         .begin()
@@ -1347,7 +1359,10 @@ pub async fn update_issue_details(
         TechReviewExitReason::Resolved,
         &mut txn,
     )
-    .await?;
+    .await
+    .wrap_api_err(
+        "executing `tech_review_sync::sync_project_tech_review_state`",
+    )?;
 
     txn.commit()
         .await
@@ -1381,7 +1396,10 @@ pub async fn update_global_issue_details(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?;
+    .await
+    .wrap_auth_err(
+        "updating database records for `update_global_issue_details`",
+    )?;
 
     let updates = update_reqs.into_inner();
 
@@ -1461,7 +1479,10 @@ pub async fn update_global_issue_details(
         TechReviewExitReason::Resolved,
         &mut txn,
     )
-    .await?;
+    .await
+    .wrap_api_err(
+        "executing `tech_review_sync::sync_detail_key_tech_review_state`",
+    )?;
 
     txn.commit()
         .await
@@ -1498,7 +1519,8 @@ pub async fn add_report(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?;
+    .await
+    .wrap_auth_err("inserting database records for `add_report`")?;
     let file_id = add_report.file_id;
 
     let mut txn = pool
diff --git a/apps/labrinth/src/routes/internal/moderation/tech_review/global.rs b/apps/labrinth/src/routes/internal/moderation/tech_review/global.rs
index c152d5c2f9..84fbe00fe3 100644
--- a/apps/labrinth/src/routes/internal/moderation/tech_review/global.rs
+++ b/apps/labrinth/src/routes/internal/moderation/tech_review/global.rs
@@ -148,7 +148,8 @@ pub async fn search_global_issue_details(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating global issue search")?;
 
     let query = search_req
         .query
@@ -370,7 +371,8 @@ pub async fn get_global_issue_detail(
         &session_queue,
         Scopes::PROJECT_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating global issue detail request")?;
 
     let detail_key = get_req.detail_key.trim();
     if detail_key.is_empty() {
@@ -404,7 +406,7 @@ pub async fn get_global_issue_detail(
     .fetch_optional(&**pool)
     .await
     .wrap_internal_err("failed to fetch global issue detail")?
-    .ok_or(ApiError::NotFound)?;
+    .wrap_not_found_err("resource not found")?;
 
     let local_rows = sqlx::query!(
         r#"
diff --git a/apps/labrinth/src/routes/internal/mural.rs b/apps/labrinth/src/routes/internal/mural.rs
index b78069de5c..ea29c29e38 100644
--- a/apps/labrinth/src/routes/internal/mural.rs
+++ b/apps/labrinth/src/routes/internal/mural.rs
@@ -22,7 +22,7 @@ pub async fn get_bank_details(
     let mural = payouts_queue.muralpay.load();
     let mural = mural
         .as_ref()
-        .wrap_internal_err("Mural API not available")?;
+        .wrap_internal_err("required Mural API is not available")?;
     let fiat_and_rail_codes = FiatAndRailCode::iter().collect::<Vec<_>>();
     let details = mural
         .client
diff --git a/apps/labrinth/src/routes/internal/pats.rs b/apps/labrinth/src/routes/internal/pats.rs
index 5c0d41b783..63e4f10eba 100644
--- a/apps/labrinth/src/routes/internal/pats.rs
+++ b/apps/labrinth/src/routes/internal/pats.rs
@@ -1,5 +1,6 @@
 use crate::database;
 use crate::database::models::generate_pat_id;
+use crate::util::error::Context as _;
 
 use crate::auth::get_user_from_headers;
 use crate::routes::ApiError;
@@ -18,7 +19,6 @@ use crate::database::models::notification_item::NotificationBuilder;
 use crate::models::notifications::NotificationBody;
 use crate::models::pats::{PersonalAccessToken, Scopes};
 use crate::queue::session::AuthQueue;
-use crate::util::validate::validation_errors_to_string;
 use serde::Deserialize;
 use validator::Validate;
 
@@ -54,7 +54,8 @@ pub async fn get_pats(
         &session_queue,
         Scopes::PAT_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let pat_ids =
@@ -63,11 +64,13 @@ pub async fn get_pats(
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching personal access tokens from database")?;
     let pats = database::models::pat_item::DBPersonalAccessToken::get_many_ids(
         &pat_ids, &**pool, &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching personal access tokens from database")?;
 
     Ok(HttpResponse::Ok().json(
         pats.into_iter()
@@ -104,19 +107,20 @@ pub async fn create_pat(
     redis: Data<RedisPool>,
     session_queue: Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    info.0.validate().map_err(|err| {
-        ApiError::InvalidInput(validation_errors_to_string(err, None))
-    })?;
+    info.0
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     if info.scopes.is_restricted() {
-        return Err(ApiError::InvalidInput(
-            "Invalid scopes requested!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Invalid scopes requested!",
+        )));
     }
     if info.expires < Utc::now() {
-        return Err(ApiError::InvalidInput(
-            "Expire date must be in the future!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Expire date must be in the future!",
+        )));
     }
 
     let user = get_user_from_headers(
@@ -126,12 +130,18 @@ pub async fn create_pat(
         &session_queue,
         Scopes::PAT_CREATE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
-    let id = generate_pat_id(&mut transaction).await?;
+    let id = generate_pat_id(&mut transaction)
+        .await
+        .wrap_internal_err("generating pat ID")?;
 
     let token = ChaCha20Rng::from_entropy()
         .sample_iter(&Alphanumeric)
@@ -152,7 +162,8 @@ pub async fn create_pat(
         last_used: None,
     }
     .insert(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `create_pat`")?;
 
     NotificationBuilder {
         body: NotificationBody::PatCreated {
@@ -160,14 +171,19 @@ pub async fn create_pat(
         },
     }
     .insert(user.id.into(), &mut transaction, &redis)
-    .await?;
-    transaction.commit().await?;
+    .await
+    .wrap_internal_err("inserting database records for `create_pat`")?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     database::models::pat_item::DBPersonalAccessToken::clear_cache(
         vec![(None, None, Some(user.id.into()))],
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::Ok().json(PersonalAccessToken {
         id: id.into(),
@@ -213,9 +229,10 @@ pub async fn edit_pat(
     redis: Data<RedisPool>,
     session_queue: Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    info.0.validate().map_err(|err| {
-        ApiError::InvalidInput(validation_errors_to_string(err, None))
-    })?;
+    info.0
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let user = get_user_from_headers(
         &req,
@@ -224,25 +241,30 @@ pub async fn edit_pat(
         &session_queue,
         Scopes::PAT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let id = id.into_inner().0;
     let pat = database::models::pat_item::DBPersonalAccessToken::get(
         &id, &**pool, &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching personal access token from database")?;
 
     if let Some(pat) = pat
         && pat.user_id == user.id.into()
     {
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         if let Some(scopes) = &info.scopes {
             if scopes.is_restricted() {
-                return Err(ApiError::InvalidInput(
-                    "Invalid scopes requested!".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "Invalid scopes requested!",
+                )));
             }
 
             sqlx::query!(
@@ -255,7 +277,8 @@ pub async fn edit_pat(
                 pat.id.0
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `edit_pat`")?;
         }
         if let Some(name) = &info.name {
             sqlx::query!(
@@ -268,13 +291,14 @@ pub async fn edit_pat(
                 pat.id.0
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `edit_pat`")?;
         }
         if let Some(expires) = &info.expires {
             if expires < &Utc::now() {
-                return Err(ApiError::InvalidInput(
-                    "Expire date must be in the future!".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "Expire date must be in the future!",
+                )));
             }
 
             sqlx::query!(
@@ -287,15 +311,20 @@ pub async fn edit_pat(
                 pat.id.0
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `edit_pat`")?;
         }
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         database::models::pat_item::DBPersonalAccessToken::clear_cache(
             vec![(Some(pat.id), Some(pat.access_token), Some(pat.user_id))],
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
     }
 
     Ok(HttpResponse::NoContent().finish())
@@ -330,29 +359,39 @@ pub async fn delete_pat(
         &session_queue,
         Scopes::PAT_DELETE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let id = id.into_inner().0;
     let pat = database::models::pat_item::DBPersonalAccessToken::get(
         &id, &**pool, &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching personal access token from database")?;
 
     if let Some(pat) = pat
         && pat.user_id == user.id.into()
     {
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
         database::models::pat_item::DBPersonalAccessToken::remove(
             pat.id,
             &mut transaction,
         )
-        .await?;
-        transaction.commit().await?;
+        .await
+        .wrap_internal_err("deleting personal access token from database")?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         database::models::pat_item::DBPersonalAccessToken::clear_cache(
             vec![(Some(pat.id), Some(pat.access_token), Some(pat.user_id))],
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
     }
 
     Ok(HttpResponse::NoContent().finish())
diff --git a/apps/labrinth/src/routes/internal/search.rs b/apps/labrinth/src/routes/internal/search.rs
index 6521a21800..04063ebfcc 100644
--- a/apps/labrinth/src/routes/internal/search.rs
+++ b/apps/labrinth/src/routes/internal/search.rs
@@ -1,3 +1,4 @@
+use crate::util::error::Context as _;
 use crate::util::guards::admin_key_guard;
 use crate::{
     routes::ApiError,
@@ -19,7 +20,12 @@ pub fn config(cfg: &mut actix_web::web::ServiceConfig) {
 pub async fn tasks(
     search: web::Data<dyn SearchBackend>,
 ) -> Result<web::Json<serde_json::Value>, ApiError> {
-    Ok(web::Json(search.tasks().await.map_err(ApiError::Internal)?))
+    Ok(web::Json(
+        search
+            .tasks()
+            .await
+            .wrap_internal_err("fetching search tasks")?,
+    ))
 }
 
 /// Cancel search tasks.  
@@ -36,6 +42,6 @@ pub async fn tasks_cancel(
     search
         .tasks_cancel(&body)
         .await
-        .map_err(ApiError::Internal)?;
+        .wrap_internal_err("cancelling search tasks")?;
     Ok(())
 }
diff --git a/apps/labrinth/src/routes/internal/server_ping.rs b/apps/labrinth/src/routes/internal/server_ping.rs
index f80961bc88..5847572ea5 100644
--- a/apps/labrinth/src/routes/internal/server_ping.rs
+++ b/apps/labrinth/src/routes/internal/server_ping.rs
@@ -44,7 +44,8 @@ pub async fn ping_minecraft_java(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let timeout = request.timeout_ms.map(Duration::from_millis);
     server_ping::ping_server(&request.address, timeout)
diff --git a/apps/labrinth/src/routes/internal/session.rs b/apps/labrinth/src/routes/internal/session.rs
index c6316a3bad..f7bd6f685c 100644
--- a/apps/labrinth/src/routes/internal/session.rs
+++ b/apps/labrinth/src/routes/internal/session.rs
@@ -9,6 +9,7 @@ use crate::models::pats::Scopes;
 use crate::models::sessions::Session;
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 use actix_web::http::header::AUTHORIZATION;
 use actix_web::web::Data;
 use actix_web::{HttpRequest, HttpResponse, delete, get, post, web};
@@ -159,20 +160,24 @@ pub async fn list(
         &session_queue,
         Scopes::SESSION_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let session = req
         .headers()
         .get(AUTHORIZATION)
         .and_then(|x| x.to_str().ok())
-        .ok_or_else(|| AuthenticationError::InvalidCredentials)?;
+        .ok_or_else(|| AuthenticationError::InvalidCredentials)
+        .wrap_auth_err("authenticating API request")?;
 
     let session_ids =
         DBSession::get_user_sessions(current_user.id.into(), &**pool, &redis)
-            .await?;
+            .await
+            .wrap_internal_err("fetching sessions from database")?;
     let sessions = DBSession::get_many_ids(&session_ids, &**pool, &redis)
-        .await?
+        .await
+        .wrap_internal_err("fetching sessions from database")?
         .into_iter()
         .filter(|x| x.expires > Utc::now())
         .map(|x| Session::from(x, false, Some(session)))
@@ -211,17 +216,28 @@ pub async fn delete(
         &session_queue,
         Scopes::SESSION_DELETE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    let session = DBSession::get(info.into_inner().0, &**pool, &redis).await?;
+    let session = DBSession::get(info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching session from database")?;
 
     if let Some(session) = session
         && session.user_id == current_user.id.into()
     {
-        let mut transaction = pool.begin().await?;
-        DBSession::remove(session.id, &mut transaction).await?;
-        transaction.commit().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
+        DBSession::remove(session.id, &mut transaction)
+            .await
+            .wrap_internal_err("deleting session from database")?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         DBSession::clear_cache(
             vec![(
                 Some(session.id),
@@ -230,7 +246,8 @@ pub async fn delete(
             )],
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
     }
 
     Ok(HttpResponse::NoContent().body(""))
@@ -258,16 +275,14 @@ pub async fn refresh(
         .headers()
         .get(AUTHORIZATION)
         .and_then(|x| x.to_str().ok())
-        .ok_or_else(|| {
-            ApiError::Authentication(AuthenticationError::InvalidCredentials)
-        })?;
+        .wrap_auth_err_with(|| AuthenticationError::InvalidCredentials)?;
 
     // We should ensure that the authorization given is a session token, and not some other type of token (like a PAT), since this endpoint is only for refreshing sessions.
     // This is done by checking the prefix of the token, which should be "mra_" for session tokens.
     if !session.starts_with("mra_") {
-        return Err(ApiError::Authentication(
+        return Err(ApiError::Auth(eyre::eyre!(
             AuthenticationError::InvalidCredentials,
-        ));
+        )));
     }
 
     let current_user = get_user_from_bearer_token(
@@ -278,23 +293,31 @@ pub async fn refresh(
         &session_queue,
         true, // Allow expired sessions, since we want to allow refreshing expired sessions
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    let session = DBSession::get(session, &**pool, &redis).await?;
+    let session = DBSession::get(session, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching session from database")?;
 
     if let Some(session) = session {
         if current_user.id != session.user_id.into()
             || session.refresh_expires < Utc::now()
         {
-            return Err(ApiError::Authentication(
+            return Err(ApiError::Auth(eyre::eyre!(
                 AuthenticationError::InvalidCredentials,
-            ));
+            )));
         }
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
-        DBSession::remove(session.id, &mut transaction).await?;
+        DBSession::remove(session.id, &mut transaction)
+            .await
+            .wrap_internal_err("deleting session from database")?;
         let new_session = issue_session(
             req,
             session.user_id,
@@ -302,8 +325,12 @@ pub async fn refresh(
             &redis,
             Some(session.refresh_expires),
         )
-        .await?;
-        transaction.commit().await?;
+        .await
+        .wrap_auth_err("authenticating API request")?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         DBSession::clear_cache(
             vec![(
                 Some(session.id),
@@ -312,12 +339,13 @@ pub async fn refresh(
             )],
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
         Ok(HttpResponse::Ok().json(Session::from(new_session, true, None)))
     } else {
-        Err(ApiError::Authentication(
+        Err(ApiError::Auth(eyre::eyre!(
             AuthenticationError::InvalidCredentials,
-        ))
+        )))
     }
 }
diff --git a/apps/labrinth/src/routes/internal/statuses.rs b/apps/labrinth/src/routes/internal/statuses.rs
index 160cdba9ba..62e4fde4d9 100644
--- a/apps/labrinth/src/routes/internal/statuses.rs
+++ b/apps/labrinth/src/routes/internal/statuses.rs
@@ -15,6 +15,7 @@ use crate::sync::friends::{FRIENDS_CHANNEL_NAME, RedisFriendsMessage};
 use crate::sync::status::{
     get_user_status, push_back_user_expiry, replace_user_status,
 };
+use crate::util::error::Context as _;
 use actix_web::web::{Data, Payload};
 use actix_web::{HttpRequest, HttpResponse, get, web};
 use actix_ws::Message;
@@ -67,15 +68,14 @@ pub async fn ws_init(
         &session_queue,
         false,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::Authentication(AuthenticationError::InvalidCredentials)
-    })?;
+    .await
+    .wrap_auth_err("authenticating API request")?
+    .wrap_auth_err_with(|| AuthenticationError::InvalidCredentials)?;
 
     if !scopes.contains(Scopes::SESSION_ACCESS) {
-        return Err(ApiError::Authentication(
+        return Err(ApiError::Auth(eyre::eyre!(
             AuthenticationError::InvalidCredentials,
-        ));
+        )));
     }
 
     let user = User::from_full(db_user);
@@ -93,7 +93,9 @@ pub async fn ws_init(
     };
 
     let friends =
-        DBFriend::get_user_friends(user.id.into(), Some(true), &**pool).await?;
+        DBFriend::get_user_friends(user.id.into(), Some(true), &**pool)
+            .await
+            .wrap_internal_err("fetching friends from database")?;
 
     let friend_statuses = if !friends.is_empty() {
         let db = db.clone();
@@ -127,11 +129,12 @@ pub async fn ws_init(
     };
 
     let _ = session
-        .text(serde_json::to_string(
-            &ServerToClientMessage::FriendStatuses {
+        .text(
+            serde_json::to_string(&ServerToClientMessage::FriendStatuses {
                 statuses: friend_statuses,
-            },
-        )?)
+            })
+            .wrap_request_err("serializing friend statuses")?,
+        )
         .await;
 
     let unread_launcher_invites =
@@ -140,7 +143,8 @@ pub async fn ws_init(
             &**pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching notifications from database")?
         .into_iter()
         .filter(|notification| {
             !notification.read
@@ -153,7 +157,12 @@ pub async fn ws_init(
         .map(Notification::from);
 
     for notification in unread_launcher_invites {
-        let _ = session.text(serde_json::to_string(&notification)?).await;
+        let _ = session
+            .text(
+                serde_json::to_string(&notification)
+                    .wrap_request_err("serializing launcher notification")?,
+            )
+            .await;
     }
 
     let db = db.clone();
@@ -168,12 +177,15 @@ pub async fn ws_init(
     #[cfg(debug_assertions)]
     tracing::info!("Connection {socket_id} opened by {}", user.id);
 
-    replace_user_status(None, Some(&status), &redis).await?;
+    replace_user_status(None, Some(&status), &redis)
+        .await
+        .wrap_internal_err("reading HTTP response body")?;
     broadcast_friends_message(
         &redis,
         RedisFriendsMessage::StatusUpdate { status },
     )
-    .await?;
+    .await
+    .wrap_internal_err("reading HTTP response body")?;
 
     let (shutdown_sender, mut shutdown_receiver) =
         tokio::sync::oneshot::channel::<()>();
diff --git a/apps/labrinth/src/routes/maven.rs b/apps/labrinth/src/routes/maven.rs
index bc351ccb03..a10e7d724c 100644
--- a/apps/labrinth/src/routes/maven.rs
+++ b/apps/labrinth/src/routes/maven.rs
@@ -11,6 +11,8 @@ use crate::models::pats::Scopes;
 use crate::models::projects::FileType;
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context;
 use crate::{auth::get_user_from_headers, database};
 use actix_web::{HttpRequest, HttpResponse, get, route, web};
 use quick_xml::escape::escape;
@@ -85,9 +87,11 @@ pub async fn maven_metadata(
 ) -> Result<HttpResponse, ApiError> {
     let project_id = params.into_inner().0;
     let Some(project) =
-        database::models::DBProject::get(&project_id, &**pool, &redis).await?
+        database::models::DBProject::get(&project_id, &**pool, &redis)
+            .await
+            .wrap_api_err("fetching Maven project")?
     else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
     let user_option = get_user_from_headers(
@@ -101,8 +105,11 @@ pub async fn maven_metadata(
     .map(|x| x.1)
     .ok();
 
-    if !is_visible_project(&project.inner, &user_option, &pool, false).await? {
-        return Err(ApiError::NotFound);
+    if !is_visible_project(&project.inner, &user_option, &pool, false)
+        .await
+        .wrap_api_err("checking project visibility")?
+    {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     let version_names = sqlx::query!(
@@ -119,7 +126,8 @@ pub async fn maven_metadata(
             .collect::<Vec<String>>(),
     )
     .fetch_all(&**pool)
-    .await?;
+    .await
+    .wrap_internal_err("fetching version names from database")?;
 
     let mut new_versions = Vec::new();
     let mut vals = HashSet::new();
@@ -162,9 +170,11 @@ pub async fn maven_metadata(
         },
     };
 
-    Ok(HttpResponse::Ok()
-        .content_type("text/xml")
-        .body(yaserde::ser::to_string(&respdata).map_err(ApiError::Xml)?))
+    Ok(HttpResponse::Ok().content_type("text/xml").body(
+        yaserde::ser::to_string(&respdata)
+            .map_err(eyre::Report::msg)
+            .wrap_internal_err("serializing Maven metadata as XML")?,
+    ))
 }
 
 async fn find_version(
@@ -179,7 +189,8 @@ async fn find_version(
 
     let all_versions =
         database::models::DBVersion::get_many(&project.versions, pool, redis)
-            .await?;
+            .await
+            .wrap_internal_err("fetching versions from database")?;
 
     let exact_matches = all_versions
         .iter()
@@ -199,7 +210,8 @@ async fn find_version(
     };
 
     let db_loaders: HashSet<String> = Loader::list(pool, redis)
-        .await?
+        .await
+        .wrap_internal_err("fetching loader from Redis")?
         .into_iter()
         .map(|x| x.loader)
         .collect();
@@ -310,9 +322,11 @@ pub async fn version_file(
 ) -> Result<HttpResponse, ApiError> {
     let (project_id, vnum, file) = params.into_inner();
     let Some(project) =
-        database::models::DBProject::get(&project_id, &**pool, &redis).await?
+        database::models::DBProject::get(&project_id, &**pool, &redis)
+            .await
+            .wrap_api_err("fetching Maven project")?
     else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
     let user_option = get_user_from_headers(
@@ -326,17 +340,25 @@ pub async fn version_file(
     .map(|x| x.1)
     .ok();
 
-    if !is_visible_project(&project.inner, &user_option, &pool, false).await? {
-        return Err(ApiError::NotFound);
+    if !is_visible_project(&project.inner, &user_option, &pool, false)
+        .await
+        .wrap_api_err("checking project visibility")?
+    {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
-    let Some(version) = find_version(&project, &vnum, &pool, &redis).await?
+    let Some(version) = find_version(&project, &vnum, &pool, &redis)
+        .await
+        .wrap_api_err("fetching Maven version")?
     else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
-    if !is_visible_version(&version.inner, &user_option, &pool, &redis).await? {
-        return Err(ApiError::NotFound);
+    if !is_visible_version(&version.inner, &user_option, &pool, &redis)
+        .await
+        .wrap_api_err("checking version visibility")?
+    {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     if file.eq_ignore_ascii_case(&format!("{}-{}.pom", &project_id, &vnum)) {
@@ -352,9 +374,11 @@ pub async fn version_file(
             name: project.inner.name,
             description: escape(project.inner.summary).into_owned(),
         };
-        return Ok(HttpResponse::Ok()
-            .content_type("text/xml")
-            .body(yaserde::ser::to_string(&respdata).map_err(ApiError::Xml)?));
+        return Ok(HttpResponse::Ok().content_type("text/xml").body(
+            yaserde::ser::to_string(&respdata)
+                .map_err(eyre::Report::msg)
+                .wrap_internal_err("serializing Maven project as XML")?,
+        ));
     } else if let Some(selected_file) =
         find_file(&project_id, &vnum, &version, &file)
     {
@@ -363,7 +387,7 @@ pub async fn version_file(
             .body(""));
     }
 
-    Err(ApiError::NotFound)
+    Err(ApiError::NotFound(eyre::eyre!("resource not found")))
 }
 
 #[utoipa::path(
@@ -385,9 +409,11 @@ pub async fn version_file_sha1(
 ) -> Result<HttpResponse, ApiError> {
     let (project_id, vnum, file) = params.into_inner();
     let Some(project) =
-        database::models::DBProject::get(&project_id, &**pool, &redis).await?
+        database::models::DBProject::get(&project_id, &**pool, &redis)
+            .await
+            .wrap_api_err("fetching Maven project")?
     else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
     let user_option = get_user_from_headers(
@@ -401,17 +427,25 @@ pub async fn version_file_sha1(
     .map(|x| x.1)
     .ok();
 
-    if !is_visible_project(&project.inner, &user_option, &pool, false).await? {
-        return Err(ApiError::NotFound);
+    if !is_visible_project(&project.inner, &user_option, &pool, false)
+        .await
+        .wrap_api_err("checking project visibility")?
+    {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
-    let Some(version) = find_version(&project, &vnum, &pool, &redis).await?
+    let Some(version) = find_version(&project, &vnum, &pool, &redis)
+        .await
+        .wrap_api_err("fetching Maven version")?
     else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
-    if !is_visible_version(&version.inner, &user_option, &pool, &redis).await? {
-        return Err(ApiError::NotFound);
+    if !is_visible_version(&version.inner, &user_option, &pool, &redis)
+        .await
+        .wrap_api_err("checking version visibility")?
+    {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     Ok(find_file(&project_id, &vnum, &version, &file)
@@ -441,9 +475,11 @@ pub async fn version_file_sha512(
 ) -> Result<HttpResponse, ApiError> {
     let (project_id, vnum, file) = params.into_inner();
     let Some(project) =
-        database::models::DBProject::get(&project_id, &**pool, &redis).await?
+        database::models::DBProject::get(&project_id, &**pool, &redis)
+            .await
+            .wrap_api_err("fetching Maven project")?
     else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
     let user_option = get_user_from_headers(
@@ -457,17 +493,25 @@ pub async fn version_file_sha512(
     .map(|x| x.1)
     .ok();
 
-    if !is_visible_project(&project.inner, &user_option, &pool, false).await? {
-        return Err(ApiError::NotFound);
+    if !is_visible_project(&project.inner, &user_option, &pool, false)
+        .await
+        .wrap_api_err("checking project visibility")?
+    {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
-    let Some(version) = find_version(&project, &vnum, &pool, &redis).await?
+    let Some(version) = find_version(&project, &vnum, &pool, &redis)
+        .await
+        .wrap_api_err("fetching Maven version")?
     else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
-    if !is_visible_version(&version.inner, &user_option, &pool, &redis).await? {
-        return Err(ApiError::NotFound);
+    if !is_visible_version(&version.inner, &user_option, &pool, &redis)
+        .await
+        .wrap_api_err("checking version visibility")?
+    {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     Ok(find_file(&project_id, &vnum, &version, &file)
diff --git a/apps/labrinth/src/routes/mod.rs b/apps/labrinth/src/routes/mod.rs
index e9e606deba..fc5f72e75c 100644
--- a/apps/labrinth/src/routes/mod.rs
+++ b/apps/labrinth/src/routes/mod.rs
@@ -1,13 +1,10 @@
-use crate::database::models::DelphiReportIssueDetailsId;
 use crate::env::ENV;
-use crate::file_hosting::FileHostingError;
 use crate::util::cors::default_cors;
 use actix_cors::Cors;
 use actix_files::Files;
 use actix_web::http::StatusCode;
 use actix_web::{HttpResponse, web};
 use futures::FutureExt;
-use serde_json::json;
 use utoipa::openapi::extensions::ExtensionsBuilder;
 use utoipa::openapi::security::{HttpAuthScheme, HttpBuilder, SecurityScheme};
 
@@ -192,84 +189,49 @@ pub enum ApiError {
     /// Caller attempted a request which they are not allowed to make.
     #[error(transparent)]
     Auth(eyre::Report),
-    #[error("Invalid input: {0}")]
-    InvalidInput(String),
-    #[error("Error while uploading file: {0}")]
-    FileHosting(#[from] FileHostingError),
-    #[error("database error")]
-    Database(#[from] crate::database::models::DatabaseError),
-    // todo: remove this variant
-    #[error("Postgres database error: {0}")]
-    SqlxDatabase(#[from] sqlx::Error),
-    #[error("redis database error")]
-    RedisDatabase(#[from] redis::RedisError),
-    #[error("Clickhouse error: {0}")]
-    Clickhouse(#[from] clickhouse::error::Error),
-    #[error("XML error: {0}")]
-    Xml(String),
-    #[error("Deserialization error: {0}")]
-    Json(#[from] serde_json::Error),
-    #[error("Authentication error: {0}")]
-    Authentication(#[from] crate::auth::AuthenticationError),
-    #[error("Authentication error: {0}")]
-    CustomAuthentication(String),
-    #[error("Error while validating input: {0}")]
-    Validation(String),
-    #[error("Search error: {0}")]
-    Search(#[from] meilisearch_sdk::errors::Error),
-    #[error("Payments error: {0}")]
-    Payments(String),
-    #[error("Discord error: {0}")]
-    Discord(String),
-    #[error("Slack webhook error: {0}")]
-    Slack(String),
-    #[error("Captcha error. Try resubmitting the form.")]
-    Turnstile,
-    #[error("Error while decoding Base62: {0}")]
-    Decoding(#[from] ariadne::ids::DecodingError),
-    #[error("Image parsing error: {0}")]
-    ImageParse(#[from] image::ImageError),
-    #[error("Password hashing error: {0}")]
-    PasswordHashing(#[from] argon2::password_hash::Error),
-    #[error("{0}")]
-    Mail(#[from] crate::queue::email::MailError),
-    #[error("Error while rerouting request: {0:?}")]
-    Reroute(#[from] reqwest::Error),
-    #[error("Unable to read zip archive: {0}")]
-    Zip(#[from] zip::result::ZipError),
-    #[error("IO Error: {0}")]
-    Io(#[from] std::io::Error),
-    #[error("Resource not found")]
-    NotFound,
-    #[error("Conflict: {0}")]
-    Conflict(String),
-    #[error("precondition required: {0}")]
-    PreconditionRequired(String),
-    #[error("precondition failed: {0}")]
-    PreconditionFailed(String),
-    #[error("External tax compliance API error")]
-    TaxComplianceApi,
+    /// The requested resource does not exist.
     #[error(transparent)]
-    TaxProcessor(#[from] crate::util::anrok::AnrokError),
-    #[error(
-        "You are being rate-limited. Please wait {0} milliseconds. 0/{1} remaining."
-    )]
-    RateLimitError(u128, u32),
-    #[error("Error while interacting with payment processor: {0}")]
-    Stripe(#[from] stripe::StripeError),
-    #[error("Error while interacting with Delphi: {0:?}")]
-    Delphi(eyre::Error),
+    NotFound(eyre::Report),
+    /// The request conflicts with the current state of the resource.
     #[error(transparent)]
-    Mural(#[from] Box<muralpay::ApiError>),
-    #[error("report still has {} issue details with no verdict", details.len())]
-    TechReviewDetailsWithNoVerdict {
-        details: Vec<DelphiReportIssueDetailsId>,
-    },
+    Conflict(eyre::Report),
+    /// A service dependency failed to complete the request.
+    #[error(transparent)]
+    FailedDependency(eyre::Report),
+    /// The request requires a precondition.
+    #[error(transparent)]
+    PreconditionRequired(eyre::Report),
+    /// A request precondition was not met.
+    #[error(transparent)]
+    PreconditionFailed(eyre::Report),
+    /// The caller exceeded a request rate limit.
+    #[error(transparent)]
+    RateLimit(eyre::Report),
 }
 
 impl ApiError {
-    pub fn delphi(err: impl Into<eyre::Error>) -> Self {
-        Self::Delphi(err.into())
+    /// Adds context to the contained report while preserving the HTTP status.
+    pub(crate) fn wrap_err<D>(self, msg: D) -> Self
+    where
+        D: Send + Sync + std::fmt::Debug + std::fmt::Display + 'static,
+    {
+        match self {
+            Self::Internal(report) => Self::Internal(report.wrap_err(msg)),
+            Self::Request(report) => Self::Request(report.wrap_err(msg)),
+            Self::Auth(report) => Self::Auth(report.wrap_err(msg)),
+            Self::NotFound(report) => Self::NotFound(report.wrap_err(msg)),
+            Self::Conflict(report) => Self::Conflict(report.wrap_err(msg)),
+            Self::FailedDependency(report) => {
+                Self::FailedDependency(report.wrap_err(msg))
+            }
+            Self::PreconditionRequired(report) => {
+                Self::PreconditionRequired(report.wrap_err(msg))
+            }
+            Self::PreconditionFailed(report) => {
+                Self::PreconditionFailed(report.wrap_err(msg))
+            }
+            Self::RateLimit(report) => Self::RateLimit(report.wrap_err(msg)),
+        }
     }
 
     pub fn as_api_error<'a>(&self) -> crate::models::error::ApiError<'a> {
@@ -278,60 +240,15 @@ impl ApiError {
                 Self::Internal(..) => "internal_error",
                 Self::Request(..) => "request_error",
                 Self::Auth(..) => "auth_error",
-                Self::Database(..) => "database_error",
-                Self::SqlxDatabase(..) => "database_error",
-                Self::RedisDatabase(..) => "database_error",
-                Self::Authentication(..) => "unauthorized",
-                Self::CustomAuthentication(..) => "unauthorized",
-                Self::Xml(..) => "xml_error",
-                Self::Json(..) => "json_error",
-                Self::Search(..) => "search_error",
-                Self::FileHosting(..) => "file_hosting_error",
-                Self::InvalidInput(..) => "invalid_input",
-                Self::Validation(..) => "invalid_input",
-                Self::Payments(..) => "payments_error",
-                Self::Discord(..) => "discord_error",
-                Self::Turnstile => "turnstile_error",
-                Self::Decoding(..) => "decoding_error",
-                Self::ImageParse(..) => "invalid_image",
-                Self::PasswordHashing(..) => "password_hashing_error",
-                Self::Mail(..) => "mail_error",
-                Self::Clickhouse(..) => "clickhouse_error",
-                Self::Reroute(..) => "reroute_error",
-                Self::NotFound => "not_found",
+                Self::NotFound(..) => "not_found",
                 Self::Conflict(..) => "conflict",
+                Self::FailedDependency(..) => "failed_dependency",
                 Self::PreconditionRequired(..) => "precondition_required",
                 Self::PreconditionFailed(..) => "precondition_failed",
-                Self::TaxComplianceApi => "tax_compliance_api_error",
-                Self::Zip(..) => "zip_error",
-                Self::Io(..) => "io_error",
-                Self::RateLimitError(..) => "ratelimit_error",
-                Self::Stripe(..) => "stripe_error",
-                Self::TaxProcessor(..) => "tax_processor_error",
-                Self::Slack(..) => "slack_error",
-                Self::Delphi(..) => "delphi_error",
-                Self::Mural(..) => "mural_error",
-                Self::TechReviewDetailsWithNoVerdict { .. } => {
-                    "tech_review_issues_with_no_verdict"
-                }
-            },
-            description: match self {
-                Self::Internal(e) => format!("{e:#}"),
-                Self::Request(e) => format!("{e:#}"),
-                Self::Auth(e) => format!("{e:#}"),
-                _ => self.to_string(),
-            },
-            details: match self {
-                Self::Mural(err) => serde_json::to_value(err.clone()).ok(),
-                Self::TechReviewDetailsWithNoVerdict { details } => {
-                    let details = serde_json::to_value(details)
-                        .expect("details should never fail to serialize");
-                    Some(json!({
-                        "issue_details": details
-                    }))
-                }
-                _ => None,
+                Self::RateLimit(..) => "ratelimit_error",
             },
+            description: format!("{self:#}"),
+            details: None,
         }
     }
 }
@@ -342,42 +259,12 @@ impl actix_web::ResponseError for ApiError {
             Self::Internal(..) => StatusCode::INTERNAL_SERVER_ERROR,
             Self::Request(..) => StatusCode::BAD_REQUEST,
             Self::Auth(..) => StatusCode::UNAUTHORIZED,
-            Self::InvalidInput(..) => StatusCode::BAD_REQUEST,
-            Self::Database(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::SqlxDatabase(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::RedisDatabase(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Clickhouse(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Authentication(..) => StatusCode::UNAUTHORIZED,
-            Self::CustomAuthentication(..) => StatusCode::UNAUTHORIZED,
-            Self::Xml(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Json(..) => StatusCode::BAD_REQUEST,
-            Self::Search(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::FileHosting(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Validation(..) => StatusCode::BAD_REQUEST,
-            Self::Payments(..) => StatusCode::FAILED_DEPENDENCY,
-            Self::Discord(..) => StatusCode::FAILED_DEPENDENCY,
-            Self::Turnstile => StatusCode::BAD_REQUEST,
-            Self::Decoding(..) => StatusCode::BAD_REQUEST,
-            Self::ImageParse(..) => StatusCode::BAD_REQUEST,
-            Self::PasswordHashing(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Mail(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Reroute(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::NotFound => StatusCode::NOT_FOUND,
+            Self::NotFound(..) => StatusCode::NOT_FOUND,
             Self::Conflict(..) => StatusCode::CONFLICT,
+            Self::FailedDependency(..) => StatusCode::FAILED_DEPENDENCY,
             Self::PreconditionRequired(..) => StatusCode::PRECONDITION_REQUIRED,
             Self::PreconditionFailed(..) => StatusCode::PRECONDITION_FAILED,
-            Self::TaxComplianceApi => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Zip(..) => StatusCode::BAD_REQUEST,
-            Self::Io(..) => StatusCode::BAD_REQUEST,
-            Self::RateLimitError(..) => StatusCode::TOO_MANY_REQUESTS,
-            Self::Stripe(..) => StatusCode::FAILED_DEPENDENCY,
-            Self::TaxProcessor(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Slack(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Delphi(..) => StatusCode::INTERNAL_SERVER_ERROR,
-            Self::Mural(..) => StatusCode::BAD_REQUEST,
-            Self::TechReviewDetailsWithNoVerdict { .. } => {
-                StatusCode::BAD_REQUEST
-            }
+            Self::RateLimit(..) => StatusCode::TOO_MANY_REQUESTS,
         }
     }
 
diff --git a/apps/labrinth/src/routes/updates.rs b/apps/labrinth/src/routes/updates.rs
index 7b287c6cf9..95db80199d 100644
--- a/apps/labrinth/src/routes/updates.rs
+++ b/apps/labrinth/src/routes/updates.rs
@@ -1,3 +1,5 @@
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use std::cmp::Reverse;
 use std::collections::HashMap;
 
@@ -55,8 +57,9 @@ pub async fn forge_updates(
     let (id,) = info.into_inner();
 
     let project = database::models::DBProject::get(&id, &**pool, &redis)
-        .await?
-        .ok_or_else(|| ApiError::InvalidInput(ERROR.to_string()))?;
+        .await
+        .wrap_api_err("fetching project from database")?
+        .wrap_request_err_with(|| ERROR.to_string())?;
 
     let user_option = get_user_from_headers(
         &req,
@@ -69,8 +72,11 @@ pub async fn forge_updates(
     .map(|x| x.1)
     .ok();
 
-    if !is_visible_project(&project.inner, &user_option, &pool, false).await? {
-        return Err(ApiError::InvalidInput(ERROR.to_string()));
+    if !is_visible_project(&project.inner, &user_option, &pool, false)
+        .await
+        .wrap_api_err("checking project visibility")?
+    {
+        return Err(ApiError::Request(eyre::eyre!("{ERROR}")));
     }
 
     let versions = database::models::DBVersion::get_many(
@@ -78,7 +84,8 @@ pub async fn forge_updates(
         &***ro_pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching versions from database")?;
 
     let loaders = match &*neo.neoforge {
         "only" => |x: &String| *x == "neoforge",
@@ -96,7 +103,8 @@ pub async fn forge_updates(
         &ro_pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching compatible update versions")?;
 
     versions.sort_by_key(|b| Reverse(b.date_published));
 
diff --git a/apps/labrinth/src/routes/v2/notifications.rs b/apps/labrinth/src/routes/v2/notifications.rs
index f84f58ab5d..52f279fa6c 100644
--- a/apps/labrinth/src/routes/v2/notifications.rs
+++ b/apps/labrinth/src/routes/v2/notifications.rs
@@ -6,6 +6,7 @@ use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
 use crate::routes::v2_reroute;
 use crate::routes::v3;
+use crate::util::error::ApiContext as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, web};
 use serde::{Deserialize, Serialize};
 use xredis::RedisPool;
@@ -65,7 +66,11 @@ pub async fn notifications_get(
     )
     .await
     .or_else(v2_reroute::flatten_404_error);
-    match v2_reroute::extract_ok_json::<Vec<Notification>>(resp?).await {
+    match v2_reroute::extract_ok_json::<Vec<Notification>>(
+        resp.wrap_api_err("extracting v2 response body")?,
+    )
+    .await
+    {
         Ok(notifications) => {
             let notifications: Vec<LegacyNotification> = notifications
                 .into_iter()
@@ -115,7 +120,8 @@ pub async fn notification_get(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
     match v2_reroute::extract_ok_json::<Notification>(response).await {
         Ok(notification) => {
             let notification = LegacyNotification::from(notification);
diff --git a/apps/labrinth/src/routes/v2/projects.rs b/apps/labrinth/src/routes/v2/projects.rs
index d36bae318f..407d6359b2 100644
--- a/apps/labrinth/src/routes/v2/projects.rs
+++ b/apps/labrinth/src/routes/v2/projects.rs
@@ -13,6 +13,8 @@ use crate::queue::session::AuthQueue;
 use crate::routes::v3::projects::ProjectIds;
 use crate::routes::{ApiError, v2_reroute, v3};
 use crate::search::{SearchBackend, SearchRequest, SearchState};
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, post, web};
 use serde::{Deserialize, Serialize};
 use std::collections::HashMap;
@@ -79,7 +81,8 @@ pub async fn project_search(
     // While the backend for this has changed, it doesnt affect much
     // in the API calls except that 'versions:x' is now 'game_versions:x'
     let facets: Option<Vec<Vec<String>>> = if let Some(facets) = info.facets {
-        let facets = serde_json::from_str::<Vec<Vec<String>>>(&facets)?;
+        let facets = serde_json::from_str::<Vec<Vec<String>>>(&facets)
+            .wrap_request_err("deserializing JSON data")?;
 
         Some(
             facets
@@ -119,7 +122,10 @@ pub async fn project_search(
         ..info
     };
 
-    let results = search_backend.search_for_project(&info, &redis).await?;
+    let results = search_backend
+        .search_for_project(&info, &redis)
+        .await
+        .wrap_api_err("searching projects")?;
 
     let results = LegacySearchResults::from(results);
 
@@ -194,12 +200,17 @@ pub async fn random_projects_get(
     )
     .await
     .or_else(v2_reroute::flatten_404_error)
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<Project>>(response).await {
         Ok(project) => {
             let legacy_projects =
-                LegacyProject::from_many(project, &**pool, &redis).await?;
+                LegacyProject::from_many(project, &**pool, &redis)
+                    .await
+                    .wrap_internal_err(
+                        "executing `LegacyProject::from_many`",
+                    )?;
             Ok(HttpResponse::Ok().json(legacy_projects))
         }
         Err(response) => Ok(response),
@@ -234,13 +245,18 @@ pub async fn projects_get(
     )
     .await
     .or_else(v2_reroute::flatten_404_error)
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<Project>>(response).await {
         Ok(project) => {
             let legacy_projects =
-                LegacyProject::from_many(project, &**pool, &redis).await?;
+                LegacyProject::from_many(project, &**pool, &redis)
+                    .await
+                    .wrap_internal_err(
+                        "executing `LegacyProject::from_many`",
+                    )?;
             Ok(HttpResponse::Ok().json(legacy_projects))
         }
         Err(response) => Ok(response),
@@ -284,14 +300,18 @@ pub async fn project_get(
     .await
     {
         Ok(resp) => resp.0,
-        Err(ApiError::NotFound) => return Ok(HttpResponse::NotFound().body("")),
+        Err(ApiError::NotFound(_)) => {
+            return Ok(HttpResponse::NotFound().body(""));
+        }
         Err(err) => return Err(err),
     };
 
     // Convert response to V2 format
     let version_item = match project.versions.first() {
         Some(vid) => {
-            version_item::DBVersion::get((*vid).into(), &**pool, &redis).await?
+            version_item::DBVersion::get((*vid).into(), &**pool, &redis)
+                .await
+                .wrap_internal_err("fetching version from database")?
         }
         None => None,
     };
@@ -371,7 +391,8 @@ pub async fn dependency_list(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     match v2_reroute::extract_ok_json::<
         crate::routes::v3::projects::DependencyInfo,
@@ -384,7 +405,10 @@ pub async fn dependency_list(
                 &**pool,
                 &redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err(
+                "converting dependency projects to legacy responses",
+            )?;
             let converted_versions = dependency_info
                 .versions
                 .into_iter()
@@ -585,7 +609,9 @@ pub async fn project_edit(
     if let Some(donation_urls) = v2_new_project.donation_urls {
         // Fetch current donation links from project so we know what to delete
         let fetched_example_project =
-            project_item::DBProject::get(&info.0, &**pool, &redis).await?;
+            project_item::DBProject::get(&info.0, &**pool, &redis)
+                .await
+                .wrap_api_err("fetching project from database")?;
         let donation_links = fetched_example_project
             .map(|x| {
                 x.urls
@@ -647,7 +673,8 @@ pub async fn project_edit(
         search_state.clone(),
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // If client and server side were set, we will call
     // the version setting route for each version to set the side types for each of them.
@@ -659,11 +686,13 @@ pub async fn project_edit(
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_api_err("fetching project from database")?;
         let version_ids = project_item.map(|x| x.versions).unwrap_or_default();
         let versions =
             version_item::DBVersion::get_many(&version_ids, &**pool, &redis)
-                .await?;
+                .await
+                .wrap_internal_err("fetching versions from database")?;
         for version in versions {
             let version = Version::from(version);
             let mut fields = version.fields;
@@ -690,7 +719,8 @@ pub async fn project_edit(
                 session_queue.clone(),
                 search_state.clone(),
             )
-            .await?;
+            .await
+            .wrap_api_err("editing project")?;
         }
     }
     Ok(response)
@@ -795,7 +825,9 @@ pub async fn projects_edit(
     // If we are *setting* donation links, we will set every possible donation link to None, as
     // setting will delete all of them then 're-add' the ones we want to keep
     if let Some(donation_url) = bulk_edit_project.donation_urls {
-        let link_platforms = LinkPlatform::list(&**pool, &redis).await?;
+        let link_platforms = LinkPlatform::list(&**pool, &redis)
+            .await
+            .wrap_internal_err("fetching link platform from Redis")?;
         for link in link_platforms {
             if link.donation {
                 link_urls.insert(link.name, None);
diff --git a/apps/labrinth/src/routes/v2/reports.rs b/apps/labrinth/src/routes/v2/reports.rs
index c50950e544..041900e5f7 100644
--- a/apps/labrinth/src/routes/v2/reports.rs
+++ b/apps/labrinth/src/routes/v2/reports.rs
@@ -3,6 +3,7 @@ use crate::models::reports::Report;
 use crate::models::v2::reports::LegacyReport;
 use crate::queue::session::AuthQueue;
 use crate::routes::{ApiError, v2_reroute, v3};
+use crate::util::error::ApiContext as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, post, web};
 use serde::Deserialize;
 use validator::Validate;
@@ -44,7 +45,8 @@ pub async fn report_create(
     let response =
         v3::reports::report_create(req, pool, body, redis, session_queue)
             .await
-            .or_else(v2_reroute::flatten_404_error)?;
+            .or_else(v2_reroute::flatten_404_error)
+            .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Report>(response).await {
@@ -109,7 +111,8 @@ pub async fn reports(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<Report>>(response).await {
@@ -164,7 +167,8 @@ pub async fn reports_get(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<Report>>(response).await {
@@ -209,7 +213,8 @@ pub async fn report_get(
     let response =
         v3::reports::report_get(req, pool, redis, info, session_queue)
             .await
-            .or_else(v2_reroute::flatten_404_error)?;
+            .or_else(v2_reroute::flatten_404_error)
+            .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Report>(response).await {
diff --git a/apps/labrinth/src/routes/v2/statistics.rs b/apps/labrinth/src/routes/v2/statistics.rs
index 94ac6f66e9..fed3166c32 100644
--- a/apps/labrinth/src/routes/v2/statistics.rs
+++ b/apps/labrinth/src/routes/v2/statistics.rs
@@ -3,6 +3,7 @@ use crate::routes::{
     ApiError, v2_reroute,
     v3::{self, statistics::V3Stats},
 };
+use crate::util::error::ApiContext as _;
 use actix_web::{HttpResponse, get, web};
 
 pub fn config(cfg: &mut actix_web::web::ServiceConfig) {
@@ -36,7 +37,8 @@ pub async fn get_stats(
 ) -> Result<HttpResponse, ApiError> {
     let response = v3::statistics::get_stats(pool)
         .await
-        .or_else(v2_reroute::flatten_404_error)?;
+        .or_else(v2_reroute::flatten_404_error)
+        .wrap_api_err("flattening v2 not-found response")?;
 
     match v2_reroute::extract_ok_json::<V3Stats>(response).await {
         Ok(stats) => {
diff --git a/apps/labrinth/src/routes/v2/tags.rs b/apps/labrinth/src/routes/v2/tags.rs
index 56a86ca46d..ac14c0b412 100644
--- a/apps/labrinth/src/routes/v2/tags.rs
+++ b/apps/labrinth/src/routes/v2/tags.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use std::collections::HashMap;
 
 use super::ApiError;
@@ -54,7 +55,9 @@ pub async fn category_list(
     pool: web::Data<PgPool>,
     redis: web::Data<RedisPool>,
 ) -> Result<HttpResponse, ApiError> {
-    let response = v3::tags::category_list(pool, redis).await?;
+    let response = v3::tags::category_list(pool, redis)
+        .await
+        .wrap_api_err("executing `tags::category_list`")?;
 
     // Convert to V2 format
     match v2_reroute::extract_ok_json::<Vec<v3::tags::CategoryData>>(response)
@@ -102,7 +105,9 @@ pub async fn loader_list(
     pool: web::Data<PgPool>,
     redis: web::Data<RedisPool>,
 ) -> Result<HttpResponse, ApiError> {
-    let response = v3::tags::loader_list(pool, redis).await?;
+    let response = v3::tags::loader_list(pool, redis)
+        .await
+        .wrap_api_err("executing `tags::loader_list`")?;
 
     // Convert to V2 format
     match v2_reroute::extract_ok_json::<Vec<v3::tags::LoaderData>>(response)
@@ -198,7 +203,8 @@ pub async fn game_version_list(
         }),
         redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching game versions")?;
 
     // Convert to V2 format
     Ok(
@@ -293,7 +299,8 @@ pub async fn license_text(
 ) -> Result<HttpResponse, ApiError> {
     let license = v3::tags::license_text(params)
         .await
-        .or_else(v2_reroute::flatten_404_error)?;
+        .or_else(v2_reroute::flatten_404_error)
+        .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert to V2 format
     Ok(
@@ -339,7 +346,9 @@ pub async fn donation_platform_list(
     pool: web::Data<PgPool>,
     redis: web::Data<RedisPool>,
 ) -> Result<HttpResponse, ApiError> {
-    let response = v3::tags::link_platform_list(pool, redis).await?;
+    let response = v3::tags::link_platform_list(pool, redis)
+        .await
+        .wrap_api_err("executing `tags::link_platform_list`")?;
 
     // Convert to V2 format
     Ok(
diff --git a/apps/labrinth/src/routes/v2/teams.rs b/apps/labrinth/src/routes/v2/teams.rs
index 36c373094e..cdd4e30665 100644
--- a/apps/labrinth/src/routes/v2/teams.rs
+++ b/apps/labrinth/src/routes/v2/teams.rs
@@ -6,6 +6,7 @@ use crate::models::teams::{
 use crate::models::v2::teams::LegacyTeamMember;
 use crate::queue::session::AuthQueue;
 use crate::routes::{ApiError, v2_reroute, v3};
+use crate::util::error::ApiContext as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, post, web};
 use ariadne::ids::UserId;
 use rust_decimal::Decimal;
@@ -63,7 +64,8 @@ pub async fn team_members_get_project(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<TeamMember>>(response).await {
         Ok(members) => {
@@ -101,7 +103,8 @@ pub async fn team_members_get(
     let response =
         v3::teams::team_members_get(req, info, pool, redis, session_queue)
             .await
-            .or_else(v2_reroute::flatten_404_error)?;
+            .or_else(v2_reroute::flatten_404_error)
+            .wrap_api_err("flattening v2 not-found response")?;
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<TeamMember>>(response).await {
         Ok(members) => {
@@ -148,7 +151,11 @@ pub async fn teams_get(
     .await
     .or_else(v2_reroute::flatten_404_error);
     // Convert response to V2 format
-    match v2_reroute::extract_ok_json::<Vec<Vec<TeamMember>>>(response?).await {
+    match v2_reroute::extract_ok_json::<Vec<Vec<TeamMember>>>(
+        response.wrap_api_err("extracting v2 response body")?,
+    )
+    .await
+    {
         Ok(members) => {
             let members = members
                 .into_iter()
diff --git a/apps/labrinth/src/routes/v2/threads.rs b/apps/labrinth/src/routes/v2/threads.rs
index 3854d4977a..e110ef5b98 100644
--- a/apps/labrinth/src/routes/v2/threads.rs
+++ b/apps/labrinth/src/routes/v2/threads.rs
@@ -5,6 +5,7 @@ use crate::models::threads::{MessageBody, Thread};
 use crate::models::v2::threads::LegacyThread;
 use crate::queue::session::AuthQueue;
 use crate::routes::{ApiError, v2_reroute, v3};
+use crate::util::error::ApiContext as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, post, web};
 use serde::Deserialize;
 use xredis::RedisPool;
@@ -88,7 +89,8 @@ pub async fn threads_get(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<Thread>>(response).await {
diff --git a/apps/labrinth/src/routes/v2/users.rs b/apps/labrinth/src/routes/v2/users.rs
index 5879315336..3c5dae8e8e 100644
--- a/apps/labrinth/src/routes/v2/users.rs
+++ b/apps/labrinth/src/routes/v2/users.rs
@@ -8,6 +8,8 @@ use crate::models::v2::projects::LegacyProject;
 use crate::models::v2::user::LegacyUser;
 use crate::queue::session::AuthQueue;
 use crate::routes::{ApiError, v2_reroute, v3};
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, web};
 use serde::{Deserialize, Serialize};
 use validator::Validate;
@@ -53,7 +55,8 @@ pub async fn user_auth_get(
 ) -> Result<HttpResponse, ApiError> {
     let response = v3::users::user_auth_get(req, pool, redis, session_queue)
         .await
-        .or_else(v2_reroute::flatten_404_error)?;
+        .or_else(v2_reroute::flatten_404_error)
+        .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<User>(response).await {
@@ -96,7 +99,8 @@ pub async fn users_get(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<User>>(response).await {
@@ -136,7 +140,8 @@ pub async fn user_get(
 ) -> Result<HttpResponse, ApiError> {
     let response = v3::users::user_get(req, info, pool, redis, session_queue)
         .await
-        .or_else(v2_reroute::flatten_404_error)?;
+        .or_else(v2_reroute::flatten_404_error)
+        .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<User>(response).await {
@@ -181,13 +186,18 @@ pub async fn projects_list(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert to V2 projects
     match v2_reroute::extract_ok_json::<Vec<Project>>(response).await {
         Ok(project) => {
             let legacy_projects =
-                LegacyProject::from_many(project, &**pool, &redis).await?;
+                LegacyProject::from_many(project, &**pool, &redis)
+                    .await
+                    .wrap_internal_err(
+                        "executing `LegacyProject::from_many`",
+                    )?;
             Ok(HttpResponse::Ok().json(legacy_projects))
         }
         Err(response) => Ok(response),
@@ -448,13 +458,18 @@ pub async fn user_follows(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert to V2 projects
     match v2_reroute::extract_ok_json::<Vec<Project>>(response).await {
         Ok(project) => {
             let legacy_projects =
-                LegacyProject::from_many(project, &**pool, &redis).await?;
+                LegacyProject::from_many(project, &**pool, &redis)
+                    .await
+                    .wrap_internal_err(
+                        "executing `LegacyProject::from_many`",
+                    )?;
             Ok(HttpResponse::Ok().json(legacy_projects))
         }
         Err(response) => Ok(response),
@@ -494,7 +509,8 @@ pub async fn user_notifications(
     let response =
         v3::users::user_notifications(req, info, pool, redis, session_queue)
             .await
-            .or_else(v2_reroute::flatten_404_error)?;
+            .or_else(v2_reroute::flatten_404_error)
+            .wrap_api_err("flattening v2 not-found response")?;
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<Notification>>(response).await {
         Ok(notifications) => {
diff --git a/apps/labrinth/src/routes/v2/version_file.rs b/apps/labrinth/src/routes/v2/version_file.rs
index a4c529b8c1..f1db94c0bf 100644
--- a/apps/labrinth/src/routes/v2/version_file.rs
+++ b/apps/labrinth/src/routes/v2/version_file.rs
@@ -7,6 +7,8 @@ use crate::queue::session::AuthQueue;
 use crate::routes::HashAlgorithm;
 use crate::routes::v3::version_file::{DownloadRedirect, HashQuery};
 use crate::routes::{FileHash, v2_reroute, v3};
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, post, web};
 use serde::{Deserialize, Serialize};
 use std::collections::HashMap;
@@ -69,7 +71,8 @@ pub async fn get_version_from_hash(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Version>(response).await {
@@ -233,7 +236,8 @@ pub async fn get_update_from_hash(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Version>(response).await {
@@ -289,7 +293,8 @@ pub async fn get_versions_from_hashes(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert to V2
     match v2_reroute::extract_ok_json::<HashMap<String, Version>>(response)
@@ -342,7 +347,8 @@ pub async fn get_projects_from_hashes(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert to V2
     match v2_reroute::extract_ok_json::<HashMap<String, Project>>(response)
@@ -361,7 +367,8 @@ pub async fn get_projects_from_hashes(
                 &**pool,
                 &redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err("converting projects to legacy responses")?;
             let legacy_projects_hashes = hash_to_project_id
                 .into_iter()
                 .filter_map(|(hash, project_id)| {
@@ -426,7 +433,9 @@ pub async fn update_files(
     .await
     {
         Ok(resp) => resp,
-        Err(ApiError::NotFound) => return Ok(HttpResponse::NotFound().body("")),
+        Err(ApiError::NotFound(_)) => {
+            return Ok(HttpResponse::NotFound().body(""));
+        }
         Err(err) => return Err(err),
     };
 
@@ -477,7 +486,9 @@ pub async fn update_files_many(
     .await
     {
         Ok(resp) => resp,
-        Err(ApiError::NotFound) => return Ok(HttpResponse::NotFound().body("")),
+        Err(ApiError::NotFound(_)) => {
+            return Ok(HttpResponse::NotFound().body(""));
+        }
         Err(err) => return Err(err),
     };
 
@@ -565,7 +576,8 @@ pub async fn update_individual_files(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<HashMap<String, Version>>(response)
diff --git a/apps/labrinth/src/routes/v2/versions.rs b/apps/labrinth/src/routes/v2/versions.rs
index 2ffb4abd93..ec94f169ba 100644
--- a/apps/labrinth/src/routes/v2/versions.rs
+++ b/apps/labrinth/src/routes/v2/versions.rs
@@ -1,3 +1,5 @@
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use std::collections::HashMap;
 
 use super::ApiError;
@@ -138,7 +140,8 @@ pub async fn version_list(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<Version>>(response).await {
@@ -191,7 +194,8 @@ pub async fn version_project_get(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Version>(response).await {
         Ok(version) => {
@@ -242,7 +246,8 @@ pub async fn versions_get(
         session_queue,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
 
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Vec<Version>>(response).await {
@@ -294,7 +299,8 @@ pub async fn version_get(
     )
     .await
     .map(|b| HttpResponse::Ok().json(b))
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("flattening v2 not-found response")?;
     // Convert response to V2 format
     match v2_reroute::extract_ok_json::<Version>(response).await {
         Ok(version) => {
@@ -396,7 +402,9 @@ pub async fn version_edit(
     .await
     {
         Ok(resp) => resp,
-        Err(ApiError::NotFound) => return Ok(HttpResponse::NotFound().body("")),
+        Err(ApiError::NotFound(_)) => {
+            return Ok(HttpResponse::NotFound().body(""));
+        }
         Err(err) => return Err(err),
     };
     let old_version = match v2_reroute::extract_ok_json::<Version>(
@@ -450,12 +458,16 @@ pub async fn version_edit(
         info,
         pool,
         redis,
-        web::Json(serde_json::to_value(new_version)?),
+        web::Json(
+            serde_json::to_value(new_version)
+                .wrap_request_err("serializing version edit")?,
+        ),
         session_queue,
         search_state,
     )
     .await
-    .or_else(v2_reroute::flatten_404_error)?;
+    .or_else(v2_reroute::flatten_404_error)
+    .wrap_api_err("editing version through v3 route")?;
     Ok(response)
 }
 
diff --git a/apps/labrinth/src/routes/v2_reroute.rs b/apps/labrinth/src/routes/v2_reroute.rs
index 0a99b0796c..5576c0f2fa 100644
--- a/apps/labrinth/src/routes/v2_reroute.rs
+++ b/apps/labrinth/src/routes/v2_reroute.rs
@@ -45,7 +45,7 @@ where
 // This should not be used on the fallback no-route-found handler
 pub fn flatten_404_error(res: ApiError) -> Result<HttpResponse, ApiError> {
     match res {
-        ApiError::NotFound => Ok(HttpResponse::NotFound().body("")),
+        ApiError::NotFound(_) => Ok(HttpResponse::NotFound().body("")),
         _ => Err(res),
     }
 }
diff --git a/apps/labrinth/src/routes/v3/analytics_get/facets/fixed.rs b/apps/labrinth/src/routes/v3/analytics_get/facets/fixed.rs
index 14b1f68911..02a37254bb 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/facets/fixed.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/facets/fixed.rs
@@ -3,6 +3,7 @@ use super::{
     AnalyticsFacets, ProjectDownloadsFacets, ProjectPlaytimeFacets,
     ProjectViewsFacets,
 };
+use crate::util::error::ApiContext as _;
 use crate::{
     database::PgPool, models::v3::analytics::DownloadReason, routes::ApiError,
     util::tags::valid_download_tags,
@@ -13,7 +14,9 @@ pub async fn fetch(
     pool: &PgPool,
     redis: &RedisPool,
 ) -> Result<AnalyticsFacets, ApiError> {
-    let tags = valid_download_tags(pool, redis).await?;
+    let tags = valid_download_tags(pool, redis)
+        .await
+        .wrap_api_err("executing `valid_download_tags`")?;
     let mut loaders = tags.loaders.iter().cloned().collect::<Vec<_>>();
     loaders.sort();
     let mut game_versions =
diff --git a/apps/labrinth/src/routes/v3/analytics_get/facets/mod.rs b/apps/labrinth/src/routes/v3/analytics_get/facets/mod.rs
index 02218bcec9..c61ea4f565 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/facets/mod.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/facets/mod.rs
@@ -1,3 +1,5 @@
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use xredis::RedisPool;
 mod fixed;
 
@@ -78,9 +80,12 @@ pub async fn fetch_facets(
         &session_queue,
         Scopes::ANALYTICS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    let facets = fixed::fetch(&pool, &redis).await?;
+    let facets = fixed::fetch(&pool, &redis)
+        .await
+        .wrap_api_err("executing `fixed::fetch`")?;
 
     Ok(web::Json(FacetsResponse { facets }))
 }
diff --git a/apps/labrinth/src/routes/v3/analytics_get/metrics/affiliate_code_conversions.rs b/apps/labrinth/src/routes/v3/analytics_get/metrics/affiliate_code_conversions.rs
index c62f1e0e0b..29e611ccab 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/metrics/affiliate_code_conversions.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/metrics/affiliate_code_conversions.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use futures::StreamExt;
 use serde::{Deserialize, Serialize};
 
@@ -91,7 +92,12 @@ pub(crate) async fn fetch(
         &filter_affiliate_code_ids,
     )
     .fetch(pool);
-    while let Some(row) = rows.next().await.transpose()? {
+    while let Some(row) = rows
+        .next()
+        .await
+        .transpose()
+        .wrap_internal_err("fetching affiliate code conversions")?
+    {
         let bucket = row
             .bucket
             .wrap_internal_err("bucket should be non-null - query bug!")?;
@@ -116,7 +122,8 @@ pub(crate) async fn fetch(
                     AffiliateCodeConversions { conversions },
                 ),
             }),
-        )?;
+        )
+        .wrap_api_err("executing `AffiliateCodeMetrics::Conversions`")?;
     }
 
     Ok(())
diff --git a/apps/labrinth/src/routes/v3/analytics_get/metrics/affiliate_code_revenue.rs b/apps/labrinth/src/routes/v3/analytics_get/metrics/affiliate_code_revenue.rs
index 9873bc15cd..791dd8a3dd 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/metrics/affiliate_code_revenue.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/metrics/affiliate_code_revenue.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use futures::StreamExt;
 use rust_decimal::Decimal;
 use serde::{Deserialize, Serialize};
@@ -86,7 +87,12 @@ pub(crate) async fn fetch(
         &filter_affiliate_code_ids,
     )
     .fetch(pool);
-    while let Some(row) = rows.next().await.transpose()? {
+    while let Some(row) = rows
+        .next()
+        .await
+        .transpose()
+        .wrap_internal_err("fetching affiliate code revenue")?
+    {
         let bucket = row
             .bucket
             .wrap_internal_err("bucket should be non-null - query bug!")?;
@@ -110,7 +116,8 @@ pub(crate) async fn fetch(
                     revenue,
                 }),
             }),
-        )?;
+        )
+        .wrap_api_err("executing `AffiliateCodeMetrics::Revenue`")?;
     }
 
     Ok(())
diff --git a/apps/labrinth/src/routes/v3/analytics_get/metrics/project_downloads.rs b/apps/labrinth/src/routes/v3/analytics_get/metrics/project_downloads.rs
index 36e8aabe16..2439d9cb5c 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/metrics/project_downloads.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/metrics/project_downloads.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use std::{
     collections::{HashMap, HashSet},
     sync::{
@@ -14,7 +15,7 @@ use serde::{Deserialize, Deserializer, Serialize, Serializer, de::Error as _};
 use crate::{
     database::{
         PgPool,
-        models::{DBProjectId, DBVersion, DBVersionId},
+        models::{DBProjectId, DBVersionId},
     },
     models::{
         ids::{ProjectId, VersionId},
@@ -326,37 +327,28 @@ async fn fetch_dependent_version_projects(
         return Ok(HashMap::new());
     }
 
-    let dependent_on_version_ids =
-        dependent_on_version_ids.into_iter().collect::<Vec<_>>();
-    let versions =
-        DBVersion::get_many(&dependent_on_version_ids, cx.pool, cx.redis)
-            .await?;
-
-    let dependent_project_ids = versions
-        .iter()
-        .map(|version| version.inner.project_id.0)
+    let dependent_on_version_ids = dependent_on_version_ids
+        .into_iter()
+        .map(|version_id| version_id.0)
         .collect::<Vec<_>>();
-    let server_projects = sqlx::query!(
+    let versions = sqlx::query!(
         "
-        SELECT id FROM mods
-        WHERE id = ANY($1)
-            AND components ? 'minecraft_server'
+        SELECT v.id, v.mod_id
+        FROM versions v
+        INNER JOIN mods m ON m.id = v.mod_id
+        WHERE
+            v.id = ANY($1)
+            AND jsonb_typeof(m.components -> 'minecraft_server') IS DISTINCT FROM 'object'
         ",
-        &dependent_project_ids,
+        &dependent_on_version_ids,
     )
     .fetch_all(cx.pool)
     .await
-    .wrap_internal_err("failed to fetch server dependent projects")?
-    .into_iter()
-    .map(|project| DBProjectId(project.id))
-    .collect::<HashSet<_>>();
+    .wrap_internal_err("failed to fetch dependent version projects")?;
 
     Ok(versions
         .into_iter()
-        .filter_map(|version| {
-            (!server_projects.contains(&version.inner.project_id))
-                .then_some((version.inner.id, version.inner.project_id))
-        })
+        .map(|version| (DBVersionId(version.id), DBProjectId(version.mod_id)))
         .collect())
 }
 
@@ -367,7 +359,9 @@ pub(crate) async fn fetch(
     use ProjectDownloadsField as F;
     let uses = |field| metrics.bucket_by.contains(&field);
     let dependent_on_version_filter =
-        fetch_dependent_on_version_filter(metrics, cx.pool).await?;
+        fetch_dependent_on_version_filter(metrics, cx.pool)
+            .await
+            .wrap_api_err("fetching dependent on version filter")?;
     if !metrics.filter_by.dependent_project_id.is_empty()
         && dependent_on_version_filter.is_empty()
     {
@@ -442,15 +436,23 @@ pub(crate) async fn fetch(
             .iter()
             .any(|(column_name, used)| *column_name == name && *used)
     };
-    let mut cursor = query.fetch::<DownloadRow>()?;
+    let mut cursor = query
+        .fetch::<DownloadRow>()
+        .wrap_internal_err("fetching project-download pagination cursor")?;
     let mut rows = Vec::new();
 
-    while let Some(row) = cursor.next().await? {
+    while let Some(row) = cursor
+        .next()
+        .await
+        .wrap_internal_err("fetching project downloads")?
+    {
         rows.push(row);
     }
 
     let dependent_version_projects =
-        fetch_dependent_version_projects(&rows, cx).await?;
+        fetch_dependent_version_projects(&rows, cx)
+            .await
+            .wrap_api_err("fetching dependent version projects")?;
     let mut buckets = HashMap::<DownloadBucket, u64>::new();
 
     for row in rows {
@@ -576,7 +578,8 @@ pub(crate) async fn fetch(
                     downloads,
                 }),
             }),
-        )?;
+        )
+        .wrap_api_err("executing `ProjectMetrics::Downloads`")?;
     }
 
     Ok(())
diff --git a/apps/labrinth/src/routes/v3/analytics_get/metrics/project_playtime.rs b/apps/labrinth/src/routes/v3/analytics_get/metrics/project_playtime.rs
index 91ce1cfc10..f5ce8767b0 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/metrics/project_playtime.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/metrics/project_playtime.rs
@@ -1,3 +1,5 @@
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use std::collections::HashMap;
 
 use const_format::formatcp;
@@ -227,10 +229,16 @@ pub(crate) async fn fetch(
         query = filter_param.bind(query);
     }
 
-    let mut cursor = query.fetch::<PlaytimeRow>()?;
+    let mut cursor = query
+        .fetch::<PlaytimeRow>()
+        .wrap_internal_err("fetching project-playtime pagination cursor")?;
     let mut buckets = HashMap::<PlaytimeBucket, u64>::new();
 
-    while let Some(row) = cursor.next().await? {
+    while let Some(row) = cursor
+        .next()
+        .await
+        .wrap_internal_err("fetching project playtime")?
+    {
         let project_id =
             if uses_column("use_project_id") && row.project_id.0 == 0 {
                 parent_version_projects
@@ -308,7 +316,8 @@ pub(crate) async fn fetch(
                     seconds,
                 }),
             }),
-        )?;
+        )
+        .wrap_api_err("executing `ProjectMetrics::Playtime`")?;
     }
 
     Ok(())
diff --git a/apps/labrinth/src/routes/v3/analytics_get/metrics/project_revenue.rs b/apps/labrinth/src/routes/v3/analytics_get/metrics/project_revenue.rs
index 0b292ae0f3..c03de3cf8c 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/metrics/project_revenue.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/metrics/project_revenue.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use futures::StreamExt;
 use rust_decimal::Decimal;
 use serde::{Deserialize, Serialize};
@@ -95,7 +96,12 @@ pub(crate) async fn fetch(
         user_id_bucket_project_ids,
     )
     .fetch(pool);
-    while let Some(row) = rows.next().await.transpose()? {
+    while let Some(row) = rows
+        .next()
+        .await
+        .transpose()
+        .wrap_internal_err("fetching project revenue")?
+    {
         let bucket = row
             .bucket
             .wrap_internal_err("bucket should be non-null - query bug!")?;
@@ -123,7 +129,8 @@ pub(crate) async fn fetch(
                         revenue,
                     }),
                 }),
-            )?;
+            )
+            .wrap_api_err("adding project revenue to time slice")?;
         }
     }
 
diff --git a/apps/labrinth/src/routes/v3/analytics_get/metrics/project_views.rs b/apps/labrinth/src/routes/v3/analytics_get/metrics/project_views.rs
index cd612c3c38..a1b276e99c 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/metrics/project_views.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/metrics/project_views.rs
@@ -1,3 +1,5 @@
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use std::collections::HashMap;
 
 use const_format::formatcp;
@@ -188,10 +190,16 @@ pub(crate) async fn fetch(
         query = filter_param.bind(query);
     }
 
-    let mut cursor = query.fetch::<ViewRow>()?;
+    let mut cursor = query
+        .fetch::<ViewRow>()
+        .wrap_internal_err("fetching project-view pagination cursor")?;
     let mut buckets = HashMap::<ViewBucket, u64>::new();
 
-    while let Some(row) = cursor.next().await? {
+    while let Some(row) = cursor
+        .next()
+        .await
+        .wrap_internal_err("fetching project views")?
+    {
         let key = ViewBucket {
             bucket: row.bucket,
             project_id: row.project_id,
@@ -252,7 +260,8 @@ pub(crate) async fn fetch(
                     views,
                 }),
             }),
-        )?;
+        )
+        .wrap_api_err("executing `ProjectMetrics::Views`")?;
     }
 
     Ok(())
diff --git a/apps/labrinth/src/routes/v3/analytics_get/mod.rs b/apps/labrinth/src/routes/v3/analytics_get/mod.rs
index 72d1831dbc..6dc980a1c7 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/mod.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/mod.rs
@@ -7,6 +7,9 @@
 //!   requests, you have to zip together M arrays of N elements
 //!   - this makes it inconvenient to have separate endpoints
 
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
+
 use xredis::RedisPool;
 
 pub mod facets;
@@ -195,36 +198,30 @@ pub async fn fetch_analytics(
         &session_queue,
         Scopes::ANALYTICS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let full_time_range = req.time_range.end - req.time_range.start;
     if full_time_range < TimeDelta::zero() {
-        return Err(ApiError::InvalidInput(
-            "End date must be after start date".into(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "End date must be after start date",
+        )));
     }
 
     let (num_time_slices, resolution) = match req.time_range.resolution {
         TimeRangeResolution::Slices(slices) => {
-            let slices = i32::try_from(slices.get()).map_err(|_| {
-                ApiError::InvalidInput(
-                    "Number of slices must fit into an `i32`".into(),
-                )
-            })?;
+            let slices = i32::try_from(slices.get())
+                .map_err(|err| eyre::eyre!(err))
+                .wrap_request_err("number of slices must fit into an `i32`")?;
             let resolution = full_time_range / slices;
             (slices as usize, resolution)
         }
         TimeRangeResolution::Minutes(resolution_minutes) => {
             let resolution_minutes = i64::try_from(resolution_minutes.get())
-                .map_err(|_| {
-                    ApiError::InvalidInput(
-                        "Resolution must fit into a `i64`".into(),
-                    )
-                })?;
+                .map_err(|err| eyre::eyre!(err))
+                .wrap_request_err("resolution must fit into a `i64`")?;
             let resolution = TimeDelta::try_minutes(resolution_minutes)
-                .ok_or_else(|| {
-                    ApiError::InvalidInput("Resolution overflow".into())
-                })?;
+                .wrap_request_err_with(|| "resolution overflow")?;
 
             let num_slices =
                 full_time_range.as_seconds_f64() / resolution.as_seconds_f64();
@@ -248,7 +245,9 @@ pub async fn fetch_analytics(
 
     let project_ids = {
         if req.project_ids.is_empty() {
-            DBUser::get_projects(user.id.into(), &**pool, &redis).await?
+            DBUser::get_projects(user.id.into(), &**pool, &redis)
+                .await
+                .wrap_internal_err("fetching users from database")?
         } else {
             req.project_ids
                 .iter()
@@ -258,7 +257,9 @@ pub async fn fetch_analytics(
     };
 
     let project_ids =
-        filter_allowed_project_ids(&project_ids, &user, &pool, &redis).await?;
+        filter_allowed_project_ids(&project_ids, &user, &pool, &redis)
+            .await
+            .wrap_api_err("filtering allowed project ids")?;
 
     let project_id_values =
         project_ids.iter().map(|id| id.0).collect::<Vec<_>>();
@@ -271,7 +272,8 @@ pub async fn fetch_analytics(
         &project_id_values,
     )
     .fetch_all(&**pool)
-    .await?;
+    .await
+    .wrap_internal_err("fetching parent versions from database")?;
     let parent_version_ids = parent_versions
         .iter()
         .map(|version| DBVersionId(version.id))
@@ -281,7 +283,9 @@ pub async fn fetch_analytics(
         .map(|version| (DBVersionId(version.id), DBProjectId(version.mod_id)))
         .collect::<HashMap<_, _>>();
     let parent_version_data =
-        DBVersion::get_many(&parent_version_ids, &**pool, &redis).await?;
+        DBVersion::get_many(&parent_version_ids, &**pool, &redis)
+            .await
+            .wrap_internal_err("fetching versions from database")?;
     let visible_version_ids = filter_visible_version_ids(
         parent_version_data
             .iter()
@@ -291,7 +295,8 @@ pub async fn fetch_analytics(
         &pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("filtering visible version ids")?;
     let mut project_events = parent_version_data
         .iter()
         .filter(|version| {
@@ -315,13 +320,15 @@ pub async fn fetch_analytics(
             &req.time_range,
             &pool,
         )
-        .await?,
+        .await
+        .wrap_api_err("fetching project status change events")?,
     );
     project_events.sort_by_key(|event| event.timestamp);
 
     let affiliate_code_ids =
         DBAffiliateCode::get_by_affiliate(user.id.into(), &**pool)
-            .await?
+            .await
+            .wrap_internal_err("fetching affiliate codes from database")?
             .into_iter()
             .map(|code| code.id)
             .collect::<Vec<_>>();
@@ -330,7 +337,6 @@ pub async fn fetch_analytics(
     let mut query_clickhouse_cx = QueryClickhouseContext {
         clickhouse: &clickhouse,
         pool: &pool,
-        redis: &redis,
         req: &req,
         time_slices: &mut time_slices,
         project_ids: &project_ids,
@@ -340,12 +346,15 @@ pub async fn fetch_analytics(
     };
 
     if let Some(metrics) = &req.return_metrics.project_views {
-        metrics::fetch_project_views(&mut query_clickhouse_cx, metrics).await?;
+        metrics::fetch_project_views(&mut query_clickhouse_cx, metrics)
+            .await
+            .wrap_api_err("fetching project views")?;
     }
 
     if let Some(metrics) = &req.return_metrics.project_downloads {
         metrics::fetch_project_downloads(&mut query_clickhouse_cx, metrics)
-            .await?;
+            .await
+            .wrap_api_err("fetching project downloads")?;
     }
 
     if let Some(metrics) = &req.return_metrics.project_playtime {
@@ -354,17 +363,21 @@ pub async fn fetch_analytics(
             &parent_version_projects,
             metrics,
         )
-        .await?;
+        .await
+        .wrap_api_err("fetching project playtime")?;
     }
 
     if let Some(metrics) = &req.return_metrics.affiliate_code_clicks {
         metrics::fetch_affiliate_code_clicks(&mut query_clickhouse_cx, metrics)
-            .await?;
+            .await
+            .wrap_api_err("fetching affiliate code clicks")?;
     }
 
     if let Some(metrics) = &req.return_metrics.project_revenue {
         if !scopes.contains(Scopes::PAYOUTS_READ) {
-            return Err(AuthenticationError::InvalidCredentials.into());
+            return Err(ApiError::Auth(eyre::eyre!(
+                AuthenticationError::InvalidCredentials
+            )));
         }
 
         let user_id_bucket_project_ids = sqlx::query!(
@@ -381,7 +394,8 @@ pub async fn fetch_analytics(
             DBUserId::from(user.id).0,
         )
         .fetch_all(&**pool)
-        .await?
+        .await
+        .wrap_internal_err("fetching user IDs from database")?
         .into_iter()
         .map(|row| row.id)
         .collect::<Vec<_>>();
@@ -396,7 +410,8 @@ pub async fn fetch_analytics(
             user.role.is_mod(),
             metrics,
         )
-        .await?;
+        .await
+        .wrap_api_err("checking mod")?;
     }
 
     if let Some(metrics) = &req.return_metrics.affiliate_code_conversions {
@@ -408,12 +423,15 @@ pub async fn fetch_analytics(
             num_time_slices,
             metrics,
         )
-        .await?;
+        .await
+        .wrap_api_err("fetching affiliate code conversions")?;
     }
 
     if let Some(metrics) = &req.return_metrics.affiliate_code_revenue {
         if !scopes.contains(Scopes::PAYOUTS_READ) {
-            return Err(AuthenticationError::InvalidCredentials.into());
+            return Err(ApiError::Auth(eyre::eyre!(
+                AuthenticationError::InvalidCredentials
+            )));
         }
 
         metrics::fetch_affiliate_code_revenue(
@@ -424,12 +442,17 @@ pub async fn fetch_analytics(
             num_time_slices,
             metrics,
         )
-        .await?;
+        .await
+        .wrap_api_err("fetching affiliate code revenue")?;
     }
 
     let projects =
-        fetch_response_projects(&mut time_slices, &user, &pool, &redis).await?;
-    let users = fetch_response_users(&time_slices, &pool, &redis).await?;
+        fetch_response_projects(&mut time_slices, &user, &pool, &redis)
+            .await
+            .wrap_api_err("fetching response projects")?;
+    let users = fetch_response_users(&time_slices, &pool, &redis)
+        .await
+        .wrap_api_err("fetching response users")?;
 
     Ok(web::Json(GetResponse {
         metrics: time_slices,
@@ -531,14 +554,17 @@ async fn fetch_response_projects(
     }
 
     let project_ids = project_ids.into_iter().collect::<Vec<_>>();
-    let projects = DBProject::get_many_ids(&project_ids, pool, redis).await?;
+    let projects = DBProject::get_many_ids(&project_ids, pool, redis)
+        .await
+        .wrap_api_err("fetching analytics projects")?;
     let visible_project_ids = filter_visible_project_ids(
         projects.iter().map(|project| &project.inner).collect(),
         &Some(user.clone()),
         pool,
         false,
     )
-    .await?
+    .await
+    .wrap_api_err("filtering visible project ids")?
     .into_iter()
     .collect::<HashSet<_>>();
 
@@ -580,7 +606,9 @@ async fn fetch_response_users(
         return Ok(HashMap::new());
     }
 
-    let users = DBUser::get_many_ids(&user_ids, pool, redis).await?;
+    let users = DBUser::get_many_ids(&user_ids, pool, redis)
+        .await
+        .wrap_internal_err("fetching users from database")?;
 
     Ok(users
         .into_iter()
@@ -649,7 +677,10 @@ async fn fetch_project_status_change_events(
         time_range.end,
     )
     .fetch_all(&**pool)
-    .await?;
+    .await
+    .wrap_internal_err(
+        "querying database for `fetch_project_status_change_events`",
+    )?;
 
     Ok(rows
         .into_iter()
@@ -677,7 +708,6 @@ async fn fetch_project_status_change_events(
 pub(crate) struct QueryClickhouseContext<'a> {
     pub(crate) clickhouse: &'a clickhouse::Client,
     pub(crate) pool: &'a PgPool,
-    pub(crate) redis: &'a RedisPool,
     pub(crate) req: &'a GetRequest,
     pub(crate) time_slices: &'a mut [TimeSlice],
     pub(crate) project_ids: &'a [DBProjectId],
@@ -798,14 +828,21 @@ where
     for filter_param in filter_params {
         query = filter_param.bind(query);
     }
-    let mut cursor = query.fetch::<Row>()?;
+    let mut cursor = query
+        .fetch::<Row>()
+        .wrap_internal_err("fetching analytics pagination cursor")?;
 
-    while let Some(row) = cursor.next().await? {
+    while let Some(row) = cursor
+        .next()
+        .await
+        .wrap_internal_err("querying database for `query_clickhouse`")?
+    {
         if !row_filter(&row) {
             continue;
         }
         let bucket = row_get_bucket(&row) as usize;
-        add_to_time_slice(cx.time_slices, bucket, row_to_analytics(row))?;
+        add_to_time_slice(cx.time_slices, bucket, row_to_analytics(row))
+            .wrap_api_err("executing `row_to_analytics`")?;
     }
 
     Ok(())
@@ -827,11 +864,7 @@ pub(crate) fn add_to_time_slice(
     };
 
     let num_time_slices = time_slices.len();
-    let slice = time_slices.get_mut(bucket).ok_or_else(|| {
-        ApiError::InvalidInput(
-            format!("bucket {bucket} returned by query out of range for {num_time_slices} - query bug!")
-        )
-    })?;
+    let slice = time_slices.get_mut(bucket).wrap_request_err_with(|| format!("bucket {bucket} returned by query out of range for {num_time_slices} - query bug!"))?;
 
     slice.0.push(data);
     Ok(())
@@ -843,7 +876,9 @@ async fn filter_allowed_project_ids(
     pool: &PgPool,
     redis: &RedisPool,
 ) -> Result<Vec<DBProjectId>, ApiError> {
-    let projects = DBProject::get_many_ids(project_ids, pool, redis).await?;
+    let projects = DBProject::get_many_ids(project_ids, pool, redis)
+        .await
+        .wrap_api_err("fetching projects for analytics authorization")?;
 
     let team_ids = projects
         .iter()
@@ -852,7 +887,8 @@ async fn filter_allowed_project_ids(
     let team_members = database::models::DBTeamMember::get_from_team_full_many(
         &team_ids, pool, redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching team members from database")?;
 
     let organization_ids = projects
         .iter()
@@ -863,7 +899,8 @@ async fn filter_allowed_project_ids(
         pool,
         redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching organizations from database")?;
 
     let organization_team_ids = organizations
         .iter()
@@ -875,7 +912,8 @@ async fn filter_allowed_project_ids(
             pool,
             redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching team members from database")?;
 
     Ok(projects
         .into_iter()
diff --git a/apps/labrinth/src/routes/v3/analytics_get/old.rs b/apps/labrinth/src/routes/v3/analytics_get/old.rs
index 060a0299d7..a164921783 100644
--- a/apps/labrinth/src/routes/v3/analytics_get/old.rs
+++ b/apps/labrinth/src/routes/v3/analytics_get/old.rs
@@ -1,5 +1,8 @@
 //! TODO: this module should be removed; it is superseded by `analytics_get`
 
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
+
 use super::ApiError;
 use crate::database;
 use crate::database::PgPool;
@@ -13,7 +16,6 @@ use crate::{
 use actix_web::{HttpRequest, HttpResponse, get, web};
 use ariadne::ids::base62_impl::to_base62;
 use chrono::{DateTime, Duration, Utc};
-use eyre::eyre;
 use serde::{Deserialize, Serialize};
 use sqlx::postgres::types::PgInterval;
 use std::collections::HashMap;
@@ -77,13 +79,15 @@ pub async fn playtimes_get(
         Scopes::ANALYTICS,
     )
     .await
-    .map(|x| x.1)?;
+    .map(|x| x.1)
+    .wrap_auth_err("authenticating API request")?;
 
     let project_ids = data
         .project_ids
         .as_ref()
         .map(|ids| serde_json::from_str::<Vec<String>>(ids))
-        .transpose()?;
+        .transpose()
+        .wrap_request_err("deserializing JSON data")?;
 
     let start_date = data.start_date.unwrap_or(Utc::now() - Duration::weeks(2));
     let end_date = data.end_date.unwrap_or(Utc::now());
@@ -95,7 +99,9 @@ pub async fn playtimes_get(
     // - Filter out unauthorized projects/versions
     // - If no project_ids or version_ids are provided, we default to all projects the user has access to
     let project_ids =
-        filter_allowed_ids(project_ids, user, &pool, &redis, None).await?;
+        filter_allowed_ids(project_ids, user, &pool, &redis, None)
+            .await
+            .wrap_api_err("filtering authorized playtime project IDs")?;
 
     // Get the views
     let playtimes = crate::clickhouse::fetch_playtimes(
@@ -105,7 +111,8 @@ pub async fn playtimes_get(
         resolution_minutes,
         clickhouse.into_inner(),
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching project playtime from ClickHouse")?;
 
     let mut hm = HashMap::new();
     for playtime in playtimes {
@@ -159,13 +166,15 @@ pub async fn views_get(
         Scopes::ANALYTICS,
     )
     .await
-    .map(|x| x.1)?;
+    .map(|x| x.1)
+    .wrap_auth_err("authenticating API request")?;
 
     let project_ids = data
         .project_ids
         .as_ref()
         .map(|ids| serde_json::from_str::<Vec<String>>(ids))
-        .transpose()?;
+        .transpose()
+        .wrap_request_err("deserializing JSON data")?;
 
     let start_date = data.start_date.unwrap_or(Utc::now() - Duration::weeks(2));
     let end_date = data.end_date.unwrap_or(Utc::now());
@@ -177,7 +186,9 @@ pub async fn views_get(
     // - Filter out unauthorized projects/versions
     // - If no project_ids or version_ids are provided, we default to all projects the user has access to
     let project_ids =
-        filter_allowed_ids(project_ids, user, &pool, &redis, None).await?;
+        filter_allowed_ids(project_ids, user, &pool, &redis, None)
+            .await
+            .wrap_api_err("filtering authorized view project IDs")?;
 
     // Get the views
     let views = crate::clickhouse::fetch_views(
@@ -187,7 +198,8 @@ pub async fn views_get(
         resolution_minutes,
         clickhouse.into_inner(),
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching project views from ClickHouse")?;
 
     let mut hm = HashMap::new();
     for views in views {
@@ -241,13 +253,15 @@ pub async fn downloads_get(
         Scopes::ANALYTICS,
     )
     .await
-    .map(|x| x.1)?;
+    .map(|x| x.1)
+    .wrap_auth_err("authenticating API request")?;
 
     let project_ids = data
         .project_ids
         .as_ref()
         .map(|ids| serde_json::from_str::<Vec<String>>(ids))
-        .transpose()?;
+        .transpose()
+        .wrap_request_err("deserializing JSON data")?;
 
     let start_date = data.start_date.unwrap_or(Utc::now() - Duration::weeks(2));
     let end_date = data.end_date.unwrap_or(Utc::now());
@@ -260,7 +274,8 @@ pub async fn downloads_get(
     // - If no project_ids or version_ids are provided, we default to all projects the user has access to
     let project_ids =
         filter_allowed_ids(project_ids, user_option, &pool, &redis, None)
-            .await?;
+            .await
+            .wrap_api_err("filtering authorized download project IDs")?;
 
     // Get the downloads
     let downloads = crate::clickhouse::fetch_downloads(
@@ -270,7 +285,8 @@ pub async fn downloads_get(
         resolution_minutes,
         clickhouse.into_inner(),
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching project downloads from ClickHouse")?;
 
     let mut hm = HashMap::new();
     for downloads in downloads {
@@ -323,13 +339,15 @@ pub async fn revenue_get(
         Scopes::PAYOUTS_READ,
     )
     .await
-    .map(|x| x.1)?;
+    .map(|x| x.1)
+    .wrap_auth_err("authenticating API request")?;
 
     let project_ids = data
         .project_ids
         .as_ref()
         .map(|ids| serde_json::from_str::<Vec<String>>(ids))
-        .transpose()?;
+        .transpose()
+        .wrap_request_err("deserializing JSON data")?;
 
     let start_date = data.start_date.unwrap_or(Utc::now() - Duration::weeks(2));
     let end_date = data.end_date.unwrap_or(Utc::now());
@@ -357,13 +375,15 @@ pub async fn revenue_get(
         &redis,
         Some(true),
     )
-    .await?;
+    .await
+    .wrap_api_err("filtering authorized revenue project IDs")?;
 
     let duration: PgInterval = Duration::minutes(resolution_minutes as i64)
         .try_into()
-        .map_err(|_| {
-            ApiError::Request(eyre!("Invalid `resolution_minutes`"))
-        })?;
+        .map_err(|err: Box<dyn std::error::Error + Send + Sync>| {
+            eyre::eyre!("{err}")
+        })
+        .wrap_request_err("invalid `resolution_minutes`")?;
     // Get the revenue data
     let project_ids = project_ids.unwrap_or_default();
 
@@ -387,7 +407,7 @@ pub async fn revenue_get(
             duration,
         )
             .fetch_all(&**pool)
-            .await?.into_iter().map(|x| PayoutValue {
+            .await.wrap_internal_err("fetching payouts values from database")?.into_iter().map(|x| PayoutValue {
             mod_id: x.mod_id,
             amount_sum: x.amount_sum,
             interval_start: x.interval_start,
@@ -406,7 +426,7 @@ pub async fn revenue_get(
             duration,
         )
             .fetch_all(&**pool)
-            .await?.into_iter().map(|x| PayoutValue {
+            .await.wrap_internal_err("querying database for `revenue_get`")?.into_iter().map(|x| PayoutValue {
             mod_id: x.mod_id,
             amount_sum: x.amount_sum,
             interval_start: x.interval_start,
@@ -476,13 +496,15 @@ pub async fn countries_downloads_get(
         Scopes::ANALYTICS,
     )
     .await
-    .map(|x| x.1)?;
+    .map(|x| x.1)
+    .wrap_auth_err("authenticating API request")?;
 
     let project_ids = data
         .project_ids
         .as_ref()
         .map(|ids| serde_json::from_str::<Vec<String>>(ids))
-        .transpose()?;
+        .transpose()
+        .wrap_request_err("deserializing JSON data")?;
 
     let start_date = data.start_date.unwrap_or(Utc::now() - Duration::weeks(2));
     let end_date = data.end_date.unwrap_or(Utc::now());
@@ -491,7 +513,11 @@ pub async fn countries_downloads_get(
     // - Filter out unauthorized projects/versions
     // - If no project_ids or version_ids are provided, we default to all projects the user has access to
     let project_ids =
-        filter_allowed_ids(project_ids, user, &pool, &redis, None).await?;
+        filter_allowed_ids(project_ids, user, &pool, &redis, None)
+            .await
+            .wrap_api_err(
+                "filtering authorized download-country project IDs",
+            )?;
 
     // Get the countries
     let countries = crate::clickhouse::fetch_countries_downloads(
@@ -500,7 +526,8 @@ pub async fn countries_downloads_get(
         end_date,
         clickhouse.into_inner(),
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching download countries from ClickHouse")?;
 
     let mut hm = HashMap::new();
     for views in countries {
@@ -562,13 +589,15 @@ pub async fn countries_views_get(
         Scopes::ANALYTICS,
     )
     .await
-    .map(|x| x.1)?;
+    .map(|x| x.1)
+    .wrap_auth_err("authenticating API request")?;
 
     let project_ids = data
         .project_ids
         .as_ref()
         .map(|ids| serde_json::from_str::<Vec<String>>(ids))
-        .transpose()?;
+        .transpose()
+        .wrap_request_err("deserializing JSON data")?;
 
     let start_date = data.start_date.unwrap_or(Utc::now() - Duration::weeks(2));
     let end_date = data.end_date.unwrap_or(Utc::now());
@@ -577,7 +606,9 @@ pub async fn countries_views_get(
     // - Filter out unauthorized projects/versions
     // - If no project_ids or version_ids are provided, we default to all projects the user has access to
     let project_ids =
-        filter_allowed_ids(project_ids, user, &pool, &redis, None).await?;
+        filter_allowed_ids(project_ids, user, &pool, &redis, None)
+            .await
+            .wrap_api_err("filtering authorized view-country project IDs")?;
 
     // Get the countries
     let countries = crate::clickhouse::fetch_countries_views(
@@ -586,7 +617,8 @@ pub async fn countries_views_get(
         end_date,
         clickhouse.into_inner(),
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching view countries from ClickHouse")?;
 
     let mut hm = HashMap::new();
     for views in countries {
@@ -635,7 +667,8 @@ async fn filter_allowed_ids(
     if project_ids.is_none() && !remove_defaults.unwrap_or(false) {
         project_ids = Some(
             user_item::DBUser::get_projects(user.id.into(), &***pool, redis)
-                .await?
+                .await
+                .wrap_internal_err("deleting user from database")?
                 .into_iter()
                 .map(|x| ProjectId::from(x).to_string())
                 .collect(),
@@ -650,7 +683,8 @@ async fn filter_allowed_ids(
             &***pool,
             redis,
         )
-        .await?;
+        .await
+        .wrap_api_err("fetching analytics projects")?;
 
         let team_ids = projects_data
             .iter()
@@ -660,7 +694,8 @@ async fn filter_allowed_ids(
             database::models::DBTeamMember::get_from_team_full_many(
                 &team_ids, &***pool, redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team members from database")?;
 
         let organization_ids = projects_data
             .iter()
@@ -671,7 +706,8 @@ async fn filter_allowed_ids(
             &***pool,
             redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching organizations from database")?;
 
         let organization_team_ids = organizations
             .iter()
@@ -683,7 +719,8 @@ async fn filter_allowed_ids(
                 &***pool,
                 redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team members from database")?;
 
         let ids = projects_data
             .into_iter()
diff --git a/apps/labrinth/src/routes/v3/blocked_users.rs b/apps/labrinth/src/routes/v3/blocked_users.rs
index 4090e3ac1c..2cdd00bbc9 100644
--- a/apps/labrinth/src/routes/v3/blocked_users.rs
+++ b/apps/labrinth/src/routes/v3/blocked_users.rs
@@ -6,6 +6,7 @@ use crate::database::models::friend_item::DBFriend;
 use crate::models::pats::Scopes;
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 use actix_web::{HttpRequest, delete, get, post, web};
 use ariadne::ids::UserId;
 use eyre::eyre;
@@ -34,30 +35,43 @@ pub async fn block_user(
         &session_queue,
         Scopes::USER_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let user_id = info.into_inner().0;
-    let Some(blocked) = DBUser::get(&user_id, &**pool, &redis).await? else {
-        return Err(ApiError::NotFound);
+    let Some(blocked) = DBUser::get(&user_id, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?
+    else {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
     if blocked.id == user.id.into() {
         return Err(ApiError::Request(eyre!("you cannot block yourself")));
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
-    DBFriend::remove(user.id.into(), blocked.id, &mut transaction).await?;
+    DBFriend::remove(user.id.into(), blocked.id, &mut transaction)
+        .await
+        .wrap_internal_err("deleting friend from database")?;
 
     DBBlockedUser {
         user_id: user.id.into(),
         blocked_id: blocked.id,
     }
     .insert(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `block_user`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(())
 }
@@ -79,15 +93,21 @@ pub async fn unblock_user(
         &session_queue,
         Scopes::USER_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let user_id = info.into_inner().0;
-    let Some(blocked) = DBUser::get(&user_id, &**pool, &redis).await? else {
-        return Err(ApiError::NotFound);
+    let Some(blocked) = DBUser::get(&user_id, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?
+    else {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
-    DBBlockedUser::remove(user.id.into(), blocked.id, &**pool).await?;
+    DBBlockedUser::remove(user.id.into(), blocked.id, &**pool)
+        .await
+        .wrap_internal_err("deleting blocked user from database")?;
 
     Ok(())
 }
@@ -108,11 +128,13 @@ pub async fn get_blocked_users(
         &session_queue,
         Scopes::USER_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let blocked = DBBlockedUser::get_blocked_for_user(user.id.into(), &**pool)
-        .await?
+        .await
+        .wrap_internal_err("fetching blocked user from database")?
         .into_iter()
         .map(UserId::from)
         .collect();
diff --git a/apps/labrinth/src/routes/v3/collections.rs b/apps/labrinth/src/routes/v3/collections.rs
index fe549298cf..b5e5d266a8 100644
--- a/apps/labrinth/src/routes/v3/collections.rs
+++ b/apps/labrinth/src/routes/v3/collections.rs
@@ -14,6 +14,7 @@ use crate::models::v3::user_limits::UserLimits;
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
 use crate::routes::v3::project_creation::CreateError;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use crate::util::img::delete_old_images;
 use crate::util::routes::read_limited_from_payload;
@@ -157,16 +158,20 @@ pub async fn collections_get(
     redis: web::Data<RedisPool>,
     session_queue: web::Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    let ids = serde_json::from_str::<Vec<&str>>(&ids.ids)?;
+    let ids = serde_json::from_str::<Vec<&str>>(&ids.ids)
+        .wrap_request_err("deserializing JSON data")?;
     let ids = ids
         .into_iter()
         .map(|x| {
             parse_base62(x).map(|x| database::models::DBCollectionId(x as i64))
         })
-        .collect::<Result<Vec<_>, _>>()?;
+        .collect::<Result<Vec<_>, _>>()
+        .wrap_request_err("parsing collection IDs")?;
 
     let collections_data =
-        database::models::DBCollection::get_many(&ids, &**pool, &redis).await?;
+        database::models::DBCollection::get_many(&ids, &**pool, &redis)
+            .await
+            .wrap_internal_err("fetching collections from database")?;
 
     let user_option = get_user_from_headers(
         &req,
@@ -181,7 +186,8 @@ pub async fn collections_get(
 
     let collections =
         filter_visible_collections(collections_data, &user_option, false)
-            .await?;
+            .await
+            .wrap_api_err("filtering visible collections")?;
 
     Ok(HttpResponse::Ok().json(collections))
 }
@@ -197,9 +203,13 @@ pub async fn collection_get(
 ) -> Result<HttpResponse, ApiError> {
     let string = info.into_inner().0;
 
-    let id = database::models::DBCollectionId(parse_base62(&string)? as i64);
+    let id = database::models::DBCollectionId(
+        parse_base62(&string).wrap_request_err("parsing collection ID")? as i64,
+    );
     let collection_data =
-        database::models::DBCollection::get(id, &**pool, &redis).await?;
+        database::models::DBCollection::get(id, &**pool, &redis)
+            .await
+            .wrap_internal_err("fetching collection from database")?;
     let user_option = get_user_from_headers(
         &req,
         &**pool,
@@ -212,11 +222,13 @@ pub async fn collection_get(
     .ok();
 
     if let Some(data) = collection_data
-        && is_visible_collection(&data, &user_option, false).await?
+        && is_visible_collection(&data, &user_option, false)
+            .await
+            .wrap_api_err("checking collection visibility")?
     {
         return Ok(HttpResponse::Ok().json(Collection::from(data)));
     }
-    Err(ApiError::NotFound)
+    Err(ApiError::NotFound(eyre::eyre!("resource not found")))
 }
 
 #[derive(Deserialize, Validate, utoipa::ToSchema)]
@@ -256,17 +268,22 @@ pub async fn collection_edit(
         &session_queue,
         Scopes::COLLECTION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    new_collection.validate().map_err(|err| {
-        ApiError::Validation(validation_errors_to_string(err, None))
-    })?;
+    new_collection
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let string = info.into_inner().0;
-    let id = database::models::DBCollectionId(parse_base62(&string)? as i64);
-    let result =
-        database::models::DBCollection::get(id, &**pool, &redis).await?;
+    let id = database::models::DBCollectionId(
+        parse_base62(&string).wrap_request_err("parsing collection ID")? as i64,
+    );
+    let result = database::models::DBCollection::get(id, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching collection from database")?;
 
     if let Some(collection_item) = result {
         if !can_modify_collection(&collection_item, &user) {
@@ -275,7 +292,10 @@ pub async fn collection_edit(
 
         let id = collection_item.id;
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         if let Some(name) = &new_collection.name {
             sqlx::query!(
@@ -288,7 +308,8 @@ pub async fn collection_edit(
                 id as database::models::ids::DBCollectionId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `collection_edit`")?;
         }
 
         if let Some(description) = &new_collection.description {
@@ -302,7 +323,8 @@ pub async fn collection_edit(
                 id as database::models::ids::DBCollectionId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `collection_edit`")?;
         }
 
         if let Some(status) = &new_collection.status {
@@ -310,9 +332,9 @@ pub async fn collection_edit(
                 || collection_item.status.is_approved()
                     && status.can_be_requested())
             {
-                return Err(ApiError::CustomAuthentication(
-                    "You don't have permission to set this status!".to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You don't have permission to set this status!",
+                )));
             }
 
             sqlx::query!(
@@ -325,7 +347,8 @@ pub async fn collection_edit(
                 id as database::models::ids::DBCollectionId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `collection_edit`")?;
         }
 
         if let Some(new_project_ids) = &new_collection.new_projects {
@@ -338,7 +361,8 @@ pub async fn collection_edit(
                 collection_item.id as database::models::ids::DBCollectionId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("fetching new project IDs from database")?;
 
             let collection_item_ids = new_project_ids
                 .iter()
@@ -349,9 +373,10 @@ pub async fn collection_edit(
                 let project = database::models::DBProject::get(
                     project_id, &**pool, &redis,
                 )
-                .await?
+                .await
+                .wrap_api_err("fetching project from database")?
                 .wrap_request_err_with(|| {
-                    eyre!("The specified project {project_id} does not exist!")
+                    eyre!("the specified project `{project_id}` does not exist")
                 })?;
                 validated_project_ids.push(project.inner.id.0);
             }
@@ -366,7 +391,8 @@ pub async fn collection_edit(
                 &validated_project_ids[..],
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `collection_edit`")?;
 
             sqlx::query!(
                 "
@@ -377,16 +403,21 @@ pub async fn collection_edit(
                 collection_item.id as database::models::ids::DBCollectionId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `collection_edit`")?;
         }
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         database::models::DBCollection::clear_cache(collection_item.id, &redis)
-            .await?;
+            .await
+            .wrap_internal_err("clearing cached data from Redis")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -420,18 +451,20 @@ pub async fn collection_icon_edit(
         &session_queue,
         Scopes::COLLECTION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let string = info.into_inner().0;
-    let id = database::models::DBCollectionId(parse_base62(&string)? as i64);
+    let id = database::models::DBCollectionId(
+        parse_base62(&string).wrap_request_err("parsing collection ID")? as i64,
+    );
     let collection_item =
         database::models::DBCollection::get(id, &**pool, &redis)
-            .await?
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "The specified collection does not exist!".to_string(),
-                )
+            .await
+            .wrap_internal_err("fetching collection from database")?
+            .wrap_request_err_with(|| {
+                "the specified collection does not exist!".to_string()
             })?;
 
     if !can_modify_collection(&collection_item, &user) {
@@ -444,14 +477,16 @@ pub async fn collection_icon_edit(
         FileHostPublicity::Public,
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("deleting old images")?;
 
     let bytes = read_limited_from_payload(
         &mut payload,
         262144,
         "Icons must be smaller than 256KiB",
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `read_limited_from_payload`")?;
 
     let collection_id: CollectionId = collection_item.id.into();
     let upload_result = crate::util::img::upload_image_optimized(
@@ -463,9 +498,13 @@ pub async fn collection_icon_edit(
         Some(1.0),
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("uploading image")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     sqlx::query!(
         "
@@ -479,11 +518,16 @@ pub async fn collection_icon_edit(
         collection_item.id as database::models::ids::DBCollectionId,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `collection_icon_edit`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     database::models::DBCollection::clear_cache(collection_item.id, &redis)
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -505,18 +549,20 @@ pub async fn delete_collection_icon(
         &session_queue,
         Scopes::COLLECTION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let string = info.into_inner().0;
-    let id = database::models::DBCollectionId(parse_base62(&string)? as i64);
+    let id = database::models::DBCollectionId(
+        parse_base62(&string).wrap_request_err("parsing collection ID")? as i64,
+    );
     let collection_item =
         database::models::DBCollection::get(id, &**pool, &redis)
-            .await?
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "The specified collection does not exist!".to_string(),
-                )
+            .await
+            .wrap_internal_err("fetching collection from database")?
+            .wrap_request_err_with(|| {
+                "the specified collection does not exist!".to_string()
             })?;
     if !can_modify_collection(&collection_item, &user) {
         return Ok(HttpResponse::Unauthorized().body(""));
@@ -528,8 +574,12 @@ pub async fn delete_collection_icon(
         FileHostPublicity::Public,
         &**file_host,
     )
-    .await?;
-    let mut transaction = pool.begin().await?;
+    .await
+    .wrap_api_err("deleting old images")?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     sqlx::query!(
         "
@@ -540,11 +590,16 @@ pub async fn delete_collection_icon(
         collection_item.id as database::models::ids::DBCollectionId,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `delete_collection_icon`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     database::models::DBCollection::clear_cache(collection_item.id, &redis)
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -565,37 +620,48 @@ pub async fn collection_delete(
         &session_queue,
         Scopes::COLLECTION_DELETE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let string = info.into_inner().0;
-    let id = database::models::DBCollectionId(parse_base62(&string)? as i64);
+    let id = database::models::DBCollectionId(
+        parse_base62(&string).wrap_request_err("parsing collection ID")? as i64,
+    );
     let collection = database::models::DBCollection::get(id, &**pool, &redis)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified collection does not exist!".to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching collection from database")?
+        .wrap_request_err_with(|| {
+            "the specified collection does not exist!".to_string()
         })?;
     if !can_modify_collection(&collection, &user) {
         return Ok(HttpResponse::Unauthorized().body(""));
     }
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let result = database::models::DBCollection::remove(
         collection.id,
         &mut transaction,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("deleting collection from database")?;
 
-    transaction.commit().await?;
-    database::models::DBCollection::clear_cache(collection.id, &redis).await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
+    database::models::DBCollection::clear_cache(collection.id, &redis)
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
     if result.is_some() {
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
diff --git a/apps/labrinth/src/routes/v3/content/mod.rs b/apps/labrinth/src/routes/v3/content/mod.rs
index 4d8cda3b91..51379b7f1b 100644
--- a/apps/labrinth/src/routes/v3/content/mod.rs
+++ b/apps/labrinth/src/routes/v3/content/mod.rs
@@ -11,6 +11,7 @@ use crate::models::pats::Scopes;
 use crate::models::projects::{DependencyType, Version};
 use crate::models::users::User;
 use crate::queue::session::AuthQueue;
+use crate::util::error::ApiContext as _;
 use actix_web::{HttpRequest, post, web};
 use ariadne::ids::base62_impl::parse_base62;
 use async_trait::async_trait;
@@ -72,7 +73,8 @@ pub async fn resolve_content(
         modrinth_content_management::resolve_content(&mut provider, request)
             .await
     }
-    .map_err(resolve_error_to_api)?;
+    .map_err(resolve_error_to_api)
+    .wrap_api_err("executing `modrinth_content_management::resolve_content`")?;
 
     Ok(web::Json(plan))
 }
diff --git a/apps/labrinth/src/routes/v3/friends.rs b/apps/labrinth/src/routes/v3/friends.rs
index 0f02c081da..5be589a6ac 100644
--- a/apps/labrinth/src/routes/v3/friends.rs
+++ b/apps/labrinth/src/routes/v3/friends.rs
@@ -13,6 +13,8 @@ use crate::routes::internal::statuses::{
 };
 use crate::sync::friends::RedisFriendsMessage;
 use crate::sync::status::get_user_status;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, post, web};
 use ariadne::networking::message::ServerToClientMessage;
 use chrono::Utc;
@@ -42,41 +44,54 @@ pub async fn add_friend(
         &session_queue,
         Scopes::USER_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let string = info.into_inner().0;
-    let Some(friend) = DBUser::get(&string, &**pool, &redis).await? else {
-        return Err(ApiError::NotFound);
+    let Some(friend) = DBUser::get(&string, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?
+    else {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
-    if DBBlockedUser::is_blocked(friend.id, user.id.into(), &**pool).await? {
-        return Err(ApiError::InvalidInput(
-            "You've been blocked the other user!".to_string(),
-        ));
-    } else if DBBlockedUser::is_blocked(user.id.into(), friend.id, &**pool)
-        .await?
+    if DBBlockedUser::is_blocked(friend.id, user.id.into(), &**pool)
+        .await
+        .wrap_internal_err("checking whether target user blocked requester")?
     {
-        return Err(ApiError::InvalidInput(
-            "You've blocked the other user!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "You've been blocked the other user!",
+        )));
+    } else if DBBlockedUser::is_blocked(user.id.into(), friend.id, &**pool)
+        .await
+        .wrap_internal_err("checking whether requester blocked target user")?
+    {
+        return Err(ApiError::Request(eyre::eyre!(
+            "You've blocked the other user!",
+        )));
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     if let Some(friend) =
-        DBFriend::get_friend(user.id.into(), friend.id, &**pool).await?
+        DBFriend::get_friend(user.id.into(), friend.id, &**pool)
+            .await
+            .wrap_internal_err("fetching friend from database")?
     {
         if friend.accepted {
-            return Err(ApiError::InvalidInput(
-                "You are already friends with this user!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You are already friends with this user!",
+            )));
         }
 
         if !friend.accepted && user.id != friend.friend_id.into() {
-            return Err(ApiError::InvalidInput(
-                "You cannot accept your own friend request!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You cannot accept your own friend request!",
+            )));
         }
 
         DBFriend::update_friend(
@@ -85,7 +100,8 @@ pub async fn add_friend(
             true,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_internal_err("updating friend in database")?;
 
         async fn send_friend_status(
             user_id: DBUserId,
@@ -103,27 +119,30 @@ pub async fn add_friend(
                         status: friend_status,
                     },
                 )
-                .await?;
+                .await
+                .wrap_internal_err("updating friend in database")?;
             }
 
             Ok(())
         }
 
         send_friend_status(friend.user_id, friend.friend_id, &db, &redis)
-            .await?;
+            .await
+            .wrap_api_err("executing `send_friend_status`")?;
         send_friend_status(friend.friend_id, friend.user_id, &db, &redis)
-            .await?;
+            .await
+            .wrap_api_err("executing `send_friend_status`")?;
     } else {
         if friend.id == user.id.into() {
-            return Err(ApiError::InvalidInput(
-                "You cannot add yourself as a friend!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You cannot add yourself as a friend!",
+            )));
         }
 
         if !friend.allow_friend_requests {
-            return Err(ApiError::InvalidInput(
-                "Friend requests are disabled for this user!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "Friend requests are disabled for this user!",
+            )));
         }
 
         DBFriend {
@@ -133,17 +152,26 @@ pub async fn add_friend(
             accepted: false,
         }
         .insert(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `send_friend_status`",
+        )?;
 
         send_message_to_user(
             &db,
             friend.id.into(),
             &ServerToClientMessage::FriendRequest { from: user.id },
         )
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `send_friend_status`",
+        )?;
     }
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -166,29 +194,41 @@ pub async fn remove_friend(
         &session_queue,
         Scopes::USER_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let string = info.into_inner().0;
-    let friend = DBUser::get(&string, &**pool, &redis).await?;
+    let friend = DBUser::get(&string, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(friend) = friend {
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
-        DBFriend::remove(user.id.into(), friend.id, &mut transaction).await?;
+        DBFriend::remove(user.id.into(), friend.id, &mut transaction)
+            .await
+            .wrap_internal_err("deleting friend from database")?;
 
         send_message_to_user(
             &db,
             friend.id.into(),
             &ServerToClientMessage::FriendRequestRejected { from: user.id },
         )
-        .await?;
+        .await
+        .wrap_internal_err("deleting friend from database")?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -208,11 +248,13 @@ pub async fn friends(
         &session_queue,
         Scopes::USER_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let friends = DBFriend::get_user_friends(user.id.into(), None, &**pool)
-        .await?
+        .await
+        .wrap_internal_err("fetching friends from database")?
         .into_iter()
         .map(UserFriend::from)
         .collect::<Vec<_>>();
diff --git a/apps/labrinth/src/routes/v3/images.rs b/apps/labrinth/src/routes/v3/images.rs
index 6b53cf0fab..7e45da50c1 100644
--- a/apps/labrinth/src/routes/v3/images.rs
+++ b/apps/labrinth/src/routes/v3/images.rs
@@ -11,6 +11,8 @@ use crate::models::ids::{ReportId, ThreadMessageId, VersionId};
 use crate::models::images::{Image, ImageContext};
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use crate::util::img::upload_image_optimized;
 use crate::util::routes::read_limited_from_payload;
 use actix_web::{HttpRequest, HttpResponse, post, web};
@@ -68,7 +70,8 @@ pub async fn images_add(
         &session_queue,
         context.relevant_scope(),
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     // Attempt to associated a supplied id with the context
@@ -77,25 +80,28 @@ pub async fn images_add(
         ImageContext::Project { project_id } => {
             if let Some(id) = data.project_id {
                 let project =
-                    project_item::DBProject::get(&id, &**pool, &redis).await?;
+                    project_item::DBProject::get(&id, &**pool, &redis)
+                        .await
+                        .wrap_api_err("fetching project from database")?;
                 if let Some(project) = project {
                     if is_team_member_project(
                         &project.inner,
                         &Some(user.clone()),
                         &pool,
                     )
-                    .await?
+                    .await
+                    .wrap_api_err("checking team member project")?
                     {
                         *project_id = Some(project.inner.id.into());
                     } else {
-                        return Err(ApiError::CustomAuthentication(
-                            "You are not authorized to upload images for this project".to_string(),
-                        ));
+                        return Err(ApiError::Auth(eyre::eyre!(
+                            "You are not authorized to upload images for this project",
+                        )));
                     }
                 } else {
-                    return Err(ApiError::InvalidInput(
-                        "The project could not be found.".to_string(),
-                    ));
+                    return Err(ApiError::Request(eyre::eyre!(
+                        "The project could not be found.",
+                    )));
                 }
             }
         }
@@ -103,7 +109,8 @@ pub async fn images_add(
             if let Some(id) = data.version_id {
                 let version =
                     version_item::DBVersion::get(id.into(), &**pool, &redis)
-                        .await?;
+                        .await
+                        .wrap_internal_err("fetching version from database")?;
                 if let Some(version) = version {
                     if is_team_member_version(
                         &version.inner,
@@ -111,18 +118,19 @@ pub async fn images_add(
                         &pool,
                         &redis,
                     )
-                    .await?
+                    .await
+                    .wrap_api_err("checking team member version")?
                     {
                         *version_id = Some(version.inner.id.into());
                     } else {
-                        return Err(ApiError::CustomAuthentication(
-                            "You are not authorized to upload images for this version".to_string(),
-                        ));
+                        return Err(ApiError::Auth(eyre::eyre!(
+                            "You are not authorized to upload images for this version",
+                        )));
                     }
                 } else {
-                    return Err(ApiError::InvalidInput(
-                        "The version could not be found.".to_string(),
-                    ));
+                    return Err(ApiError::Request(eyre::eyre!(
+                        "The version could not be found.",
+                    )));
                 }
             }
         }
@@ -130,60 +138,63 @@ pub async fn images_add(
             if let Some(id) = data.thread_message_id {
                 let thread_message =
                     thread_item::DBThreadMessage::get(id.into(), &**pool)
-                        .await?
-                        .ok_or_else(|| {
-                            ApiError::InvalidInput(
-                                "The thread message could not found."
-                                    .to_string(),
-                            )
+                        .await
+                        .wrap_internal_err(
+                            "fetching thread message from database",
+                        )?
+                        .wrap_request_err_with(|| {
+                            "the thread message could not found.".to_string()
                         })?;
                 let thread = thread_item::DBThread::get(thread_message.thread_id, &**pool)
-                    .await?
-                    .ok_or_else(|| {
-                        ApiError::InvalidInput(
-                            "The thread associated with the thread message could not be found"
-                                .to_string(),
-                        )
-                    })?;
-                if is_authorized_thread(&thread, &user, &pool).await? {
+                    .await.wrap_internal_err("fetching thread from database")?
+                    .wrap_request_err_with(|| "the thread associated with the thread message could not be found"
+                                .to_string())?;
+                if is_authorized_thread(&thread, &user, &pool)
+                    .await
+                    .wrap_api_err("checking thread authorization")?
+                {
                     *thread_message_id = Some(thread_message.id.into());
                 } else {
-                    return Err(ApiError::CustomAuthentication(
-                        "You are not authorized to upload images for this thread message"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You are not authorized to upload images for this thread message",
+                    )));
                 }
             }
         }
         ImageContext::Report { report_id } => {
             if let Some(id) = data.report_id {
                 let report = report_item::DBReport::get(id.into(), &**pool)
-                    .await?
-                    .ok_or_else(|| {
-                        ApiError::InvalidInput(
-                            "The report could not be found.".to_string(),
-                        )
+                    .await
+                    .wrap_internal_err("fetching report from database")?
+                    .wrap_request_err_with(|| {
+                        "the report could not be found.".to_string()
                     })?;
-                let thread = thread_item::DBThread::get(report.thread_id, &**pool)
-                    .await?
-                    .ok_or_else(|| {
-                        ApiError::InvalidInput(
-                            "The thread associated with the report could not be found.".to_string(),
-                        )
-                    })?;
-                if is_authorized_thread(&thread, &user, &pool).await? {
+                let thread = thread_item::DBThread::get(
+                    report.thread_id,
+                    &**pool,
+                )
+                .await
+                .wrap_internal_err("fetching thread from database")?
+                .wrap_request_err_with(|| {
+                    "the thread associated with the report could not be found."
+                        .to_string()
+                })?;
+                if is_authorized_thread(&thread, &user, &pool)
+                    .await
+                    .wrap_api_err("checking thread authorization")?
+                {
                     *report_id = Some(report.id.into());
                 } else {
-                    return Err(ApiError::CustomAuthentication(
-                        "You are not authorized to upload images for this report".to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You are not authorized to upload images for this report",
+                    )));
                 }
             }
         }
         ImageContext::Unknown => {
-            return Err(ApiError::InvalidInput(
-                "Context must be one of: project, version, thread_message, report".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "Context must be one of: project, version, thread_message, report",
+            )));
         }
     }
 
@@ -193,7 +204,8 @@ pub async fn images_add(
         1_048_576,
         "Icons must be smaller than 1MiB",
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `read_limited_from_payload`")?;
 
     let content_length = bytes.len();
     let upload_result = upload_image_optimized(
@@ -205,12 +217,18 @@ pub async fn images_add(
         None,
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("uploading image")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let db_image: database::models::DBImage = database::models::DBImage {
-        id: database::models::generate_image_id(&mut transaction).await?,
+        id: database::models::generate_image_id(&mut transaction)
+            .await
+            .wrap_internal_err("generating image ID")?,
         url: upload_result.url,
         raw_url: upload_result.raw_url,
         size: content_length as u64,
@@ -252,7 +270,10 @@ pub async fn images_add(
     };
 
     // Insert
-    db_image.insert(&mut transaction).await?;
+    db_image
+        .insert(&mut transaction)
+        .await
+        .wrap_internal_err("inserting database records for `images_add`")?;
 
     let image = Image {
         id: db_image.id.into(),
@@ -263,7 +284,10 @@ pub async fn images_add(
         context,
     };
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::Ok().json(image))
 }
diff --git a/apps/labrinth/src/routes/v3/limits.rs b/apps/labrinth/src/routes/v3/limits.rs
index f7ef89a48f..ab11d37a8e 100644
--- a/apps/labrinth/src/routes/v3/limits.rs
+++ b/apps/labrinth/src/routes/v3/limits.rs
@@ -1,4 +1,5 @@
 use crate::database::PgPool;
+use crate::util::error::Context as _;
 use crate::{
     auth::get_user_from_headers,
     models::{pats::Scopes, v3::user_limits::UserLimits},
@@ -29,9 +30,12 @@ pub async fn get_project_limits(
         &session_queue,
         Scopes::empty(),
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    let limits = UserLimits::get_for_projects(&user, &pool).await?;
+    let limits = UserLimits::get_for_projects(&user, &pool)
+        .await
+        .wrap_internal_err("fetching user limits from Redis")?;
     Ok(web::Json(limits))
 }
 
@@ -50,9 +54,12 @@ pub async fn get_organization_limits(
         &session_queue,
         Scopes::empty(),
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    let limits = UserLimits::get_for_organizations(&user, &pool).await?;
+    let limits = UserLimits::get_for_organizations(&user, &pool)
+        .await
+        .wrap_internal_err("fetching user limits from Redis")?;
     Ok(web::Json(limits))
 }
 
@@ -71,8 +78,11 @@ pub async fn get_collection_limits(
         &session_queue,
         Scopes::empty(),
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    let limits = UserLimits::get_for_collections(&user, &pool).await?;
+    let limits = UserLimits::get_for_collections(&user, &pool)
+        .await
+        .wrap_internal_err("fetching user limits from Redis")?;
     Ok(web::Json(limits))
 }
diff --git a/apps/labrinth/src/routes/v3/notifications.rs b/apps/labrinth/src/routes/v3/notifications.rs
index bab2519802..1daa7acf3e 100644
--- a/apps/labrinth/src/routes/v3/notifications.rs
+++ b/apps/labrinth/src/routes/v3/notifications.rs
@@ -6,6 +6,7 @@ use crate::models::notifications::Notification;
 use crate::models::pats::Scopes;
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, web};
 use serde::{Deserialize, Serialize};
 use xredis::RedisPool;
@@ -54,14 +55,16 @@ pub async fn notifications_get(
         &session_queue,
         Scopes::NOTIFICATION_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     use database::models::DBNotificationId;
     use database::models::notification_item::DBNotification;
 
     let notification_ids: Vec<DBNotificationId> =
-        serde_json::from_str::<Vec<NotificationId>>(ids.ids.as_str())?
+        serde_json::from_str::<Vec<NotificationId>>(ids.ids.as_str())
+            .wrap_request_err("deserializing JSON data")?
             .into_iter()
             .map(DBNotificationId::from)
             .collect();
@@ -71,7 +74,8 @@ pub async fn notifications_get(
             &notification_ids,
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching notifications from database")?;
 
     let notifications: Vec<Notification> = notifications_data
         .into_iter()
@@ -108,7 +112,8 @@ pub async fn notification_get(
         &session_queue,
         Scopes::NOTIFICATION_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let id = info.into_inner().0;
@@ -118,16 +123,17 @@ pub async fn notification_get(
             id.into(),
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching notification from database")?;
 
     if let Some(data) = notification_data {
         if user.id == data.user_id.into() || user.role.is_admin() {
             Ok(HttpResponse::Ok().json(Notification::from(data)))
         } else {
-            Err(ApiError::NotFound)
+            Err(ApiError::NotFound(eyre::eyre!("resource not found")))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -157,7 +163,8 @@ pub async fn notification_read(
         &session_queue,
         Scopes::NOTIFICATION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let id = info.into_inner().0;
@@ -167,29 +174,37 @@ pub async fn notification_read(
             id.into(),
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching notification from database")?;
 
     if let Some(data) = notification_data {
         if data.user_id == user.id.into() || user.role.is_admin() {
-            let mut transaction = pool.begin().await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
 
             database::models::notification_item::DBNotification::read(
                 id.into(),
                 &mut transaction,
                 &redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err("executing `DBNotification::read`")?;
 
-            transaction.commit().await?;
+            transaction
+                .commit()
+                .await
+                .wrap_internal_err("committing database transaction")?;
 
             Ok(HttpResponse::NoContent().body(""))
         } else {
-            Err(ApiError::CustomAuthentication(
-                "You are not authorized to read this notification!".to_string(),
-            ))
+            Err(ApiError::Auth(eyre::eyre!(
+                "You are not authorized to read this notification!",
+            )))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -219,7 +234,8 @@ pub async fn notification_delete(
         &session_queue,
         Scopes::NOTIFICATION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let id = info.into_inner().0;
@@ -229,30 +245,37 @@ pub async fn notification_delete(
             id.into(),
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching notification from database")?;
 
     if let Some(data) = notification_data {
         if data.user_id == user.id.into() || user.role.is_admin() {
-            let mut transaction = pool.begin().await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
 
             database::models::notification_item::DBNotification::remove(
                 id.into(),
                 &mut transaction,
                 &redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err("deleting notification from database")?;
 
-            transaction.commit().await?;
+            transaction
+                .commit()
+                .await
+                .wrap_internal_err("committing database transaction")?;
 
             Ok(HttpResponse::NoContent().body(""))
         } else {
-            Err(ApiError::CustomAuthentication(
-                "You are not authorized to delete this notification!"
-                    .to_string(),
-            ))
+            Err(ApiError::Auth(eyre::eyre!(
+                "You are not authorized to delete this notification!",
+            )))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -286,23 +309,29 @@ pub async fn notifications_read(
         &session_queue,
         Scopes::NOTIFICATION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let notification_ids =
-        serde_json::from_str::<Vec<NotificationId>>(&ids.ids)?
+        serde_json::from_str::<Vec<NotificationId>>(&ids.ids)
+            .wrap_request_err("deserializing JSON data")?
             .into_iter()
             .map(|x| x.into())
             .collect::<Vec<_>>();
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let notifications_data =
         database::models::notification_item::DBNotification::get_many(
             &notification_ids,
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching notifications from database")?;
 
     let mut notifications: Vec<database::models::ids::DBNotificationId> =
         Vec::new();
@@ -318,9 +347,13 @@ pub async fn notifications_read(
         &mut transaction,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("marking notifications as read")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -355,23 +388,29 @@ pub async fn notifications_delete(
         &session_queue,
         Scopes::NOTIFICATION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let notification_ids =
-        serde_json::from_str::<Vec<NotificationId>>(&ids.ids)?
+        serde_json::from_str::<Vec<NotificationId>>(&ids.ids)
+            .wrap_request_err("deserializing JSON data")?
             .into_iter()
             .map(|x| x.into())
             .collect::<Vec<_>>();
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let notifications_data =
         database::models::notification_item::DBNotification::get_many(
             &notification_ids,
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching notifications from database")?;
 
     let mut notifications: Vec<database::models::ids::DBNotificationId> =
         Vec::new();
@@ -387,9 +426,13 @@ pub async fn notifications_delete(
         &mut transaction,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("deleting notifications from database")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
diff --git a/apps/labrinth/src/routes/v3/oauth_clients.rs b/apps/labrinth/src/routes/v3/oauth_clients.rs
index a2b3a5c52b..039045f28d 100644
--- a/apps/labrinth/src/routes/v3/oauth_clients.rs
+++ b/apps/labrinth/src/routes/v3/oauth_clients.rs
@@ -1,3 +1,5 @@
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use std::{collections::HashSet, fmt::Display};
 use xredis::RedisPool;
 
@@ -71,23 +73,27 @@ pub async fn get_user_clients(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    let target_user = DBUser::get(&info.into_inner(), &**pool, &redis).await?;
+    let target_user = DBUser::get(&info.into_inner(), &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(target_user) = target_user {
         if target_user.id != current_user.id.into()
             && !current_user.role.is_admin()
         {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have permission to see the OAuth clients of this user!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have permission to see the OAuth clients of this user!",
+            )));
         }
 
         let clients =
             DBOAuthClient::get_all_user_clients(target_user.id, &**pool)
-                .await?;
+                .await
+                .wrap_internal_err("fetching OAuth clients from database")?;
 
         let response = clients
             .into_iter()
@@ -96,7 +102,7 @@ pub async fn get_user_clients(
 
         Ok(HttpResponse::Ok().json(response))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -112,11 +118,13 @@ pub async fn get_client(
     id: web::Path<OAuthClientId>,
     pool: web::Data<PgPool>,
 ) -> Result<HttpResponse, ApiError> {
-    let clients = get_clients_inner(&[id.into_inner()], pool).await?;
+    let clients = get_clients_inner(&[id.into_inner()], pool)
+        .await
+        .wrap_api_err("fetching OAuth client")?;
     if let Some(client) = clients.into_iter().next() {
         Ok(HttpResponse::Ok().json(client))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -136,9 +144,12 @@ pub async fn get_clients(
         .ids
         .iter()
         .map(|id| parse_base62(id).map(OAuthClientId))
-        .collect::<Result<_, _>>()?;
+        .collect::<Result<_, _>>()
+        .wrap_request_err("parsing OAuth client IDs")?;
 
-    let clients = get_clients_inner(&ids, pool).await?;
+    let clients = get_clients_inner(&ids, pool)
+        .await
+        .wrap_api_err("fetching clients inner")?;
 
     Ok(HttpResponse::Ok().json(clients))
 }
@@ -257,18 +268,24 @@ pub async fn oauth_client_delete(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    let client =
-        DBOAuthClient::get(client_id.into_inner().into(), &**pool).await?;
+    let client = DBOAuthClient::get(client_id.into_inner().into(), &**pool)
+        .await
+        .wrap_internal_err("fetching OAuth client from database")?;
     if let Some(client) = client {
-        client.validate_authorized(Some(&current_user))?;
-        DBOAuthClient::remove(client.id, &**pool).await?;
+        client
+            .validate_authorized(Some(&current_user))
+            .wrap_api_err("validating authorized")?;
+        DBOAuthClient::remove(client.id, &**pool)
+            .await
+            .wrap_internal_err("validating oauth client")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -321,17 +338,23 @@ pub async fn oauth_client_edit(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    client_updates.validate().map_err(|e| {
-        ApiError::Validation(validation_errors_to_string(e, None))
-    })?;
+    client_updates
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     if let Some(existing_client) =
-        DBOAuthClient::get(client_id.into_inner().into(), &**pool).await?
+        DBOAuthClient::get(client_id.into_inner().into(), &**pool)
+            .await
+            .wrap_internal_err("fetching OAuth client from database")?
     {
-        existing_client.validate_authorized(Some(&current_user))?;
+        existing_client
+            .validate_authorized(Some(&current_user))
+            .wrap_api_err("authorizing OAuth client update")?;
 
         let mut updated_client = existing_client.clone();
         let OAuthClientEdit {
@@ -357,21 +380,31 @@ pub async fn oauth_client_edit(
             updated_client.description = description;
         }
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
         updated_client
             .update_editable_fields(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "updating database records for `oauth_client_edit`",
+            )?;
 
         if let Some(redirects) = redirect_uris {
             edit_redirects(redirects, &existing_client, &mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("updating redirects in database")?;
         }
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::Ok().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -410,18 +443,20 @@ pub async fn oauth_client_icon_edit(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let client = DBOAuthClient::get((*client_id).into(), &**pool)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified client does not exist!".to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching OAuth client from database")?
+        .wrap_request_err_with(|| {
+            "the specified client does not exist!".to_string()
         })?;
 
-    client.validate_authorized(Some(&user))?;
+    client
+        .validate_authorized(Some(&user))
+        .wrap_api_err("validating authorized")?;
 
     delete_old_images(
         client.icon_url.clone(),
@@ -429,14 +464,16 @@ pub async fn oauth_client_icon_edit(
         FileHostPublicity::Public,
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("deleting old images")?;
 
     let bytes = read_limited_from_payload(
         &mut payload,
         262144,
         "Icons must be smaller than 256KiB",
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `read_limited_from_payload`")?;
     let upload_result = upload_image_optimized(
         &format!("data/{client_id}"),
         FileHostPublicity::Public,
@@ -446,9 +483,13 @@ pub async fn oauth_client_icon_edit(
         Some(1.0),
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("uploading image")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let mut editable_client = client.clone();
     editable_client.icon_url = Some(upload_result.url);
@@ -456,9 +497,15 @@ pub async fn oauth_client_icon_edit(
 
     editable_client
         .update_editable_fields(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "updating database records for `oauth_client_icon_edit`",
+        )?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -486,17 +533,19 @@ pub async fn oauth_client_icon_delete(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let client = DBOAuthClient::get((*client_id).into(), &**pool)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified client does not exist!".to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching OAuth client from database")?
+        .wrap_request_err_with(|| {
+            "the specified client does not exist!".to_string()
         })?;
-    client.validate_authorized(Some(&user))?;
+    client
+        .validate_authorized(Some(&user))
+        .wrap_api_err("validating authorized")?;
 
     delete_old_images(
         client.icon_url.clone(),
@@ -504,9 +553,13 @@ pub async fn oauth_client_icon_delete(
         FileHostPublicity::Public,
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("deleting old images")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let mut editable_client = client.clone();
     editable_client.icon_url = None;
@@ -514,8 +567,14 @@ pub async fn oauth_client_icon_delete(
 
     editable_client
         .update_editable_fields(&mut transaction)
-        .await?;
-    transaction.commit().await?;
+        .await
+        .wrap_internal_err(
+            "updating database records for `oauth_client_icon_delete`",
+        )?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -540,14 +599,16 @@ pub async fn get_user_oauth_authorizations(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let authorizations = DBOAuthClientAuthorization::get_all_for_user(
         current_user.id.into(),
         &**pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching OAuth client authorizations from database")?;
 
     let mapped: Vec<models::oauth_clients::OAuthClientAuthorization> =
         authorizations.into_iter().map(|a| a.into()).collect_vec();
@@ -577,7 +638,8 @@ pub async fn revoke_oauth_authorization(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     DBOAuthClientAuthorization::remove(
@@ -585,7 +647,8 @@ pub async fn revoke_oauth_authorization(
         current_user.id.into(),
         &**pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("deleting oauth client authorization from database")?;
 
     Ok(HttpResponse::Ok().body(""))
 }
@@ -653,7 +716,9 @@ pub async fn get_clients_inner(
     pool: web::Data<PgPool>,
 ) -> Result<Vec<models::oauth_clients::OAuthClient>, ApiError> {
     let ids: Vec<DBOAuthClientId> = ids.iter().map(|i| (*i).into()).collect();
-    let clients = DBOAuthClient::get_many(&ids, &**pool).await?;
+    let clients = DBOAuthClient::get_many(&ids, &**pool)
+        .await
+        .wrap_internal_err("fetching OAuth clients from database")?;
 
     Ok(clients.into_iter().map(|c| c.into()).collect_vec())
 }
diff --git a/apps/labrinth/src/routes/v3/organizations.rs b/apps/labrinth/src/routes/v3/organizations.rs
index 91f9e04b43..3ff46b06e3 100644
--- a/apps/labrinth/src/routes/v3/organizations.rs
+++ b/apps/labrinth/src/routes/v3/organizations.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use std::collections::HashMap;
 
 use super::ApiError;
@@ -18,6 +19,7 @@ use crate::models::v3::user_limits::UserLimits;
 use crate::queue::session::AuthQueue;
 use crate::routes::v3::project_creation::CreateError;
 use crate::search::SearchState;
+use crate::util::error::Context;
 use crate::util::img::delete_old_images;
 use crate::util::routes::read_limited_from_payload;
 use crate::util::validate::validation_errors_to_string;
@@ -65,10 +67,13 @@ pub async fn organization_projects_get(
     .map(|x| x.1)
     .ok();
 
-    let organization_data = DBOrganization::get(&id, &**pool, &redis).await?;
+    let organization_data = DBOrganization::get(&id, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching organization from database")?;
     if let Some(organization) = organization_data
         && is_visible_organization(&organization, &current_user, &pool, &redis)
-            .await?
+            .await
+            .wrap_api_err("checking organization visibility")?
     {
         let project_ids = sqlx::query!(
             "
@@ -81,22 +86,25 @@ pub async fn organization_projects_get(
         .fetch(&**pool)
         .map_ok(|m| database::models::DBProjectId(m.id))
         .try_collect::<Vec<_>>()
-        .await?;
+        .await
+        .wrap_internal_err("fetching project IDs from database")?;
 
         let projects_data = crate::database::models::DBProject::get_many_ids(
             &project_ids,
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_api_err("fetching organization projects")?;
 
         let projects =
             filter_visible_projects(projects_data, &current_user, &pool, true)
-                .await?;
+                .await
+                .wrap_api_err("filtering visible projects")?;
 
         Ok(HttpResponse::Ok().json(projects))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -242,20 +250,26 @@ pub async fn organization_get(
     .ok();
     let user_id = current_user.as_ref().map(|x| x.id.into());
 
-    let organization_data = DBOrganization::get(&id, &**pool, &redis).await?;
+    let organization_data = DBOrganization::get(&id, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching organization from database")?;
     if let Some(data) = organization_data
-        && is_visible_organization(&data, &current_user, &pool, &redis).await?
+        && is_visible_organization(&data, &current_user, &pool, &redis)
+            .await
+            .wrap_api_err("checking organization visibility")?
     {
         let members_data =
             DBTeamMember::get_from_team_full(data.team_id, &**pool, &redis)
-                .await?;
+                .await
+                .wrap_internal_err("fetching team members from database")?;
 
         let users = crate::database::models::DBUser::get_many_ids(
             &members_data.iter().map(|x| x.user_id).collect::<Vec<_>>(),
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching users from database")?;
         let logged_in = current_user
             .as_ref()
             .and_then(|user| {
@@ -292,12 +306,13 @@ pub async fn organization_get(
                 &**pool,
                 &redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching moderation note from database")?;
             organization.moderation_notes = Some(note.map(Into::into));
         }
         return Ok(HttpResponse::Ok().json(organization));
     }
-    Err(ApiError::NotFound)
+    Err(ApiError::NotFound(eyre::eyre!("resource not found")))
 }
 
 #[utoipa::path(tag = "organizations", responses((status = NO_CONTENT)))]
@@ -317,25 +332,35 @@ pub async fn organization_notes_edit(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if !user.role.is_mod() {
-        return Err(ApiError::CustomAuthentication(
-            "you do not have permission to edit moderation notes".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "you do not have permission to edit moderation notes",
+        )));
     }
 
-    new_note.validate_not_empty()?;
+    new_note
+        .validate_not_empty()
+        .wrap_api_err("validating not empty")?;
     let expected_version =
-        crate::models::moderation_notes::parse_if_match_header(&req)?;
+        crate::models::moderation_notes::parse_if_match_header(&req)
+            .wrap_api_err(
+                "executing `moderation_notes::parse_if_match_header`",
+            )?;
 
     let organization =
         DBOrganization::get(&info.into_inner().0, &**pool, &redis)
-            .await?
-            .ok_or(ApiError::NotFound)?;
+            .await
+            .wrap_internal_err("fetching organization from database")?
+            .wrap_not_found_err("resource not found")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
     if let Some(expected) = expected_version {
         let updated = DBModerationNote::update(
             None,
@@ -346,12 +371,13 @@ pub async fn organization_notes_edit(
             new_note.user_rating,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_internal_err("updating moderation note in database")?;
 
         if updated.is_none() {
-            return Err(ApiError::PreconditionFailed(
-                "moderation note version does not match".to_string(),
-            ));
+            return Err(ApiError::PreconditionFailed(eyre::eyre!(
+                "moderation note version does not match",
+            )));
         }
     } else {
         let updated = DBModerationNote::insert(
@@ -362,17 +388,23 @@ pub async fn organization_notes_edit(
             new_note.user_rating,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_internal_err("inserting moderation note into database")?;
 
         if updated.is_none() {
-            return Err(ApiError::PreconditionRequired(
-                "moderation note version does not match".to_string(),
-            ));
+            return Err(ApiError::PreconditionRequired(eyre::eyre!(
+                "moderation note version does not match",
+            )));
         }
     };
 
-    transaction.commit().await?;
-    DBModerationNote::clear_organization_cache(organization.id, &redis).await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
+    DBModerationNote::clear_organization_cache(organization.id, &redis)
+        .await
+        .wrap_internal_err("clearing cached moderation note in Redis")?;
 
     Ok(HttpResponse::NoContent().finish())
 }
@@ -395,9 +427,11 @@ pub async fn organizations_get(
     redis: web::Data<RedisPool>,
     session_queue: web::Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    let ids = serde_json::from_str::<Vec<&str>>(&ids.ids)?;
-    let organizations_data =
-        DBOrganization::get_many(&ids, &**pool, &redis).await?;
+    let ids = serde_json::from_str::<Vec<&str>>(&ids.ids)
+        .wrap_request_err("deserializing JSON data")?;
+    let organizations_data = DBOrganization::get_many(&ids, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching organizations from database")?;
     let team_ids = organizations_data
         .iter()
         .map(|x| x.team_id)
@@ -405,13 +439,15 @@ pub async fn organizations_get(
 
     let teams_data =
         DBTeamMember::get_from_team_full_many(&team_ids, &**pool, &redis)
-            .await?;
+            .await
+            .wrap_internal_err("fetching team members from database")?;
     let users = crate::database::models::DBUser::get_many_ids(
         &teams_data.iter().map(|x| x.user_id).collect::<Vec<_>>(),
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching users from database")?;
 
     let current_user = get_user_from_headers(
         &req,
@@ -431,7 +467,8 @@ pub async fn organizations_get(
             &**pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching moderation notes from database")?
     } else {
         HashMap::new()
     };
@@ -444,7 +481,9 @@ pub async fn organizations_get(
     }
 
     for data in organizations_data {
-        if !is_visible_organization(&data, &current_user, &pool, &redis).await?
+        if !is_visible_organization(&data, &current_user, &pool, &redis)
+            .await
+            .wrap_api_err("checking organization visibility")?
         {
             continue;
         }
@@ -522,16 +561,20 @@ pub async fn organizations_edit(
         &session_queue,
         Scopes::ORGANIZATION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    new_organization.validate().map_err(|err| {
-        ApiError::Validation(validation_errors_to_string(err, None))
-    })?;
+    new_organization
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let string = info.into_inner().0;
     let result =
-        database::models::DBOrganization::get(&string, &**pool, &redis).await?;
+        database::models::DBOrganization::get(&string, &**pool, &redis)
+            .await
+            .wrap_internal_err("fetching organization from database")?;
     if let Some(organization_item) = result {
         let id = organization_item.id;
 
@@ -540,7 +583,8 @@ pub async fn organizations_edit(
             user.id.into(),
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching team member from database")?;
 
         let permissions = OrganizationPermissions::get_permissions_by_role(
             &user.role,
@@ -548,13 +592,15 @@ pub async fn organizations_edit(
         );
 
         if let Some(perms) = permissions {
-            let mut transaction = pool.begin().await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
             if let Some(description) = &new_organization.description {
                 if !perms.contains(OrganizationPermissions::EDIT_DETAILS) {
-                    return Err(ApiError::CustomAuthentication(
-                        "You do not have the permissions to edit the description of this organization!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You do not have the permissions to edit the description of this organization!",
+                    )));
                 }
                 sqlx::query!(
                     "
@@ -566,15 +612,17 @@ pub async fn organizations_edit(
                     id as database::models::ids::DBOrganizationId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `organizations_edit`",
+                )?;
             }
 
             if let Some(name) = &new_organization.name {
                 if !perms.contains(OrganizationPermissions::EDIT_DETAILS) {
-                    return Err(ApiError::CustomAuthentication(
-                        "You do not have the permissions to edit the name of this organization!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You do not have the permissions to edit the name of this organization!",
+                    )));
                 }
                 sqlx::query!(
                     "
@@ -586,15 +634,17 @@ pub async fn organizations_edit(
                     id as database::models::ids::DBOrganizationId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `organizations_edit`",
+                )?;
             }
 
             if let Some(slug) = &new_organization.slug {
                 if !perms.contains(OrganizationPermissions::EDIT_DETAILS) {
-                    return Err(ApiError::CustomAuthentication(
-                        "You do not have the permissions to edit the slug of this organization!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You do not have the permissions to edit the slug of this organization!",
+                    )));
                 }
 
                 let existing = DBOrganization::get(
@@ -602,12 +652,12 @@ pub async fn organizations_edit(
                     &mut transaction,
                     &redis,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("fetching organization from database")?;
                 if existing.is_some() {
-                    return Err(ApiError::InvalidInput(
-                        "Slug collides with other organization's id!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Request(eyre::eyre!(
+                        "Slug collides with other organization's id!",
+                    )));
                 }
 
                 // Make sure the new name is different from the old one
@@ -625,13 +675,15 @@ pub async fn organizations_edit(
                         slug
                     )
                     .fetch_one(&mut transaction)
-                    .await?;
+                    .await
+                    .wrap_internal_err(
+                        "querying database for `organizations_edit`",
+                    )?;
 
                     if results.exists.unwrap_or(true) {
-                        return Err(ApiError::InvalidInput(
-                            "Slug collides with other organization's id!"
-                                .to_string(),
-                        ));
+                        return Err(ApiError::Request(eyre::eyre!(
+                            "Slug collides with other organization's id!",
+                        )));
                     }
                 }
 
@@ -645,26 +697,32 @@ pub async fn organizations_edit(
                     id as database::models::ids::DBOrganizationId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `organizations_edit`",
+                )?;
             }
 
-            transaction.commit().await?;
+            transaction
+                .commit()
+                .await
+                .wrap_internal_err("committing database transaction")?;
             database::models::DBOrganization::clear_cache(
                 organization_item.id,
                 Some(organization_item.slug),
                 &redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err("clearing cached data from Redis")?;
 
             Ok(HttpResponse::NoContent().body(""))
         } else {
-            Err(ApiError::CustomAuthentication(
-                "You do not have permission to edit this organization!"
-                    .to_string(),
-            ))
+            Err(ApiError::Auth(eyre::eyre!(
+                "You do not have permission to edit this organization!",
+            )))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -685,17 +743,17 @@ pub async fn organization_delete(
         &session_queue,
         Scopes::ORGANIZATION_DELETE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let string = info.into_inner().0;
 
     let organization =
         database::models::DBOrganization::get(&string, &**pool, &redis)
-            .await?
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "The specified organization does not exist!".to_string(),
-                )
+            .await
+            .wrap_internal_err("fetching organization from database")?
+            .wrap_request_err_with(|| {
+                "the specified organization does not exist!".to_string()
             })?;
 
     if !user.role.is_admin() {
@@ -707,11 +765,9 @@ pub async fn organization_delete(
                 &**pool,
             )
             .await
-            .map_err(ApiError::Database)?
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "The specified organization does not exist!".to_string(),
-                )
+            .wrap_internal_err("fetching organization team member")?
+            .wrap_request_err_with(|| {
+                "the specified organization does not exist!".to_string()
             })?;
 
         let permissions = OrganizationPermissions::get_permissions_by_role(
@@ -721,10 +777,9 @@ pub async fn organization_delete(
         .unwrap_or_default();
 
         if !permissions.contains(OrganizationPermissions::DELETE_ORGANIZATION) {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to delete this organization!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to delete this organization!",
+            )));
         }
     }
 
@@ -736,11 +791,15 @@ pub async fn organization_delete(
         organization.team_id as database::models::ids::DBTeamId
     )
     .fetch_one(&**pool)
-    .await?
+    .await
+    .wrap_internal_err("fetching owner ID from database")?
     .user_id;
     let owner_id = database::models::ids::DBUserId(owner_id);
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     // Handle projects- every project that is in this organization needs to have its owner changed the organization owner
     // Now, no project should have an owner if it is in an organization, and also
@@ -762,7 +821,8 @@ pub async fn organization_delete(
         )
     })
     .try_collect::<Vec<_>>()
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `organization_delete`")?;
     let organization_project_teams = organization_projects
         .iter()
         .map(|(team_id, _)| *team_id)
@@ -776,7 +836,8 @@ pub async fn organization_delete(
         let new_id = crate::database::models::ids::generate_team_member_id(
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching query results from database")?;
         let member = DBTeamMember {
             id: new_id,
             team_id: *organization_project_team,
@@ -789,7 +850,9 @@ pub async fn organization_delete(
             payouts_split: Decimal::ZERO,
             ordering: 0,
         };
-        member.insert(&mut transaction).await?;
+        member.insert(&mut transaction).await.wrap_internal_err(
+            "inserting database records for `organization_delete`",
+        )?;
     }
     // Safely remove the organization
     let result = database::models::DBOrganization::remove(
@@ -797,19 +860,26 @@ pub async fn organization_delete(
         &mut transaction,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching query results from database")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     database::models::DBOrganization::clear_cache(
         organization.id,
         Some(organization.slug),
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
 
     for team_id in &organization_project_teams {
-        database::models::DBTeamMember::clear_cache(*team_id, &redis).await?;
+        database::models::DBTeamMember::clear_cache(*team_id, &redis)
+            .await
+            .wrap_internal_err("clearing cached data from Redis")?;
     }
 
     for project_id in organization_project_ids {
@@ -820,18 +890,22 @@ pub async fn organization_delete(
             None,
             None,
         )
-        .await?;
+        .await
+        .wrap_api_err(
+            "executing `projects::clear_project_cache_and_queue_search`",
+        )?;
     }
 
     if !organization_project_teams.is_empty() {
         database::models::DBUser::clear_project_cache(&[owner_id], &redis)
-            .await?;
+            .await
+            .wrap_internal_err("clearing cached user in Redis")?;
     }
 
     if result.is_some() {
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -858,16 +932,16 @@ pub async fn organization_projects_add(
         &session_queue,
         Scopes::PROJECT_WRITE | Scopes::ORGANIZATION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let organization =
         database::models::DBOrganization::get(&info, &**pool, &redis)
-            .await?
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "The specified organization does not exist!".to_string(),
-                )
+            .await
+            .wrap_internal_err("fetching organization from database")?
+            .wrap_request_err_with(|| {
+                "the specified organization does not exist!".to_string()
             })?;
 
     let project_item = database::models::DBProject::get(
@@ -875,17 +949,15 @@ pub async fn organization_projects_add(
         &**pool,
         &redis,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(
-            "The specified project does not exist!".to_string(),
-        )
+    .await
+    .wrap_api_err("fetching project from database")?
+    .wrap_request_err_with(|| {
+        "the specified project does not exist!".to_string()
     })?;
     if project_item.inner.organization_id.is_some() {
-        return Err(ApiError::InvalidInput(
-            "The specified project is already owned by an organization!"
-                .to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "The specified project is already owned by an organization!",
+        )));
     }
 
     let project_team_member =
@@ -895,11 +967,10 @@ pub async fn organization_projects_add(
             false,
             &**pool,
         )
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "You are not a member of this project!".to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching team member from database")?
+        .wrap_request_err_with(|| {
+            "you are not a member of this project!".to_string()
         })?;
     let organization_team_member =
         database::models::DBTeamMember::get_from_user_id_organization(
@@ -908,18 +979,17 @@ pub async fn organization_projects_add(
             false,
             &**pool,
         )
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "You are not a member of this organization!".to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching team member from database")?
+        .wrap_request_err_with(|| {
+            "you are not a member of this organization!".to_string()
         })?;
 
     // Require ownership of a project to add it to an organization
     if !current_user.role.is_admin() && !project_team_member.is_owner {
-        return Err(ApiError::CustomAuthentication(
-            "You need to be an owner of a project to add it to an organization!".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You need to be an owner of a project to add it to an organization!",
+        )));
     }
 
     let permissions = OrganizationPermissions::get_permissions_by_role(
@@ -928,7 +998,10 @@ pub async fn organization_projects_add(
     )
     .unwrap_or_default();
     if permissions.contains(OrganizationPermissions::ADD_PROJECT) {
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
         sqlx::query!(
             "
             UPDATE mods
@@ -939,7 +1012,10 @@ pub async fn organization_projects_add(
             project_item.inner.id as database::models::ids::DBProjectId
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `organization_projects_add`",
+        )?;
 
         // The former owner is no longer an owner (as it is now 'owned' by the organization, 'given' to them)
         // The former owner is still a member of the project, but not an owner
@@ -955,7 +1031,10 @@ pub async fn organization_projects_add(
             organization.team_id as database::models::ids::DBTeamId
         )
         .fetch_one(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "fetching organization owner user ID from database",
+        )?;
         let organization_owner_user_id =
             database::models::ids::DBUserId(organization_owner_user_id.id);
 
@@ -968,20 +1047,28 @@ pub async fn organization_projects_add(
             organization_owner_user_id as database::models::ids::DBUserId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `organization_projects_add`",
+        )?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         database::models::DBUser::clear_project_cache(
             &[current_user.id.into()],
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached user in Redis")?;
         database::models::DBTeamMember::clear_cache(
             project_item.inner.team_id,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
         super::projects::clear_project_cache_and_queue_search(
             &redis,
             &search_state,
@@ -989,12 +1076,14 @@ pub async fn organization_projects_add(
             project_item.inner.slug,
             None,
         )
-        .await?;
+        .await
+        .wrap_api_err(
+            "executing `projects::clear_project_cache_and_queue_search`",
+        )?;
     } else {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to add projects to this organization!"
-                .to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to add projects to this organization!",
+        )));
     }
     Ok(HttpResponse::Ok().finish())
 }
@@ -1025,7 +1114,8 @@ pub async fn organization_projects_remove(
         &session_queue,
         Scopes::PROJECT_WRITE | Scopes::ORGANIZATION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let organization = database::models::DBOrganization::get(
@@ -1033,20 +1123,18 @@ pub async fn organization_projects_remove(
         &**pool,
         &redis,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(
-            "The specified organization does not exist!".to_string(),
-        )
+    .await
+    .wrap_internal_err("fetching organization from database")?
+    .wrap_request_err_with(|| {
+        "the specified organization does not exist!".to_string()
     })?;
 
     let project_item =
         database::models::DBProject::get(&project_id, &**pool, &redis)
-            .await?
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "The specified project does not exist!".to_string(),
-                )
+            .await
+            .wrap_api_err("fetching project from database")?
+            .wrap_request_err_with(|| {
+                "the specified project does not exist!".to_string()
             })?;
 
     if !project_item
@@ -1054,10 +1142,9 @@ pub async fn organization_projects_remove(
         .organization_id
         .eq(&Some(organization.id))
     {
-        return Err(ApiError::InvalidInput(
-            "The specified project is not owned by this organization!"
-                .to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "The specified project is not owned by this organization!",
+        )));
     }
 
     let organization_team_member =
@@ -1067,11 +1154,10 @@ pub async fn organization_projects_remove(
             false,
             &**pool,
         )
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "You are not a member of this organization!".to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching team member from database")?
+        .wrap_request_err_with(|| {
+            "you are not a member of this organization!".to_string()
         })?;
 
     let permissions = OrganizationPermissions::get_permissions_by_role(
@@ -1087,12 +1173,11 @@ pub async fn organization_projects_remove(
             false,
             &**pool,
         )
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified user is not a member of this organization!"
-                    .to_string(),
-            )
+        .await
+        .wrap_internal_err("deleting team member from database")?
+        .wrap_request_err_with(|| {
+            "the specified user is not a member of this organization!"
+                .to_string()
         })?;
 
         // Then, we get the team member of the project and that user (if it exists)
@@ -1104,9 +1189,13 @@ pub async fn organization_projects_remove(
                 true,
                 &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team member from database")?;
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         // If the user is not a member of the project, we add them
         let new_owner = match new_owner {
@@ -1116,7 +1205,8 @@ pub async fn organization_projects_remove(
                     crate::database::models::ids::generate_team_member_id(
                         &mut transaction,
                     )
-                    .await?;
+                    .await
+                    .wrap_internal_err("generating team member ID")?;
                 let member = DBTeamMember {
                     id: new_id,
                     team_id: project_item.inner.team_id,
@@ -1129,7 +1219,10 @@ pub async fn organization_projects_remove(
                     payouts_split: Decimal::ZERO,
                     ordering: 0,
                 };
-                member.insert(&mut transaction).await?;
+                member
+                    .insert(&mut transaction)
+                    .await
+                    .wrap_internal_err("inserting database records for `organization_projects_remove`")?;
                 member
             }
         };
@@ -1150,7 +1243,10 @@ pub async fn organization_projects_remove(
             ProjectPermissions::all().bits() as i64
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `organization_projects_remove`",
+        )?;
 
         sqlx::query!(
             "
@@ -1161,19 +1257,27 @@ pub async fn organization_projects_remove(
             project_item.inner.id as database::models::ids::DBProjectId
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `organization_projects_remove`",
+        )?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
         database::models::DBUser::clear_project_cache(
             &[current_user.id.into()],
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached user in Redis")?;
         database::models::DBTeamMember::clear_cache(
             project_item.inner.team_id,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
         super::projects::clear_project_cache_and_queue_search(
             &redis,
             &search_state,
@@ -1181,12 +1285,14 @@ pub async fn organization_projects_remove(
             project_item.inner.slug,
             None,
         )
-        .await?;
+        .await
+        .wrap_api_err(
+            "executing `projects::clear_project_cache_and_queue_search`",
+        )?;
     } else {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to add projects to this organization!"
-                .to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to add projects to this organization!",
+        )));
     }
     Ok(HttpResponse::Ok().finish())
 }
@@ -1221,17 +1327,17 @@ pub async fn organization_icon_edit(
         &session_queue,
         Scopes::ORGANIZATION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let string = info.into_inner().0;
 
     let organization_item =
         database::models::DBOrganization::get(&string, &**pool, &redis)
-            .await?
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "The specified organization does not exist!".to_string(),
-                )
+            .await
+            .wrap_internal_err("fetching organization from database")?
+            .wrap_request_err_with(|| {
+                "the specified organization does not exist!".to_string()
             })?;
 
     if !user.role.is_mod() {
@@ -1241,7 +1347,7 @@ pub async fn organization_icon_edit(
             &**pool,
         )
         .await
-        .map_err(ApiError::Database)?;
+        .wrap_internal_err("fetching organization team member")?;
 
         let permissions = OrganizationPermissions::get_permissions_by_role(
             &user.role,
@@ -1250,10 +1356,9 @@ pub async fn organization_icon_edit(
         .unwrap_or_default();
 
         if !permissions.contains(OrganizationPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit this organization's icon."
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit this organization's icon.",
+            )));
         }
     }
 
@@ -1263,14 +1368,16 @@ pub async fn organization_icon_edit(
         FileHostPublicity::Public,
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("deleting old images")?;
 
     let bytes = read_limited_from_payload(
         &mut payload,
         262144,
         "Icons must be smaller than 256KiB",
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `read_limited_from_payload`")?;
 
     let organization_id: OrganizationId = organization_item.id.into();
     let upload_result = crate::util::img::upload_image_optimized(
@@ -1282,9 +1389,13 @@ pub async fn organization_icon_edit(
         Some(1.0),
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("uploading image")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     sqlx::query!(
         "
@@ -1298,15 +1409,20 @@ pub async fn organization_icon_edit(
         organization_item.id as database::models::ids::DBOrganizationId,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `organization_icon_edit`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     database::models::DBOrganization::clear_cache(
         organization_item.id,
         Some(organization_item.slug),
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -1328,17 +1444,17 @@ pub async fn delete_organization_icon(
         &session_queue,
         Scopes::ORGANIZATION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let string = info.into_inner().0;
 
     let organization_item =
         database::models::DBOrganization::get(&string, &**pool, &redis)
-            .await?
-            .ok_or_else(|| {
-                ApiError::InvalidInput(
-                    "The specified organization does not exist!".to_string(),
-                )
+            .await
+            .wrap_internal_err("fetching organization from database")?
+            .wrap_request_err_with(|| {
+                "the specified organization does not exist!".to_string()
             })?;
 
     if !user.role.is_mod() {
@@ -1348,7 +1464,7 @@ pub async fn delete_organization_icon(
             &**pool,
         )
         .await
-        .map_err(ApiError::Database)?;
+        .wrap_internal_err("fetching organization team member")?;
 
         let permissions = OrganizationPermissions::get_permissions_by_role(
             &user.role,
@@ -1357,10 +1473,9 @@ pub async fn delete_organization_icon(
         .unwrap_or_default();
 
         if !permissions.contains(OrganizationPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit this organization's icon."
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit this organization's icon.",
+            )));
         }
     }
 
@@ -1370,9 +1485,13 @@ pub async fn delete_organization_icon(
         FileHostPublicity::Public,
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("deleting old images")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     sqlx::query!(
         "
@@ -1383,16 +1502,21 @@ pub async fn delete_organization_icon(
         organization_item.id as database::models::ids::DBOrganizationId,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `delete_organization_icon`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     database::models::DBOrganization::clear_cache(
         organization_item.id,
         Some(organization_item.slug),
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
diff --git a/apps/labrinth/src/routes/v3/payouts.rs b/apps/labrinth/src/routes/v3/payouts.rs
index 8f9cb8a447..b0deabbb83 100644
--- a/apps/labrinth/src/routes/v3/payouts.rs
+++ b/apps/labrinth/src/routes/v3/payouts.rs
@@ -14,6 +14,7 @@ use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
 use crate::routes::internal::globals::tax_compliance_payout_threshold;
 use crate::util::avalara1099;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use crate::util::gotenberg::GotenbergClient;
 use actix_web::{HttpRequest, HttpResponse, delete, get, post, web};
@@ -70,16 +71,21 @@ pub async fn post_compliance_form(
         &session_queue,
         Scopes::PAYOUTS_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let user_id = DBUserId(user.id.0 as i64);
 
-    let mut txn = pool.begin().await?;
+    let mut txn = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let maybe_compliance =
         users_compliance::UserCompliance::get_by_user_id(&mut txn, user_id)
-            .await?;
+            .await
+            .wrap_internal_err("fetching user compliance from Redis")?;
 
     let mut compliance = match maybe_compliance {
         Some(c) => {
@@ -87,9 +93,9 @@ pub async fn post_compliance_form(
                 && c.form_type.is_some_and(|f| f.requires_domestic_tin_match())
                 && !c.tin_matched
             {
-                return Err(ApiError::InvalidInput(
+                return Err(ApiError::Request(eyre::eyre!(
                     "Your TIN/SSN did not match the IRS records. Please contact support https://support.modrinth.com".to_owned(),
-                ));
+                )));
             }
 
             c
@@ -109,7 +115,9 @@ pub async fn post_compliance_form(
         },
     };
 
-    let result = avalara1099::request_form(user_id, body.0.form_type).await?;
+    let result = avalara1099::request_form(user_id, body.0.form_type)
+        .await
+        .wrap_api_err("executing `avalara1099::request_form`")?;
 
     match result {
         Ok(
@@ -132,15 +140,20 @@ pub async fn post_compliance_form(
             compliance.form_type = Some(body.0.form_type);
             compliance.last_checked = Utc::now() - COMPLIANCE_CHECK_DEBOUNCE;
 
-            compliance.upsert_partial(&mut txn).await?;
-            txn.commit().await?;
+            compliance
+                .upsert_partial(&mut txn)
+                .await
+                .wrap_internal_err("updating user compliance request")?;
+            txn.commit()
+                .await
+                .wrap_internal_err("committing database transaction")?;
 
             Ok(HttpResponse::Ok().json(toplevel))
         }
 
         Ok(_) => {
             error!("Missing form request ID in Avalara response");
-            Err(ApiError::TaxComplianceApi)
+            Err(ApiError::Internal(eyre::eyre!("tax compliance API failed")))
         }
 
         Err(json_error) => {
@@ -148,7 +161,7 @@ pub async fn post_compliance_form(
                 "Error sending request to Avalara: {}",
                 serde_json::to_string_pretty(&json_error).unwrap()
             );
-            Err(ApiError::TaxComplianceApi)
+            Err(ApiError::Internal(eyre::eyre!("tax compliance API failed")))
         }
     }
 }
@@ -171,37 +184,27 @@ pub async fn paypal_webhook(
         .headers()
         .get("PAYPAL-AUTH-ALGO")
         .and_then(|x| x.to_str().ok())
-        .ok_or_else(|| {
-            ApiError::InvalidInput("missing auth algo".to_string())
-        })?;
+        .wrap_request_err_with(|| "missing auth algo".to_string())?;
     let cert_url = req
         .headers()
         .get("PAYPAL-CERT-URL")
         .and_then(|x| x.to_str().ok())
-        .ok_or_else(|| {
-            ApiError::InvalidInput("missing cert url".to_string())
-        })?;
+        .wrap_request_err_with(|| "missing cert url".to_string())?;
     let transmission_id = req
         .headers()
         .get("PAYPAL-TRANSMISSION-ID")
         .and_then(|x| x.to_str().ok())
-        .ok_or_else(|| {
-            ApiError::InvalidInput("missing transmission ID".to_string())
-        })?;
+        .wrap_request_err_with(|| "missing transmission ID".to_string())?;
     let transmission_sig = req
         .headers()
         .get("PAYPAL-TRANSMISSION-SIG")
         .and_then(|x| x.to_str().ok())
-        .ok_or_else(|| {
-            ApiError::InvalidInput("missing transmission sig".to_string())
-        })?;
+        .wrap_request_err_with(|| "missing transmission sig".to_string())?;
     let transmission_time = req
         .headers()
         .get("PAYPAL-TRANSMISSION-TIME")
         .and_then(|x| x.to_str().ok())
-        .ok_or_else(|| {
-            ApiError::InvalidInput("missing transmission time".to_string())
-        })?;
+        .wrap_request_err_with(|| "missing transmission time".to_string())?;
 
     #[derive(Deserialize)]
     struct WebHookResponse {
@@ -228,12 +231,13 @@ pub async fn paypal_webhook(
             )),
             None,
         )
-        .await?;
+        .await
+        .wrap_api_err("verifying PayPal webhook signature")?;
 
     if &webhook_res.verification_status != "SUCCESS" {
-        return Err(ApiError::InvalidInput(
-            "Invalid webhook signature".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Invalid webhook signature",
+        )));
     }
 
     #[derive(Deserialize)]
@@ -247,7 +251,8 @@ pub async fn paypal_webhook(
         pub resource: PayPalResource,
     }
 
-    let webhook = serde_json::from_str::<PayPalWebhook>(&body)?;
+    let webhook = serde_json::from_str::<PayPalWebhook>(&body)
+        .wrap_request_err("deserializing JSON data")?;
 
     match &*webhook.event_type {
         "PAYMENT.PAYOUTS-ITEM.BLOCKED"
@@ -255,7 +260,10 @@ pub async fn paypal_webhook(
         | "PAYMENT.PAYOUTS-ITEM.REFUNDED"
         | "PAYMENT.PAYOUTS-ITEM.RETURNED"
         | "PAYMENT.PAYOUTS-ITEM.CANCELED" => {
-            let mut transaction = pool.begin().await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
 
             let result = sqlx::query!(
                 "SELECT user_id, amount, fee FROM payouts WHERE platform_id = $1 AND status = $2",
@@ -263,7 +271,7 @@ pub async fn paypal_webhook(
                 PayoutStatus::InTransit.as_str()
             )
             .fetch_optional(&mut transaction)
-            .await?;
+            .await.wrap_internal_err("querying database for `paypal_webhook`")?;
 
             if let Some(result) = result {
                 sqlx::query!(
@@ -281,9 +289,13 @@ pub async fn paypal_webhook(
                     webhook.resource.payout_item_id
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("querying database for `paypal_webhook`")?;
 
-                transaction.commit().await?;
+                transaction
+                    .commit()
+                    .await
+                    .wrap_internal_err("committing database transaction")?;
 
                 crate::database::models::user_item::DBUser::clear_caches(
                     &[(
@@ -292,11 +304,15 @@ pub async fn paypal_webhook(
                     )],
                     &redis,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("clearing cached data from Redis")?;
             }
         }
         "PAYMENT.PAYOUTS-ITEM.SUCCEEDED" => {
-            let mut transaction = pool.begin().await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
             sqlx::query!(
                 "
                 UPDATE payouts
@@ -307,8 +323,12 @@ pub async fn paypal_webhook(
                 webhook.resource.payout_item_id
             )
             .execute(&mut transaction)
-            .await?;
-            transaction.commit().await?;
+            .await
+            .wrap_internal_err("querying database for `paypal_webhook`")?;
+            transaction
+                .commit()
+                .await
+                .wrap_internal_err("committing database transaction")?;
         }
         _ => {}
     }
@@ -334,21 +354,21 @@ pub async fn tremendous_webhook(
         .get("Tremendous-Webhook-Signature")
         .and_then(|x| x.to_str().ok())
         .and_then(|x| x.split('=').next_back())
-        .ok_or_else(|| {
-            ApiError::InvalidInput("missing webhook signature".to_string())
-        })?;
+        .wrap_request_err_with(|| "missing webhook signature".to_string())?;
 
-    let mut mac: Hmac<Sha256> = Hmac::new_from_slice(
-        ENV.TREMENDOUS_PRIVATE_KEY.as_bytes(),
-    )
-    .map_err(|_| ApiError::Payments("error initializing HMAC".to_string()))?;
+    let mut mac: Hmac<Sha256> =
+        Hmac::new_from_slice(ENV.TREMENDOUS_PRIVATE_KEY.as_bytes())
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_failed_dependency_err(
+                "error initializing HMAC".to_string(),
+            )?;
     mac.update(body.as_bytes());
     let request_signature = mac.finalize().into_bytes().encode_hex::<String>();
 
     if &*request_signature != signature {
-        return Err(ApiError::InvalidInput(
-            "Invalid webhook signature".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Invalid webhook signature",
+        )));
     }
 
     #[derive(Deserialize)]
@@ -367,11 +387,15 @@ pub async fn tremendous_webhook(
         pub payload: TremendousPayload,
     }
 
-    let webhook = serde_json::from_str::<TremendousWebhook>(&body)?;
+    let webhook = serde_json::from_str::<TremendousWebhook>(&body)
+        .wrap_request_err("deserializing JSON data")?;
 
     match &*webhook.event {
         "REWARDS.CANCELED" | "REWARDS.DELIVERY.FAILED" => {
-            let mut transaction = pool.begin().await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
 
             let result = sqlx::query!(
                 "SELECT user_id, amount, fee FROM payouts WHERE platform_id = $1 AND status = $2",
@@ -379,7 +403,7 @@ pub async fn tremendous_webhook(
                 PayoutStatus::InTransit.as_str()
             )
             .fetch_optional(&mut transaction)
-            .await?;
+            .await.wrap_internal_err("querying database for `tremendous_webhook`")?;
 
             if let Some(result) = result {
                 sqlx::query!(
@@ -397,9 +421,15 @@ pub async fn tremendous_webhook(
                     webhook.payload.resource.id
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `tremendous_webhook`",
+                )?;
 
-                transaction.commit().await?;
+                transaction
+                    .commit()
+                    .await
+                    .wrap_internal_err("committing database transaction")?;
 
                 crate::database::models::user_item::DBUser::clear_caches(
                     &[(
@@ -408,11 +438,15 @@ pub async fn tremendous_webhook(
                     )],
                     &redis,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("clearing cached data from Redis")?;
             }
         }
         "REWARDS.DELIVERY.SUCCEEDED" => {
-            let mut transaction = pool.begin().await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
             sqlx::query!(
                 "
                 UPDATE payouts
@@ -423,8 +457,12 @@ pub async fn tremendous_webhook(
                 webhook.payload.resource.id
             )
             .execute(&mut transaction)
-            .await?;
-            transaction.commit().await?;
+            .await
+            .wrap_internal_err("querying database for `tremendous_webhook`")?;
+            transaction
+                .commit()
+                .await
+                .wrap_internal_err("committing database transaction")?;
         }
         _ => {}
     }
@@ -463,12 +501,14 @@ pub async fn calculate_fees(
         &session_queue,
         false,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::Authentication(AuthenticationError::InvalidCredentials)
-    })?;
+    .await
+    .wrap_auth_err("authenticating API request")?
+    .wrap_auth_err_with(|| AuthenticationError::InvalidCredentials)?;
 
-    let payout_flow = payouts_queue.create_payout_flow(body.0).await?;
+    let payout_flow = payouts_queue
+        .create_payout_flow(body.0)
+        .await
+        .wrap_api_err("creating payout flow")?;
 
     Ok(web::Json(WithdrawalFees {
         net_usd: payout_flow.net_usd,
@@ -500,18 +540,20 @@ pub async fn create_payout(
         &session_queue,
         false,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::Authentication(AuthenticationError::InvalidCredentials)
-    })?;
+    .await
+    .wrap_auth_err("authenticating API request")?
+    .wrap_auth_err_with(|| AuthenticationError::InvalidCredentials)?;
 
     if !scopes.contains(Scopes::PAYOUTS_WRITE) {
-        return Err(ApiError::Authentication(
+        return Err(ApiError::Auth(eyre::eyre!(
             AuthenticationError::InvalidCredentials,
-        ));
+        )));
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     sqlx::query!(
         "
@@ -528,8 +570,8 @@ pub async fn create_payout(
         .wrap_internal_err("failed to calculate user balance")?;
 
     if body.amount < Decimal::ZERO {
-        return Err(ApiError::InvalidInput(
-            "Amount must be positive!".to_string(),
+        return Err(ApiError::Request(
+            eyre::eyre!("Amount must be positive!",),
         ));
     }
 
@@ -537,13 +579,18 @@ pub async fn create_payout(
     // for tax threshold checks. body.amount may be in local currency for
     // gift cards (e.g. INR), so we must not compare it directly against
     // USD thresholds.
-    let payout_flow = payouts_queue.create_payout_flow(body.0).await?;
+    let payout_flow = payouts_queue
+        .create_payout_flow(body.0)
+        .await
+        .wrap_api_err("creating payout flow")?;
     let amount_usd = payout_flow.net_usd.get();
 
     let requires_manual_review;
 
     if let Some(threshold) = tax_compliance_payout_threshold() {
-        let maybe_compliance = update_compliance_status(&pool, user.id).await?;
+        let maybe_compliance = update_compliance_status(&pool, user.id)
+            .await
+            .wrap_api_err("updating compliance status")?;
 
         let (tin_matched, signed, requested, api_check_failed) =
             match maybe_compliance {
@@ -575,14 +622,16 @@ pub async fn create_payout(
             // error with the API, as this is more accurate than saying the form wasn't completed
             // properly as this might be wrong!
             if api_check_failed {
-                return Err(ApiError::TaxComplianceApi);
+                return Err(ApiError::Internal(eyre::eyre!(
+                    "tax compliance API failed"
+                )));
             }
 
-            return Err(ApiError::InvalidInput(match (tin_matched, signed, requested) {
+            return Err(ApiError::Request(eyre::eyre!(match (tin_matched, signed, requested) {
                 (_, false, true) => "Tax form isn't signed yet!",
                 (false, true, true) => "Tax form is signed, but the Tax Identification Number/SSN didn't match the IRS records. Withdrawals are blocked until the TIN/SSN matches.",
                 _ => "Tax compliance form is required to withdraw more!",
-            }.to_owned()));
+            }.to_owned())));
         }
     } else {
         requires_manual_review = None;
@@ -592,19 +641,22 @@ pub async fn create_payout(
         r
     } else {
         users_compliance::UserCompliance::get_by_user_id(&**pool, user.id)
-            .await?
+            .await
+            .wrap_internal_err("fetching user compliance from database")?
             .is_some_and(|x| x.requires_manual_review)
     };
 
     if requires_manual_review {
-        return Err(ApiError::InvalidInput(
-            "More information is required to proceed. Please contact support (https://support.modrinth.com, support@modrinth.com)".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "More information is required to proceed. Please contact support (https://support.modrinth.com, support@modrinth.com)",
+        )));
     }
 
     let payout_flow = match payout_flow.validate(balance.available) {
         Ok(flow) => flow,
-        Err(err) => return Err(ApiError::InvalidInput(err.to_string())),
+        Err(err) => {
+            return Err(ApiError::Request(eyre::eyre!("{err}")));
+        }
     };
 
     let payout_id = generate_payout_id(&mut transaction)
@@ -613,7 +665,8 @@ pub async fn create_payout(
 
     payout_flow
         .execute(&payouts_queue, &user, payout_id, transaction, &gotenberg)
-        .await?;
+        .await
+        .wrap_api_err("executing `execute`")?;
 
     crate::database::models::DBUser::clear_caches(&[(user.id, None)], &redis)
         .await
@@ -714,19 +767,22 @@ pub async fn transaction_history(
         &session_queue,
         Scopes::PAYOUTS_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     let payout_ids =
         crate::database::models::payout_item::DBPayout::get_all_for_user(
             user.id.into(),
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching payouts from database")?;
     let payouts = crate::database::models::payout_item::DBPayout::get_many(
         &payout_ids,
         &**pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching payouts from database")?;
     let withdrawals =
         payouts
             .into_iter()
@@ -802,13 +858,15 @@ pub async fn cancel_payout(
         &session_queue,
         Scopes::PAYOUTS_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let id = info.into_inner().0;
     let payout =
         crate::database::models::payout_item::DBPayout::get(id.into(), &**pool)
-            .await?;
+            .await
+            .wrap_internal_err("fetching payout from database")?;
 
     if let Some(payout) = payout {
         if payout.user_id != user.id.into() && !user.role.is_admin() {
@@ -818,9 +876,9 @@ pub async fn cancel_payout(
         if let Some(platform_id) = payout.platform_id {
             if let Some(method) = payout.method {
                 if payout.status != PayoutStatus::InTransit {
-                    return Err(ApiError::InvalidInput(
-                        "Payout cannot be cancelled!".to_string(),
-                    ));
+                    return Err(ApiError::Request(eyre::eyre!(
+                        "Payout cannot be cancelled!",
+                    )));
                 }
 
                 match method {
@@ -835,7 +893,8 @@ pub async fn cancel_payout(
                                 None,
                                 None,
                             )
-                            .await?;
+                            .await
+                            .wrap_api_err("cancelling PayPal payout")?;
                     }
                     PayoutMethodType::Tremendous => {
                         payouts
@@ -844,7 +903,8 @@ pub async fn cancel_payout(
                                 &format!("rewards/{platform_id}/cancel"),
                                 None,
                             )
-                            .await?;
+                            .await
+                            .wrap_api_err("cancelling Tremendous payout")?;
                     }
                     PayoutMethodType::MuralPay => {
                         let payout_request_id = platform_id
@@ -859,7 +919,10 @@ pub async fn cancel_payout(
                     }
                 }
 
-                let mut transaction = pool.begin().await?;
+                let mut transaction = pool
+                    .begin()
+                    .await
+                    .wrap_internal_err("starting database transaction")?;
                 sqlx::query!(
                     "
                     UPDATE payouts
@@ -870,19 +933,23 @@ pub async fn cancel_payout(
                     platform_id
                 )
                 .execute(&mut transaction)
-                .await?;
-                transaction.commit().await?;
+                .await
+                .wrap_internal_err("querying database for `cancel_payout`")?;
+                transaction
+                    .commit()
+                    .await
+                    .wrap_internal_err("committing database transaction")?;
 
                 Ok(HttpResponse::NoContent().finish())
             } else {
-                Err(ApiError::InvalidInput(
-                    "Payout cannot be cancelled!".to_string(),
-                ))
+                Err(ApiError::Request(eyre::eyre!(
+                    "Payout cannot be cancelled!",
+                )))
             }
         } else {
-            Err(ApiError::InvalidInput(
-                "Payout cannot be cancelled!".to_string(),
-            ))
+            Err(ApiError::Request(eyre::eyre!(
+                "Payout cannot be cancelled!",
+            )))
         }
     } else {
         Ok(HttpResponse::NotFound().finish())
@@ -920,7 +987,8 @@ pub async fn payment_methods(
 ) -> Result<HttpResponse, ApiError> {
     let methods = payouts_queue
         .get_payout_methods()
-        .await?
+        .await
+        .wrap_api_err("fetching payout methods")?
         .into_iter()
         .filter(|x| {
             let mut val = true;
@@ -973,10 +1041,13 @@ pub async fn get_balance(
         &session_queue,
         Scopes::PAYOUTS_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    let balance = get_user_balance(user.id.into(), &pool).await?;
+    let balance = get_user_balance(user.id.into(), &pool)
+        .await
+        .wrap_api_err("fetching user balance")?;
 
     let mut requested_form_type = None;
     let mut form_completion_status = None;
@@ -985,7 +1056,8 @@ pub async fn get_balance(
     if tax_compliance_payout_threshold().is_some() {
         form_completion_status = Some(
             update_compliance_status(&pool, user.id.into())
-                .await?
+                .await
+                .wrap_api_err("updating compliance status")?
                 .filter(|x| x.model.form_type.is_some())
                 .map_or(FormCompletionStatus::Unrequested, |compliance| {
                     requested_form_type = compliance.model.form_type;
@@ -1031,7 +1103,8 @@ async fn get_user_balance(
         user_id.0
     )
     .fetch_all(pool)
-    .await?;
+    .await
+    .wrap_internal_err("fetching payouts from database")?;
 
     let available = payouts
         .iter()
@@ -1054,7 +1127,7 @@ async fn get_user_balance(
         user_id.0
     )
     .fetch_optional(pool)
-    .await?;
+    .await.wrap_internal_err("fetching withdrawn from database")?;
 
     let (withdrawn, fees, withdrawn_this_year) =
         withdrawn.map_or((Decimal::ZERO, Decimal::ZERO, Decimal::ZERO), |x| {
@@ -1152,7 +1225,9 @@ async fn update_compliance_status(
             }
         }
 
-        compliance.update(pg).await?;
+        compliance.update(pg).await.wrap_internal_err(
+            "updating database records for `update_compliance_status`",
+        )?;
 
         Ok(Some(ComplianceCheck {
             model: compliance,
@@ -1202,7 +1277,8 @@ pub async fn platform_revenue(
         ",
     )
     .fetch_optional(&**pool)
-    .await?
+    .await
+    .wrap_internal_err("fetching all time payouts from database")?
     .and_then(|x| x.sum)
     .unwrap_or(Decimal::ZERO);
 
@@ -1212,7 +1288,8 @@ pub async fn platform_revenue(
         ",
     )
     .fetch_optional(&**pool)
-    .await?
+    .await
+    .wrap_internal_err("fetching all available from database")?
     .and_then(|x| x.sum)
     .unwrap_or(Decimal::ZERO);
 
@@ -1232,7 +1309,8 @@ pub async fn platform_revenue(
         end
     )
     .fetch_all(&**pool)
-    .await?
+    .await
+    .wrap_internal_err("fetching revenue from database")?
     .into_iter()
     .map(|x| RevenueData {
         time: x.created.timestamp() as u64,
diff --git a/apps/labrinth/src/routes/v3/project_creation.rs b/apps/labrinth/src/routes/v3/project_creation.rs
index f7c383a8ca..e8f5adc972 100644
--- a/apps/labrinth/src/routes/v3/project_creation.rs
+++ b/apps/labrinth/src/routes/v3/project_creation.rs
@@ -99,25 +99,14 @@ pub enum CreateError {
 impl From<crate::routes::ApiError> for CreateError {
     fn from(value: crate::routes::ApiError) -> Self {
         match value {
-            crate::routes::ApiError::Database(err) => Self::DatabaseError(err),
-            crate::routes::ApiError::SqlxDatabase(err) => {
-                Self::SqlxDatabaseError(err)
-            }
-            crate::routes::ApiError::Authentication(err) => {
-                Self::Unauthorized(err)
-            }
-            crate::routes::ApiError::CustomAuthentication(err) => {
-                Self::CustomAuthenticationError(err)
-            }
             crate::routes::ApiError::Auth(err) => {
                 Self::CustomAuthenticationError(format!("{err:#}"))
             }
-            crate::routes::ApiError::InvalidInput(err)
-            | crate::routes::ApiError::Validation(err) => {
-                Self::InvalidInput(err)
+            crate::routes::ApiError::Request(err) => {
+                Self::InvalidInput(format!("{err:#}"))
             }
             err => Self::DatabaseError(models::DatabaseError::SchemaError(
-                err.to_string(),
+                format!("{err:#}"),
             )),
         }
     }
diff --git a/apps/labrinth/src/routes/v3/project_creation/new.rs b/apps/labrinth/src/routes/v3/project_creation/new.rs
index 5112807803..2922375796 100644
--- a/apps/labrinth/src/routes/v3/project_creation/new.rs
+++ b/apps/labrinth/src/routes/v3/project_creation/new.rs
@@ -138,13 +138,13 @@ pub async fn create(
         Scopes::PROJECT_CREATE,
     )
     .await
-    .map_err(ApiError::from)?;
+    .wrap_auth_err("authenticating project creator")?;
 
     require_verified_email(&user)?;
 
     let limits = UserLimits::get_for_projects(&user, &db)
         .await
-        .map_err(ApiError::from)?;
+        .wrap_internal_err("fetching project limits")?;
     if limits.current >= limits.max {
         return Err(CreateError::LimitReached);
     }
diff --git a/apps/labrinth/src/routes/v3/projects.rs b/apps/labrinth/src/routes/v3/projects.rs
index 8c7074a4ba..4af79d0635 100644
--- a/apps/labrinth/src/routes/v3/projects.rs
+++ b/apps/labrinth/src/routes/v3/projects.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use std::any::type_name;
 use std::cmp::Reverse;
 use std::collections::HashMap;
@@ -34,7 +35,6 @@ use crate::util::error::Context;
 use crate::util::img;
 use crate::util::img::{delete_old_images, upload_image_optimized};
 use crate::util::routes::read_limited_from_payload;
-use crate::util::validate::validation_errors_to_string;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, post, web};
 use chrono::Utc;
 use eyre::eyre;
@@ -84,7 +84,8 @@ pub async fn clear_project_cache_and_queue_search(
         clear_dependencies,
         redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
 
     search_state
         .queue
@@ -119,9 +120,10 @@ pub async fn random_projects_get(
     pool: web::Data<PgPool>,
     redis: web::Data<RedisPool>,
 ) -> Result<HttpResponse, ApiError> {
-    count.validate().map_err(|err| {
-        ApiError::Validation(validation_errors_to_string(err, None))
-    })?;
+    count
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let project_ids = sqlx::query!(
         // IDs are randomly generated (see the `generate_ids` macro), so fetching a
@@ -143,11 +145,12 @@ pub async fn random_projects_get(
     .fetch(&**pool)
     .map_ok(|m| db_ids::DBProjectId(m.id))
     .try_collect::<Vec<_>>()
-    .await?;
+    .await.wrap_internal_err("querying random project IDs")?;
 
     let projects_data =
         db_models::DBProject::get_many_ids(&project_ids, &**pool, &redis)
-            .await?
+            .await
+            .wrap_api_err("fetching projects by ID")?
             .into_iter()
             .map(Project::from)
             .collect::<Vec<_>>();
@@ -188,9 +191,11 @@ pub async fn projects_get(
     redis: web::Data<RedisPool>,
     session_queue: web::Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    let ids = serde_json::from_str::<Vec<&str>>(&ids.ids)?;
-    let projects_data =
-        db_models::DBProject::get_many(&ids, &**pool, &redis).await?;
+    let ids = serde_json::from_str::<Vec<&str>>(&ids.ids)
+        .wrap_request_err("deserializing JSON data")?;
+    let projects_data = db_models::DBProject::get_many(&ids, &**pool, &redis)
+        .await
+        .wrap_api_err("fetching requested projects")?;
 
     let user_option = get_user_from_headers(
         &req,
@@ -205,7 +210,8 @@ pub async fn projects_get(
 
     let projects =
         filter_visible_projects(projects_data, &user_option, &pool, false)
-            .await?;
+            .await
+            .wrap_api_err("filtering visible projects")?;
 
     Ok(HttpResponse::Ok().json(projects))
 }
@@ -256,7 +262,7 @@ pub async fn project_get_internal(
     {
         return Ok(web::Json(Project::from(data)));
     }
-    Err(ApiError::NotFound)
+    Err(ApiError::NotFound(eyre::eyre!("resource not found")))
 }
 
 #[derive(Debug, Serialize, Deserialize, Validate, utoipa::ToSchema)]
@@ -388,18 +394,21 @@ pub async fn project_edit_internal(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    new_project.validate().map_err(|err| {
-        ApiError::Validation(validation_errors_to_string(err, None))
-    })?;
+    new_project
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let Some(mut project_item) =
         db_models::DBProject::get(&info.into_inner().0, &**pool, &redis)
-            .await?
+            .await
+            .wrap_api_err("fetching project")?
     else {
-        return Err(ApiError::NotFound);
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     };
 
     let id = project_item.inner.id;
@@ -410,26 +419,29 @@ pub async fn project_edit_internal(
             user.id.into(),
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching team member from database")?;
 
     let Some(perms) = ProjectPermissions::get_permissions_by_role(
         &user.role,
         &team_member,
         &organization_team_member,
     ) else {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to edit this project!".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to edit this project!",
+        )));
     };
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     if let Some(name) = &new_project.name {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the name of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the name of this project!",
+            )));
         }
 
         sqlx::query!(
@@ -442,15 +454,15 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(summary) = &new_project.summary {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the summary of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the summary of this project!",
+            )));
         }
 
         sqlx::query!(
@@ -463,15 +475,15 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(status) = &new_project.status {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the status of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the status of this project!",
+            )));
         }
 
         if !(user.role.is_mod()
@@ -480,9 +492,9 @@ pub async fn project_edit_internal(
             || project_item.inner.status.is_approved()
                 && status.can_be_requested())
         {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to set this status!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to set this status!",
+            )));
         }
 
         // If a moderator (non-admin) is completing a review while another moderator holds an
@@ -493,21 +505,24 @@ pub async fn project_edit_internal(
             && status != &ProjectStatus::Processing
             && let Some(lock) =
                 DBModerationLock::get_with_user(project_item.inner.id, &pool)
-                    .await?
+                    .await
+                    .wrap_internal_err(
+                        "fetching moderation lock from database",
+                    )?
             && lock.moderator_id != db_ids::DBUserId::from(user.id)
             && !lock.expired
         {
-            return Err(ApiError::CustomAuthentication(format!(
+            return Err(ApiError::Auth(eyre::eyre!(format!(
                 "This project is currently being moderated by @{}. Please wait for them to finish or for the lock to expire.",
                 lock.moderator_username
-            )));
+            ))));
         }
 
         if status == &ProjectStatus::Processing {
             if project_item.versions.is_empty() {
-                return Err(ApiError::InvalidInput(String::from(
+                return Err(ApiError::Request(eyre::eyre!(String::from(
                     "Project submitted for review with no initial versions",
-                )));
+                ))));
             }
 
             sqlx::query!(
@@ -519,7 +534,7 @@ pub async fn project_edit_internal(
                 id as db_ids::DBProjectId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await.wrap_internal_err("querying database for `project_edit_internal`")?;
         }
 
         if status.is_approved() && !project_item.inner.status.is_approved() {
@@ -532,7 +547,10 @@ pub async fn project_edit_internal(
                 id as db_ids::DBProjectId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "querying database for `project_edit_internal`",
+            )?;
         }
 
         if status.is_searchable()
@@ -559,7 +577,10 @@ pub async fn project_edit_internal(
                 id as db_ids::DBProjectId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "querying database for `project_edit_internal`",
+            )?;
         }
 
         if user.role.is_mod() && !ENV.MODERATION_SLACK_WEBHOOK.is_empty() {
@@ -596,7 +617,8 @@ pub async fn project_edit_internal(
             .fetch(&mut transaction)
             .map_ok(|c| db_models::DBUserId(c.id))
             .try_collect::<Vec<_>>()
-            .await?;
+            .await
+            .wrap_internal_err("fetching notified members from database")?;
 
             NotificationBuilder {
                 body: NotificationBody::StatusChange {
@@ -606,7 +628,10 @@ pub async fn project_edit_internal(
                 },
             }
             .insert_many(notified_members.clone(), &mut transaction, &redis)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "inserting database records for `project_edit_internal`",
+            )?;
 
             NotificationBuilder {
                 body: if status.is_approved() {
@@ -622,7 +647,10 @@ pub async fn project_edit_internal(
                 },
             }
             .insert_many(notified_members, &mut transaction, &redis)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "inserting database records for `project_edit_internal`",
+            )?;
         }
 
         ThreadMessageBuilder {
@@ -635,7 +663,10 @@ pub async fn project_edit_internal(
             hide_identity: user.role.is_mod(),
         }
         .insert(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `project_edit_internal`",
+        )?;
 
         sqlx::query!(
             "
@@ -647,24 +678,24 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(requested_status) = &new_project.requested_status {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the requested status of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the requested status of this project!",
+            )));
         }
 
         if !requested_status
             .map(|x| x.can_be_requested())
             .unwrap_or(true)
         {
-            return Err(ApiError::InvalidInput(String::from(
+            return Err(ApiError::Request(eyre::eyre!(String::from(
                 "Specified status cannot be requested!",
-            )));
+            ))));
         }
 
         sqlx::query!(
@@ -677,7 +708,8 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if perms.contains(ProjectPermissions::EDIT_DETAILS) {
@@ -690,7 +722,10 @@ pub async fn project_edit_internal(
                 id as db_ids::DBProjectId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "updating database records for `project_edit_internal`",
+            )?;
         }
 
         if new_project.additional_categories.is_some() {
@@ -702,7 +737,10 @@ pub async fn project_edit_internal(
                 id as db_ids::DBProjectId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "querying database for `project_edit_internal`",
+            )?;
         }
     }
 
@@ -714,7 +752,8 @@ pub async fn project_edit_internal(
             false,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_api_err("executing `edit_project_categories`")?;
     }
 
     if let Some(categories) = &new_project.additional_categories {
@@ -725,15 +764,15 @@ pub async fn project_edit_internal(
             true,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_api_err("executing `edit_project_categories`")?;
     }
 
     if let Some(license_url) = &new_project.license_url {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the license URL of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the license URL of this project!",
+            )));
         }
 
         sqlx::query!(
@@ -746,15 +785,15 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(slug) = &new_project.slug {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the slug of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the slug of this project!",
+            )));
         }
 
         let existing = db_models::DBProject::get(
@@ -762,11 +801,12 @@ pub async fn project_edit_internal(
             &mut transaction,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_api_err("checking project slug availability")?;
         if existing.is_some() {
-            return Err(ApiError::InvalidInput(
-                "Slug collides with other project's id!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "Slug collides with other project's id!",
+            )));
         }
 
         // Make sure the new slug is different from the old one
@@ -784,12 +824,15 @@ pub async fn project_edit_internal(
                 slug
             )
             .fetch_one(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "querying database for `project_edit_internal`",
+            )?;
 
             if results.exists.unwrap_or(true) {
-                return Err(ApiError::InvalidInput(
-                    "Slug collides with other project's id!".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "Slug collides with other project's id!",
+                )));
             }
         }
 
@@ -803,15 +846,15 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(license) = &new_project.license_id {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the license of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the license of this project!",
+            )));
         }
 
         let mut license = license.clone();
@@ -820,11 +863,9 @@ pub async fn project_edit_internal(
             license = models::projects::DEFAULT_LICENSE_ID.to_string();
         }
 
-        spdx::Expression::parse(&license).map_err(|err| {
-            ApiError::InvalidInput(format!(
-                "Invalid SPDX license identifier: {err}"
-            ))
-        })?;
+        spdx::Expression::parse(&license)
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_request_err("parsing request value")?;
 
         sqlx::query!(
             "
@@ -836,17 +877,17 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(links) = &new_project.link_urls
         && !links.is_empty()
     {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                    "You do not have the permissions to edit the links of this project!"
-                        .to_string(),
-                ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the links of this project!",
+            )));
         }
 
         let ids_to_delete = links.keys().cloned().collect::<Vec<String>>();
@@ -862,7 +903,8 @@ pub async fn project_edit_internal(
             &ids_to_delete
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
 
         for (platform, url) in links {
             if let Some(url) = url {
@@ -870,12 +912,10 @@ pub async fn project_edit_internal(
                     platform,
                     &mut transaction,
                 )
-                .await?
-                .ok_or_else(|| {
-                    ApiError::InvalidInput(format!(
-                        "Platform {} does not exist.",
-                        platform.clone()
-                    ))
+                .await
+                .wrap_internal_err("fetching link platform from database")?
+                .wrap_request_err_with(|| {
+                    format!("platform `{}` does not exist", platform.clone())
                 })?;
                 sqlx::query!(
                         "
@@ -887,7 +927,7 @@ pub async fn project_edit_internal(
                         url
                     )
                     .execute(&mut transaction)
-                    .await?;
+                    .await.wrap_internal_err("querying database for `project_edit_internal`")?;
             }
         }
     }
@@ -896,10 +936,9 @@ pub async fn project_edit_internal(
             && (!project_item.inner.status.is_approved()
                 || moderation_message.is_some())
         {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the moderation message of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the moderation message of this project!",
+            )));
         }
 
         sqlx::query!(
@@ -912,7 +951,8 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(moderation_message_body) = &new_project.moderation_message_body
@@ -921,10 +961,9 @@ pub async fn project_edit_internal(
             && (!project_item.inner.status.is_approved()
                 || moderation_message_body.is_some())
         {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the moderation message body of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the moderation message body of this project!",
+            )));
         }
 
         sqlx::query!(
@@ -937,15 +976,15 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(description) = &new_project.description {
         if !perms.contains(ProjectPermissions::EDIT_BODY) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the description (body) of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the description (body) of this project!",
+            )));
         }
 
         sqlx::query!(
@@ -958,15 +997,15 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(monetization_status) = &new_project.monetization_status {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the monetization status of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the monetization status of this project!",
+            )));
         }
 
         if (*monetization_status == MonetizationStatus::ForceDemonetized
@@ -974,10 +1013,9 @@ pub async fn project_edit_internal(
                 == MonetizationStatus::ForceDemonetized)
             && !user.role.is_mod()
         {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the monetization status of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the monetization status of this project!",
+            )));
         }
 
         sqlx::query!(
@@ -990,17 +1028,17 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if let Some(side_types_migration_review_status) =
         &new_project.side_types_migration_review_status
     {
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the side types migration review status of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the side types migration review status of this project!",
+            )));
         }
 
         sqlx::query!(
@@ -1013,7 +1051,8 @@ pub async fn project_edit_internal(
             id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_edit_internal`")?;
     }
 
     if !new_project.loader_fields.is_empty() {
@@ -1022,7 +1061,8 @@ pub async fn project_edit_internal(
             &**pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching versions from database")?
         {
             match super::versions::version_edit_helper(
                 req.clone(),
@@ -1043,7 +1083,7 @@ pub async fn project_edit_internal(
                 // the loaders defined for this version, which is a common case for
                 // projects with heterogeneous loaders across versions and is best
                 // handled with opportunistic update semantics
-                Ok(_) | Err(ApiError::InvalidInput(_)) => continue,
+                Ok(_) | Err(ApiError::Request(_)) => continue,
                 err => return err,
             }
         }
@@ -1064,10 +1104,9 @@ pub async fn project_edit_internal(
         };
 
         if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have the permissions to edit the components of this project!"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have the permissions to edit the components of this project!",
+            )));
         }
 
         match (&mut component, edit) {
@@ -1112,7 +1151,8 @@ pub async fn project_edit_internal(
         &mut project_item.inner.components.minecraft_server,
         perms,
     )
-    .await?;
+    .await
+    .wrap_api_err("updating Minecraft server component")?;
     reindex_versions |= update(
         &mut transaction,
         id,
@@ -1120,7 +1160,8 @@ pub async fn project_edit_internal(
         &mut project_item.inner.components.minecraft_java_server,
         perms,
     )
-    .await?;
+    .await
+    .wrap_api_err("updating Minecraft Java server component")?;
     reindex_versions |= update(
         &mut transaction,
         id,
@@ -1128,7 +1169,8 @@ pub async fn project_edit_internal(
         &mut project_item.inner.components.minecraft_bedrock_server,
         perms,
     )
-    .await?;
+    .await
+    .wrap_api_err("updating Minecraft Bedrock server component")?;
 
     let components_serial = project_item.inner.components.clone();
 
@@ -1170,9 +1212,13 @@ pub async fn project_edit_internal(
         &mut transaction,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("deleting unused images")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     if reindex_versions {
         db_models::DBProject::clear_cache(
@@ -1181,7 +1227,8 @@ pub async fn project_edit_internal(
             None,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
         search_state
             .queue
             .push_version_changes(
@@ -1197,7 +1244,8 @@ pub async fn project_edit_internal(
             project_item.inner.slug,
             None,
         )
-        .await?;
+        .await
+        .wrap_api_err("executing `clear_project_cache_and_queue_search`")?;
     }
 
     // Remove no longer searchable projects from search index
@@ -1223,9 +1271,9 @@ pub async fn edit_project_categories(
 ) -> Result<(), ApiError> {
     if !perms.contains(ProjectPermissions::EDIT_DETAILS) {
         let additional_str = if is_additional { "additional " } else { "" };
-        return Err(ApiError::CustomAuthentication(format!(
+        return Err(ApiError::Auth(eyre::eyre!(format!(
             "You do not have the permissions to edit the {additional_str}categories of this project!"
-        )));
+        ))));
     }
 
     let mut mod_categories = Vec::new();
@@ -1234,7 +1282,8 @@ pub async fn edit_project_categories(
             category,
             &mut *transaction,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching category from Redis")?;
         // TODO: We should filter out categories that don't match the project type of any of the versions
         // ie: if mod and modpack both share a name this should only have modpack if it only has a modpack as a version
 
@@ -1248,7 +1297,9 @@ pub async fn edit_project_categories(
             .collect::<Vec<_>>();
         mod_categories.extend(mcategories);
     }
-    DBModCategory::insert_many(mod_categories, &mut *transaction).await?;
+    DBModCategory::insert_many(mod_categories, &mut *transaction)
+        .await
+        .wrap_internal_err("inserting mod categories into database")?;
 
     Ok(())
 }
@@ -1290,7 +1341,8 @@ pub async fn project_search(
 ) -> Result<web::Json<SearchResults>, ApiError> {
     let results = search_backend
         .search_for_project(&SearchRequest::from(info), &redis)
-        .await?;
+        .await
+        .wrap_api_err("searching projects")?;
 
     // TODO: add this back
     // let results = ReturnSearchResults {
@@ -1320,7 +1372,10 @@ pub async fn project_search_post(
     search_backend: web::Data<dyn SearchBackend>,
     redis: web::Data<RedisPool>,
 ) -> Result<web::Json<SearchResults>, ApiError> {
-    let results = search_backend.search_for_project(&info, &redis).await?;
+    let results = search_backend
+        .search_for_project(&info, &redis)
+        .await
+        .wrap_api_err("searching projects")?;
     Ok(web::Json(results))
 }
 
@@ -1346,15 +1401,16 @@ pub async fn project_get_check_internal(
 ) -> Result<HttpResponse, ApiError> {
     let slug = info.into_inner().0;
 
-    let project_data =
-        db_models::DBProject::get(&slug, &**pool, &redis).await?;
+    let project_data = db_models::DBProject::get(&slug, &**pool, &redis)
+        .await
+        .wrap_api_err("fetching project from database")?;
 
     if let Some(project) = project_data {
         Ok(HttpResponse::Ok().json(ProjectCheckResponse {
             id: models::ids::ProjectId::from(project.inner.id),
         }))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1392,8 +1448,9 @@ pub async fn dependency_list_internal(
 ) -> Result<HttpResponse, ApiError> {
     let string = info.into_inner().0;
 
-    let result =
-        db_models::DBProject::get(&string, &***ro_pool, &redis).await?;
+    let result = db_models::DBProject::get(&string, &***ro_pool, &redis)
+        .await
+        .wrap_api_err("fetching project from database")?;
 
     let user_option = get_user_from_headers(
         &req,
@@ -1408,9 +1465,10 @@ pub async fn dependency_list_internal(
 
     if let Some(project) = result {
         if !is_visible_project(&project.inner, &user_option, &pool, false)
-            .await?
+            .await
+            .wrap_api_err("checking project visibility")?
         {
-            return Err(ApiError::NotFound);
+            return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
         }
 
         let dependencies = database::DBProject::get_dependencies(
@@ -1418,7 +1476,8 @@ pub async fn dependency_list_internal(
             &***ro_pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching projects from database")?;
         let project_ids = dependencies
             .iter()
             .filter_map(|x| {
@@ -1456,7 +1515,8 @@ pub async fn dependency_list_internal(
                 .wrap_internal_err("failed to fetch dependency versions")
             },
         )
-        .await?;
+        .await
+        .wrap_api_err("fetching project dependencies")?;
 
         let mut projects = filter_visible_projects(
             projects_result,
@@ -1464,7 +1524,8 @@ pub async fn dependency_list_internal(
             &pool,
             false,
         )
-        .await?;
+        .await
+        .wrap_api_err("filtering visible projects")?;
         let mut versions = filter_visible_versions(
             versions_result,
             &user_option,
@@ -1472,7 +1533,8 @@ pub async fn dependency_list_internal(
             &ro_pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_api_err("filtering visible versions")?;
 
         projects.sort_by_key(|b| Reverse(b.published));
         projects.dedup_by(|a, b| a.id == b.id);
@@ -1482,7 +1544,7 @@ pub async fn dependency_list_internal(
 
         Ok(HttpResponse::Ok().json(DependencyInfo { projects, versions }))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1555,31 +1617,35 @@ pub async fn projects_edit(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    bulk_edit_project.validate().map_err(|err| {
-        ApiError::Validation(validation_errors_to_string(err, None))
-    })?;
+    bulk_edit_project
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let project_ids: Vec<db_ids::DBProjectId> =
-        serde_json::from_str::<Vec<ProjectId>>(&ids.ids)?
+        serde_json::from_str::<Vec<ProjectId>>(&ids.ids)
+            .wrap_request_err("deserializing JSON data")?
             .into_iter()
             .map(|x| x.into())
             .collect();
 
     let projects_data =
         db_models::DBProject::get_many_ids(&project_ids, &**pool, &redis)
-            .await?;
+            .await
+            .wrap_api_err("fetching projects to edit")?;
 
     if let Some(id) = project_ids
         .iter()
         .find(|x| !projects_data.iter().any(|y| x == &&y.inner.id))
     {
-        return Err(ApiError::InvalidInput(format!(
+        return Err(ApiError::Request(eyre::eyre!(format!(
             "Project {} not found",
             ProjectId(id.0 as u64)
-        )));
+        ))));
     }
 
     let team_ids = projects_data
@@ -1589,7 +1655,8 @@ pub async fn projects_edit(
     let team_members = db_models::DBTeamMember::get_from_team_full_many(
         &team_ids, &**pool, &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching team members from database")?;
 
     let organization_ids = projects_data
         .iter()
@@ -1600,7 +1667,8 @@ pub async fn projects_edit(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching organizations from database")?;
 
     let organization_team_ids = organizations
         .iter()
@@ -1612,14 +1680,21 @@ pub async fn projects_edit(
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching team members from database")?;
 
-    let categories =
-        db_models::categories::Category::list(&**pool, &redis).await?;
+    let categories = db_models::categories::Category::list(&**pool, &redis)
+        .await
+        .wrap_internal_err("fetching category from Redis")?;
     let link_platforms =
-        db_models::categories::LinkPlatform::list(&**pool, &redis).await?;
+        db_models::categories::LinkPlatform::list(&**pool, &redis)
+            .await
+            .wrap_internal_err("fetching link platform from Redis")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
     let mut changed_projects = Vec::new();
 
     for project in projects_data {
@@ -1653,21 +1728,21 @@ pub async fn projects_edit(
 
             if team_member.is_some() {
                 if !permissions.contains(ProjectPermissions::EDIT_DETAILS) {
-                    return Err(ApiError::CustomAuthentication(format!(
+                    return Err(ApiError::Auth(eyre::eyre!(format!(
                         "You do not have the permissions to bulk edit project {}!",
                         project.inner.name
-                    )));
+                    ))));
                 }
             } else if project.inner.status.is_hidden() {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "Project {} not found",
                     ProjectId(project.inner.id.0 as u64)
-                )));
+                ))));
             } else {
-                return Err(ApiError::CustomAuthentication(format!(
+                return Err(ApiError::Auth(eyre::eyre!(format!(
                     "You are not a member of project {}!",
                     project.inner.name
-                )));
+                ))));
             };
         }
 
@@ -1684,7 +1759,8 @@ pub async fn projects_edit(
             false,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_api_err("executing `bulk_edit_project_categories`")?;
 
         reindex_versions |= bulk_edit_project_categories(
             &categories,
@@ -1700,7 +1776,8 @@ pub async fn projects_edit(
             true,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_api_err("executing `bulk_edit_project_categories`")?;
 
         if let Some(links) = &bulk_edit_project.link_urls {
             let ids_to_delete = links.keys().cloned().collect::<Vec<String>>();
@@ -1716,18 +1793,19 @@ pub async fn projects_edit(
                 &ids_to_delete
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `projects_edit`")?;
 
             for (platform, url) in links {
                 if let Some(url) = url {
                     let platform_id = link_platforms
                         .iter()
                         .find(|x| &x.name == platform)
-                        .ok_or_else(|| {
-                            ApiError::InvalidInput(format!(
-                                "Platform {} does not exist.",
+                        .wrap_request_err_with(|| {
+                            format!(
+                                "platform `{}` does not exist",
                                 platform.clone()
-                            ))
+                            )
                         })?
                         .id;
                     sqlx::query!(
@@ -1740,7 +1818,7 @@ pub async fn projects_edit(
                         url
                     )
                     .execute(&mut transaction)
-                    .await?;
+                    .await.wrap_internal_err("querying database for `projects_edit`")?;
                 }
             }
         }
@@ -1753,12 +1831,16 @@ pub async fn projects_edit(
         ));
     }
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     for (project_id, slug, versions, reindex_versions) in changed_projects {
         if reindex_versions {
             db_models::DBProject::clear_cache(project_id, slug, None, &redis)
-                .await?;
+                .await
+                .wrap_internal_err("clearing cached data from Redis")?;
             search_state
                 .queue
                 .push_version_changes(
@@ -1774,7 +1856,8 @@ pub async fn projects_edit(
                 slug,
                 None,
             )
-            .await?;
+            .await
+            .wrap_api_err("executing `clear_project_cache_and_queue_search`")?;
         }
     }
 
@@ -1827,18 +1910,18 @@ pub async fn bulk_edit_project_categories(
             is_additional
         )
         .execute(&mut *transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `bulk_edit_project_categories`",
+        )?;
 
         let mut mod_categories = Vec::new();
         for category in set_categories {
             let category_id = all_db_categories
                 .iter()
                 .find(|x| x.category == category)
-                .ok_or_else(|| {
-                    ApiError::InvalidInput(format!(
-                        "Category {} does not exist.",
-                        category.clone()
-                    ))
+                .wrap_request_err_with(|| {
+                    format!("category `{}` does not exist", category.clone())
                 })?
                 .id;
             mod_categories.push(DBModCategory {
@@ -1847,7 +1930,9 @@ pub async fn bulk_edit_project_categories(
                 is_additional,
             });
         }
-        DBModCategory::insert_many(mod_categories, &mut *transaction).await?;
+        DBModCategory::insert_many(mod_categories, &mut *transaction)
+            .await
+            .wrap_internal_err("inserting mod categories into database")?;
     }
 
     Ok(changed)
@@ -1913,16 +1998,16 @@ pub async fn project_icon_edit_internal(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let string = info.into_inner().0;
 
     let project_item = db_models::DBProject::get(&string, &**pool, &redis)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified project does not exist!".to_string(),
-            )
+        .await
+        .wrap_api_err("fetching project from database")?
+        .wrap_request_err_with(|| {
+            "the specified project does not exist!".to_string()
         })?;
 
     if !user.role.is_mod() {
@@ -1932,13 +2017,14 @@ pub async fn project_icon_edit_internal(
                 user.id.into(),
                 &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team member from database")?;
 
         // Hide the project
         if team_member.is_none() && organization_team_member.is_none() {
-            return Err(ApiError::CustomAuthentication(
-                "The specified project does not exist!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "The specified project does not exist!",
+            )));
         }
 
         let permissions = ProjectPermissions::get_permissions_by_role(
@@ -1949,10 +2035,9 @@ pub async fn project_icon_edit_internal(
         .unwrap_or_default();
 
         if !permissions.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit this project's icon."
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit this project's icon.",
+            )));
         }
     }
 
@@ -1962,14 +2047,16 @@ pub async fn project_icon_edit_internal(
         FileHostPublicity::Public,
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("deleting old images")?;
 
     let bytes = read_limited_from_payload(
         &mut payload,
         262144,
         "Icons must be smaller than 256KiB",
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `read_limited_from_payload`")?;
 
     let project_id: ProjectId = project_item.inner.id.into();
     let upload_result = upload_image_optimized(
@@ -1981,9 +2068,13 @@ pub async fn project_icon_edit_internal(
         Some(1.0),
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("uploading image")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     sqlx::query!(
         "
@@ -1997,9 +2088,13 @@ pub async fn project_icon_edit_internal(
         project_item.inner.id as db_ids::DBProjectId,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("querying database for `project_icon_edit_internal`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     clear_project_cache_and_queue_search(
         &redis,
         &search_state,
@@ -2007,7 +2102,8 @@ pub async fn project_icon_edit_internal(
         project_item.inner.slug,
         None,
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `clear_project_cache_and_queue_search`")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -2055,16 +2151,16 @@ pub async fn delete_project_icon_internal(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let string = info.into_inner().0;
 
     let project_item = db_models::DBProject::get(&string, &**pool, &redis)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified project does not exist!".to_string(),
-            )
+        .await
+        .wrap_api_err("fetching project from database")?
+        .wrap_request_err_with(|| {
+            "the specified project does not exist!".to_string()
         })?;
 
     if !user.role.is_mod() {
@@ -2074,13 +2170,14 @@ pub async fn delete_project_icon_internal(
                 user.id.into(),
                 &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team member from database")?;
 
         // Hide the project
         if team_member.is_none() && organization_team_member.is_none() {
-            return Err(ApiError::CustomAuthentication(
-                "The specified project does not exist!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "The specified project does not exist!",
+            )));
         }
         let permissions = ProjectPermissions::get_permissions_by_role(
             &user.role,
@@ -2090,10 +2187,9 @@ pub async fn delete_project_icon_internal(
         .unwrap_or_default();
 
         if !permissions.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit this project's icon."
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit this project's icon.",
+            )));
         }
     }
 
@@ -2103,9 +2199,13 @@ pub async fn delete_project_icon_internal(
         FileHostPublicity::Public,
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("deleting old images")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     sqlx::query!(
         "
@@ -2116,9 +2216,15 @@ pub async fn delete_project_icon_internal(
         project_item.inner.id as db_ids::DBProjectId,
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err(
+        "querying database for `delete_project_icon_internal`",
+    )?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     clear_project_cache_and_queue_search(
         &redis,
         &search_state,
@@ -2126,7 +2232,8 @@ pub async fn delete_project_icon_internal(
         project_item.inner.slug,
         None,
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `clear_project_cache_and_queue_search`")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -2196,9 +2303,9 @@ pub async fn add_gallery_item_internal(
     session_queue: web::Data<AuthQueue>,
     search_state: web::Data<SearchState>,
 ) -> Result<HttpResponse, ApiError> {
-    item.validate().map_err(|err| {
-        ApiError::Validation(validation_errors_to_string(err, None))
-    })?;
+    item.validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let user = get_user_from_headers(
         &req,
@@ -2207,23 +2314,22 @@ pub async fn add_gallery_item_internal(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let string = info.into_inner().0;
 
     let project_item = db_models::DBProject::get(&string, &**pool, &redis)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified project does not exist!".to_string(),
-            )
+        .await
+        .wrap_api_err("fetching project from database")?
+        .wrap_request_err_with(|| {
+            "the specified project does not exist!".to_string()
         })?;
 
     if project_item.gallery_items.len() > 64 {
-        return Err(ApiError::CustomAuthentication(
-            "You have reached the maximum of gallery images to upload."
-                .to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You have reached the maximum of gallery images to upload.",
+        )));
     }
 
     if !user.role.is_admin() {
@@ -2233,13 +2339,14 @@ pub async fn add_gallery_item_internal(
                 user.id.into(),
                 &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team member from database")?;
 
         // Hide the project
         if team_member.is_none() && organization_team_member.is_none() {
-            return Err(ApiError::CustomAuthentication(
-                "The specified project does not exist!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "The specified project does not exist!",
+            )));
         }
 
         let permissions = ProjectPermissions::get_permissions_by_role(
@@ -2250,10 +2357,9 @@ pub async fn add_gallery_item_internal(
         .unwrap_or_default();
 
         if !permissions.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit this project's gallery."
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit this project's gallery.",
+            )));
         }
     }
 
@@ -2262,7 +2368,8 @@ pub async fn add_gallery_item_internal(
         5 * (1 << 20),
         "Gallery image exceeds the maximum of 5MiB.",
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `read_limited_from_payload`")?;
 
     let id: ProjectId = project_item.inner.id.into();
     let upload_result = upload_image_optimized(
@@ -2274,19 +2381,23 @@ pub async fn add_gallery_item_internal(
         Some(1.0),
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("uploading image")?;
 
     if project_item
         .gallery_items
         .iter()
         .any(|x| x.image_url == upload_result.url)
     {
-        return Err(ApiError::InvalidInput(
-            "You may not upload duplicate gallery images!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "You may not upload duplicate gallery images!",
+        )));
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     if item.featured {
         sqlx::query!(
@@ -2299,7 +2410,10 @@ pub async fn add_gallery_item_internal(
             false,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `add_gallery_item_internal`",
+        )?;
     }
 
     let gallery_item = vec![db_models::project_item::DBGalleryItem {
@@ -2316,9 +2430,13 @@ pub async fn add_gallery_item_internal(
         project_item.inner.id,
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_internal_err("inserting galleries into database")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
     clear_project_cache_and_queue_search(
         &redis,
         &search_state,
@@ -2326,7 +2444,8 @@ pub async fn add_gallery_item_internal(
         project_item.inner.slug,
         None,
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `clear_project_cache_and_queue_search`")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -2401,12 +2520,13 @@ pub async fn edit_gallery_item_internal(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    item.validate().map_err(|err| {
-        ApiError::Validation(validation_errors_to_string(err, None))
-    })?;
+    item.validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let result = sqlx::query!(
         "
@@ -2416,12 +2536,13 @@ pub async fn edit_gallery_item_internal(
         item.url
     )
     .fetch_optional(&**pool)
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(format!(
-            "Gallery item at URL {} is not part of the project's gallery.",
+    .await
+    .wrap_internal_err("querying database for `edit_gallery_item_internal`")?
+    .wrap_request_err_with(|| {
+        format!(
+            "gallery item at URL `{}` is not part of the project's gallery",
             item.url
-        ))
+        )
     })?;
 
     let project_item = db_models::DBProject::get_id(
@@ -2429,11 +2550,10 @@ pub async fn edit_gallery_item_internal(
         &**pool,
         &redis,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(
-            "The specified project does not exist!".to_string(),
-        )
+    .await
+    .wrap_api_err("fetching project from database")?
+    .wrap_request_err_with(|| {
+        "the specified project does not exist!".to_string()
     })?;
 
     if !user.role.is_mod() {
@@ -2443,13 +2563,14 @@ pub async fn edit_gallery_item_internal(
                 user.id.into(),
                 &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team member from database")?;
 
         // Hide the project
         if team_member.is_none() && organization_team_member.is_none() {
-            return Err(ApiError::CustomAuthentication(
-                "The specified project does not exist!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "The specified project does not exist!",
+            )));
         }
         let permissions = ProjectPermissions::get_permissions_by_role(
             &user.role,
@@ -2459,14 +2580,16 @@ pub async fn edit_gallery_item_internal(
         .unwrap_or_default();
 
         if !permissions.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit this project's gallery."
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit this project's gallery.",
+            )));
         }
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     if let Some(featured) = item.featured {
         if featured {
@@ -2480,7 +2603,8 @@ pub async fn edit_gallery_item_internal(
                 false,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("fetching featured status from database")?;
         }
 
         sqlx::query!(
@@ -2493,7 +2617,10 @@ pub async fn edit_gallery_item_internal(
             featured
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `edit_gallery_item_internal`",
+        )?;
     }
     if let Some(name) = item.name {
         sqlx::query!(
@@ -2506,7 +2633,10 @@ pub async fn edit_gallery_item_internal(
             name
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `edit_gallery_item_internal`",
+        )?;
     }
     if let Some(description) = item.description {
         sqlx::query!(
@@ -2519,7 +2649,10 @@ pub async fn edit_gallery_item_internal(
             description
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `edit_gallery_item_internal`",
+        )?;
     }
     if let Some(ordering) = item.ordering {
         sqlx::query!(
@@ -2532,10 +2665,16 @@ pub async fn edit_gallery_item_internal(
             ordering
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `edit_gallery_item_internal`",
+        )?;
     }
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     clear_project_cache_and_queue_search(
         &redis,
@@ -2544,7 +2683,8 @@ pub async fn edit_gallery_item_internal(
         project_item.inner.slug,
         None,
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `clear_project_cache_and_queue_search`")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -2601,7 +2741,8 @@ pub async fn delete_gallery_item_internal(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let item = sqlx::query!(
@@ -2612,12 +2753,13 @@ pub async fn delete_gallery_item_internal(
         item.url
     )
     .fetch_optional(&**pool)
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(format!(
-            "Gallery item at URL {} is not part of the project's gallery.",
+    .await
+    .wrap_internal_err("querying database for `delete_gallery_item_internal`")?
+    .wrap_request_err_with(|| {
+        format!(
+            "gallery item at URL `{}` is not part of the project's gallery",
             item.url
-        ))
+        )
     })?;
 
     let project_item = db_models::DBProject::get_id(
@@ -2625,11 +2767,10 @@ pub async fn delete_gallery_item_internal(
         &**pool,
         &redis,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(
-            "The specified project does not exist!".to_string(),
-        )
+    .await
+    .wrap_api_err("fetching project from database")?
+    .wrap_request_err_with(|| {
+        "the specified project does not exist!".to_string()
     })?;
 
     if !user.role.is_mod() {
@@ -2639,13 +2780,14 @@ pub async fn delete_gallery_item_internal(
                 user.id.into(),
                 &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team member from database")?;
 
         // Hide the project
         if team_member.is_none() && organization_team_member.is_none() {
-            return Err(ApiError::CustomAuthentication(
-                "The specified project does not exist!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "The specified project does not exist!",
+            )));
         }
 
         let permissions = ProjectPermissions::get_permissions_by_role(
@@ -2656,10 +2798,9 @@ pub async fn delete_gallery_item_internal(
         .unwrap_or_default();
 
         if !permissions.contains(ProjectPermissions::EDIT_DETAILS) {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit this project's gallery."
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit this project's gallery.",
+            )));
         }
     }
 
@@ -2669,9 +2810,13 @@ pub async fn delete_gallery_item_internal(
         FileHostPublicity::Public,
         &**file_host,
     )
-    .await?;
+    .await
+    .wrap_api_err("deleting old images")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     sqlx::query!(
         "
@@ -2681,9 +2826,15 @@ pub async fn delete_gallery_item_internal(
         item.id
     )
     .execute(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err(
+        "querying database for `delete_gallery_item_internal`",
+    )?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     clear_project_cache_and_queue_search(
         &redis,
@@ -2692,7 +2843,8 @@ pub async fn delete_gallery_item_internal(
         project_item.inner.slug,
         None,
     )
-    .await?;
+    .await
+    .wrap_api_err("executing `clear_project_cache_and_queue_search`")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -2730,7 +2882,8 @@ pub async fn project_delete_internal(
         &session_queue,
         Scopes::PROJECT_DELETE,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
     let string = info.into_inner().0;
 
     // In two cases, we return `The specified project does not exist!`:
@@ -2744,7 +2897,7 @@ pub async fn project_delete_internal(
     let project = db_models::DBProject::get(&string, &**pool, &redis)
         .await
         .wrap_internal_err("failed to get project")?
-        .wrap_auth_err("The specified project does not exist!")?;
+        .wrap_auth_err("the specified project does not exist")?;
 
     if !user.role.is_admin() {
         let (team_member, organization_team_member) =
@@ -2771,9 +2924,9 @@ pub async fn project_delete_internal(
         .unwrap_or_default();
 
         if !permissions.contains(ProjectPermissions::DELETE_PROJECT) {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to delete this project!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to delete this project!",
+            )));
         }
     }
 
@@ -2785,7 +2938,10 @@ pub async fn project_delete_internal(
         project.inner.id,
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_api_err(
+        "executing `tech_review_sync::sync_deleted_project_tech_review_exit`",
+    )?;
 
     let context = ImageContext::Project {
         project_id: Some(project.inner.id.into()),
@@ -2833,14 +2989,15 @@ pub async fn project_delete_internal(
             None,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
         search_state
             .queue
             .push_project_removal(project.inner.id.into())
             .await;
         Ok(())
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -2874,23 +3031,26 @@ pub async fn project_follow_internal(
         &session_queue,
         Scopes::USER_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let string = info.into_inner().0;
 
     let result = db_models::DBProject::get(&string, &**pool, &redis)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified project does not exist!".to_string(),
-            )
+        .await
+        .wrap_api_err("fetching project from database")?
+        .wrap_request_err_with(|| {
+            "the specified project does not exist!".to_string()
         })?;
 
     let user_id: db_ids::DBUserId = user.id.into();
     let project_id: db_ids::DBProjectId = result.inner.id;
 
-    if !is_visible_project(&result.inner, &Some(user), &pool, false).await? {
-        return Err(ApiError::NotFound);
+    if !is_visible_project(&result.inner, &Some(user), &pool, false)
+        .await
+        .wrap_api_err("checking project visibility")?
+    {
+        return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
     }
 
     let following = sqlx::query!(
@@ -2901,12 +3061,15 @@ pub async fn project_follow_internal(
         project_id as db_ids::DBProjectId
     )
     .fetch_one(&**pool)
-    .await?
+    .await.wrap_internal_err("fetching project follow status from database")?
     .exists
     .unwrap_or(false);
 
     if !following {
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         sqlx::query!(
             "
@@ -2917,7 +3080,8 @@ pub async fn project_follow_internal(
             project_id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_follow_internal`")?;
 
         sqlx::query!(
             "
@@ -2928,15 +3092,19 @@ pub async fn project_follow_internal(
             project_id as db_ids::DBProjectId
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `project_follow_internal`")?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::InvalidInput(
-            "You are already following this project!".to_string(),
-        ))
+        Err(ApiError::Request(eyre::eyre!(
+            "You are already following this project!",
+        )))
     }
 }
 
@@ -2970,16 +3138,16 @@ pub async fn project_unfollow_internal(
         &session_queue,
         Scopes::USER_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let string = info.into_inner().0;
 
     let result = db_models::DBProject::get(&string, &**pool, &redis)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified project does not exist!".to_string(),
-            )
+        .await
+        .wrap_api_err("fetching project from database")?
+        .wrap_request_err_with(|| {
+            "the specified project does not exist!".to_string()
         })?;
 
     let user_id: db_ids::DBUserId = user.id.into();
@@ -2993,12 +3161,15 @@ pub async fn project_unfollow_internal(
         project_id as db_ids::DBProjectId
     )
     .fetch_one(&**pool)
-    .await?
+    .await.wrap_internal_err("fetching project follow status from database")?
     .exists
     .unwrap_or(false);
 
     if following {
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         sqlx::query!(
             "
@@ -3009,7 +3180,10 @@ pub async fn project_unfollow_internal(
             project_id as db_ids::DBProjectId,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `project_unfollow_internal`",
+        )?;
 
         sqlx::query!(
             "
@@ -3020,15 +3194,21 @@ pub async fn project_unfollow_internal(
             project_id as db_ids::DBProjectId
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "querying database for `project_unfollow_internal`",
+        )?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::InvalidInput(
-            "You are not following this project!".to_string(),
-        ))
+        Err(ApiError::Request(eyre::eyre!(
+            "You are not following this project!",
+        )))
     }
 }
 
@@ -3059,25 +3239,26 @@ pub async fn project_get_organization(
 
     let string = info.into_inner().0;
     let result = db_models::DBProject::get(&string, &**pool, &redis)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified project does not exist!".to_string(),
-            )
+        .await
+        .wrap_api_err("fetching project from database")?
+        .wrap_request_err_with(|| {
+            "the specified project does not exist!".to_string()
         })?;
 
-    if !is_visible_project(&result.inner, &current_user, &pool, false).await? {
-        Err(ApiError::InvalidInput(
-            "The specified project does not exist!".to_string(),
-        ))
+    if !is_visible_project(&result.inner, &current_user, &pool, false)
+        .await
+        .wrap_api_err("checking project visibility")?
+    {
+        Err(ApiError::Request(eyre::eyre!(
+            "The specified project does not exist!",
+        )))
     } else if let Some(organization_id) = result.inner.organization_id {
         let organization =
             db_models::DBOrganization::get_id(organization_id, &**pool, &redis)
-                .await?
-                .ok_or_else(|| {
-                    ApiError::InvalidInput(
-                        "The attached organization does not exist!".to_string(),
-                    )
+                .await
+                .wrap_internal_err("fetching organization from database")?
+                .wrap_request_err_with(|| {
+                    "the attached organization does not exist!".to_string()
                 })?;
 
         let members_data = DBTeamMember::get_from_team_full(
@@ -3085,14 +3266,16 @@ pub async fn project_get_organization(
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching team members from database")?;
 
         let users = crate::database::models::DBUser::get_many_ids(
             &members_data.iter().map(|x| x.user_id).collect::<Vec<_>>(),
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching users from database")?;
         let logged_in = current_user
             .as_ref()
             .and_then(|user| {
@@ -3127,6 +3310,6 @@ pub async fn project_get_organization(
         );
         Ok(HttpResponse::Ok().json(organization))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
diff --git a/apps/labrinth/src/routes/v3/reports.rs b/apps/labrinth/src/routes/v3/reports.rs
index 04dc2b3028..a3bba51279 100644
--- a/apps/labrinth/src/routes/v3/reports.rs
+++ b/apps/labrinth/src/routes/v3/reports.rs
@@ -17,6 +17,7 @@ use crate::models::reports::{ItemType, Report};
 use crate::models::threads::{MessageBody, ThreadType};
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use crate::util::http::HTTP_CLIENT;
 use crate::util::img;
@@ -73,7 +74,10 @@ pub async fn report_create(
     redis: web::Data<RedisPool>,
     session_queue: web::Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let current_user = get_user_from_headers(
         &req,
@@ -82,23 +86,25 @@ pub async fn report_create(
         &session_queue,
         Scopes::REPORT_CREATE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    let new_report: CreateReport = read_typed_from_payload(&mut body).await?;
+    let new_report: CreateReport = read_typed_from_payload(&mut body)
+        .await
+        .wrap_api_err("reading request payload")?;
 
-    let id =
-        crate::database::models::generate_report_id(&mut transaction).await?;
+    let id = crate::database::models::generate_report_id(&mut transaction)
+        .await
+        .wrap_internal_err("generating report ID")?;
     let report_type = crate::database::models::categories::ReportType::get_id(
         &new_report.report_type,
         &mut transaction,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(format!(
-            "Invalid report type: {}",
-            new_report.report_type
-        ))
+    .await
+    .wrap_internal_err("generating report ID")?
+    .wrap_request_err_with(|| {
+        format!("invalid report type: `{}`", new_report.report_type)
     })?;
 
     let mut report = crate::database::models::report_item::DBReport {
@@ -117,60 +123,70 @@ pub async fn report_create(
 
     match new_report.item_type {
         ItemType::Project => {
-            let project_id =
-                ProjectId(parse_base62(new_report.item_id.as_str())?);
+            let project_id = ProjectId(
+                parse_base62(new_report.item_id.as_str())
+                    .wrap_request_err("parsing reported project ID")?,
+            );
 
             let result = sqlx::query!(
                 "SELECT EXISTS(SELECT 1 FROM mods WHERE id = $1)",
                 project_id.0 as i64
             )
             .fetch_one(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `report_create`")?;
 
             if !result.exists.unwrap_or(false) {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "Project could not be found: {}",
                     new_report.item_id
-                )));
+                ))));
             }
 
             report.project_id = Some(project_id.into())
         }
         ItemType::Version => {
-            let version_id =
-                VersionId(parse_base62(new_report.item_id.as_str())?);
+            let version_id = VersionId(
+                parse_base62(new_report.item_id.as_str())
+                    .wrap_request_err("parsing reported version ID")?,
+            );
 
             let result = sqlx::query!(
                 "SELECT EXISTS(SELECT 1 FROM versions WHERE id = $1)",
                 version_id.0 as i64
             )
             .fetch_one(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `report_create`")?;
 
             if !result.exists.unwrap_or(false) {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "Version could not be found: {}",
                     new_report.item_id
-                )));
+                ))));
             }
 
             report.version_id = Some(version_id.into())
         }
         ItemType::User => {
-            let user_id = UserId(parse_base62(new_report.item_id.as_str())?);
+            let user_id = UserId(
+                parse_base62(new_report.item_id.as_str())
+                    .wrap_request_err("parsing reported user ID")?,
+            );
 
             let result = sqlx::query!(
                 "SELECT EXISTS(SELECT 1 FROM users WHERE id = $1)",
                 user_id.0 as i64
             )
             .fetch_one(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `report_create`")?;
 
             if !result.exists.unwrap_or(false) {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "User could not be found: {}",
                     new_report.item_id
-                )));
+                ))));
             }
 
             report.user_id = Some(user_id.into())
@@ -180,21 +196,18 @@ pub async fn report_create(
             let (instance_part, version_part) = new_report
                 .item_id
                 .split_once('/')
-                .ok_or_else(|| {
-                    ApiError::InvalidInput(
-                        "Shared instance reports must format the item ID as `instance_id/version_id`"
-                            .to_string(),
-                    )
-                })?;
+                .wrap_request_err_with(|| "shared instance reports must format the item ID as `instance_id/version_id`"
+                            .to_string())?;
 
-            let shared_instance_id =
-                SharedInstanceId(parse_base62(instance_part)? as i64);
+            let shared_instance_id = SharedInstanceId(
+                parse_base62(instance_part)
+                    .wrap_request_err("parsing reported shared instance ID")?
+                    as i64,
+            );
             let shared_instance_version_id: i32 =
-                version_part.parse().map_err(|_| {
-                    ApiError::InvalidInput(format!(
-                        "Shared instance version is not a number: {version_part}"
-                    ))
-                })?;
+                version_part.parse().wrap_request_err(format!(
+                    "shared instance version is not a number: `{version_part}`"
+                ))?;
 
             // validation
             let url = format!(
@@ -212,9 +225,9 @@ pub async fn report_create(
                 )?;
 
             if !instance_response.status().is_success() {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "Shared instance could not be found: {instance_part}"
-                )));
+                ))));
             }
 
             let version_response = HTTP_CLIENT
@@ -225,36 +238,40 @@ pub async fn report_create(
                 .wrap_internal_err("failed to reach the shared instance service (version lookup)")?;
 
             if !version_response.status().is_success() {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "Shared instance version could not be found: {instance_part}/{version_part}"
-                )));
+                ))));
             }
 
             report.shared_instance_id = Some(shared_instance_id);
             report.shared_instance_version_id = Some(shared_instance_version_id)
         }
         ItemType::Unknown => {
-            return Err(ApiError::InvalidInput(format!(
+            return Err(ApiError::Request(eyre::eyre!(format!(
                 "Invalid report item type: {}",
                 new_report.item_type.as_str()
-            )));
+            ))));
         }
     }
 
-    report.insert(&mut transaction).await?;
+    report
+        .insert(&mut transaction)
+        .await
+        .wrap_internal_err("inserting database records for `report_create`")?;
 
     for image_id in new_report.uploaded_images {
         if let Some(db_image) =
             image_item::DBImage::get(image_id.into(), &mut transaction, &redis)
-                .await?
+                .await
+                .wrap_internal_err("fetching image from database")?
         {
             let image: Image = db_image.into();
             if !matches!(image.context, ImageContext::Report { .. })
                 || image.context.inner_id().is_some()
             {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "Image {image_id} is not unused and in the 'report' context"
-                )));
+                ))));
             }
 
             sqlx::query!(
@@ -267,13 +284,16 @@ pub async fn report_create(
                 image_id.0 as i64
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("querying database for `report_create`")?;
 
-            image_item::DBImage::clear_cache(image.id.into(), &redis).await?;
+            image_item::DBImage::clear_cache(image.id.into(), &redis)
+                .await
+                .wrap_internal_err("clearing cached data from Redis")?;
         } else {
-            return Err(ApiError::InvalidInput(format!(
+            return Err(ApiError::Request(eyre::eyre!(format!(
                 "Image {image_id} could not be found"
-            )));
+            ))));
         }
     }
 
@@ -284,7 +304,8 @@ pub async fn report_create(
         report_id: Some(report.id),
     }
     .insert(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `report_create`")?;
 
     // Notify the reporter that the report has been submitted
     NotificationBuilder {
@@ -293,9 +314,13 @@ pub async fn report_create(
         },
     }
     .insert(current_user.id.into(), &mut transaction, &redis)
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `report_create`")?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     Ok(HttpResponse::Ok().json(Report {
         id: id.into(),
@@ -362,7 +387,8 @@ pub async fn reports(
         &session_queue,
         Scopes::REPORT_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     use futures::stream::TryStreamExt;
@@ -382,7 +408,8 @@ pub async fn reports(
         .fetch(&**pool)
         .map_ok(|m| crate::database::models::ids::DBReportId(m.id))
         .try_collect::<Vec<crate::database::models::ids::DBReportId>>()
-        .await?
+        .await
+        .wrap_internal_err("fetching report IDs from database")?
     } else {
         sqlx::query!(
             "
@@ -399,7 +426,8 @@ pub async fn reports(
         .fetch(&**pool)
         .map_ok(|m| crate::database::models::ids::DBReportId(m.id))
         .try_collect::<Vec<crate::database::models::ids::DBReportId>>()
-        .await?
+        .await
+        .wrap_internal_err("querying database for `reports`")?
     };
 
     let query_reports =
@@ -407,7 +435,8 @@ pub async fn reports(
             &report_ids,
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching reports from database")?;
 
     let mut reports: Vec<Report> = Vec::new();
 
@@ -447,7 +476,8 @@ pub async fn reports_get(
     session_queue: web::Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
     let report_ids: Vec<crate::database::models::ids::DBReportId> =
-        serde_json::from_str::<Vec<crate::models::ids::ReportId>>(&ids.ids)?
+        serde_json::from_str::<Vec<crate::models::ids::ReportId>>(&ids.ids)
+            .wrap_request_err("deserializing JSON data")?
             .into_iter()
             .map(|x| x.into())
             .collect();
@@ -457,7 +487,8 @@ pub async fn reports_get(
             &report_ids,
             &**pool,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching reports from database")?;
 
     let user = get_user_from_headers(
         &req,
@@ -466,7 +497,8 @@ pub async fn reports_get(
         &session_queue,
         Scopes::REPORT_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let all_reports = reports_data
@@ -504,23 +536,25 @@ pub async fn report_get(
         &session_queue,
         Scopes::REPORT_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let id = info.into_inner().0.into();
 
     let report =
         crate::database::models::report_item::DBReport::get(id, &**pool)
-            .await?;
+            .await
+            .wrap_internal_err("fetching report from database")?;
 
     if let Some(report) = report {
         if !user.role.is_mod() && report.reporter != user.id.into() {
-            return Err(ApiError::NotFound);
+            return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
         }
 
         let report: Report = report.into();
         Ok(HttpResponse::Ok().json(report))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -559,20 +593,25 @@ pub async fn report_edit(
         &session_queue,
         Scopes::REPORT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let id = info.into_inner().0.into();
 
     let report =
         crate::database::models::report_item::DBReport::get(id, &**pool)
-            .await?;
+            .await
+            .wrap_internal_err("fetching report from database")?;
 
     if let Some(report) = report {
         if !user.role.is_mod() && report.reporter != user.id.into() {
-            return Err(ApiError::NotFound);
+            return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
         }
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         if let Some(edit_body) = &edit_report.body {
             sqlx::query!(
@@ -585,14 +624,15 @@ pub async fn report_edit(
                 id as crate::database::models::ids::DBReportId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("updating edit body in database")?;
         }
 
         if let Some(edit_closed) = edit_report.closed {
             if !user.role.is_mod() {
-                return Err(ApiError::InvalidInput(
-                    "You cannot reopen a report!".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "You cannot reopen a report!",
+                )));
             }
 
             ThreadMessageBuilder {
@@ -606,7 +646,10 @@ pub async fn report_edit(
                 hide_identity: user.role.is_mod(),
             }
             .insert(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "inserting database records for `report_edit`",
+            )?;
 
             NotificationBuilder {
                 body: NotificationBody::ReportStatusUpdated {
@@ -614,7 +657,10 @@ pub async fn report_edit(
                 },
             }
             .insert(report.reporter, &mut transaction, &redis)
-            .await?;
+            .await
+            .wrap_internal_err(
+                "inserting database records for `report_edit`",
+            )?;
 
             sqlx::query!(
                 "
@@ -626,7 +672,8 @@ pub async fn report_edit(
                 id as crate::database::models::ids::DBReportId,
             )
             .execute(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("updating database records for `report_edit`")?;
         }
 
         // delete any images no longer in the body
@@ -643,13 +690,17 @@ pub async fn report_edit(
             &mut transaction,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_api_err("deleting unused images")?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -679,9 +730,13 @@ pub async fn report_delete(
         &session_queue,
         Scopes::REPORT_DELETE,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let id = info.into_inner().0;
     let context = ImageContext::Report {
@@ -691,21 +746,28 @@ pub async fn report_delete(
         context,
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching images from database")?;
     for image in uploaded_images {
-        image_item::DBImage::remove(image.id, &mut transaction, &redis).await?;
+        image_item::DBImage::remove(image.id, &mut transaction, &redis)
+            .await
+            .wrap_internal_err("deleting image from database")?;
     }
 
     let result = crate::database::models::report_item::DBReport::remove_full(
         id.into(),
         &mut transaction,
     )
-    .await?;
-    transaction.commit().await?;
+    .await
+    .wrap_internal_err("deleting report from database")?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     if result.is_some() {
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
diff --git a/apps/labrinth/src/routes/v3/statistics.rs b/apps/labrinth/src/routes/v3/statistics.rs
index c09797e5de..b607eac5ab 100644
--- a/apps/labrinth/src/routes/v3/statistics.rs
+++ b/apps/labrinth/src/routes/v3/statistics.rs
@@ -1,5 +1,6 @@
 use crate::database::PgPool;
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 use actix_web::{HttpResponse, get, web};
 
 pub fn config(cfg: &mut actix_web::web::ServiceConfig) {
@@ -37,7 +38,8 @@ pub async fn get_stats(
             .collect::<Vec<String>>(),
     )
     .fetch_one(&**pool)
-    .await?;
+    .await
+    .wrap_internal_err("counting projects")?;
 
     let versions = sqlx::query!(
         "
@@ -56,7 +58,8 @@ pub async fn get_stats(
             .collect::<Vec<String>>(),
     )
     .fetch_one(&**pool)
-    .await?;
+    .await
+    .wrap_internal_err("counting versions")?;
 
     let authors = sqlx::query!(
         "
@@ -71,7 +74,8 @@ pub async fn get_stats(
             .collect::<Vec<String>>(),
     )
     .fetch_one(&**pool)
-    .await?;
+    .await
+    .wrap_internal_err("counting project authors")?;
 
     let files = sqlx::query!(
         "
@@ -89,7 +93,8 @@ pub async fn get_stats(
             .collect::<Vec<String>>(),
     )
     .fetch_one(&**pool)
-    .await?;
+    .await
+    .wrap_internal_err("counting version files")?;
 
     let v3_stats = V3Stats {
         projects: projects.count,
diff --git a/apps/labrinth/src/routes/v3/tags.rs b/apps/labrinth/src/routes/v3/tags.rs
index 4c1589cbbc..2a2b638fb9 100644
--- a/apps/labrinth/src/routes/v3/tags.rs
+++ b/apps/labrinth/src/routes/v3/tags.rs
@@ -1,3 +1,4 @@
+use crate::util::error::Context as _;
 use std::collections::HashMap;
 
 use super::ApiError;
@@ -49,7 +50,8 @@ pub async fn games_list(
     redis: web::Data<RedisPool>,
 ) -> Result<HttpResponse, ApiError> {
     let results = Game::list(&**pool, &redis)
-        .await?
+        .await
+        .wrap_internal_err("fetching game from Redis")?
         .into_iter()
         .map(|x| GameData {
             slug: x.slug,
@@ -84,7 +86,8 @@ pub async fn category_list(
     redis: web::Data<RedisPool>,
 ) -> Result<HttpResponse, ApiError> {
     let results = Category::list(&**pool, &redis)
-        .await?
+        .await
+        .wrap_internal_err("fetching category from Redis")?
         .into_iter()
         .map(|x| CategoryData {
             icon: x.icon,
@@ -120,14 +123,17 @@ pub async fn loader_list(
     pool: web::Data<PgPool>,
     redis: web::Data<RedisPool>,
 ) -> Result<HttpResponse, ApiError> {
-    let loaders = Loader::list(&**pool, &redis).await?;
+    let loaders = Loader::list(&**pool, &redis)
+        .await
+        .wrap_internal_err("fetching loader from Redis")?;
 
     let loader_fields = LoaderField::get_fields_per_loader(
         &loaders.iter().map(|x| x.id).collect_vec(),
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching loader field from Redis")?;
 
     let mut results = loaders
         .into_iter()
@@ -180,25 +186,23 @@ pub async fn loader_fields_list(
 ) -> Result<HttpResponse, ApiError> {
     let query = query.into_inner();
     let loader_field = LoaderField::get_fields_all(&**pool, &redis)
-        .await?
+        .await
+        .wrap_internal_err("fetching loader field from Redis")?
         .into_iter()
         .find(|x| x.field == query.loader_field)
-        .ok_or_else(|| {
-            ApiError::InvalidInput(format!(
-                "'{}' was not a valid loader field.",
-                query.loader_field
-            ))
+        .wrap_request_err_with(|| {
+            format!("'{}' was not a valid loader field.", query.loader_field)
         })?;
 
     let (LoaderFieldType::Enum(loader_field_enum_id)
     | LoaderFieldType::ArrayEnum(loader_field_enum_id)) =
         loader_field.field_type
     else {
-        return Err(ApiError::InvalidInput(format!(
+        return Err(ApiError::Request(eyre::eyre!(format!(
             "'{}' is not an enumerable field, but an '{}' field.",
             query.loader_field,
             loader_field.field_type.to_str()
-        )));
+        ))));
     };
 
     let results: Vec<_> = if let Some(filters) = query.filters {
@@ -208,10 +212,12 @@ pub async fn loader_fields_list(
             &**pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching loader field enum value from Redis")?
     } else {
         LoaderFieldEnumValue::list(loader_field_enum_id, &**pool, &redis)
-            .await?
+            .await
+            .wrap_internal_err("fetching loader field enum value from Redis")?
     };
 
     Ok(HttpResponse::Ok().json(results))
@@ -276,9 +282,9 @@ pub async fn license_text(
         }));
     }
 
-    Err(ApiError::InvalidInput(
-        "Invalid SPDX identifier specified".to_string(),
-    ))
+    Err(ApiError::Request(eyre::eyre!(
+        "Invalid SPDX identifier specified",
+    )))
 }
 
 #[derive(serde::Serialize, serde::Deserialize)]
@@ -302,7 +308,8 @@ pub async fn link_platform_list(
 ) -> Result<HttpResponse, ApiError> {
     let results: Vec<LinkPlatformQueryData> =
         LinkPlatform::list(&**pool, &redis)
-            .await?
+            .await
+            .wrap_internal_err("reading HTTP response body")?
             .into_iter()
             .map(|x| LinkPlatformQueryData {
                 name: x.name,
@@ -325,7 +332,9 @@ pub async fn report_type_list(
     pool: web::Data<PgPool>,
     redis: web::Data<RedisPool>,
 ) -> Result<HttpResponse, ApiError> {
-    let results = ReportType::list(&**pool, &redis).await?;
+    let results = ReportType::list(&**pool, &redis)
+        .await
+        .wrap_internal_err("reading HTTP response body")?;
     Ok(HttpResponse::Ok().json(results))
 }
 
@@ -342,6 +351,8 @@ pub async fn project_type_list(
     pool: web::Data<PgPool>,
     redis: web::Data<RedisPool>,
 ) -> Result<HttpResponse, ApiError> {
-    let results = ProjectType::list(&**pool, &redis).await?;
+    let results = ProjectType::list(&**pool, &redis)
+        .await
+        .wrap_internal_err("fetching project type from Redis")?;
     Ok(HttpResponse::Ok().json(results))
 }
diff --git a/apps/labrinth/src/routes/v3/teams.rs b/apps/labrinth/src/routes/v3/teams.rs
index 3cc0b127e8..5cb8e173bb 100644
--- a/apps/labrinth/src/routes/v3/teams.rs
+++ b/apps/labrinth/src/routes/v3/teams.rs
@@ -11,6 +11,7 @@ use crate::models::pats::Scopes;
 use crate::models::teams::{OrganizationPermissions, ProjectPermissions};
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, post, web};
 use ariadne::ids::UserId;
@@ -61,7 +62,8 @@ pub async fn team_members_get_project_internal(
     let string = info.into_inner().0;
     let project_data =
         crate::database::models::DBProject::get(&string, &**pool, &redis)
-            .await?;
+            .await
+            .wrap_api_err("fetching project from database")?;
 
     if let Some(project) = project_data {
         let current_user = get_user_from_headers(
@@ -76,22 +78,25 @@ pub async fn team_members_get_project_internal(
         .ok();
 
         if !is_visible_project(&project.inner, &current_user, &pool, false)
-            .await?
+            .await
+            .wrap_api_err("checking project visibility")?
         {
-            return Err(ApiError::NotFound);
+            return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
         }
         let members_data = DBTeamMember::get_from_team_full(
             project.inner.team_id,
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching team members from database")?;
         let users = DBUser::get_many_ids(
             &members_data.iter().map(|x| x.user_id).collect::<Vec<_>>(),
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching users from database")?;
 
         let user_id = current_user.as_ref().map(|x| x.id.into());
         let logged_in = if let Some(user_id) = user_id {
@@ -101,7 +106,8 @@ pub async fn team_members_get_project_internal(
                     user_id,
                     &**pool,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("fetching team member from database")?;
 
             team_member.is_some() || organization_team_member.is_some()
         } else {
@@ -130,7 +136,7 @@ pub async fn team_members_get_project_internal(
 
         Ok(HttpResponse::Ok().json(team_members))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -146,7 +152,8 @@ pub async fn team_members_get_organization(
     let string = info.into_inner().0;
     let organization_data =
         crate::database::models::DBOrganization::get(&string, &**pool, &redis)
-            .await?;
+            .await
+            .wrap_internal_err("fetching organization from database")?;
 
     let current_user = get_user_from_headers(
         &req,
@@ -161,20 +168,23 @@ pub async fn team_members_get_organization(
 
     if let Some(organization) = organization_data
         && is_visible_organization(&organization, &current_user, &pool, &redis)
-            .await?
+            .await
+            .wrap_api_err("checking organization visibility")?
     {
         let members_data = DBTeamMember::get_from_team_full(
             organization.team_id,
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching team members from database")?;
         let users = crate::database::models::DBUser::get_many_ids(
             &members_data.iter().map(|x| x.user_id).collect::<Vec<_>>(),
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching users from database")?;
 
         let user_id = current_user.as_ref().map(|x| x.id.into());
 
@@ -208,7 +218,7 @@ pub async fn team_members_get_organization(
 
         Ok(HttpResponse::Ok().json(team_members))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -234,13 +244,16 @@ pub async fn team_members_get(
 ) -> Result<HttpResponse, ApiError> {
     let id = info.into_inner().0;
     let members_data =
-        DBTeamMember::get_from_team_full(id.into(), &**pool, &redis).await?;
+        DBTeamMember::get_from_team_full(id.into(), &**pool, &redis)
+            .await
+            .wrap_internal_err("fetching team members from database")?;
     let users = crate::database::models::DBUser::get_many_ids(
         &members_data.iter().map(|x| x.user_id).collect::<Vec<_>>(),
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching users from database")?;
 
     let current_user = get_user_from_headers(
         &req,
@@ -315,20 +328,23 @@ pub async fn teams_get(
 ) -> Result<HttpResponse, ApiError> {
     use itertools::Itertools;
 
-    let team_ids = serde_json::from_str::<Vec<TeamId>>(&ids.ids)?
+    let team_ids = serde_json::from_str::<Vec<TeamId>>(&ids.ids)
+        .wrap_request_err("deserializing JSON data")?
         .into_iter()
         .map(|x| x.into())
         .collect::<Vec<crate::database::models::ids::DBTeamId>>();
 
     let teams_data =
         DBTeamMember::get_from_team_full_many(&team_ids, &**pool, &redis)
-            .await?;
+            .await
+            .wrap_internal_err("fetching team members from database")?;
     let users = crate::database::models::DBUser::get_many_ids(
         &teams_data.iter().map(|x| x.user_id).collect::<Vec<_>>(),
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching users from database")?;
 
     let current_user = get_user_from_headers(
         &req,
@@ -403,7 +419,8 @@ pub async fn join_team(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let member = DBTeamMember::get_from_user_id_pending(
@@ -411,15 +428,19 @@ pub async fn join_team(
         current_user.id.into(),
         &**pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching team member from database")?;
 
     if let Some(member) = member {
         if member.accepted {
-            return Err(ApiError::InvalidInput(
-                "You are already a member of this team".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You are already a member of this team",
+            )));
         }
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         // Edit Team Member to set Accepted to True
         DBTeamMember::edit_team_member(
@@ -434,16 +455,24 @@ pub async fn join_team(
             None,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_internal_err("updating team member in database")?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
-        DBUser::clear_project_cache(&[current_user.id.into()], &redis).await?;
-        DBTeamMember::clear_cache(team_id, &redis).await?;
+        DBUser::clear_project_cache(&[current_user.id.into()], &redis)
+            .await
+            .wrap_internal_err("clearing cached user in Redis")?;
+        DBTeamMember::clear_cache(team_id, &redis)
+            .await
+            .wrap_internal_err("clearing cached data from Redis")?;
     } else {
-        return Err(ApiError::InvalidInput(
-            "There is no pending request from this team".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "There is no pending request from this team",
+        )));
     }
 
     Ok(HttpResponse::NoContent().body(""))
@@ -496,7 +525,10 @@ pub async fn add_team_member(
 ) -> Result<HttpResponse, ApiError> {
     let team_id = info.into_inner().0.into();
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let current_user = get_user_from_headers(
         &req,
@@ -505,21 +537,22 @@ pub async fn add_team_member(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let team_association = DBTeam::get_association(team_id, &**pool)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The team specified does not exist".to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching team from database")?
+        .wrap_request_err_with(|| {
+            "the team specified does not exist".to_string()
         })?;
     let member = DBTeamMember::get_from_user_id(
         team_id,
         current_user.id.into(),
         &**pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching team member from database")?;
     match team_association {
         // If team is associated with a project, check if they have permissions to invite users to that project
         TeamAssociationId::Project(pid) => {
@@ -527,7 +560,8 @@ pub async fn add_team_member(
                 DBOrganization::get_associated_organization_project_id(
                     pid, &**pool,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("fetching organization from database")?;
             let organization_team_member =
                 if let Some(organization) = &organization {
                     DBTeamMember::get_from_user_id(
@@ -535,7 +569,8 @@ pub async fn add_team_member(
                         current_user.id.into(),
                         &**pool,
                     )
-                    .await?
+                    .await
+                    .wrap_internal_err("fetching team member from database")?
                 } else {
                     None
                 };
@@ -547,23 +582,20 @@ pub async fn add_team_member(
             .unwrap_or_default();
 
             if !permissions.contains(ProjectPermissions::MANAGE_INVITES) {
-                return Err(ApiError::CustomAuthentication(
-                    "You don't have permission to invite users to this team"
-                        .to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You don't have permission to invite users to this team",
+                )));
             }
             if !permissions.contains(new_member.permissions) {
-                return Err(ApiError::InvalidInput(
-                    "The new member has permissions that you don't have"
-                        .to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "The new member has permissions that you don't have",
+                )));
             }
 
             if new_member.organization_permissions.is_some() {
-                return Err(ApiError::InvalidInput(
-                    "The organization permissions of a project team member cannot be set"
-                        .to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "The organization permissions of a project team member cannot be set",
+                )));
             }
         }
         // If team is associated with an organization, check if they have permissions to invite users to that organization
@@ -577,25 +609,24 @@ pub async fn add_team_member(
             if !organization_permissions
                 .contains(OrganizationPermissions::MANAGE_INVITES)
             {
-                return Err(ApiError::CustomAuthentication(
-                    "You don't have permission to invite users to this organization".to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You don't have permission to invite users to this organization",
+                )));
             }
             if !organization_permissions.contains(
                 new_member.organization_permissions.unwrap_or_default(),
             ) {
-                return Err(ApiError::InvalidInput(
-                    "The new member has organization permissions that you don't have".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "The new member has organization permissions that you don't have",
+                )));
             }
             if !organization_permissions.contains(
                 OrganizationPermissions::EDIT_MEMBER_DEFAULT_PERMISSIONS,
             ) && !new_member.permissions.is_empty()
             {
-                return Err(ApiError::CustomAuthentication(
-                    "You do not have permission to give this user default project permissions. Ensure 'permissions' is set if it is not, and empty (0)."
-                        .to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You do not have permission to give this user default project permissions. Ensure 'permissions' is set if it is not, and empty (0).",
+                )));
             }
         }
     }
@@ -603,9 +634,9 @@ pub async fn add_team_member(
     if new_member.payouts_split < Decimal::ZERO
         || new_member.payouts_split > Decimal::from(5000)
     {
-        return Err(ApiError::InvalidInput(
-            "Payouts split must be between 0 and 5000!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Payouts split must be between 0 and 5000!",
+        )));
     }
 
     let request = DBTeamMember::get_from_user_id_pending(
@@ -613,18 +644,18 @@ pub async fn add_team_member(
         new_member.user_id.into(),
         &**pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching team member from database")?;
 
     if let Some(req) = request {
         if req.accepted {
-            return Err(ApiError::InvalidInput(
-                "The user is already a member of that team".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "The user is already a member of that team",
+            )));
         } else {
-            return Err(ApiError::InvalidInput(
-                "There is already a pending member request for this user"
-                    .to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "There is already a pending member request for this user",
+            )));
         }
     }
     let new_user = crate::database::models::DBUser::get_id(
@@ -632,10 +663,9 @@ pub async fn add_team_member(
         &**pool,
         &redis,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput("An invalid User ID specified".to_string())
-    })?;
+    .await
+    .wrap_internal_err("fetching user from database")?
+    .wrap_request_err_with(|| "an invalid User ID specified".to_string())?;
 
     let mut force_accepted = false;
     if let TeamAssociationId::Project(pid) = team_association {
@@ -644,7 +674,8 @@ pub async fn add_team_member(
             DBOrganization::get_associated_organization_project_id(
                 pid, &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching organization from database")?;
         let new_user_organization_team_member =
             if let Some(organization) = &organization {
                 DBTeamMember::get_from_user_id(
@@ -652,7 +683,8 @@ pub async fn add_team_member(
                     new_user.id,
                     &**pool,
                 )
-                .await?
+                .await
+                .wrap_internal_err("fetching team member from database")?
             } else {
                 None
             };
@@ -661,10 +693,9 @@ pub async fn add_team_member(
             .is_some_and(|tm| tm.is_owner)
             && new_member.permissions != ProjectPermissions::all()
         {
-            return Err(ApiError::InvalidInput(
-                "You cannot override the owner of an organization's permissions in a project team"
-                    .to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You cannot override the owner of an organization's permissions in a project team",
+            )));
         }
 
         // In the case of adding a user that is in an org, to a project that is owned by that same org,
@@ -678,7 +709,8 @@ pub async fn add_team_member(
 
     let new_id =
         crate::database::models::ids::generate_team_member_id(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("generating team member ID")?;
     DBTeamMember {
         id: new_id,
         team_id,
@@ -692,7 +724,8 @@ pub async fn add_team_member(
         ordering: new_member.ordering,
     }
     .insert(&mut transaction)
-    .await?;
+    .await
+    .wrap_internal_err("inserting database records for `add_team_member`")?;
 
     // If the user has an opportunity to accept the invite, send a notification
     if !force_accepted {
@@ -707,7 +740,10 @@ pub async fn add_team_member(
                     },
                 }
                 .insert(new_member.user_id.into(), &mut transaction, &redis)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "inserting database records for `add_team_member`",
+                )?;
             }
             TeamAssociationId::Organization(oid) => {
                 NotificationBuilder {
@@ -719,14 +755,24 @@ pub async fn add_team_member(
                     },
                 }
                 .insert(new_member.user_id.into(), &mut transaction, &redis)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "inserting database records for `add_team_member`",
+                )?;
             }
         }
     }
 
-    transaction.commit().await?;
-    DBTeamMember::clear_cache(team_id, &redis).await?;
-    DBUser::clear_project_cache(&[new_member.user_id.into()], &redis).await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
+    DBTeamMember::clear_cache(team_id, &redis)
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
+    DBUser::clear_project_cache(&[new_member.user_id.into()], &redis)
+        .await
+        .wrap_internal_err("clearing cached user in Redis")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -777,7 +823,8 @@ pub async fn edit_team_member(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let team_association = DBTeam::get_association(id, &**pool)
@@ -786,7 +833,8 @@ pub async fn edit_team_member(
         .wrap_request_err("the specified team does not exist")?;
     let member =
         DBTeamMember::get_from_user_id(id, current_user.id.into(), &**pool)
-            .await?;
+            .await
+            .wrap_internal_err("fetching team member from database")?;
     let edit_member_db =
         DBTeamMember::get_from_user_id_pending(id, user_id, &**pool)
             .await
@@ -796,15 +844,18 @@ pub async fn edit_team_member(
 				the member must first be created via `POST`",
             )?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     if edit_member_db.is_owner
         && (edit_member.permissions.is_some()
             || edit_member.organization_permissions.is_some())
     {
-        return Err(ApiError::InvalidInput(
-            "The owner's permission's in a team cannot be edited".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "The owner's permission's in a team cannot be edited",
+        )));
     }
 
     match team_association {
@@ -813,7 +864,8 @@ pub async fn edit_team_member(
                 DBOrganization::get_associated_organization_project_id(
                     project_id, &**pool,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("fetching organization from database")?;
             let organization_team_member =
                 if let Some(organization) = &organization {
                     DBTeamMember::get_from_user_id(
@@ -821,7 +873,8 @@ pub async fn edit_team_member(
                         current_user.id.into(),
                         &**pool,
                     )
-                    .await?
+                    .await
+                    .wrap_internal_err("fetching team member from database")?
                 } else {
                     None
                 };
@@ -833,7 +886,8 @@ pub async fn edit_team_member(
                         user_id,
                         &**pool,
                     )
-                    .await?
+                    .await
+                    .wrap_internal_err("fetching team member from database")?
                 } else {
                     None
                 };
@@ -845,10 +899,9 @@ pub async fn edit_team_member(
                     .permissions
                     .is_some_and(|x| x != ProjectPermissions::all())
             {
-                return Err(ApiError::CustomAuthentication(
-                    "You cannot override the project permissions of the organization owner!"
-                        .to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You cannot override the project permissions of the organization owner!",
+                )));
             }
 
             let permissions = ProjectPermissions::get_permissions_by_role(
@@ -858,26 +911,23 @@ pub async fn edit_team_member(
             )
             .unwrap_or_default();
             if !permissions.contains(ProjectPermissions::EDIT_MEMBER) {
-                return Err(ApiError::CustomAuthentication(
-                    "You don't have permission to edit members of this team"
-                        .to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You don't have permission to edit members of this team",
+                )));
             }
 
             if let Some(new_permissions) = edit_member.permissions
                 && !permissions.contains(new_permissions)
             {
-                return Err(ApiError::InvalidInput(
-                    "The new permissions have permissions that you don't have"
-                        .to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "The new permissions have permissions that you don't have",
+                )));
             }
 
             if edit_member.organization_permissions.is_some() {
-                return Err(ApiError::InvalidInput(
-                    "The organization permissions of a project team member cannot be edited"
-                        .to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "The organization permissions of a project team member cannot be edited",
+                )));
             }
         }
         TeamAssociationId::Organization(_) => {
@@ -891,19 +941,17 @@ pub async fn edit_team_member(
             if !organization_permissions
                 .contains(OrganizationPermissions::EDIT_MEMBER)
             {
-                return Err(ApiError::CustomAuthentication(
-                    "You don't have permission to edit members of this team"
-                        .to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You don't have permission to edit members of this team",
+                )));
             }
 
             if let Some(new_permissions) = edit_member.organization_permissions
                 && !organization_permissions.contains(new_permissions)
             {
-                return Err(ApiError::InvalidInput(
-                        "The new organization permissions have permissions that you don't have"
-                            .to_string(),
-                    ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "The new organization permissions have permissions that you don't have",
+                )));
             }
 
             if edit_member.permissions.is_some()
@@ -911,10 +959,9 @@ pub async fn edit_team_member(
                     OrganizationPermissions::EDIT_MEMBER_DEFAULT_PERMISSIONS,
                 )
             {
-                return Err(ApiError::CustomAuthentication(
-                    "You do not have permission to give this user default project permissions."
-                        .to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You do not have permission to give this user default project permissions.",
+                )));
             }
         }
     }
@@ -923,9 +970,9 @@ pub async fn edit_team_member(
         && (payouts_split < Decimal::ZERO
             || payouts_split > Decimal::from(5000))
     {
-        return Err(ApiError::InvalidInput(
-            "Payouts split must be between 0 and 5000!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "Payouts split must be between 0 and 5000!",
+        )));
     }
 
     DBTeamMember::edit_team_member(
@@ -940,10 +987,16 @@ pub async fn edit_team_member(
         None,
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_internal_err("updating team member in database")?;
 
-    transaction.commit().await?;
-    DBTeamMember::clear_cache(id, &redis).await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
+    DBTeamMember::clear_cache(id, &redis)
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
 
     Ok(HttpResponse::NoContent().body(""))
 }
@@ -983,23 +1036,26 @@ pub async fn transfer_ownership(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     // Forbid transferring ownership of a project team that is owned by an organization
     // These are owned by the organization owner, and must be removed from the organization first
     // There shouldnt be an owner on these projects in these cases, but just in case.
-    let team_association_id =
-        DBTeam::get_association(id.into(), &**pool).await?;
+    let team_association_id = DBTeam::get_association(id.into(), &**pool)
+        .await
+        .wrap_internal_err("fetching team from database")?;
     if let Some(TeamAssociationId::Project(pid)) = team_association_id {
-        let result = DBProject::get_id(pid, &**pool, &redis).await?;
+        let result = DBProject::get_id(pid, &**pool, &redis)
+            .await
+            .wrap_api_err("fetching project for ownership transfer")?;
         if let Some(project_item) = result
             && project_item.inner.organization_id.is_some()
         {
-            return Err(ApiError::InvalidInput(
-                    "You cannot transfer ownership of a project team that is owned by an organization"
-                        .to_string(),
-                ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You cannot transfer ownership of a project team that is owned by an organization",
+            )));
         }
     }
 
@@ -1009,19 +1065,16 @@ pub async fn transfer_ownership(
             current_user.id.into(),
             &**pool,
         )
-        .await?
-        .ok_or_else(|| {
-            ApiError::CustomAuthentication(
-                "You don't have permission to edit members of this team"
-                    .to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching team member from database")?
+        .wrap_auth_err_with(|| {
+            "you don't have permission to edit members of this team".to_string()
         })?;
 
         if !member.is_owner {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit the ownership of this team"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit the ownership of this team",
+            )));
         }
     }
 
@@ -1030,25 +1083,28 @@ pub async fn transfer_ownership(
         new_owner.user_id.into(),
         &**pool,
     )
-    .await?
-    .ok_or_else(|| {
-        ApiError::InvalidInput(
-            "The new owner specified does not exist".to_string(),
-        )
+    .await
+    .wrap_internal_err("fetching team member from database")?
+    .wrap_request_err_with(|| {
+        "the new owner specified does not exist".to_string()
     })?;
 
     if !new_member.accepted {
-        return Err(ApiError::InvalidInput(
-            "You can only transfer ownership to members who are currently in your team".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "You can only transfer ownership to members who are currently in your team",
+        )));
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     // The following are the only places new_is_owner is modified.
     if let Some(former_owner) =
         DBTeamMember::get_from_team_full(id.into(), &**pool, &redis)
-            .await?
+            .await
+            .wrap_internal_err("fetching team member from database")?
             .into_iter()
             .find(|x| x.is_owner)
     {
@@ -1064,7 +1120,8 @@ pub async fn transfer_ownership(
             Some(false),
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_internal_err("updating team member in database")?;
     }
 
     DBTeamMember::edit_team_member(
@@ -1086,7 +1143,8 @@ pub async fn transfer_ownership(
         Some(true),
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_internal_err("updating database records for `transfer_ownership`")?;
 
     let project_teams_edited =
         if let Some(TeamAssociationId::Organization(oid)) = team_association_id
@@ -1105,7 +1163,8 @@ pub async fn transfer_ownership(
                 oid.0 as i64
             )
             .fetch_all(&mut transaction)
-            .await?;
+            .await
+            .wrap_internal_err("fetching team IDs from database")?;
 
             let team_ids: Vec<crate::database::models::ids::DBTeamId> =
                 team_ids
@@ -1120,7 +1179,8 @@ pub async fn transfer_ownership(
                     new_owner.user_id.into(),
                     &mut transaction,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("deleting team member from database")?;
             }
 
             team_ids
@@ -1138,14 +1198,24 @@ pub async fn transfer_ownership(
             },
         }
         .insert(new_owner.user_id.into(), &mut transaction, &redis)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `transfer_ownership`",
+        )?;
     }
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
-    DBTeamMember::clear_cache(id.into(), &redis).await?;
+    DBTeamMember::clear_cache(id.into(), &redis)
+        .await
+        .wrap_internal_err("clearing cached data from Redis")?;
     for team_id in project_teams_edited {
-        DBTeamMember::clear_cache(team_id, &redis).await?;
+        DBTeamMember::clear_cache(team_id, &redis)
+            .await
+            .wrap_internal_err("clearing cached data from Redis")?;
     }
 
     Ok(HttpResponse::NoContent().body(""))
@@ -1181,31 +1251,38 @@ pub async fn remove_team_member(
         &session_queue,
         Scopes::PROJECT_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    let team_association =
-        DBTeam::get_association(id, &**pool).await?.ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The team specified does not exist".to_string(),
-            )
+    let team_association = DBTeam::get_association(id, &**pool)
+        .await
+        .wrap_internal_err("fetching team from database")?
+        .wrap_request_err_with(|| {
+            "the team specified does not exist".to_string()
         })?;
     let member =
         DBTeamMember::get_from_user_id(id, current_user.id.into(), &**pool)
-            .await?;
+            .await
+            .wrap_internal_err("fetching team member from database")?;
 
     let delete_member =
-        DBTeamMember::get_from_user_id_pending(id, user_id, &**pool).await?;
+        DBTeamMember::get_from_user_id_pending(id, user_id, &**pool)
+            .await
+            .wrap_internal_err("deleting team member from database")?;
 
     if let Some(delete_member) = delete_member {
         if delete_member.is_owner {
             // The owner cannot be removed from a team
-            return Err(ApiError::CustomAuthentication(
-                "The owner can't be removed from a team".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "The owner can't be removed from a team",
+            )));
         }
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         // Organization attached to a project this team is attached to
         match team_association {
@@ -1214,18 +1291,21 @@ pub async fn remove_team_member(
                     DBOrganization::get_associated_organization_project_id(
                         pid, &**pool,
                     )
-                    .await?;
-                let organization_team_member =
-                    if let Some(organization) = &organization {
-                        DBTeamMember::get_from_user_id(
-                            organization.team_id,
-                            current_user.id.into(),
-                            &**pool,
-                        )
-                        .await?
-                    } else {
-                        None
-                    };
+                    .await
+                    .wrap_internal_err("fetching organization from database")?;
+                let organization_team_member = if let Some(organization) =
+                    &organization
+                {
+                    DBTeamMember::get_from_user_id(
+                        organization.team_id,
+                        current_user.id.into(),
+                        &**pool,
+                    )
+                    .await
+                    .wrap_internal_err("fetching team member from database")?
+                } else {
+                    None
+                };
                 let permissions = ProjectPermissions::get_permissions_by_role(
                     &current_user.role,
                     &member,
@@ -1243,12 +1323,14 @@ pub async fn remove_team_member(
                     // true as if the permission exists, but the member does not, they are part of an org
                     {
                         DBTeamMember::delete(id, user_id, &mut transaction)
-                            .await?;
+                            .await
+                            .wrap_internal_err(
+                                "deleting team member from database",
+                            )?;
                     } else {
-                        return Err(ApiError::CustomAuthentication(
-                            "You do not have permission to remove a member from this team"
-                                .to_string(),
-                        ));
+                        return Err(ApiError::Auth(eyre::eyre!(
+                            "You do not have permission to remove a member from this team",
+                        )));
                     }
                 } else if Some(delete_member.user_id)
                     == member.as_ref().map(|m| m.user_id)
@@ -1258,12 +1340,13 @@ pub async fn remove_team_member(
                     // This is a pending invite rather than a member, so the
                     // user being invited or team members with the MANAGE_INVITES
                     // permission can remove it.
-                    DBTeamMember::delete(id, user_id, &mut transaction).await?;
+                    DBTeamMember::delete(id, user_id, &mut transaction)
+                        .await
+                        .wrap_internal_err("deleting team member from database")?;
                 } else {
-                    return Err(ApiError::CustomAuthentication(
-                        "You do not have permission to cancel a team invite"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You do not have permission to cancel a team invite",
+                    )));
                 }
             }
             TeamAssociationId::Organization(_) => {
@@ -1282,12 +1365,14 @@ pub async fn remove_team_member(
                             .contains(OrganizationPermissions::REMOVE_MEMBER)
                     {
                         DBTeamMember::delete(id, user_id, &mut transaction)
-                            .await?;
+                            .await
+                            .wrap_internal_err(
+                                "deleting team member from database",
+                            )?;
                     } else {
-                        return Err(ApiError::CustomAuthentication(
-                            "You do not have permission to remove a member from this organization"
-                                .to_string(),
-                        ));
+                        return Err(ApiError::Auth(eyre::eyre!(
+                            "You do not have permission to remove a member from this organization",
+                        )));
                     }
                 } else if Some(delete_member.user_id)
                     == member.map(|m| m.user_id)
@@ -1297,22 +1382,31 @@ pub async fn remove_team_member(
                     // This is a pending invite rather than a member, so the
                     // user being invited or team members with the MANAGE_INVITES
                     // permission can remove it.
-                    DBTeamMember::delete(id, user_id, &mut transaction).await?;
+                    DBTeamMember::delete(id, user_id, &mut transaction)
+                        .await
+                        .wrap_internal_err("deleting team member from database")?;
                 } else {
-                    return Err(ApiError::CustomAuthentication(
-                        "You do not have permission to cancel an organization invite".to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You do not have permission to cancel an organization invite",
+                    )));
                 }
             }
         }
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
-        DBTeamMember::clear_cache(id, &redis).await?;
-        DBUser::clear_project_cache(&[delete_member.user_id], &redis).await?;
+        DBTeamMember::clear_cache(id, &redis)
+            .await
+            .wrap_internal_err("clearing cached data from Redis")?;
+        DBUser::clear_project_cache(&[delete_member.user_id], &redis)
+            .await
+            .wrap_internal_err("deleting user from database")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
diff --git a/apps/labrinth/src/routes/v3/threads.rs b/apps/labrinth/src/routes/v3/threads.rs
index cfca3fdb67..4d7d82167d 100644
--- a/apps/labrinth/src/routes/v3/threads.rs
+++ b/apps/labrinth/src/routes/v3/threads.rs
@@ -15,6 +15,8 @@ use crate::models::threads::{MessageBody, Thread, ThreadType};
 use crate::models::users::User;
 use crate::queue::session::AuthQueue;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use actix_web::{HttpRequest, HttpResponse, delete, get, post, web};
 use futures::TryStreamExt;
 use serde::Deserialize;
@@ -46,7 +48,7 @@ pub async fn is_authorized_thread(
                     user_id as database::models::ids::DBUserId,
                 )
                 .fetch_one(pool)
-                .await?
+                .await.wrap_internal_err("fetching report exists from database")?
                 .exists;
 
                 report_exists.unwrap_or(false)
@@ -62,7 +64,7 @@ pub async fn is_authorized_thread(
                     user_id as database::models::ids::DBUserId,
                 )
                     .fetch_one(pool)
-                    .await?
+                    .await.wrap_internal_err("fetching project exists from database")?
                     .exists;
 
                 if !project_exists.unwrap_or(false) {
@@ -72,7 +74,7 @@ pub async fn is_authorized_thread(
                         user_id as database::models::ids::DBUserId,
                     )
                         .fetch_one(pool)
-                        .await?
+                        .await.wrap_internal_err("fetching organization exists from database")?
                         .exists;
 
                     org_exists.unwrap_or(false)
@@ -139,7 +141,7 @@ pub async fn filter_authorized_threads(
                 });
             })
             .try_collect::<Vec<()>>()
-            .await?;
+            .await.wrap_internal_err("fetching query results from database")?;
         }
 
         let mut org_project_thread_ids = check_threads
@@ -171,7 +173,7 @@ pub async fn filter_authorized_threads(
                 });
             })
             .try_collect::<Vec<()>>()
-            .await?;
+            .await.wrap_internal_err("fetching query results from database")?;
         }
 
         let report_thread_ids = check_threads
@@ -202,7 +204,8 @@ pub async fn filter_authorized_threads(
                 });
             })
             .try_collect::<Vec<()>>()
-            .await?;
+            .await
+            .wrap_internal_err("fetching query results from database")?;
         }
     }
 
@@ -224,7 +227,8 @@ pub async fn filter_authorized_threads(
 
     let users: Vec<User> =
         database::models::DBUser::get_many_ids(&user_ids, &***pool, redis)
-            .await?
+            .await
+            .wrap_internal_err("fetching users from database")?
             .into_iter()
             .map(From::from)
             .collect();
@@ -283,7 +287,9 @@ pub async fn thread_get(
 ) -> Result<HttpResponse, ApiError> {
     let string = info.into_inner().0.into();
 
-    let thread_data = database::models::DBThread::get(string, &**pool).await?;
+    let thread_data = database::models::DBThread::get(string, &**pool)
+        .await
+        .wrap_internal_err("fetching thread from database")?;
 
     let user = get_user_from_headers(
         &req,
@@ -292,11 +298,14 @@ pub async fn thread_get(
         &session_queue,
         Scopes::THREAD_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     if let Some(mut data) = thread_data
-        && is_authorized_thread(&data, &user, &pool).await?
+        && is_authorized_thread(&data, &user, &pool)
+            .await
+            .wrap_api_err("checking thread authorization")?
     {
         let authors = &mut data.members;
 
@@ -316,14 +325,15 @@ pub async fn thread_get(
 
         let users: Vec<User> =
             database::models::DBUser::get_many_ids(authors, &**pool, &redis)
-                .await?
+                .await
+                .wrap_internal_err("fetching users from database")?
                 .into_iter()
                 .map(From::from)
                 .collect();
 
         return Ok(HttpResponse::Ok().json(Thread::from(data, users, &user)));
     }
-    Err(ApiError::NotFound)
+    Err(ApiError::NotFound(eyre::eyre!("resource not found")))
 }
 
 #[derive(Deserialize)]
@@ -361,20 +371,25 @@ pub async fn threads_get(
         &session_queue,
         Scopes::THREAD_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let thread_ids: Vec<database::models::ids::DBThreadId> =
-        serde_json::from_str::<Vec<ThreadId>>(&ids.ids)?
+        serde_json::from_str::<Vec<ThreadId>>(&ids.ids)
+            .wrap_request_err("deserializing JSON data")?
             .into_iter()
             .map(|x| x.into())
             .collect();
 
     let threads_data =
-        database::models::DBThread::get_many(&thread_ids, &**pool).await?;
+        database::models::DBThread::get_many(&thread_ids, &**pool)
+            .await
+            .wrap_internal_err("fetching threads from database")?;
 
-    let threads =
-        filter_authorized_threads(threads_data, &user, &pool, &redis).await?;
+    let threads = filter_authorized_threads(threads_data, &user, &pool, &redis)
+        .await
+        .wrap_api_err("filtering authorized threads")?;
 
     Ok(HttpResponse::Ok().json(threads))
 }
@@ -413,7 +428,8 @@ pub async fn thread_send_message(
         &session_queue,
         Scopes::THREAD_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     thread_send_message_internal(
@@ -423,7 +439,8 @@ pub async fn thread_send_message(
         new_message.into_inner(),
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("sending thread message")?;
     Ok(HttpResponse::NoContent().finish())
 }
 
@@ -446,15 +463,15 @@ pub async fn thread_send_message_internal(
     } = &new_message.body
     {
         if body.len() > 65536 {
-            return Err(ApiError::InvalidInput(
-                "Input body is too long!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "Input body is too long!",
+            )));
         }
 
         if *private && !user.role.is_mod() {
-            return Err(ApiError::InvalidInput(
-                "You are not allowed to send private messages!".to_string(),
-            ));
+            return Err(ApiError::Request(eyre::eyre!(
+                "You are not allowed to send private messages!",
+            )));
         }
 
         if let Some(replying_to) = replying_to {
@@ -462,37 +479,45 @@ pub async fn thread_send_message_internal(
                 (*replying_to).into(),
                 pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching thread message from database")?;
 
             if let Some(thread_message) = thread_message {
                 if thread_message.thread_id != string {
-                    return Err(ApiError::InvalidInput(
-                        "Message replied to is from another thread!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Request(eyre::eyre!(
+                        "Message replied to is from another thread!",
+                    )));
                 }
             } else {
-                return Err(ApiError::InvalidInput(
-                    "Message replied to does not exist!".to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "Message replied to does not exist!",
+                )));
             }
         }
 
         is_private = *private;
     } else {
-        return Err(ApiError::InvalidInput(
-            "You may only send text messages through this route!".to_string(),
-        ));
+        return Err(ApiError::Request(eyre::eyre!(
+            "You may only send text messages through this route!",
+        )));
     }
 
-    let result = database::models::DBThread::get(string, pool).await?;
+    let result = database::models::DBThread::get(string, pool)
+        .await
+        .wrap_internal_err("fetching thread from database")?;
 
     if let Some(thread) = result {
-        if !is_authorized_thread(&thread, user, pool).await? {
-            return Err(ApiError::NotFound);
+        if !is_authorized_thread(&thread, user, pool)
+            .await
+            .wrap_api_err("checking thread authorization")?
+        {
+            return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
         }
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         let id = ThreadMessageBuilder {
             author_id: Some(user.id.into()),
@@ -501,12 +526,16 @@ pub async fn thread_send_message_internal(
             hide_identity: user.role.is_mod(),
         }
         .insert(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err(
+            "inserting database records for `thread_send_message_internal`",
+        )?;
 
         if let Some(project_id) = thread.project_id {
             let project =
                 database::models::DBProject::get_id(project_id, pool, redis)
-                    .await?;
+                    .await
+                    .wrap_api_err("fetching thread project")?;
 
             if let Some(project) = project
                 && project.inner.status != ProjectStatus::Processing
@@ -519,7 +548,8 @@ pub async fn thread_send_message_internal(
                         pool,
                         redis,
                     )
-                    .await?;
+                    .await
+                    .wrap_internal_err("fetching team members from database")?;
 
                 NotificationBuilder {
                     body: NotificationBody::ModeratorMessage {
@@ -534,7 +564,8 @@ pub async fn thread_send_message_internal(
                     &mut transaction,
                     redis,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("inserting database records for `thread_send_message_internal`")?;
 
                 NotificationBuilder {
                     body: NotificationBody::ModerationMessageReceived {
@@ -546,18 +577,20 @@ pub async fn thread_send_message_internal(
                     &mut transaction,
                     redis,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("inserting database records for `thread_send_message_internal`")?;
             }
         } else if let Some(report_id) = thread.report_id {
             let report =
                 database::models::report_item::DBReport::get(report_id, pool)
-                    .await?;
+                    .await
+                    .wrap_internal_err("fetching report from database")?;
 
             if let Some(report) = report {
                 if report.closed && !user.role.is_mod() {
-                    return Err(ApiError::InvalidInput(
-                        "You may not reply to a closed report".to_string(),
-                    ));
+                    return Err(ApiError::Request(eyre::eyre!(
+                        "You may not reply to a closed report",
+                    )));
                 }
 
                 if user.id != report.reporter.into() && !is_private {
@@ -570,7 +603,8 @@ pub async fn thread_send_message_internal(
                         },
                     }
                     .insert(report.reporter, &mut transaction, redis)
-                    .await?;
+                    .await
+                    .wrap_internal_err("inserting database records for `thread_send_message_internal`")?;
                 }
             }
         }
@@ -585,7 +619,8 @@ pub async fn thread_send_message_internal(
                     &mut transaction,
                     redis,
                 )
-                .await?
+                .await
+                .wrap_internal_err("fetching image from database")?
                 {
                     let image: Image = db_image.into();
                     if !matches!(
@@ -593,9 +628,9 @@ pub async fn thread_send_message_internal(
                         ImageContext::ThreadMessage { .. }
                     ) || image.context.inner_id().is_some()
                     {
-                        return Err(ApiError::InvalidInput(format!(
+                        return Err(ApiError::Request(eyre::eyre!(format!(
                             "Image {image_id} is not unused and in the 'thread_message' context"
-                        )));
+                        ))));
                     }
 
                     sqlx::query!(
@@ -608,23 +643,30 @@ pub async fn thread_send_message_internal(
                         image_id.0 as i64
                     )
                     .execute(&mut transaction)
-                    .await?;
+                    .await
+                    .wrap_internal_err(
+                        "querying database for `thread_send_message_internal`",
+                    )?;
 
                     image_item::DBImage::clear_cache(image.id.into(), redis)
-                        .await?;
+                        .await
+                        .wrap_internal_err("clearing cached data from Redis")?;
                 } else {
-                    return Err(ApiError::InvalidInput(format!(
+                    return Err(ApiError::Request(eyre::eyre!(format!(
                         "Image {image_id} does not exist"
-                    )));
+                    ))));
                 }
             }
         }
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(())
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -656,30 +698,36 @@ pub async fn message_delete(
         &session_queue,
         Scopes::THREAD_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let result = database::models::DBThreadMessage::get(
         info.into_inner().0.into(),
         &**pool,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching thread message from database")?;
 
     if let Some(thread) = result {
         if !user.role.is_mod() && thread.author_id != Some(user.id.into()) {
-            return Err(ApiError::CustomAuthentication(
-                "You cannot delete this message!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You cannot delete this message!",
+            )));
         }
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         let context = ImageContext::ThreadMessage {
             thread_message_id: Some(thread.id.into()),
         };
         let images =
             database::DBImage::get_many_contexted(context, &mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("fetching images from database")?;
         for image in images {
             let name = image.url.split(&format!("{}/", ENV.CDN_URL)).nth(1);
             if let Some(icon_path) = name {
@@ -688,10 +736,12 @@ pub async fn message_delete(
                         icon_path,
                         FileHostPublicity::Public, // FIXME: Consider using private file storage?
                     )
-                    .await?;
+                    .await
+                    .wrap_internal_err("deleting file from file host")?;
             }
             database::DBImage::remove(image.id, &mut transaction, &redis)
-                .await?;
+                .await
+                .wrap_internal_err("deleting image from database")?;
         }
 
         let private = thread.body.is_private();
@@ -700,11 +750,15 @@ pub async fn message_delete(
             private,
             &mut transaction,
         )
-        .await?;
-        transaction.commit().await?;
+        .await
+        .wrap_internal_err("deleting thread message from database")?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
diff --git a/apps/labrinth/src/routes/v3/users.rs b/apps/labrinth/src/routes/v3/users.rs
index 59a452c4de..ce5215d4ce 100644
--- a/apps/labrinth/src/routes/v3/users.rs
+++ b/apps/labrinth/src/routes/v3/users.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use std::{
     cmp::Reverse,
     collections::{HashMap, HashSet},
@@ -24,10 +25,7 @@ use crate::{
         users::{Badges, Role},
     },
     queue::session::AuthQueue,
-    util::{
-        img::delete_old_images, routes::read_limited_from_payload,
-        validate::validation_errors_to_string,
-    },
+    util::{img::delete_old_images, routes::read_limited_from_payload},
 };
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, web};
 use ariadne::ids::UserId;
@@ -85,16 +83,21 @@ pub async fn all_projects(
     .map(|x| x.1)
     .ok();
     let target_user = DBUser::get(&info.into_inner().0, &**pool, &redis)
-        .await?
-        .ok_or(ApiError::NotFound)?;
+        .await
+        .wrap_internal_err("fetching user from database")?
+        .wrap_not_found_err("resource not found")?;
 
     let user_project_ids =
-        DBUser::get_projects(target_user.id, &**pool, &redis).await?;
-    let organization_ids =
-        DBUser::get_organizations(target_user.id, &**pool).await?;
+        DBUser::get_projects(target_user.id, &**pool, &redis)
+            .await
+            .wrap_internal_err("fetching users from database")?;
+    let organization_ids = DBUser::get_organizations(target_user.id, &**pool)
+        .await
+        .wrap_internal_err("fetching users from database")?;
     let organizations_data =
         DBOrganization::get_many_ids(&organization_ids, &**pool, &redis)
-            .await?;
+            .await
+            .wrap_internal_err("fetching organizations from database")?;
 
     let team_ids = organizations_data
         .iter()
@@ -104,7 +107,8 @@ pub async fn all_projects(
         crate::database::models::DBTeamMember::get_from_team_full_many(
             &team_ids, &**pool, &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching team members from database")?;
     let users = DBUser::get_many_ids(
         &teams_data
             .iter()
@@ -113,7 +117,8 @@ pub async fn all_projects(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching users from database")?;
 
     let mut team_groups = HashMap::new();
     for member in teams_data {
@@ -126,7 +131,10 @@ pub async fn all_projects(
     let mut organizations = HashMap::new();
     let mut visible_organization_ids = Vec::new();
     for data in organizations_data {
-        if !is_visible_organization(&data, &user, &pool, &redis).await? {
+        if !is_visible_organization(&data, &user, &pool, &redis)
+            .await
+            .wrap_api_err("checking organization visibility")?
+        {
             continue;
         }
 
@@ -173,7 +181,8 @@ pub async fn all_projects(
         &organization_id_values,
     )
     .fetch_all(&**pool)
-    .await?
+    .await
+    .wrap_internal_err("fetching organization project IDs from database")?
     .into_iter()
     .map(|row| DBProjectId(row.id))
     .collect::<Vec<_>>();
@@ -186,9 +195,11 @@ pub async fn all_projects(
         .collect::<Vec<_>>();
     let projects_data =
         crate::database::DBProject::get_many_ids(&project_ids, &**pool, &redis)
-            .await?;
-    let projects =
-        filter_visible_projects(projects_data, &user, &pool, true).await?;
+            .await
+            .wrap_api_err("fetching user and organization projects")?;
+    let projects = filter_visible_projects(projects_data, &user, &pool, true)
+        .await
+        .wrap_api_err("filtering visible projects")?;
 
     Ok(web::Json(AllProjectsResponse {
         projects,
@@ -217,13 +228,13 @@ pub async fn admin_user_email(
         Scopes::SESSION_ACCESS,
     )
     .await
-    .map(|x| x.1)?;
+    .map(|x| x.1)
+    .wrap_auth_err("authenticating API request")?;
 
     if !user.role.is_admin() {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to get a user from their email!"
-                .to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to get a user from their email!",
+        )));
     }
 
     let user_id = sqlx::query!(
@@ -234,12 +245,11 @@ pub async fn admin_user_email(
         email.email
     )
     .fetch_optional(&**pool)
-    .await?
+    .await
+    .wrap_internal_err("fetching user ID from database")?
     .map(|x| x.id)
-    .ok_or_else(|| {
-        ApiError::InvalidInput(
-            "The email provided is not associated with a user!".to_string(),
-        )
+    .wrap_request_err_with(|| {
+        "the email provided is not associated with a user!".to_string()
     })?;
 
     let user = DBUser::get_id(
@@ -247,12 +257,13 @@ pub async fn admin_user_email(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching user from database")?;
 
     if let Some(user) = user {
         Ok(HttpResponse::Ok().json(user))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -286,22 +297,28 @@ pub async fn projects_list(
     .map(|x| x.1)
     .ok();
 
-    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis).await?;
+    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(id) = id_option.map(|x| x.id) {
-        let project_data = DBUser::get_projects(id, &**pool, &redis).await?;
+        let project_data = DBUser::get_projects(id, &**pool, &redis)
+            .await
+            .wrap_internal_err("fetching user from database")?;
 
         let projects: Vec<_> = crate::database::DBProject::get_many_ids(
             &project_data,
             &**pool,
             &redis,
         )
-        .await?;
-        let projects =
-            filter_visible_projects(projects, &user, &pool, true).await?;
+        .await
+        .wrap_api_err("fetching organization projects")?;
+        let projects = filter_visible_projects(projects, &user, &pool, true)
+            .await
+            .wrap_api_err("filtering visible projects")?;
         Ok(HttpResponse::Ok().json(projects))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -329,7 +346,8 @@ pub async fn user_auth_get(
         &session_queue,
         Scopes::USER_READ,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
     if !scopes.contains(Scopes::USER_READ_EMAIL) {
         user.email = None;
@@ -340,8 +358,9 @@ pub async fn user_auth_get(
     }
 
     if user.role.is_mod() {
-        let note =
-            DBModerationNote::get_user(user.id.into(), &**pool, &redis).await?;
+        let note = DBModerationNote::get_user(user.id.into(), &**pool, &redis)
+            .await
+            .wrap_internal_err("fetching moderation note from database")?;
         user.moderation_notes = Some(note.map(Into::into));
     }
 
@@ -402,9 +421,12 @@ pub async fn users_get(
     redis: web::Data<RedisPool>,
     session_queue: web::Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    let user_ids = serde_json::from_str::<Vec<String>>(&ids.ids)?;
+    let user_ids = serde_json::from_str::<Vec<String>>(&ids.ids)
+        .wrap_request_err("deserializing JSON data")?;
 
-    let users_data = DBUser::get_many(&user_ids, &**pool, &redis).await?;
+    let users_data = DBUser::get_many(&user_ids, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching users from database")?;
 
     let auth_user = get_user_from_headers(
         &req,
@@ -423,7 +445,8 @@ pub async fn users_get(
             &**pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching moderation notes from database")?
     } else {
         HashMap::new()
     };
@@ -462,7 +485,9 @@ pub async fn user_get(
     redis: web::Data<RedisPool>,
     session_queue: web::Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    let user_data = DBUser::get(&info.into_inner().0, &**pool, &redis).await?;
+    let user_data = DBUser::get(&info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(data) = user_data {
         let auth_user = get_user_from_headers(
@@ -495,14 +520,15 @@ pub async fn user_get(
         };
 
         if is_mod {
-            let note =
-                DBModerationNote::get_user(user_id, &**pool, &redis).await?;
+            let note = DBModerationNote::get_user(user_id, &**pool, &redis)
+                .await
+                .wrap_internal_err("fetching moderation note from database")?;
             response.moderation_notes = Some(note.map(Into::into));
         }
 
         Ok(HttpResponse::Ok().json(response))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -523,17 +549,27 @@ pub async fn user_notes_edit(
         &session_queue,
         Scopes::SESSION_ACCESS,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    new_note.validate_not_empty()?;
+    new_note
+        .validate_not_empty()
+        .wrap_api_err("validating not empty")?;
     let expected_version =
-        crate::models::moderation_notes::parse_if_match_header(&req)?;
+        crate::models::moderation_notes::parse_if_match_header(&req)
+            .wrap_api_err(
+                "executing `moderation_notes::parse_if_match_header`",
+            )?;
 
     let user_data = DBUser::get(&info.into_inner().0, &**pool, &redis)
-        .await?
-        .ok_or(ApiError::NotFound)?;
+        .await
+        .wrap_internal_err("fetching user from database")?
+        .wrap_not_found_err("resource not found")?;
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
     if let Some(expected) = expected_version {
         let updated = DBModerationNote::update(
             Some(user_data.id),
@@ -544,12 +580,13 @@ pub async fn user_notes_edit(
             new_note.user_rating,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_internal_err("updating moderation note in database")?;
 
         if updated.is_none() {
-            return Err(ApiError::PreconditionFailed(
-                "moderation note version does not match".to_string(),
-            ));
+            return Err(ApiError::PreconditionFailed(eyre::eyre!(
+                "moderation note version does not match",
+            )));
         }
     } else {
         let updated = DBModerationNote::insert(
@@ -560,17 +597,23 @@ pub async fn user_notes_edit(
             new_note.user_rating,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_internal_err("inserting moderation note into database")?;
 
         if updated.is_none() {
-            return Err(ApiError::PreconditionRequired(
-                "moderation note version does not match".to_string(),
-            ));
+            return Err(ApiError::PreconditionRequired(eyre::eyre!(
+                "moderation note version does not match",
+            )));
         }
     };
 
-    transaction.commit().await?;
-    DBModerationNote::clear_user_cache(user_data.id, &redis).await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
+    DBModerationNote::clear_user_cache(user_data.id, &redis)
+        .await
+        .wrap_internal_err("clearing cached moderation note in Redis")?;
 
     Ok(HttpResponse::NoContent().finish())
 }
@@ -595,24 +638,30 @@ pub async fn collections_list(
     .map(|x| x.1)
     .ok();
 
-    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis).await?;
+    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(id) = id_option.map(|x| x.id) {
-        let collection_data = DBUser::get_collections(id, &**pool).await?;
+        let collection_data = DBUser::get_collections(id, &**pool)
+            .await
+            .wrap_internal_err("fetching user from database")?;
 
         let response: Vec<_> = crate::database::models::DBCollection::get_many(
             &collection_data,
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching collections from database")?;
 
-        let collections =
-            filter_visible_collections(response, &user, true).await?;
+        let collections = filter_visible_collections(response, &user, true)
+            .await
+            .wrap_api_err("filtering visible collections")?;
 
         Ok(HttpResponse::Ok().json(collections))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -636,16 +685,20 @@ pub async fn orgs_list(
     .map(|x| x.1)
     .ok();
 
-    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis).await?;
+    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(id) = id_option.map(|x| x.id) {
-        let org_data = DBUser::get_organizations(id, &**pool).await?;
+        let org_data = DBUser::get_organizations(id, &**pool)
+            .await
+            .wrap_internal_err("fetching user from database")?;
 
         let organizations_data =
             crate::database::models::organization_item::DBOrganization::get_many_ids(
                 &org_data, &**pool, &redis,
             )
-            .await?;
+            .await.wrap_internal_err("fetching organizations from database")?;
 
         let team_ids = organizations_data
             .iter()
@@ -656,13 +709,15 @@ pub async fn orgs_list(
             crate::database::models::DBTeamMember::get_from_team_full_many(
                 &team_ids, &**pool, &redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team members from database")?;
         let users = DBUser::get_many_ids(
             &teams_data.iter().map(|x| x.user_id).collect::<Vec<_>>(),
             &**pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching users from database")?;
 
         let mut organizations = vec![];
         let mut team_groups = HashMap::new();
@@ -671,7 +726,10 @@ pub async fn orgs_list(
         }
 
         for data in organizations_data {
-            if !is_visible_organization(&data, &user, &pool, &redis).await? {
+            if !is_visible_organization(&data, &user, &pool, &redis)
+                .await
+                .wrap_api_err("checking organization visibility")?
+            {
                 continue;
             }
 
@@ -709,7 +767,7 @@ pub async fn orgs_list(
 
         Ok(HttpResponse::Ok().json(organizations))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -759,24 +817,33 @@ pub async fn user_edit(
         &session_queue,
         Scopes::USER_WRITE,
     )
-    .await?;
+    .await
+    .wrap_auth_err("authenticating API request")?;
 
-    new_user.validate().map_err(|err| {
-        ApiError::Validation(validation_errors_to_string(err, None))
-    })?;
+    new_user
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
-    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis).await?;
+    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(actual_user) = id_option {
         let id = actual_user.id;
         let user_id: UserId = id.into();
 
         if user.id == user_id || user.role.is_mod() {
-            let mut transaction = pool.begin().await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
 
             if let Some(username) = &new_user.username {
                 let existing_user_id_option =
-                    DBUser::get(username, &**pool, &redis).await?;
+                    DBUser::get(username, &**pool, &redis)
+                        .await
+                        .wrap_internal_err("fetching user from database")?;
 
                 if existing_user_id_option
                     .map(|x| UserId::from(x.id))
@@ -792,11 +859,12 @@ pub async fn user_edit(
                         id as crate::database::models::ids::DBUserId,
                     )
                     .execute(&mut transaction)
-                    .await?;
+                    .await
+                    .wrap_internal_err("querying database for `user_edit`")?;
                 } else {
-                    return Err(ApiError::InvalidInput(format!(
+                    return Err(ApiError::Request(eyre::eyre!(format!(
                         "Username {username} is taken!"
-                    )));
+                    ))));
                 }
             }
 
@@ -811,15 +879,15 @@ pub async fn user_edit(
                     id as crate::database::models::ids::DBUserId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("fetching bio from database")?;
             }
 
             if let Some(role) = &new_user.role {
                 if !user.role.is_admin() {
-                    return Err(ApiError::CustomAuthentication(
-                        "You do not have the permissions to edit the role of this user!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You do not have the permissions to edit the role of this user!",
+                    )));
                 }
 
                 let role = role.to_string();
@@ -834,15 +902,15 @@ pub async fn user_edit(
                     id as crate::database::models::ids::DBUserId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("querying database for `user_edit`")?;
             }
 
             if let Some(badges) = &new_user.badges {
                 if !user.role.is_admin() {
-                    return Err(ApiError::CustomAuthentication(
-                        "You do not have the permissions to edit the badges of this user!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You do not have the permissions to edit the badges of this user!",
+                    )));
                 }
 
                 sqlx::query!(
@@ -855,15 +923,15 @@ pub async fn user_edit(
                     id as crate::database::models::ids::DBUserId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("querying database for `user_edit`")?;
             }
 
             if let Some(venmo_handle) = &new_user.venmo_handle {
                 if !scopes.contains(Scopes::PAYOUTS_WRITE) {
-                    return Err(ApiError::CustomAuthentication(
-                        "You do not have the permissions to edit the venmo handle of this user!"
-                            .to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You do not have the permissions to edit the venmo handle of this user!",
+                    )));
                 }
 
                 sqlx::query!(
@@ -876,7 +944,8 @@ pub async fn user_edit(
                     id as crate::database::models::ids::DBUserId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("querying database for `user_edit`")?;
             }
 
             if let Some(allow_friend_requests) = &user.allow_friend_requests {
@@ -890,20 +959,27 @@ pub async fn user_edit(
                     id as crate::database::models::ids::DBUserId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "fetching allow friend requests from database",
+                )?;
             }
 
-            transaction.commit().await?;
+            transaction
+                .commit()
+                .await
+                .wrap_internal_err("committing database transaction")?;
             DBUser::clear_caches(&[(id, Some(actual_user.username))], &redis)
-                .await?;
+                .await
+                .wrap_internal_err("clearing cached data from Redis")?;
             Ok(HttpResponse::NoContent().body(""))
         } else {
-            Err(ApiError::CustomAuthentication(
-                "You do not have permission to edit this user!".to_string(),
-            ))
+            Err(ApiError::Auth(eyre::eyre!(
+                "You do not have permission to edit this user!",
+            )))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -960,16 +1036,18 @@ pub async fn user_icon_edit(
         &session_queue,
         Scopes::USER_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
-    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis).await?;
+    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(actual_user) = id_option {
         if user.id != actual_user.id.into() && !user.role.is_mod() {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit this user's icon."
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit this user's icon.",
+            )));
         }
 
         delete_old_images(
@@ -978,14 +1056,16 @@ pub async fn user_icon_edit(
             FileHostPublicity::Public,
             &**file_host,
         )
-        .await?;
+        .await
+        .wrap_api_err("deleting old images")?;
 
         let bytes = read_limited_from_payload(
             &mut payload,
             262144,
             "Icons must be smaller than 256KiB",
         )
-        .await?;
+        .await
+        .wrap_api_err("executing `read_limited_from_payload`")?;
 
         let user_id: UserId = actual_user.id.into();
         let upload_result = crate::util::img::upload_image_optimized(
@@ -997,7 +1077,8 @@ pub async fn user_icon_edit(
             Some(1.0),
             &**file_host,
         )
-        .await?;
+        .await
+        .wrap_api_err("uploading image")?;
 
         sqlx::query!(
             "
@@ -1010,12 +1091,15 @@ pub async fn user_icon_edit(
             actual_user.id as crate::database::models::ids::DBUserId,
         )
         .execute(&**pool)
-        .await?;
-        DBUser::clear_caches(&[(actual_user.id, None)], &redis).await?;
+        .await
+        .wrap_internal_err("querying database for `user_icon_edit`")?;
+        DBUser::clear_caches(&[(actual_user.id, None)], &redis)
+            .await
+            .wrap_internal_err("clearing cached data from Redis")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1047,16 +1131,18 @@ pub async fn user_icon_delete(
         &session_queue,
         Scopes::USER_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
-    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis).await?;
+    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(actual_user) = id_option {
         if user.id != actual_user.id.into() && !user.role.is_mod() {
-            return Err(ApiError::CustomAuthentication(
-                "You don't have permission to edit this user's icon."
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You don't have permission to edit this user's icon.",
+            )));
         }
 
         delete_old_images(
@@ -1065,7 +1151,8 @@ pub async fn user_icon_delete(
             FileHostPublicity::Public,
             &**file_host,
         )
-        .await?;
+        .await
+        .wrap_api_err("deleting old images")?;
 
         sqlx::query!(
             "
@@ -1076,13 +1163,16 @@ pub async fn user_icon_delete(
             actual_user.id as crate::database::models::ids::DBUserId,
         )
         .execute(&**pool)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `user_icon_delete`")?;
 
-        DBUser::clear_caches(&[(actual_user.id, None)], &redis).await?;
+        DBUser::clear_caches(&[(actual_user.id, None)], &redis)
+            .await
+            .wrap_internal_err("clearing cached data from Redis")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1112,17 +1202,20 @@ pub async fn user_delete(
         &session_queue,
         Scopes::USER_DELETE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis)
         .await
         .wrap_internal_err("failed to get user")?;
 
-    let id = id_option.map(|x| x.id).ok_or(ApiError::NotFound)?;
+    let id = id_option
+        .map(|x| x.id)
+        .wrap_not_found_err("resource not found")?;
     if !user.role.is_admin() && user.id != id.into() {
-        return Err(ApiError::CustomAuthentication(
-            "You do not have permission to delete this user!".to_string(),
-        ));
+        return Err(ApiError::Auth(eyre::eyre!(
+            "You do not have permission to delete this user!",
+        )));
     }
 
     let mut transaction = pool
@@ -1142,7 +1235,7 @@ pub async fn user_delete(
     if result.is_some() {
         Ok(())
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1172,31 +1265,37 @@ pub async fn user_follows(
         &session_queue,
         Scopes::USER_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
-    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis).await?;
+    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(id) = id_option.map(|x| x.id) {
         if !user.role.is_admin() && user.id != id.into() {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have permission to see the projects this user follows!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have permission to see the projects this user follows!",
+            )));
         }
 
-        let project_ids = DBUser::get_follows(id, &**pool).await?;
+        let project_ids = DBUser::get_follows(id, &**pool)
+            .await
+            .wrap_internal_err("fetching users from database")?;
         let projects: Vec<_> = crate::database::DBProject::get_many_ids(
             &project_ids,
             &**pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_api_err("fetching followed projects")?
         .into_iter()
         .map(Project::from)
         .collect();
 
         Ok(HttpResponse::Ok().json(projects))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1226,22 +1325,25 @@ pub async fn user_notifications(
         &session_queue,
         Scopes::NOTIFICATION_READ,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
-    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis).await?;
+    let id_option = DBUser::get(&info.into_inner().0, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching user from database")?;
 
     if let Some(id) = id_option.map(|x| x.id) {
         if !user.role.is_admin() && user.id != id.into() {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have permission to see the notifications of this user!".to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have permission to see the notifications of this user!",
+            )));
         }
 
         let mut notifications: Vec<Notification> =
             crate::database::models::notification_item::DBNotification::get_many_user_exposed_on_site(
                 id, &**pool, &redis,
             )
-            .await?
+            .await.wrap_internal_err("fetching notifications from database")?
             .into_iter()
             .map(Into::into)
             .collect();
@@ -1249,6 +1351,6 @@ pub async fn user_notifications(
         notifications.sort_by_key(|b| Reverse(b.created));
         Ok(HttpResponse::Ok().json(notifications))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
diff --git a/apps/labrinth/src/routes/v3/version_file.rs b/apps/labrinth/src/routes/v3/version_file.rs
index efda1648ad..929416b0c5 100644
--- a/apps/labrinth/src/routes/v3/version_file.rs
+++ b/apps/labrinth/src/routes/v3/version_file.rs
@@ -10,6 +10,8 @@ use crate::models::teams::ProjectPermissions;
 use crate::queue::session::AuthQueue;
 use crate::routes::internal::delphi;
 use crate::routes::{FileHash, HashAlgorithm};
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context;
 use crate::{database, models};
 use actix_web::{HttpRequest, HttpResponse, delete, get, post, web};
 use dashmap::DashMap;
@@ -91,25 +93,30 @@ pub async fn get_version_from_hash(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching version from database")?;
     if let Some(file) = file {
         let version =
             database::models::DBVersion::get(file.version_id, &**pool, &redis)
-                .await?;
+                .await
+                .wrap_internal_err("fetching version from database")?;
         if let Some(version) = version {
             if !is_visible_version(&version.inner, &user_option, &pool, &redis)
-                .await?
+                .await
+                .wrap_api_err("checking version visibility")?
             {
-                return Err(ApiError::NotFound);
+                return Err(ApiError::NotFound(eyre::eyre!(
+                    "resource not found"
+                )));
             }
 
             Ok(HttpResponse::Ok()
                 .json(models::projects::Version::from(version)))
         } else {
-            Err(ApiError::NotFound)
+            Err(ApiError::NotFound(eyre::eyre!("resource not found")))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -217,20 +224,23 @@ pub async fn get_update_from_hash(
         &***pool,
         &redis,
     )
-    .await?
+    .await
+    .wrap_internal_err("querying database for `get_update_from_hash`")?
         && let Some(project) = database::models::DBProject::get_id(
             file.project_id,
             &***pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_api_err("fetching project for version file")?
     {
         let mut versions = database::models::DBVersion::get_many(
             &project.versions,
             &***pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching versions from database")?
         .into_iter()
         .filter(|x| {
             let mut bool = true;
@@ -259,9 +269,12 @@ pub async fn get_update_from_hash(
 
         if let Some(first) = versions.next_back() {
             if !is_visible_version(&first.inner, &user_option, &pool, &redis)
-                .await?
+                .await
+                .wrap_api_err("checking version visibility")?
             {
-                return Err(ApiError::NotFound);
+                return Err(ApiError::NotFound(eyre::eyre!(
+                    "resource not found"
+                )));
             }
 
             return Ok(
@@ -269,7 +282,7 @@ pub async fn get_update_from_hash(
             );
         }
     }
-    Err(ApiError::NotFound)
+    Err(ApiError::NotFound(eyre::eyre!("resource not found")))
 }
 
 // Requests above with multiple versions below
@@ -336,18 +349,21 @@ pub async fn get_versions_from_hashes(
         &***pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching versions from database")?;
 
     let version_ids = files.iter().map(|x| x.version_id).collect::<Vec<_>>();
     let versions_data = filter_visible_versions(
         database::models::DBVersion::get_many(&version_ids, &***pool, &redis)
-            .await?,
+            .await
+            .wrap_internal_err("fetching versions from database")?,
         &user_option,
         &pool,
         pool.as_ref(),
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("filtering visible versions")?;
 
     let mut response = HashMap::new();
 
@@ -415,7 +431,8 @@ pub async fn get_projects_from_hashes(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching versions from database")?;
 
     let project_ids = files.iter().map(|x| x.project_id).collect::<Vec<_>>();
 
@@ -425,12 +442,14 @@ pub async fn get_projects_from_hashes(
             &**pool,
             &redis,
         )
-        .await?,
+        .await
+        .wrap_api_err("fetching projects for visibility filtering")?,
         &user_option,
         &pool,
         false,
     )
-    .await?;
+    .await
+    .wrap_api_err("filtering visible projects")?;
 
     let mut response = HashMap::new();
 
@@ -531,7 +550,9 @@ pub async fn update_files(
     update_data: web::Json<ManyUpdateData>,
 ) -> Result<web::Json<HashMap<String, models::projects::Version>>, ApiError> {
     let file_hashes_to_versions =
-        update_files_internal(pool, redis, update_data).await?;
+        update_files_internal(pool, redis, update_data)
+            .await
+            .wrap_api_err("updating files internal")?;
     let resp = file_hashes_to_versions
         .into_iter()
         .filter_map(|(hash, versions)| {
@@ -557,7 +578,8 @@ async fn update_files_internal(
         &***pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("updating versions in database")?;
 
     // TODO: de-hardcode this and actually use version fields system
     let update_version_ids = sqlx::query!(
@@ -592,7 +614,8 @@ async fn update_files_internal(
                 .push(database::models::DBVersionId(m.version_id));
             async move { Ok(acc) }
         })
-        .await?;
+        .await
+        .wrap_internal_err("fetching project version IDs from database")?;
 
     let versions = database::models::DBVersion::get_many(
         &update_version_ids
@@ -602,7 +625,8 @@ async fn update_files_internal(
         &***pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("updating versions in database")?;
 
     let mut response = HashMap::<String, Vec<models::projects::Version>>::new();
     for file in files {
@@ -697,14 +721,16 @@ pub async fn update_individual_files(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("updating versions in database")?;
 
     let projects = database::models::DBProject::get_many_ids(
         &files.iter().map(|x| x.project_id).collect::<Vec<_>>(),
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching projects for version files")?;
     let all_versions = database::models::DBVersion::get_many(
         &projects
             .iter()
@@ -713,7 +739,8 @@ pub async fn update_individual_files(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching versions from database")?;
 
     let mut response = HashMap::new();
 
@@ -766,7 +793,8 @@ pub async fn update_individual_files(
                         &pool,
                         &redis,
                     )
-                    .await?
+                    .await
+                    .wrap_api_err("checking version visibility")?
                 {
                     response.insert(
                         hash.clone(),
@@ -830,7 +858,8 @@ pub async fn delete_file(
         &session_queue,
         Scopes::VERSION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
     let hash = info.into_inner().0.to_lowercase();
@@ -844,7 +873,8 @@ pub async fn delete_file(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching version from database")?;
 
     if let Some(row) = file {
         if !user.role.is_admin() {
@@ -855,7 +885,7 @@ pub async fn delete_file(
                     &**pool,
                 )
                 .await
-                .map_err(ApiError::Database)?;
+                .wrap_internal_err("fetching version team member")?;
 
             let organization =
                 database::models::DBOrganization::get_associated_organization_project_id(
@@ -863,7 +893,7 @@ pub async fn delete_file(
                     &**pool,
                 )
                 .await
-                .map_err(ApiError::Database)?;
+                .wrap_internal_err("fetching project organization")?;
 
             let organization_team_member = if let Some(organization) =
                 &organization
@@ -875,7 +905,7 @@ pub async fn delete_file(
                     &**pool,
                 )
                 .await
-                .map_err(ApiError::Database)?
+                .wrap_internal_err("fetching organization team member")?
             } else {
                 None
             };
@@ -888,28 +918,32 @@ pub async fn delete_file(
             .unwrap_or_default();
 
             if !permissions.contains(ProjectPermissions::DELETE_VERSION) {
-                return Err(ApiError::CustomAuthentication(
-                    "You don't have permission to delete this file!"
-                        .to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You don't have permission to delete this file!",
+                )));
             }
         }
 
         let version =
             database::models::DBVersion::get(row.version_id, &**pool, &redis)
-                .await?;
+                .await
+                .wrap_internal_err("fetching version from database")?;
         if let Some(version) = version {
             if version.files.len() < 2 {
-                return Err(ApiError::InvalidInput(
-                    "Versions must have at least one file uploaded to them"
-                        .to_string(),
-                ));
+                return Err(ApiError::Request(eyre::eyre!(
+                    "Versions must have at least one file uploaded to them",
+                )));
             }
 
-            database::models::DBVersion::clear_cache(&version, &redis).await?;
+            database::models::DBVersion::clear_cache(&version, &redis)
+                .await
+                .wrap_internal_err("clearing cached data from Redis")?;
         }
 
-        let mut transaction = pool.begin().await?;
+        let mut transaction = pool
+            .begin()
+            .await
+            .wrap_internal_err("starting database transaction")?;
 
         sqlx::query!(
             "
@@ -919,7 +953,8 @@ pub async fn delete_file(
             row.id.0
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `delete_file`")?;
 
         sqlx::query!(
             "
@@ -929,23 +964,30 @@ pub async fn delete_file(
             row.id.0,
         )
         .execute(&mut transaction)
-        .await?;
+        .await
+        .wrap_internal_err("querying database for `delete_file`")?;
 
         database::models::version_item::cleanup_unused_attribution_files_and_groups(&mut transaction)
-            .await?;
+            .await.wrap_internal_err("deleting version item from database")?;
 
         delphi::tech_review_sync::sync_project_tech_review_state(
             &[row.project_id],
             delphi::tech_review_sync::TechReviewExitReason::FileDeleted,
             &mut transaction,
         )
-        .await?;
+        .await
+        .wrap_api_err(
+            "executing `tech_review_sync::sync_project_tech_review_state`",
+        )?;
 
-        transaction.commit().await?;
+        transaction
+            .commit()
+            .await
+            .wrap_internal_err("committing database transaction")?;
 
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1015,27 +1057,32 @@ pub async fn download_version(
         &**pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching version from database")?;
 
     if let Some(file) = file {
         let version =
             database::models::DBVersion::get(file.version_id, &**pool, &redis)
-                .await?;
+                .await
+                .wrap_internal_err("fetching version from database")?;
 
         if let Some(version) = version {
             if !is_visible_version(&version.inner, &user_option, &pool, &redis)
-                .await?
+                .await
+                .wrap_api_err("checking version visibility")?
             {
-                return Err(ApiError::NotFound);
+                return Err(ApiError::NotFound(eyre::eyre!(
+                    "resource not found"
+                )));
             }
 
             Ok(HttpResponse::TemporaryRedirect()
                 .append_header(("Location", &*file.url))
                 .json(DownloadRedirect { url: file.url }))
         } else {
-            Err(ApiError::NotFound)
+            Err(ApiError::NotFound(eyre::eyre!("resource not found")))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
diff --git a/apps/labrinth/src/routes/v3/versions.rs b/apps/labrinth/src/routes/v3/versions.rs
index c09489bec3..377071142c 100644
--- a/apps/labrinth/src/routes/v3/versions.rs
+++ b/apps/labrinth/src/routes/v3/versions.rs
@@ -1,3 +1,4 @@
+use crate::util::error::ApiContext as _;
 use std::collections::HashMap;
 
 use super::ApiError;
@@ -27,8 +28,8 @@ use crate::queue::file_scan::get_files_missing_attribution;
 use crate::queue::session::AuthQueue;
 use crate::routes::internal::delphi;
 use crate::search::SearchState;
+use crate::util::error::Context;
 use crate::util::img;
-use crate::util::validate::validation_errors_to_string;
 use actix_web::{HttpRequest, HttpResponse, delete, get, patch, web};
 use ariadne::ids::base62_impl::parse_base62;
 use itertools::Itertools;
@@ -79,8 +80,9 @@ pub async fn version_project_get_helper(
     redis: web::Data<RedisPool>,
     session_queue: web::Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
-    let result =
-        database::models::DBProject::get(&id.0, &***ro_pool, &redis).await?;
+    let result = database::models::DBProject::get(&id.0, &***ro_pool, &redis)
+        .await
+        .wrap_api_err("fetching project from database")?;
 
     let user_option = get_user_from_headers(
         &req,
@@ -95,9 +97,10 @@ pub async fn version_project_get_helper(
 
     if let Some(project) = result {
         if !is_visible_project(&project.inner, &user_option, &pool, false)
-            .await?
+            .await
+            .wrap_api_err("checking project visibility")?
         {
-            return Err(ApiError::NotFound);
+            return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
         }
 
         let versions = database::models::DBVersion::get_many(
@@ -105,7 +108,8 @@ pub async fn version_project_get_helper(
             &***ro_pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_internal_err("fetching versions from database")?;
 
         let id_opt = parse_base62(&id.1).ok();
         let version = versions.into_iter().find(|x| {
@@ -115,7 +119,8 @@ pub async fn version_project_get_helper(
 
         if let Some(version) = version
             && is_visible_version(&version.inner, &user_option, &pool, &redis)
-                .await?
+                .await
+                .wrap_api_err("checking version visibility")?
         {
             let version_id = version.inner.id;
             let mut v = models::projects::Version::from(version);
@@ -148,7 +153,7 @@ pub async fn version_project_get_helper(
         }
     }
 
-    Err(ApiError::NotFound)
+    Err(ApiError::NotFound(eyre::eyre!("resource not found")))
 }
 
 #[derive(Serialize, Deserialize)]
@@ -193,7 +198,8 @@ pub async fn versions_get(
     session_queue: web::Data<AuthQueue>,
 ) -> Result<HttpResponse, ApiError> {
     let version_ids =
-        serde_json::from_str::<Vec<models::ids::VersionId>>(&ids.ids)?
+        serde_json::from_str::<Vec<models::ids::VersionId>>(&ids.ids)
+            .wrap_request_err("deserializing JSON data")?
             .into_iter()
             .map(|x| x.into())
             .collect::<Vec<database::models::DBVersionId>>();
@@ -202,7 +208,8 @@ pub async fn versions_get(
         &***ro_pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching versions from database")?;
 
     let user_option = get_user_from_headers(
         &req,
@@ -222,7 +229,8 @@ pub async fn versions_get(
         &ro_pool,
         &redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("filtering visible versions")?;
 
     if !ids.include_changelog {
         for version in &mut versions {
@@ -282,7 +290,8 @@ pub async fn version_get_helper(
 ) -> Result<web::Json<models::projects::Version>, ApiError> {
     let version_data =
         database::models::DBVersion::get(id.into(), &***ro_pool, &redis)
-            .await?;
+            .await
+            .wrap_internal_err("fetching version from database")?;
 
     let user_option = get_user_from_headers(
         &req,
@@ -296,7 +305,9 @@ pub async fn version_get_helper(
     .ok();
 
     if let Some(data) = version_data
-        && is_visible_version(&data.inner, &user_option, &pool, &redis).await?
+        && is_visible_version(&data.inner, &user_option, &pool, &redis)
+            .await
+            .wrap_api_err("checking version visibility")?
     {
         let version_id = data.inner.id;
         let mut version = models::projects::Version::from(data);
@@ -329,7 +340,7 @@ pub async fn version_get_helper(
         return Ok(web::Json(version));
     }
 
-    Err(ApiError::NotFound)
+    Err(ApiError::NotFound(eyre::eyre!("resource not found")))
 }
 
 #[derive(Serialize, Deserialize, Validate, Default, Debug)]
@@ -431,7 +442,8 @@ pub async fn version_edit(
     search_state: web::Data<SearchState>,
 ) -> Result<HttpResponse, ApiError> {
     let new_version: EditVersion =
-        serde_json::from_value(new_version.into_inner())?;
+        serde_json::from_value(new_version.into_inner())
+            .wrap_request_err("deserializing JSON data")?;
     version_edit_helper(
         req,
         info.into_inner(),
@@ -459,17 +471,20 @@ pub async fn version_edit_helper(
         &session_queue,
         Scopes::VERSION_WRITE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
 
-    new_version.validate().map_err(|err| {
-        ApiError::Validation(validation_errors_to_string(err, None))
-    })?;
+    new_version
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
 
     let version_id = info.0.into();
 
-    let result =
-        database::models::DBVersion::get(version_id, &**pool, &redis).await?;
+    let result = database::models::DBVersion::get(version_id, &**pool, &redis)
+        .await
+        .wrap_internal_err("fetching version from database")?;
 
     if let Some(version_item) = result {
         let team_member =
@@ -479,14 +494,16 @@ pub async fn version_edit_helper(
                 false,
                 &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching team member from database")?;
 
         let organization =
             DBOrganization::get_associated_organization_project_id(
                 version_item.inner.project_id,
                 &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching organization from database")?;
 
         let organization_team_member = if let Some(organization) = &organization
         {
@@ -495,7 +512,8 @@ pub async fn version_edit_helper(
                 user.id.into(),
                 &**pool,
             )
-            .await?
+            .await
+            .wrap_internal_err("fetching team member from database")?
         } else {
             None
         };
@@ -508,13 +526,15 @@ pub async fn version_edit_helper(
 
         if let Some(perms) = permissions {
             if !perms.contains(ProjectPermissions::UPLOAD_VERSION) {
-                return Err(ApiError::CustomAuthentication(
-                    "You do not have the permissions to edit this version!"
-                        .to_string(),
-                ));
+                return Err(ApiError::Auth(eyre::eyre!(
+                    "You do not have the permissions to edit this version!",
+                )));
             }
 
-            let mut transaction = pool.begin().await?;
+            let mut transaction = pool
+                .begin()
+                .await
+                .wrap_internal_err("starting database transaction")?;
 
             if let Some(name) = &new_version.name {
                 sqlx::query!(
@@ -527,7 +547,10 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `version_edit_helper`",
+                )?;
             }
 
             if let Some(number) = &new_version.version_number {
@@ -541,7 +564,10 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `version_edit_helper`",
+                )?;
             }
 
             if let Some(version_type) = &new_version.version_type {
@@ -555,7 +581,8 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("fetching version type from database")?;
             }
 
             if let Some(dependencies) = &new_version.dependencies {
@@ -566,7 +593,8 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("fetching dependencies from database")?;
 
                 let builders = dependencies
                     .iter()
@@ -583,7 +611,10 @@ pub async fn version_edit_helper(
                     version_item.inner.id,
                     &mut transaction,
                 )
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "inserting database records for `version_edit_helper`",
+                )?;
             }
 
             if !new_version.fields.is_empty() {
@@ -595,7 +626,8 @@ pub async fn version_edit_helper(
 
                 let all_loaders =
                     loader_fields::Loader::list(&mut transaction, &redis)
-                        .await?;
+                        .await
+                        .wrap_internal_err("fetching loader from Redis")?;
                 let loader_ids = version_item
                     .loaders
                     .iter()
@@ -612,7 +644,8 @@ pub async fn version_edit_helper(
                     &mut transaction,
                     &redis,
                 )
-                .await?
+                .await
+                .wrap_internal_err("fetching loader field from Redis")?
                 .into_iter()
                 .filter(|lf| version_fields_names.contains(&lf.field))
                 .collect::<Vec<LoaderField>>();
@@ -631,7 +664,10 @@ pub async fn version_edit_helper(
                     &loader_field_ids
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `version_edit_helper`",
+                )?;
 
                 let mut loader_field_enum_values =
                     LoaderFieldEnumValue::list_many_loader_fields(
@@ -639,18 +675,19 @@ pub async fn version_edit_helper(
                         &mut transaction,
                         &redis,
                     )
-                    .await?;
+                    .await
+                    .wrap_internal_err(
+                        "fetching loader field enum value from Redis",
+                    )?;
 
                 let mut version_fields = Vec::new();
                 for (vf_name, vf_value) in new_version.fields {
                     let loader_field = loader_fields
                         .iter()
                         .find(|lf| lf.field == vf_name)
-                        .ok_or_else(|| {
-                            ApiError::InvalidInput(format!(
-                                "Loader field '{vf_name}' does not exist for any loaders supplied."
-                            ))
-                        })?;
+                        .wrap_request_err_with(|| format!(
+                                "loader field `{vf_name}` does not exist for any loaders supplied"
+                            ))?;
                     let enum_variants = loader_field_enum_values
                         .remove(&loader_field.id)
                         .unwrap_or_default();
@@ -660,11 +697,15 @@ pub async fn version_edit_helper(
                         vf_value.clone(),
                         enum_variants,
                     )
-                    .map_err(ApiError::InvalidInput)?;
+                    .map_err(eyre::Report::msg)
+                    .wrap_request_err("parsing version field")?;
                     version_fields.push(vf);
                 }
                 VersionField::insert_many(version_fields, &mut transaction)
-                    .await?;
+                    .await
+                    .wrap_internal_err(
+                        "inserting database records for `version_edit_helper`",
+                    )?;
             }
 
             if let Some(loaders) = &new_version.loaders {
@@ -675,7 +716,8 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("fetching loaders from database")?;
 
                 let mut loader_versions = Vec::new();
                 for loader in loaders {
@@ -685,20 +727,24 @@ pub async fn version_edit_helper(
                             &mut transaction,
                             &redis,
                         )
-                        .await?
-                        .ok_or_else(|| {
-                            ApiError::InvalidInput(
-                                "No database entry for loader provided."
-                                    .to_string(),
-                            )
-                        })?;
+                        .await
+                        .wrap_internal_err("fetching loader from Redis")?
+                        .wrap_request_err_with(
+                            || {
+                                "no database entry for loader provided."
+                                    .to_string()
+                            },
+                        )?;
                     loader_versions.push(DBLoaderVersion {
                         loader_id,
                         version_id,
                     });
                 }
                 DBLoaderVersion::insert_many(loader_versions, &mut transaction)
-                    .await?;
+                    .await
+                    .wrap_internal_err(
+                        "inserting loader versions into database",
+                    )?;
             }
 
             if let Some(featured) = &new_version.featured {
@@ -712,7 +758,8 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err("fetching featured status from database")?;
             }
 
             if let Some(body) = &new_version.changelog {
@@ -726,14 +773,17 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `version_edit_helper`",
+                )?;
             }
 
             if let Some(downloads) = &new_version.downloads {
                 if !user.role.is_mod() {
-                    return Err(ApiError::CustomAuthentication(
-                        "You don't have permission to set the downloads of this mod".to_string(),
-                    ));
+                    return Err(ApiError::Auth(eyre::eyre!(
+                        "You don't have permission to set the downloads of this mod",
+                    )));
                 }
 
                 sqlx::query!(
@@ -746,7 +796,10 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `version_edit_helper`",
+                )?;
 
                 let diff = *downloads - (version_item.inner.downloads as u32);
 
@@ -761,14 +814,17 @@ pub async fn version_edit_helper(
                         as database::models::ids::DBProjectId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `version_edit_helper`",
+                )?;
             }
 
             if let Some(status) = &new_version.status {
                 if !status.can_be_requested() {
-                    return Err(ApiError::InvalidInput(
-                        "The requested status cannot be set!".to_string(),
-                    ));
+                    return Err(ApiError::Request(eyre::eyre!(
+                        "The requested status cannot be set!",
+                    )));
                 }
 
                 sqlx::query!(
@@ -781,7 +837,10 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `version_edit_helper`",
+                )?;
             }
 
             if let Some(file_types) = &new_version.file_types {
@@ -796,12 +855,15 @@ pub async fn version_edit_helper(
                         file_type.algorithm
                     )
                     .fetch_optional(&**pool)
-                    .await?
-                    .ok_or_else(|| {
-                        ApiError::InvalidInput(format!(
-                            "Specified file with hash {} does not exist.",
+                    .await
+                    .wrap_internal_err(
+                        "querying database for `version_edit_helper`",
+                    )?
+                    .wrap_request_err_with(|| {
+                        format!(
+                            "specified file with hash `{}` does not exist",
                             file_type.algorithm.clone()
-                        ))
+                        )
                     })?;
 
                     sqlx::query!(
@@ -814,7 +876,10 @@ pub async fn version_edit_helper(
                         file_type.file_type.as_ref().map(|x| x.as_str()),
                     )
                     .execute(&mut transaction)
-                    .await?;
+                    .await
+                    .wrap_internal_err(
+                        "querying database for `version_edit_helper`",
+                    )?;
                 }
             }
 
@@ -829,7 +894,10 @@ pub async fn version_edit_helper(
                     version_id as database::models::ids::DBVersionId,
                 )
                 .execute(&mut transaction)
-                .await?;
+                .await
+                .wrap_internal_err(
+                    "querying database for `version_edit_helper`",
+                )?;
             }
 
             // delete any images no longer in the changelog
@@ -847,18 +915,24 @@ pub async fn version_edit_helper(
                 &mut transaction,
                 &redis,
             )
-            .await?;
+            .await
+            .wrap_api_err("deleting unused images")?;
 
-            transaction.commit().await?;
+            transaction
+                .commit()
+                .await
+                .wrap_internal_err("committing database transaction")?;
             database::models::DBVersion::clear_cache(&version_item, &redis)
-                .await?;
+                .await
+                .wrap_internal_err("clearing cached data from Redis")?;
             database::models::DBProject::clear_cache(
                 version_item.inner.project_id,
                 None,
                 Some(true),
                 &redis,
             )
-            .await?;
+            .await
+            .wrap_internal_err("clearing cached data from Redis")?;
             search_state
                 .queue
                 .push_version_changes(
@@ -868,12 +942,12 @@ pub async fn version_edit_helper(
                 .await;
             Ok(HttpResponse::NoContent().body(""))
         } else {
-            Err(ApiError::CustomAuthentication(
-                "You do not have permission to edit this version!".to_string(),
-            ))
+            Err(ApiError::Auth(eyre::eyre!(
+                "You do not have permission to edit this version!",
+            )))
         }
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -949,8 +1023,9 @@ pub async fn version_list_internal(
 ) -> Result<HttpResponse, ApiError> {
     let string = info.into_inner().0;
 
-    let result =
-        database::models::DBProject::get(&string, &***ro_pool, &redis).await?;
+    let result = database::models::DBProject::get(&string, &***ro_pool, &redis)
+        .await
+        .wrap_api_err("fetching project from database")?;
 
     let user_option = get_user_from_headers(
         &req,
@@ -965,9 +1040,10 @@ pub async fn version_list_internal(
 
     if let Some(project) = result {
         if !is_visible_project(&project.inner, &user_option, &pool, false)
-            .await?
+            .await
+            .wrap_api_err("checking project visibility")?
         {
-            return Err(ApiError::NotFound);
+            return Err(ApiError::NotFound(eyre::eyre!("resource not found")));
         }
 
         let loader_field_filters = filters.loader_fields.as_ref().map(|x| {
@@ -982,7 +1058,8 @@ pub async fn version_list_internal(
             &***ro_pool,
             &redis,
         )
-        .await?
+        .await
+        .wrap_internal_err("fetching versions from database")?
         .into_iter()
         .filter(|x| {
             let mut bool = true;
@@ -1048,7 +1125,7 @@ pub async fn version_list_internal(
                     &redis,
                 ),
             )
-            .await?;
+            .await.wrap_internal_err("fetching minecraft game version from Redis")?;
 
             let mut joined_filters = Vec::new();
             for game_version in &game_versions {
@@ -1093,7 +1170,8 @@ pub async fn version_list_internal(
             &ro_pool,
             &redis,
         )
-        .await?;
+        .await
+        .wrap_api_err("filtering visible versions")?;
 
         if !filters.include_changelog {
             for version in &mut response {
@@ -1103,7 +1181,7 @@ pub async fn version_list_internal(
 
         Ok(HttpResponse::Ok().json(response))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
 
@@ -1154,16 +1232,16 @@ pub async fn version_delete(
         &session_queue,
         Scopes::VERSION_DELETE,
     )
-    .await?
+    .await
+    .wrap_auth_err("authenticating API request")?
     .1;
     let id = info.into_inner().0;
 
     let version = database::models::DBVersion::get(id.into(), &**pool, &redis)
-        .await?
-        .ok_or_else(|| {
-            ApiError::InvalidInput(
-                "The specified version does not exist!".to_string(),
-            )
+        .await
+        .wrap_internal_err("fetching version from database")?
+        .wrap_request_err_with(|| {
+            "the specified version does not exist!".to_string()
         })?;
 
     if !user.role.is_admin() {
@@ -1175,14 +1253,15 @@ pub async fn version_delete(
                 &**pool,
             )
             .await
-            .map_err(ApiError::Database)?;
+            .wrap_internal_err("fetching project team member")?;
 
         let organization =
             DBOrganization::get_associated_organization_project_id(
                 version.inner.project_id,
                 &**pool,
             )
-            .await?;
+            .await
+            .wrap_internal_err("fetching organization from database")?;
 
         let organization_team_member = if let Some(organization) = &organization
         {
@@ -1191,7 +1270,8 @@ pub async fn version_delete(
                 user.id.into(),
                 &**pool,
             )
-            .await?
+            .await
+            .wrap_internal_err("fetching team member from database")?
         } else {
             None
         };
@@ -1203,14 +1283,16 @@ pub async fn version_delete(
         .unwrap_or_default();
 
         if !permissions.contains(ProjectPermissions::DELETE_VERSION) {
-            return Err(ApiError::CustomAuthentication(
-                "You do not have permission to delete versions in this team"
-                    .to_string(),
-            ));
+            return Err(ApiError::Auth(eyre::eyre!(
+                "You do not have permission to delete versions in this team",
+            )));
         }
     }
 
-    let mut transaction = pool.begin().await?;
+    let mut transaction = pool
+        .begin()
+        .await
+        .wrap_internal_err("starting database transaction")?;
 
     let context = ImageContext::Version {
         version_id: Some(version.inner.id.into()),
@@ -1219,9 +1301,12 @@ pub async fn version_delete(
         context,
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_internal_err("fetching images from database")?;
     for image in uploaded_images {
-        image_item::DBImage::remove(image.id, &mut transaction, &redis).await?;
+        image_item::DBImage::remove(image.id, &mut transaction, &redis)
+            .await
+            .wrap_internal_err("deleting image from database")?;
     }
 
     let result = database::models::DBVersion::remove_full(
@@ -1229,16 +1314,23 @@ pub async fn version_delete(
         &redis,
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_internal_err("deleting version from database")?;
 
     delphi::tech_review_sync::sync_project_tech_review_state(
         &[version.inner.project_id],
         delphi::tech_review_sync::TechReviewExitReason::FileDeleted,
         &mut transaction,
     )
-    .await?;
+    .await
+    .wrap_api_err(
+        "executing `tech_review_sync::sync_project_tech_review_state`",
+    )?;
 
-    transaction.commit().await?;
+    transaction
+        .commit()
+        .await
+        .wrap_internal_err("committing database transaction")?;
 
     database::models::DBProject::clear_cache(
         version.inner.project_id,
@@ -1246,7 +1338,8 @@ pub async fn version_delete(
         Some(true),
         &redis,
     )
-    .await?;
+    .await
+    .wrap_internal_err("clearing cached data from Redis")?;
     search_state
         .queue
         .push_version_changes(
@@ -1257,6 +1350,6 @@ pub async fn version_delete(
     if result.is_some() {
         Ok(HttpResponse::NoContent().body(""))
     } else {
-        Err(ApiError::NotFound)
+        Err(ApiError::NotFound(eyre::eyre!("resource not found")))
     }
 }
diff --git a/apps/labrinth/src/search/backend/elasticsearch/mod.rs b/apps/labrinth/src/search/backend/elasticsearch/mod.rs
index 7e41cd93f9..b6474bd61d 100644
--- a/apps/labrinth/src/search/backend/elasticsearch/mod.rs
+++ b/apps/labrinth/src/search/backend/elasticsearch/mod.rs
@@ -4,6 +4,7 @@
 //! This keeps version filters correlated without duplicating every version
 //! into its project document.
 
+use crate::util::error::ApiContext as _;
 use async_trait::async_trait;
 use eyre::{Result, eyre};
 use itertools::Itertools;
@@ -388,7 +389,7 @@ impl Elasticsearch {
             .wrap_internal_err("failed to execute Elasticsearch search")?;
         let mut body = response_json(response, "execute Elasticsearch search")
             .await
-            .map_err(ApiError::Internal)?;
+            .wrap_internal_err("parsing Elasticsearch search response")?;
         if sort_only && !body["hits"]["hits"].is_array() {
             body["hits"]["hits"] = Value::Array(Vec::new());
         }
@@ -410,12 +411,15 @@ impl Elasticsearch {
             .wrap_internal_err("failed to open Elasticsearch point in time")?;
         let body = response_json(response, "open Elasticsearch point in time")
             .await
-            .map_err(ApiError::Internal)?;
-        body["id"].as_str().map(ToOwned::to_owned).ok_or_else(|| {
-            ApiError::Internal(eyre!(
-                "Elasticsearch point in time response did not contain an ID"
-            ))
-        })
+            .wrap_internal_err(
+                "parsing Elasticsearch point-in-time response",
+            )?;
+        body["id"]
+            .as_str()
+            .map(ToOwned::to_owned)
+            .wrap_internal_err(
+                "finding ID in Elasticsearch point-in-time response",
+            )
     }
 
     async fn close_point_in_time(&self, id: &str) -> Result<(), ApiError> {
@@ -428,7 +432,9 @@ impl Elasticsearch {
             .wrap_internal_err("failed to close Elasticsearch point in time")?;
         response_json(response, "close Elasticsearch point in time")
             .await
-            .map_err(ApiError::Internal)?;
+            .wrap_internal_err(
+                "parsing Elasticsearch point-in-time response",
+            )?;
         Ok(())
     }
 
@@ -456,7 +462,9 @@ impl Elasticsearch {
             "execute Elasticsearch point in time search",
         )
         .await
-        .map_err(ApiError::Internal)?;
+        .wrap_internal_err(
+            "parsing Elasticsearch point-in-time search response",
+        )?;
         if sort_only && !body["hits"]["hits"].is_array() {
             body["hits"]["hits"] = Value::Array(Vec::new());
         }
@@ -472,7 +480,10 @@ impl Elasticsearch {
         offset: usize,
         size: usize,
     ) -> Result<Value, ApiError> {
-        let mut point_in_time_id = self.open_point_in_time(alias).await?;
+        let mut point_in_time_id = self
+            .open_point_in_time(alias)
+            .await
+            .wrap_api_err("executing `open_point_in_time`")?;
         let result = self
             .execute_deep_search_with_point_in_time(
                 query,
@@ -517,7 +528,10 @@ impl Elasticsearch {
                 "id": point_in_time_id,
                 "keep_alive": "1m"
             });
-            let body = self.execute_point_in_time_search(&body, true).await?;
+            let body = self
+                .execute_point_in_time_search(&body, true)
+                .await
+                .wrap_api_err("executing `execute_point_in_time_search`")?;
             if let Some(id) = body["pit_id"].as_str() {
                 *point_in_time_id = id.to_string();
             }
@@ -579,7 +593,10 @@ impl Elasticsearch {
             "id": point_in_time_id,
             "keep_alive": "1m"
         });
-        let body = self.execute_point_in_time_search(&body, false).await?;
+        let body = self
+            .execute_point_in_time_search(&body, false)
+            .await
+            .wrap_api_err("executing `execute_point_in_time_search`")?;
         if let Some(id) = body["pit_id"].as_str() {
             *point_in_time_id = id.to_string();
         }
@@ -832,10 +849,13 @@ impl Elasticsearch {
         &self,
         info: &SearchRequest,
     ) -> Result<SearchResults, ApiError> {
-        let parsed = parse_search_request(info)?;
+        let parsed = parse_search_request(info)
+            .wrap_api_err("executing `parse_search_request`")?;
         let search_sort =
-            parse_search_index(parsed.index, info.new_filters.as_deref())?;
-        let filter = Self::build_filter(info)?;
+            parse_search_index(parsed.index, info.new_filters.as_deref())
+                .wrap_api_err("executing `parse_search_index`")?;
+        let filter = Self::build_filter(info)
+            .wrap_api_err("executing `Self::build_filter`")?;
         let mut filters = vec![json!({"term": {"document_type": "project"}})];
         if let Some(filter) = &filter {
             filters.push(filter.query.clone());
@@ -858,7 +878,8 @@ impl Elasticsearch {
                 parsed.offset,
                 parsed.hits_per_page,
             )
-            .await?
+            .await
+            .wrap_api_err("executing `execute_deep_search`")?
         } else {
             let body = Self::search_body(
                 &query,
@@ -869,7 +890,9 @@ impl Elasticsearch {
                 None,
                 true,
             );
-            self.execute_search(&alias, &body, false).await?
+            self.execute_search(&alias, &body, false)
+                .await
+                .wrap_api_err("executing `execute_search`")?
         };
         let total_hits = body["hits"]["total"]["value"]
             .as_u64()
diff --git a/apps/labrinth/src/search/backend/typesense/mod.rs b/apps/labrinth/src/search/backend/typesense/mod.rs
index e65232106c..6c7e407730 100644
--- a/apps/labrinth/src/search/backend/typesense/mod.rs
+++ b/apps/labrinth/src/search/backend/typesense/mod.rs
@@ -137,6 +137,7 @@
 //! enabled. This avoids repeating joins for popular queries at the cost of
 //! results remaining stale for Typesense's default 60-second cache lifetime.
 
+use crate::util::error::ApiContext as _;
 use std::sync::LazyLock;
 
 use async_trait::async_trait;
@@ -911,7 +912,8 @@ impl Typesense {
         new_filters: Option<&str>,
         request_config: &RequestConfig,
     ) -> Result<(String, String), ApiError> {
-        let sort = parse_search_index(index, new_filters)?;
+        let sort = parse_search_index(index, new_filters)
+            .wrap_api_err("executing `parse_search_index`")?;
         let alias = self.config.get_alias_name("projects");
         Ok((alias, self.get_sort_fields(sort.index, request_config)))
     }
@@ -1047,14 +1049,18 @@ impl SearchBackend for Typesense {
         &self,
         info: &SearchRequest,
     ) -> Result<SearchResults, ApiError> {
-        let parsed = parse_search_request(info)?;
-        let (collection_alias, sort_by) = self.get_sort_index(
-            parsed.index,
-            info.new_filters.as_deref(),
-            &info.typesense_config,
-        )?;
+        let parsed = parse_search_request(info)
+            .wrap_api_err("executing `parse_search_request`")?;
+        let (collection_alias, sort_by) = self
+            .get_sort_index(
+                parsed.index,
+                info.new_filters.as_deref(),
+                &info.typesense_config,
+            )
+            .wrap_api_err("fetching sort index")?;
         let versions_alias = self.config.get_alias_name("versions");
-        let filter_by = Self::build_filter(info, &versions_alias)?;
+        let filter_by = Self::build_filter(info, &versions_alias)
+            .wrap_api_err("executing `Self::build_filter`")?;
 
         let q = if parsed.query.is_empty() {
             "*"
diff --git a/apps/labrinth/src/search/mod.rs b/apps/labrinth/src/search/mod.rs
index 690efe149a..9df4220e71 100644
--- a/apps/labrinth/src/search/mod.rs
+++ b/apps/labrinth/src/search/mod.rs
@@ -4,6 +4,8 @@ use crate::models::ids::{ProjectId, VersionId};
 use crate::models::projects::DependencyType;
 use crate::queue::server_ping;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use crate::{database::PgPool, env::ENV};
 use ariadne::ids::base62_impl::parse_base62;
 use async_trait::async_trait;
@@ -94,10 +96,13 @@ pub trait SearchBackend: Send + Sync {
         info: &SearchRequest,
         redis: &RedisPool,
     ) -> Result<SearchResults, ApiError> {
-        let mut results = self.search_for_project_raw(info).await?;
+        let mut results = self
+            .search_for_project_raw(info)
+            .await
+            .wrap_api_err("searching projects")?;
         hydrate_search_results(&mut results.hits, redis)
             .await
-            .map_err(ApiError::Internal)?;
+            .wrap_internal_err("hydrating search results from database")?;
         Ok(results)
     }
 
diff --git a/apps/labrinth/src/util/avalara1099.rs b/apps/labrinth/src/util/avalara1099.rs
index d36e5edf62..8b9ebfb329 100644
--- a/apps/labrinth/src/util/avalara1099.rs
+++ b/apps/labrinth/src/util/avalara1099.rs
@@ -1,6 +1,8 @@
 use crate::database::models::{DBUserId, users_compliance::FormType};
 use crate::env::ENV;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use ariadne::ids::base62_impl::to_base62;
 use chrono::Datelike;
 use serde::{Deserialize, Serialize};
@@ -62,7 +64,8 @@ pub async fn request_form(
     }
 
     let (request_builder, company_id) =
-        team_request(reqwest::Method::POST, "/form_requests")?;
+        team_request(reqwest::Method::POST, "/form_requests")
+            .wrap_api_err("executing `team_request`")?;
 
     let response = request_builder
         .json(&DataWrapper {
@@ -84,12 +87,19 @@ pub async fn request_form(
             },
         })
         .send()
-        .await?;
+        .await
+        .wrap_internal_err("deserializing HTTP response")?;
 
     Ok(if response.status().is_success() {
-        Ok(response.json::<DataWrapper<FormResponse>>().await?)
+        Ok(response
+            .json::<DataWrapper<FormResponse>>()
+            .await
+            .wrap_internal_err("deserializing HTTP response")?)
     } else {
-        Err(response.json().await?)
+        Err(response
+            .json()
+            .await
+            .wrap_internal_err("deserializing HTTP response")?)
     })
 }
 
@@ -104,12 +114,18 @@ pub async fn check_form(
         &format!(
             "/w9forms?filter[reference_id_eq]={reference_id}&page[number]=1&page[size]=1"
         ),
-    )?;
+    ).wrap_api_err("executing `team_request`")?;
 
-    let response = request_builder.send().await?;
+    let response = request_builder
+        .send()
+        .await
+        .wrap_internal_err("sending HTTP request")?;
 
     Ok(if response.status().is_success() {
-        let body = response.text().await?;
+        let body = response
+            .text()
+            .await
+            .wrap_internal_err("reading HTTP response body")?;
         let serde_result =
             serde_json::from_str::<ListWrapper<W9FormsResponse>>(&body);
 
@@ -118,13 +134,16 @@ pub async fn check_form(
                 Ok(list_wrapper.data.pop().map(|data| DataWrapper { data }))
             }
             Err(e) => {
-                return Err(ApiError::InvalidInput(format!(
+                return Err(ApiError::Request(eyre::eyre!(format!(
                     "Error parsing avalara1099 response: {e}. Actual response body: {body}"
-                )));
+                ))));
             }
         }
     } else {
-        Err(response.json().await?)
+        Err(response
+            .json()
+            .await
+            .wrap_internal_err("deserializing HTTP response")?)
     })
 }
 
diff --git a/apps/labrinth/src/util/captcha.rs b/apps/labrinth/src/util/captcha.rs
index af32e51927..b2cabe52c0 100644
--- a/apps/labrinth/src/util/captcha.rs
+++ b/apps/labrinth/src/util/captcha.rs
@@ -1,5 +1,6 @@
 use crate::env::ENV;
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 use actix_web::HttpRequest;
 use serde::Deserialize;
 use std::collections::HashMap;
@@ -26,7 +27,7 @@ pub async fn check_hcaptcha(
         conn_info.peer_addr()
     };
 
-    let ip_addr = ip_addr.ok_or(ApiError::Turnstile)?;
+    let ip_addr = ip_addr.wrap_request_err("captcha validation failed")?;
 
     let client = reqwest::Client::new();
 
@@ -46,10 +47,11 @@ pub async fn check_hcaptcha(
         .form(&form)
         .send()
         .await
-        .map_err(|_| ApiError::Turnstile)?
+        .wrap_request_err("captcha validation failed")?
         .json()
         .await
-        .map_err(|_| ApiError::Turnstile)?;
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("captcha validation failed")?;
 
     Ok(val.success)
 }
diff --git a/apps/labrinth/src/util/error.rs b/apps/labrinth/src/util/error.rs
index 5f9ff343c2..8b52a20c7b 100644
--- a/apps/labrinth/src/util/error.rs
+++ b/apps/labrinth/src/util/error.rs
@@ -5,6 +5,31 @@ use std::{
 
 use crate::routes::ApiError;
 
+/// Adds context to an [`ApiError`] while preserving its HTTP status variant.
+pub trait ApiContext<T>: Sized {
+    /// Wraps the report held by the error variant with a lazily-created message.
+    fn wrap_api_err_with<D>(self, f: impl FnOnce() -> D) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static;
+
+    /// Wraps the report held by the error variant with the given message.
+    fn wrap_api_err<D>(self, msg: D) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_api_err_with(|| msg)
+    }
+}
+
+impl<T> ApiContext<T> for Result<T, ApiError> {
+    fn wrap_api_err_with<D>(self, f: impl FnOnce() -> D) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.map_err(|error| error.wrap_err(f()))
+    }
+}
+
 /// Allows wrapping [`Result`]s and [`Option`]s into [`Result<T, ApiError>`]s.
 #[allow(
     clippy::missing_errors_doc,
@@ -85,6 +110,133 @@ pub trait Context<T, E>: Sized {
     {
         self.wrap_auth_err_with(|| msg)
     }
+
+    /// Maps the error variant into an [`ApiError::NotFound`] using the closure to create the message.
+    #[inline]
+    fn wrap_not_found_err_with<D>(
+        self,
+        f: impl FnOnce() -> D,
+    ) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_err_with(f).map_err(ApiError::NotFound)
+    }
+
+    /// Maps the error variant into an [`ApiError::NotFound`] with the given message.
+    #[inline]
+    fn wrap_not_found_err<D>(self, msg: D) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_not_found_err_with(|| msg)
+    }
+
+    /// Maps the error variant into an [`ApiError::Conflict`] using the closure to create the message.
+    #[inline]
+    fn wrap_conflict_err_with<D>(
+        self,
+        f: impl FnOnce() -> D,
+    ) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_err_with(f).map_err(ApiError::Conflict)
+    }
+
+    /// Maps the error variant into an [`ApiError::Conflict`] with the given message.
+    #[inline]
+    fn wrap_conflict_err<D>(self, msg: D) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_conflict_err_with(|| msg)
+    }
+
+    /// Maps the error variant into an [`ApiError::FailedDependency`] using the closure to create the message.
+    #[inline]
+    fn wrap_failed_dependency_err_with<D>(
+        self,
+        f: impl FnOnce() -> D,
+    ) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_err_with(f).map_err(ApiError::FailedDependency)
+    }
+
+    /// Maps the error variant into an [`ApiError::FailedDependency`] with the given message.
+    #[inline]
+    fn wrap_failed_dependency_err<D>(self, msg: D) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_failed_dependency_err_with(|| msg)
+    }
+
+    /// Maps the error variant into an [`ApiError::PreconditionRequired`] using the closure to create the message.
+    #[inline]
+    fn wrap_precondition_required_err_with<D>(
+        self,
+        f: impl FnOnce() -> D,
+    ) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_err_with(f)
+            .map_err(ApiError::PreconditionRequired)
+    }
+
+    /// Maps the error variant into an [`ApiError::PreconditionRequired`] with the given message.
+    #[inline]
+    fn wrap_precondition_required_err<D>(self, msg: D) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_precondition_required_err_with(|| msg)
+    }
+
+    /// Maps the error variant into an [`ApiError::PreconditionFailed`] using the closure to create the message.
+    #[inline]
+    fn wrap_precondition_failed_err_with<D>(
+        self,
+        f: impl FnOnce() -> D,
+    ) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_err_with(f).map_err(ApiError::PreconditionFailed)
+    }
+
+    /// Maps the error variant into an [`ApiError::PreconditionFailed`] with the given message.
+    #[inline]
+    fn wrap_precondition_failed_err<D>(self, msg: D) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_precondition_failed_err_with(|| msg)
+    }
+
+    /// Maps the error variant into an [`ApiError::RateLimit`] using the closure to create the message.
+    #[inline]
+    fn wrap_rate_limit_err_with<D>(
+        self,
+        f: impl FnOnce() -> D,
+    ) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_err_with(f).map_err(ApiError::RateLimit)
+    }
+
+    /// Maps the error variant into an [`ApiError::RateLimit`] with the given message.
+    #[inline]
+    fn wrap_rate_limit_err<D>(self, msg: D) -> Result<T, ApiError>
+    where
+        D: Send + Sync + Debug + Display + 'static,
+    {
+        self.wrap_rate_limit_err_with(|| msg)
+    }
 }
 
 impl<T, E> Context<T, E> for Result<T, E>
@@ -146,6 +298,40 @@ mod tests {
 
         let auth_error = ApiError::Auth(eyre::eyre!("auth error"));
         assert_eq!(auth_error.status_code(), StatusCode::UNAUTHORIZED);
+
+        let not_found_error =
+            ApiError::NotFound(eyre::eyre!("not found error"));
+        assert_eq!(not_found_error.status_code(), StatusCode::NOT_FOUND);
+
+        let conflict_error = ApiError::Conflict(eyre::eyre!("conflict error"));
+        assert_eq!(conflict_error.status_code(), StatusCode::CONFLICT);
+
+        let dependency_error =
+            ApiError::FailedDependency(eyre::eyre!("dependency error"));
+        assert_eq!(
+            dependency_error.status_code(),
+            StatusCode::FAILED_DEPENDENCY
+        );
+
+        let required_error = ApiError::PreconditionRequired(eyre::eyre!(
+            "precondition required error"
+        ));
+        assert_eq!(
+            required_error.status_code(),
+            StatusCode::PRECONDITION_REQUIRED
+        );
+
+        let failed_error = ApiError::PreconditionFailed(eyre::eyre!(
+            "precondition failed error"
+        ));
+        assert_eq!(failed_error.status_code(), StatusCode::PRECONDITION_FAILED);
+
+        let rate_limit_error =
+            ApiError::RateLimit(eyre::eyre!("rate limit error"));
+        assert_eq!(
+            rate_limit_error.status_code(),
+            StatusCode::TOO_MANY_REQUESTS
+        );
     }
 
     #[test]
@@ -237,6 +423,68 @@ mod tests {
         }
     }
 
+    #[test]
+    fn test_context_trait_status_errors() {
+        let not_found: Option<i32> = None;
+        assert!(matches!(
+            not_found.wrap_not_found_err("missing value").unwrap_err(),
+            ApiError::NotFound(_)
+        ));
+
+        let conflict: Option<i32> = None;
+        assert!(matches!(
+            conflict.wrap_conflict_err("conflicting value").unwrap_err(),
+            ApiError::Conflict(_)
+        ));
+
+        let dependency: Option<i32> = None;
+        assert!(matches!(
+            dependency
+                .wrap_failed_dependency_err("dependency failed")
+                .unwrap_err(),
+            ApiError::FailedDependency(_)
+        ));
+
+        let required: Option<i32> = None;
+        assert!(matches!(
+            required
+                .wrap_precondition_required_err("precondition required")
+                .unwrap_err(),
+            ApiError::PreconditionRequired(_)
+        ));
+
+        let failed: Option<i32> = None;
+        assert!(matches!(
+            failed
+                .wrap_precondition_failed_err("precondition failed")
+                .unwrap_err(),
+            ApiError::PreconditionFailed(_)
+        ));
+
+        let rate_limit: Option<i32> = None;
+        assert!(matches!(
+            rate_limit
+                .wrap_rate_limit_err("rate limit exceeded")
+                .unwrap_err(),
+            ApiError::RateLimit(_)
+        ));
+    }
+
+    #[test]
+    fn test_api_context_preserves_status_variant() {
+        let result: Result<(), ApiError> =
+            Err(ApiError::NotFound(eyre::eyre!("missing value")));
+        let error = result.wrap_api_err("fetching test value").unwrap_err();
+
+        match error {
+            ApiError::NotFound(report) => {
+                assert_eq!(report.to_string(), "fetching test value");
+                assert!(format!("{report:#}").contains("missing value"));
+            }
+            _ => panic!("expected NotFound error"),
+        }
+    }
+
     #[test]
     fn test_context_trait_with_closure() {
         let result: Result<i32, std::io::Error> = Err(std::io::Error::new(
diff --git a/apps/labrinth/src/util/gotenberg.rs b/apps/labrinth/src/util/gotenberg.rs
index 0c1a3248b0..6fd4f3661b 100644
--- a/apps/labrinth/src/util/gotenberg.rs
+++ b/apps/labrinth/src/util/gotenberg.rs
@@ -2,6 +2,7 @@ use crate::env::ENV;
 use crate::models::ids::PayoutId;
 use crate::routes::ApiError;
 use crate::routes::internal::gotenberg::{GotenbergDocument, GotenbergError};
+use crate::util::error::ApiContext as _;
 use crate::util::error::Context;
 use actix_web::http::header::HeaderName;
 use chrono::{DateTime, Datelike, Utc};
@@ -166,7 +167,7 @@ impl GotenbergClient {
             .await
             .wrap_internal_err("failed to submit HTML to Gotenberg")?
             .error_for_status()
-            .wrap_internal_err("Gotenberg returned an error status")?;
+            .wrap_internal_err("received an error status from Gotenberg")?;
 
         Ok(())
     }
@@ -190,7 +191,9 @@ impl GotenbergClient {
         &self,
         statement: &PaymentStatement,
     ) -> Result<GotenbergDocument, ApiError> {
-        self.generate_payment_statement(statement).await?;
+        self.generate_payment_statement(statement)
+            .await
+            .wrap_api_err("executing `generate_payment_statement`")?;
 
         let timeout_ms = ENV.GOTENBERG_TIMEOUT;
         let redis_timeout_ms =
@@ -205,7 +208,7 @@ impl GotenbergClient {
                 .brpop(&response_key, Duration::from_millis(redis_timeout_ms)),
         )
         .await
-        .wrap_internal_err("Gotenberg document generation timed out")?
+        .wrap_internal_err("timed out generating Gotenberg document")?
         .wrap_internal_err("failed to get document over Redis")?
         .wrap_internal_err("no document was returned from Redis")?;
 
@@ -213,7 +216,7 @@ impl GotenbergClient {
             Result<GotenbergDocument, GotenbergError>,
         >(&document)
         .wrap_internal_err("failed to deserialize Redis document response")?
-        .wrap_internal_err("Gotenberg document generation failed")?;
+        .wrap_internal_err("failed to generate Gotenberg document")?;
 
         Ok(document)
     }
diff --git a/apps/labrinth/src/util/img.rs b/apps/labrinth/src/util/img.rs
index ecbecb3470..613d86666e 100644
--- a/apps/labrinth/src/util/img.rs
+++ b/apps/labrinth/src/util/img.rs
@@ -4,6 +4,7 @@ use crate::env::ENV;
 use crate::file_hosting::{FileHost, FileHostPublicity};
 use crate::models::images::ImageContext;
 use crate::routes::ApiError;
+use crate::util::error::Context as _;
 use color_thief::ColorFormat;
 use hex::ToHex;
 use image::imageops::FilterType;
@@ -54,10 +55,8 @@ pub async fn upload_image_optimized(
     file_host: &dyn FileHost,
 ) -> Result<UploadImageResult, ApiError> {
     let content_type = crate::util::ext::get_image_content_type(file_extension)
-        .ok_or_else(|| {
-            ApiError::InvalidInput(format!(
-                "Invalid format for image: {file_extension}"
-            ))
+        .wrap_request_err_with(|| {
+            format!("invalid format for image: {file_extension}")
         })?;
 
     let cdn_url = &ENV.CDN_URL;
@@ -68,8 +67,10 @@ pub async fn upload_image_optimized(
         content_type,
         target_width,
         min_aspect_ratio,
-    )?;
-    let color = get_color_from_img(&bytes)?;
+    )
+    .wrap_request_err("processing uploaded image")?;
+    let color = get_color_from_img(&bytes)
+        .wrap_request_err("extracting color from uploaded image")?;
 
     // Only upload the processed image if it's smaller than the original
     let processed_upload_data = if processed_image.len() < bytes.len() {
@@ -87,7 +88,8 @@ pub async fn upload_image_optimized(
                     publicity,
                     processed_image,
                 )
-                .await?,
+                .await
+                .wrap_internal_err("uploading file to file host")?,
         )
     } else {
         None
@@ -100,7 +102,8 @@ pub async fn upload_image_optimized(
             publicity,
             bytes,
         )
-        .await?;
+        .await
+        .wrap_internal_err("uploading file to file host")?;
 
     let url = format!("{}/{}", cdn_url, upload_data.file_name);
     Ok(UploadImageResult {
@@ -182,7 +185,10 @@ pub async fn delete_old_images(
         let name = image_url.split(&cdn_url_start).nth(1);
 
         if let Some(icon_path) = name {
-            file_host.delete_file(icon_path, publicity).await?;
+            file_host
+                .delete_file(icon_path, publicity)
+                .await
+                .wrap_internal_err("deleting file from file host")?;
         }
     }
 
@@ -190,7 +196,10 @@ pub async fn delete_old_images(
         let name = raw_image_url.split(&cdn_url_start).nth(1);
 
         if let Some(icon_path) = name {
-            file_host.delete_file(icon_path, publicity).await?;
+            file_host
+                .delete_file(icon_path, publicity)
+                .await
+                .wrap_internal_err("deleting file from file host")?;
         }
     }
 
@@ -208,7 +217,8 @@ pub async fn delete_unused_images(
 ) -> Result<(), ApiError> {
     let uploaded_images =
         database::models::DBImage::get_many_contexted(context, transaction)
-            .await?;
+            .await
+            .wrap_internal_err("fetching images from database")?;
 
     for image in uploaded_images {
         let mut should_delete = true;
@@ -220,8 +230,12 @@ pub async fn delete_unused_images(
         }
 
         if should_delete {
-            image_item::DBImage::remove(image.id, transaction, redis).await?;
-            image_item::DBImage::clear_cache(image.id, redis).await?;
+            image_item::DBImage::remove(image.id, transaction, redis)
+                .await
+                .wrap_internal_err("deleting image from database")?;
+            image_item::DBImage::clear_cache(image.id, redis)
+                .await
+                .wrap_internal_err("clearing cached data from Redis")?;
         }
     }
 
diff --git a/apps/labrinth/src/util/ratelimit.rs b/apps/labrinth/src/util/ratelimit.rs
index 3bac6cabe8..8bb340080f 100644
--- a/apps/labrinth/src/util/ratelimit.rs
+++ b/apps/labrinth/src/util/ratelimit.rs
@@ -178,10 +178,10 @@ pub async fn rate_limit_middleware(
 
             Ok(service_response.map_into_left_body())
         } else {
-            let mut response = ApiError::RateLimitError(
-                decision.retry_after_ms.unwrap_or(0) as u128,
-                decision.limit,
-            )
+            let retry_after_ms = decision.retry_after_ms.unwrap_or(0);
+            let mut response = ApiError::RateLimit(eyre::eyre!(
+                "rate limit exceeded; retry after {retry_after_ms} milliseconds"
+            ))
             .error_response();
 
             // Add rate limit headers
@@ -220,10 +220,9 @@ pub async fn rate_limit_middleware(
             Ok(req.into_response(response.map_into_right_body()))
         }
     } else {
-        let response = ApiError::CustomAuthentication(
-            "Unable to obtain user IP address!".to_string(),
-        )
-        .error_response();
+        let response =
+            ApiError::Auth(eyre::eyre!("Unable to obtain user IP address!",))
+                .error_response();
 
         Ok(req.into_response(response.map_into_right_body()))
     }
diff --git a/apps/labrinth/src/util/routes.rs b/apps/labrinth/src/util/routes.rs
index c963937213..c753988375 100644
--- a/apps/labrinth/src/util/routes.rs
+++ b/apps/labrinth/src/util/routes.rs
@@ -1,6 +1,6 @@
 use crate::routes::ApiError;
 use crate::routes::v3::project_creation::CreateError;
-use crate::util::validate::validation_errors_to_string;
+use crate::util::error::Context as _;
 use actix_multipart::Field;
 use actix_web::web::Payload;
 use bytes::BytesMut;
@@ -16,13 +16,13 @@ pub async fn read_limited_from_payload(
     let mut bytes = BytesMut::new();
     while let Some(item) = payload.next().await {
         if bytes.len() >= cap {
-            return Err(ApiError::InvalidInput(String::from(err_msg)));
+            return Err(ApiError::Request(eyre::eyre!(String::from(err_msg))));
         } else {
-            bytes.extend_from_slice(&item.map_err(|_| {
-                ApiError::InvalidInput(
-                    "Unable to parse bytes in payload sent!".to_string(),
-                )
-            })?);
+            bytes.extend_from_slice(
+                &item.map_err(|err| eyre::eyre!(err)).wrap_request_err(
+                    "unable to parse bytes in payload sent!".to_string(),
+                )?,
+            );
         }
     }
     Ok(bytes)
@@ -36,17 +36,19 @@ where
 {
     let mut bytes = BytesMut::new();
     while let Some(item) = payload.next().await {
-        bytes.extend_from_slice(&item.map_err(|_| {
-            ApiError::InvalidInput(
-                "Unable to parse bytes in payload sent!".to_string(),
-            )
-        })?);
+        bytes.extend_from_slice(
+            &item.map_err(|err| eyre::eyre!(err)).wrap_request_err(
+                "unable to parse bytes in payload sent!".to_string(),
+            )?,
+        );
     }
 
-    let parsed: T = serde_json::from_slice(&bytes)?;
-    parsed.validate().map_err(|err| {
-        ApiError::InvalidInput(validation_errors_to_string(err, None))
-    })?;
+    let parsed: T = serde_json::from_slice(&bytes)
+        .wrap_request_err("deserializing JSON data")?;
+    parsed
+        .validate()
+        .map_err(|err| eyre::eyre!(err))
+        .wrap_request_err("validating request")?;
     Ok(parsed)
 }
 
diff --git a/apps/labrinth/src/util/webhook.rs b/apps/labrinth/src/util/webhook.rs
index aa0978ee5a..8ce75b6afe 100644
--- a/apps/labrinth/src/util/webhook.rs
+++ b/apps/labrinth/src/util/webhook.rs
@@ -1,6 +1,8 @@
 use crate::database::models::legacy_loader_fields::MinecraftGameVersion;
 use crate::models::ids::ProjectId;
 use crate::routes::ApiError;
+use crate::util::error::ApiContext as _;
+use crate::util::error::Context as _;
 use crate::{database::PgPool, env::ENV};
 use ariadne::ids::base62_impl::to_base62;
 use chrono::{DateTime, Utc};
@@ -51,7 +53,8 @@ async fn get_webhook_metadata(
         pool,
         redis,
     )
-    .await?;
+    .await
+    .wrap_api_err("fetching webhook project")?;
 
     if let Some(mut project) = project {
         let mut owner = None;
@@ -62,7 +65,7 @@ async fn get_webhook_metadata(
                 pool,
                 redis,
             )
-            .await?;
+            .await.wrap_internal_err("fetching organization from database")?;
 
             if let Some(organization) = organization {
                 owner = Some(WebhookAuthor {
@@ -81,7 +84,7 @@ async fn get_webhook_metadata(
                 pool,
                 redis,
             )
-            .await?;
+            .await.wrap_internal_err("fetching team member from database")?;
 
             if let Some(member) = team.into_iter().find(|x| x.is_owner) {
                 let user = crate::database::models::user_item::DBUser::get_id(
@@ -89,7 +92,8 @@ async fn get_webhook_metadata(
                     pool,
                     redis,
                 )
-                .await?;
+                .await
+                .wrap_internal_err("fetching user from database")?;
 
                 if let Some(user) = user {
                     owner = Some(WebhookAuthor {
@@ -106,7 +110,11 @@ async fn get_webhook_metadata(
         };
 
         let all_game_versions =
-            MinecraftGameVersion::list(None, None, pool, redis).await?;
+            MinecraftGameVersion::list(None, None, pool, redis)
+                .await
+                .wrap_internal_err(
+                    "fetching minecraft game version from Redis",
+                )?;
 
         let versions = project
             .aggregate_version_fields
@@ -249,9 +257,7 @@ pub async fn send_slack_payout_source_alert_webhook(
         }))
         .send()
         .await
-        .map_err(|_| {
-            ApiError::Slack("Error while sending projects webhook".to_string())
-        })?;
+        .map_err(|err| eyre::eyre!(err)).wrap_internal_err("error while sending projects webhook".to_string())?;
 
     Ok(())
 }
@@ -263,7 +269,9 @@ pub async fn send_slack_project_webhook(
     webhook_url: &str,
     message: Option<String>,
 ) -> Result<(), ApiError> {
-    let metadata = get_webhook_metadata(project_id, pool, redis).await?;
+    let metadata = get_webhook_metadata(project_id, pool, redis)
+        .await
+        .wrap_api_err("fetching webhook metadata")?;
 
     if let Some(metadata) = metadata {
         let mut blocks = vec![];
@@ -365,11 +373,10 @@ pub async fn send_slack_project_webhook(
             }))
             .send()
             .await
-            .map_err(|_| {
-                ApiError::Slack(
-                    "Error while sending projects webhook".to_string(),
-                )
-            })?;
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_internal_err(
+                "error while sending projects webhook".to_string(),
+            )?;
     }
 
     Ok(())
@@ -434,7 +441,9 @@ pub async fn send_discord_webhook(
     webhook_url: &str,
     message: Option<String>,
 ) -> Result<(), ApiError> {
-    let metadata = get_webhook_metadata(project_id, pool, redis).await?;
+    let metadata = get_webhook_metadata(project_id, pool, redis)
+        .await
+        .wrap_api_err("fetching webhook metadata")?;
 
     if let Some(project) = metadata {
         let mut fields = vec![];
@@ -503,11 +512,10 @@ pub async fn send_discord_webhook(
             })
             .send()
             .await
-            .map_err(|_| {
-                ApiError::Discord(
-                    "Error while sending projects webhook".to_string(),
-                )
-            })?;
+            .map_err(|err| eyre::eyre!(err))
+            .wrap_failed_dependency_err(
+                "error while sending projects webhook".to_string(),
+            )?;
     }
 
     Ok(())
diff --git a/docker-compose.yml b/docker-compose.yml
index 64112bdbc0..a488c7fee0 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -415,6 +415,7 @@ services:
     ports:
       - '127.0.0.1:8123:8123'
     environment:
+      CLICKHOUSE_DB: staging_ariadne
       CLICKHOUSE_USER: default
       CLICKHOUSE_PASSWORD: default
     healthcheck:
diff --git a/packages/assets/icons/tags/loaders/neoforge.svg b/packages/assets/icons/tags/loaders/neoforge.svg
index afd5420fb5..ca55ea9203 100644
--- a/packages/assets/icons/tags/loaders/neoforge.svg
+++ b/packages/assets/icons/tags/loaders/neoforge.svg
@@ -1 +1 @@
-<svg enable-background="new 0 0 24 24" version="1.1" viewBox="0 0 24 24" xml:space="preserve" xmlns="http://www.w3.org/2000/svg"><g fill="none" stroke="currentColor" stroke-linecap="round" stroke-linejoin="round" stroke-width="2"><path d="m12 19.2v2m0-2v2"/><path d="m8.4 1.3c0.5 1.5 0.7 3 0.1 4.6-0.2 0.5-0.9 1.5-1.6 1.5m8.7-6.1c-0.5 1.5-0.7 3-0.1 4.6 0.2 0.6 0.9 1.5 1.6 1.5"/><path d="m3.6 15.8h-1.7m18.5 0h1.7"/><path d="m3.2 12.1h-1.7m19.3 0h1.8"/><path d="m8.1 12.7v1.6m7.8-1.6v1.6"/><path d="m10.8 18h1.2m0 1.2-1.2-1.2m2.4 0h-1.2m0 1.2 1.2-1.2"/><path d="m4 9.7c-0.5 1.2-0.8 2.4-0.8 3.7 0 3.1 2.9 6.3 5.3 8.2 0.9 0.7 2.2 1.1 3.4 1.1m0.1-17.8c-1.1 0-2.1 0.2-3.2 0.7m11.2 4.1c0.5 1.2 0.8 2.4 0.8 3.7 0 3.1-2.9 6.3-5.3 8.2-0.9 0.7-2.2 1.1-3.4 1.1m-0.1-17.8c1.1 0 2.1 0.2 3.2 0.7"/><path d="m4 9.7c-0.2-1.8-0.3-3.7 0.5-5.5s2.2-2.6 3.9-3m11.6 8.5c0.2-1.9 0.3-3.7-0.5-5.5s-2.2-2.6-3.9-3"/><path d="m12 21.2-2.4 0.4m2.4-0.4 2.4 0.4"/></g></svg>
\ No newline at end of file
+<svg xmlns="http://www.w3.org/2000/svg" xml:space="preserve" fill-rule="evenodd" stroke-linecap="round" stroke-linejoin="round" stroke-miterlimit="1.5" clip-rule="evenodd" viewBox="0 0 100 100"><g fill="none" stroke="currentColor" stroke-width="8.33"><path d="M61.098 32.028V6.529L84.001 26.74v52.944L50.38 93.608 16.759 79.684V26.74L39.662 6.529v25.499M39.805 25.427h21.15M34.23 54.498v7.815M65.77 54.498v7.815M47.035 77.633h6.692M21.719 51.608 6.492 44.885M21.719 63.582 6.492 70.305M79.043 51.608l15.227-6.723M79.043 63.582l15.227 6.723"/></g></svg>
\ No newline at end of file
diff --git a/packages/blog/changelog.ts b/packages/blog/changelog.ts
index 979ffff830..186f72224c 100644
--- a/packages/blog/changelog.ts
+++ b/packages/blog/changelog.ts
@@ -10,6 +10,35 @@ export type VersionEntry = {
 }
 
 const VERSIONS: VersionEntry[] = [
+	{
+		date: `2026-08-07T20:41:51+00:00`,
+		product: 'app',
+		version: '0.17.4',
+		body: `## Changed
+- Added loading states for project members and server details, to make it feel smoother.
+- Improved popout menu animations.
+- Updated NeoForge icon to be closer to the actual logo and look more like a fox.
+- Updated design of buttons.
+
+## Fixed
+- Fixed "Licensed Unknown" showing up under details on server projects.
+- Fixed project types sometimes appearing in random orders on some pages.`,
+	},
+	{
+		date: `2026-08-07T20:41:51+00:00`,
+		product: 'web',
+		body: `## Changed
+- Added loading states for project members and server details, to make it feel smoother.
+- Improved popout menu animations.
+- Updated project tag settings page to new design.
+- Updated NeoForge icon to be closer to the actual logo and look more like a fox.
+
+## Fixed
+- Fixed "Licensed Unknown" showing up under details on server projects.
+- Fixed tags settings page being broken.
+- Fixed project types sometimes appearing in random orders on some pages.
+- Fixed when the project download UI has two compatible versions and no additional content, it showed as radio buttons.`,
+	},
 	{
 		date: `2026-07-31T06:10:23+00:00`,
 		product: 'web',
diff --git a/packages/moderation/src/data/keybinds.ts b/packages/moderation/src/data/keybinds.ts
index 25b2994374..d4eb0fab10 100644
--- a/packages/moderation/src/data/keybinds.ts
+++ b/packages/moderation/src/data/keybinds.ts
@@ -115,6 +115,18 @@ const keybinds: { [id: string]: KeybindListener } = {
 		scope: 'checklist',
 		action: (ctx) => ctx.actions.tryReject(),
 	},
+	'tech-review-top': {
+		keybind: 'ArrowUp',
+		description: 'Go to top of the tech review card',
+		scope: 'tech-review',
+		action: (ctx) => ctx.actions.goToTop(),
+	},
+	'tech-review-bottom': {
+		keybind: 'ArrowDown',
+		description: 'Go to bottom of the tech review card',
+		scope: 'tech-review',
+		action: (ctx) => ctx.actions.goToBottom(),
+	},
 }
 
 export default keybinds
diff --git a/packages/moderation/src/data/settings.ts b/packages/moderation/src/data/settings.ts
index 25c8ccff4a..d62436821c 100644
--- a/packages/moderation/src/data/settings.ts
+++ b/packages/moderation/src/data/settings.ts
@@ -1,8 +1,8 @@
-import type { EnumSettingDefinition, ToggleSettingDefinition } from '../types/settings.ts'
+import { setting } from '../types/settings.ts'
 
 const settings = {
 	General: {
-		ChecklistPosition: {
+		ChecklistPosition: setting.asEnum({
 			type: 'enum',
 			id: 'checklist-position',
 			title: 'Checklist Position',
@@ -12,21 +12,41 @@ const settings = {
 				{ value: 'right', label: 'Right' },
 			],
 			default: 'right',
-		} as EnumSettingDefinition,
-		ProjectKeybinds: {
+		}),
+		ProjectKeybinds: setting.asToggle({
 			type: 'toggle',
 			id: 'project-keybinds',
 			title: 'Enable Project Keybinds',
 			description: 'Weather certain keybinds should work without the checklist visible.',
 			default: false,
-		} as ToggleSettingDefinition,
-		PrivateMessageHighlight: {
+		}),
+		PrivateMessageHighlight: setting.asToggle({
 			type: 'toggle',
 			id: 'private-message-highlight',
 			title: 'Highlight Private Messages',
 			description: 'Whether private messages should be highlighted in the chat.',
 			default: true,
-		} as ToggleSettingDefinition,
+		}),
+		SlicerButtonInVersions: setting.asToggle({
+			type: 'toggle',
+			id: 'slicer-button-in-versions',
+			title: 'Show Slicer Button in Versions Table and Page',
+			description: 'Whether the slicer button should be shown in the versions table and page.',
+			default: false,
+		}),
+		AdjustPageAlignment: setting.asEnum({
+			type: 'enum',
+			id: 'adjust-page-alignment',
+			title: 'Adjust Page Alignment',
+			description:
+				'Whether the main page elements should be centered or offset opposite to the Checklist Position.',
+			entries: [
+				{ value: 'never', label: 'Never' },
+				{ value: 'checklist-present', label: 'Checklist Needed' },
+				{ value: 'always', label: 'Always' },
+			],
+			default: 'never',
+		}),
 	},
 } as const
 
diff --git a/packages/moderation/src/handles/settings.ts b/packages/moderation/src/handles/settings.ts
index 6109596d8b..8b48c79ddb 100644
--- a/packages/moderation/src/handles/settings.ts
+++ b/packages/moderation/src/handles/settings.ts
@@ -1,4 +1,5 @@
-import type { SettingDefinitionBase } from '../types/settings.ts'
+import { isValidFor, type SettingDefinitionBase } from '../types/settings.ts'
+import { moderationSettings } from '../index.ts'
 
 export class Settings {
 	private readonly settings: { [id: string]: any }
@@ -13,7 +14,9 @@ export class Settings {
 	}
 
 	get<T>(definition: SettingDefinitionBase<T>): T {
-		return this.settings[definition.id] ?? definition.default
+		const value = this.settings[definition.id]
+
+		return (isValidFor(definition, value) ? value : undefined) ?? definition.default
 	}
 
 	set<T>(definition: SettingDefinitionBase<T>, value?: T): void {
@@ -23,3 +26,11 @@ export class Settings {
 		this.onChange()
 	}
 }
+
+export function getMarginTarget(settings: Settings): string {
+	return settings.get(moderationSettings.General.AdjustPageAlignment) == 'always'
+		? settings.get(moderationSettings.General.ChecklistPosition) == 'right'
+			? 'r'
+			: 'l'
+		: 'x'
+}
diff --git a/packages/moderation/src/types/keybinds.ts b/packages/moderation/src/types/keybinds.ts
index 529eaccc86..cb57be2368 100644
--- a/packages/moderation/src/types/keybinds.ts
+++ b/packages/moderation/src/types/keybinds.ts
@@ -16,6 +16,11 @@ export interface ModerationActions {
 	tryEditMessage: () => void
 }
 
+export interface TechReviewActions {
+	goToTop: () => void
+	goToBottom: () => void
+}
+
 export interface ModerationState {
 	currentStage: number
 	totalStages: number
@@ -44,7 +49,15 @@ export type ModerationChecklistContext = {
 	actions: ModerationActions
 }
 
-export type ModerationContext = ModerationProjectContext | ModerationChecklistContext
+export type ModerationTechReviewContext = {
+	scope: 'tech-review'
+	actions: TechReviewActions
+}
+
+export type ModerationContext =
+	| ModerationProjectContext
+	| ModerationChecklistContext
+	| ModerationTechReviewContext
 
 export interface KeybindDefinition {
 	key: string
@@ -58,7 +71,7 @@ export interface KeybindDefinition {
 export type BaseKeybindListener<T> = {
 	keybind: KeybindDefinition | KeybindDefinition[] | string | string[]
 	description: string
-	scope: 'project' | 'checklist'
+	scope: 'project' | 'checklist' | 'tech-review'
 	enabled?: (ctx: T) => boolean
 	action: (ctx: T) => void
 }
@@ -69,7 +82,13 @@ export type KeybindProjectListener = BaseKeybindListener<ModerationProjectContex
 export type KeybindChecklistListener = BaseKeybindListener<ModerationChecklistContext> & {
 	scope: 'checklist'
 }
-export type KeybindListener = KeybindProjectListener | KeybindChecklistListener
+export type KeybindTechReviewListener = BaseKeybindListener<ModerationTechReviewContext> & {
+	scope: 'tech-review'
+}
+export type KeybindListener =
+	| KeybindProjectListener
+	| KeybindChecklistListener
+	| KeybindTechReviewListener
 
 export function parseKeybind(keybindString: string): KeybindDefinition {
 	const parts = keybindString.split('+').map((p) => p.trim().toLowerCase())
diff --git a/packages/moderation/src/types/settings.ts b/packages/moderation/src/types/settings.ts
index 7cf1f91ee7..1bdbb64d6a 100644
--- a/packages/moderation/src/types/settings.ts
+++ b/packages/moderation/src/types/settings.ts
@@ -1,5 +1,5 @@
 export interface SettingDefinitionBase<T> {
-	type: string
+	type: SettingDefinitionTypes
 	id: string
 	title: string
 	description: string
@@ -11,16 +11,53 @@ export interface ToggleSettingDefinition extends SettingDefinitionBase<boolean>
 	type: 'toggle'
 }
 
-export interface EnumSettingDefinition extends SettingDefinitionBase<string> {
+export interface EnumSettingDefinition<T extends string = string> extends SettingDefinitionBase<T> {
 	type: 'enum'
 	entries: {
 		label: string
-		value: string
+		value: T
 	}[]
 }
 
 export interface StringSettingDefinition extends SettingDefinitionBase<string> {
 	type: 'string'
+	regex?: RegExp
+}
+
+export type SettingDefinitions = ReturnType<(typeof setting)[keyof typeof setting]>
+export type SettingDefinitionTypes = SettingDefinitions['type']
+
+export const setting = {
+	asEnum: <const E extends ReadonlyArray<{ label: string; value: string }>>(
+		data: EnumSettingDefinition<E[number]['value']> & { entries: E },
+	): EnumSettingDefinition<E[number]['value']> => {
+		return data as EnumSettingDefinition<E[number]['value']>
+	},
+	asToggle: (data: ToggleSettingDefinition) => data,
+	asString: (data: StringSettingDefinition) => data,
+}
+
+export function isValidFor(definitionBase: SettingDefinitionBase<any>, value: any): boolean {
+	if (value != null) {
+		// Tried my best with type safety but sadly having the `SettingDefinitions` as the type leads to issues handling types else where...
+		const definition = definitionBase as SettingDefinitions
+		if (
+			definition.type == 'enum' &&
+			definition.entries.map((entry) => entry.value).includes(value)
+		) {
+			return true
+		} else if (definition.type == 'toggle' && typeof value === 'boolean') {
+			return true
+		} else if (
+			definition.type == 'string' &&
+			typeof value === 'string' &&
+			(!definition.regex || value.match(definition.regex))
+		) {
+			return true
+		}
+	}
+
+	return false
 }
 
 export type SettingDefinition =
diff --git a/packages/muralpay/src/payout.rs b/packages/muralpay/src/payout.rs
index 7fb215aaf1..5b3cdc0957 100644
--- a/packages/muralpay/src/payout.rs
+++ b/packages/muralpay/src/payout.rs
@@ -319,7 +319,7 @@ pub struct FiatPayoutDetails {
 
 #[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
 #[cfg_attr(feature = "utoipa", derive(utoipa::ToSchema))]
-#[serde(tag = "type", rename_all = "kebab-case")]
+#[serde(tag = "type", rename_all = "camelCase")]
 pub enum FiatPayoutStatus {
     Created,
     #[serde(rename_all = "camelCase")]
@@ -999,3 +999,22 @@ pub struct CurrenciesBankDetails {
 pub struct CurrencyBankDetails {
     pub bank_names: Vec<String>,
 }
+
+#[cfg(test)]
+mod tests {
+    use super::FiatPayoutStatus;
+
+    #[test]
+    fn deserializes_refund_in_progress_status() -> Result<(), serde_json::Error>
+    {
+        let status = serde_json::from_value(serde_json::json!({
+            "type": "refundInProgress",
+            "errorCode": "UNKNOWN",
+            "failureReason": "The receiving bank rejected the payout",
+            "refundInitiatedAt": "2026-08-07T00:00:00Z"
+        }))?;
+
+        assert!(matches!(status, FiatPayoutStatus::RefundInProgress { .. }));
+        Ok(())
+    }
+}
diff --git a/packages/ui/src/components/base/CollapsibleAdmonition.vue b/packages/ui/src/components/base/CollapsibleAdmonition.vue
index 6df8073d40..30acebedee 100644
--- a/packages/ui/src/components/base/CollapsibleAdmonition.vue
+++ b/packages/ui/src/components/base/CollapsibleAdmonition.vue
@@ -132,51 +132,51 @@ const buttonColors: Record<string, 'blue' | 'orange' | 'red' | 'green'> = {
 
 <style scoped>
 .collapsible-admonition[data-type='critical'] {
-	border-color: rgba(255, 73, 110, 0.6);
+	border-color: color-mix(in srgb, var(--color-red) 60%, transparent);
 }
 
 .collapsible-admonition[data-type='critical'] .collapsible-admonition__item {
-	background: rgba(255, 73, 110, 0.1);
+	background: var(--color-red-bg);
 }
 
 .collapsible-admonition[data-type='critical'] .collapsible-admonition__item--bordered {
-	border-top: 1px solid rgba(255, 73, 110, 0.6);
+	border-top: 1px solid color-mix(in srgb, var(--color-red) 60%, transparent);
 }
 
 .collapsible-admonition[data-type='info'] {
-	border-color: rgba(47, 158, 255, 0.6);
+	border-color: color-mix(in srgb, var(--color-blue) 60%, transparent);
 }
 
 .collapsible-admonition[data-type='info'] .collapsible-admonition__item {
-	background: rgba(47, 158, 255, 0.1);
+	background: var(--color-blue-bg);
 }
 
 .collapsible-admonition[data-type='info'] .collapsible-admonition__item--bordered {
-	border-top: 1px solid rgba(47, 158, 255, 0.6);
+	border-top: 1px solid color-mix(in srgb, var(--color-blue) 60%, transparent);
 }
 
 .collapsible-admonition[data-type='warning'] {
-	border-color: rgba(255, 163, 71, 0.6);
+	border-color: color-mix(in srgb, var(--color-orange) 60%, transparent);
 }
 
 .collapsible-admonition[data-type='warning'] .collapsible-admonition__item {
-	background: rgba(255, 163, 71, 0.1);
+	background: var(--color-orange-bg);
 }
 
 .collapsible-admonition[data-type='warning'] .collapsible-admonition__item--bordered {
-	border-top: 1px solid rgba(255, 163, 71, 0.6);
+	border-top: 1px solid color-mix(in srgb, var(--color-orange) 60%, transparent);
 }
 
 .collapsible-admonition[data-type='success'] {
-	border-color: rgba(27, 217, 106, 0.6);
+	border-color: color-mix(in srgb, var(--color-green) 60%, transparent);
 }
 
 .collapsible-admonition[data-type='success'] .collapsible-admonition__item {
-	background: rgba(27, 217, 106, 0.1);
+	background: var(--color-green-bg);
 }
 
 .collapsible-admonition[data-type='success'] .collapsible-admonition__item--bordered {
-	border-top: 1px solid rgba(27, 217, 106, 0.6);
+	border-top: 1px solid color-mix(in srgb, var(--color-green) 60%, transparent);
 }
 
 .collapsible-admonition-enter-active,
diff --git a/packages/ui/src/components/base/Combobox.vue b/packages/ui/src/components/base/Combobox.vue
index 4a0c6bcd0a..750238a9e1 100644
--- a/packages/ui/src/components/base/Combobox.vue
+++ b/packages/ui/src/components/base/Combobox.vue
@@ -97,12 +97,7 @@
 		</ButtonFrame>
 
 		<Teleport to="#teleports">
-			<Transition
-				enter-active-class="transition-opacity duration-150"
-				leave-active-class="transition-opacity duration-150"
-				enter-from-class="opacity-0"
-				leave-to-class="opacity-0"
-			>
+			<Transition name="floating-expand">
 				<div
 					v-if="shouldRenderDropdown"
 					ref="dropdownRef"
@@ -110,7 +105,6 @@
 					:class="[
 						props.dropdownClass,
 						openDirection === 'up' ? 'shadow-[0_-25px_50px_-12px_rgb(0,0,0,0.25)]' : 'shadow-2xl',
-						props.dropdownClass,
 					]"
 					:style="dropdownStyle"
 					:role="listbox ? 'listbox' : 'menu'"
diff --git a/packages/ui/src/components/base/DropdownFilterBar.vue b/packages/ui/src/components/base/DropdownFilterBar.vue
index 90163795c1..796b8907f7 100644
--- a/packages/ui/src/components/base/DropdownFilterBar.vue
+++ b/packages/ui/src/components/base/DropdownFilterBar.vue
@@ -128,12 +128,7 @@
 	</div>
 
 	<Teleport to="#teleports">
-		<Transition
-			:enter-active-class="addMenuTransitionEnterActiveClass"
-			leave-active-class="transition-none duration-0"
-			:enter-from-class="addMenuTransitionEnterFromClass"
-			leave-to-class="opacity-0"
-		>
+		<Transition name="floating-expand" :css="!isMobileAddMenuLayout">
 			<div
 				v-if="isAddMenuOpen && !isMobileActiveSubmenu"
 				ref="menuContainer"
@@ -166,207 +161,214 @@
 	</Teleport>
 
 	<Teleport to="#teleports">
-		<div
-			v-if="isAddMenuOpen && activeCategory && (isMobileAddMenuLayout || hasSubmenuPosition)"
-			ref="submenu"
-			class="fixed z-[10000] flex max-h-[min(70vh,32rem)] max-w-[calc(100vw-1rem)] flex-col overflow-hidden rounded-[14px] border border-solid border-surface-5 bg-surface-4 shadow-2xl"
-			:class="activeCategory.submenuClass ?? DEFAULT_SUBMENU_CLASS"
-			:style="submenuStyle"
-			@mouseenter="handleSubmenuMouseEnter"
-			@mouseleave="handleSubmenuMouseLeave"
-			@keydown="handleAddMenuKeydown"
-			@mousemove="(event) => handleMenuMouseMove(event, 'submenu')"
-		>
+		<Transition name="floating-expand" :css="!isMobileAddMenuLayout">
 			<div
-				v-if="isMobileAddMenuLayout"
-				class="flex items-center border-0 border-b border-solid border-b-surface-5 bg-surface-4"
-			>
-				<button
-					type="button"
-					class="flex h-12 w-full items-center gap-2 border-0 bg-transparent px-4 text-left text-base font-semibold text-primary shadow-none transition-all hover:brightness-110 focus-visible:brightness-110"
-					@click="returnToCategoryMenu"
-				>
-					<ChevronLeftIcon class="size-5 shrink-0 text-secondary" />
-					<span class="min-w-0 truncate">{{ activeCategory.label }}</span>
-				</button>
-			</div>
-			<div
-				v-if="activeCategory.searchable"
-				class="flex justify-between border-0 border-b border-solid border-b-surface-5 py-1.5 w-full"
-			>
-				<StyledInput
-					v-model="categorySearchQuery"
-					:icon="SearchIcon"
-					type="text"
-					:placeholder="activeCategory.searchPlaceholder ?? 'Search...'"
-					wrapper-class="grow bg-surface-4 mx-1"
-					input-class="ps-9 mx-1.5"
-				/>
-				<slot
-					name="search-actions"
-					:category="activeCategory"
-					:selected-values="activeCategorySelectedValues"
-					:set-selected-values="setActiveCategorySelectedValues"
-					:close-menu="closeAddMenu"
-				></slot>
-			</div>
-
-			<div v-if="$slots['category-top']" class="border-0 border-b border-solid border-b-surface-5">
-				<slot
-					name="category-top"
-					:category="activeCategory"
-					:selected-values="activeCategorySelectedValues"
-					:set-selected-values="setActiveCategorySelectedValues"
-					:close-menu="closeAddMenu"
-				></slot>
-			</div>
-
-			<div
-				class="flex items-center justify-between gap-3 border-0 border-b border-solid border-b-surface-5 px-4 py-2.5 text-sm"
-			>
-				<span class="font-semibold text-secondary">{{ activeCategorySelectionLabel }}</span>
-				<button
-					type="button"
-					class="border-0 bg-transparent p-0 text-sm font-semibold text-secondary shadow-none transition-colors"
-					:class="
-						hasActiveCategorySelection
-							? 'hover:bg-transparent hover:text-contrast'
-							: 'cursor-not-allowed opacity-50'
-					"
-					:disabled="!hasActiveCategorySelection"
-					@click="clearActiveCategorySelection"
-					@keydown.enter.stop
-					@keydown.space.stop
-				>
-					Clear
-				</button>
-			</div>
-			<div
-				ref="activeCategoryOptionsScrollbar"
-				class="dropdown-filter-bar-options-scrollbar min-h-0 flex-1 bg-surface-4"
-				data-overlayscrollbars-initialize
+				v-if="isAddMenuOpen && activeCategory && (isMobileAddMenuLayout || hasSubmenuPosition)"
+				ref="submenu"
+				class="fixed z-[10000] flex max-h-[min(70vh,32rem)] max-w-[calc(100vw-1rem)] flex-col overflow-hidden rounded-[14px] border border-solid border-surface-5 bg-surface-4 shadow-2xl"
+				:class="activeCategory.submenuClass ?? DEFAULT_SUBMENU_CLASS"
+				:style="submenuStyle"
+				@mouseenter="handleSubmenuMouseEnter"
+				@mouseleave="handleSubmenuMouseLeave"
+				@keydown="handleAddMenuKeydown"
+				@mousemove="(event) => handleMenuMouseMove(event, 'submenu')"
 			>
 				<div
-					ref="activeCategoryOptionsContainer"
-					class="h-full min-h-0 overflow-y-auto"
-					data-overlayscrollbars-viewport
+					v-if="isMobileAddMenuLayout"
+					class="flex items-center border-0 border-b border-solid border-b-surface-5 bg-surface-4"
+				>
+					<button
+						type="button"
+						class="flex h-12 w-full items-center gap-2 border-0 bg-transparent px-4 text-left text-base font-semibold text-primary shadow-none transition-all hover:brightness-110 focus-visible:brightness-110"
+						@click="returnToCategoryMenu"
+					>
+						<ChevronLeftIcon class="size-5 shrink-0 text-secondary" />
+						<span class="min-w-0 truncate">{{ activeCategory.label }}</span>
+					</button>
+				</div>
+				<div
+					v-if="activeCategory.searchable"
+					class="flex justify-between border-0 border-b border-solid border-b-surface-5 py-1.5 w-full"
+				>
+					<StyledInput
+						v-model="categorySearchQuery"
+						:icon="SearchIcon"
+						type="text"
+						:placeholder="activeCategory.searchPlaceholder ?? 'Search...'"
+						wrapper-class="grow bg-surface-4 mx-1"
+						input-class="ps-9 mx-1.5"
+					/>
+					<slot
+						name="search-actions"
+						:category="activeCategory"
+						:selected-values="activeCategorySelectedValues"
+						:set-selected-values="setActiveCategorySelectedValues"
+						:close-menu="closeAddMenu"
+					></slot>
+				</div>
+
+				<div
+					v-if="$slots['category-top']"
+					class="border-0 border-b border-solid border-b-surface-5"
+				>
+					<slot
+						name="category-top"
+						:category="activeCategory"
+						:selected-values="activeCategorySelectedValues"
+						:set-selected-values="setActiveCategorySelectedValues"
+						:close-menu="closeAddMenu"
+					></slot>
+				</div>
+
+				<div
+					class="flex items-center justify-between gap-3 border-0 border-b border-solid border-b-surface-5 px-4 py-2.5 text-sm"
+				>
+					<span class="font-semibold text-secondary">{{ activeCategorySelectionLabel }}</span>
+					<button
+						type="button"
+						class="border-0 bg-transparent p-0 text-sm font-semibold text-secondary shadow-none transition-colors"
+						:class="
+							hasActiveCategorySelection
+								? 'hover:bg-transparent hover:text-contrast'
+								: 'cursor-not-allowed opacity-50'
+						"
+						:disabled="!hasActiveCategorySelection"
+						@click="clearActiveCategorySelection"
+						@keydown.enter.stop
+						@keydown.space.stop
+					>
+						Clear
+					</button>
+				</div>
+				<div
+					ref="activeCategoryOptionsScrollbar"
+					class="dropdown-filter-bar-options-scrollbar min-h-0 flex-1 bg-surface-4"
+					data-overlayscrollbars-initialize
 				>
 					<div
-						v-if="filteredActiveCategoryOptions.length === 0"
-						class="px-4 py-3.5 text-base font-medium text-secondary"
-					>
-						{{ activeCategoryEmptyStateLabel }}
-					</div>
-					<div
-						v-else
-						ref="activeCategoryOptionsListContainer"
-						:class="shouldVirtualizeActiveCategoryOptions ? 'relative' : 'flex flex-col'"
-						:style="activeCategoryOptionsListStyle"
+						ref="activeCategoryOptionsContainer"
+						class="h-full min-h-0 overflow-y-auto"
+						data-overlayscrollbars-viewport
 					>
 						<div
-							v-for="{ item, index } in renderedVisibleActiveCategoryOptions"
-							:key="getActiveCategoryItemKey(item, index)"
-							:class="shouldVirtualizeActiveCategoryOptions ? 'absolute left-0 right-0' : undefined"
-							:style="getActiveCategoryOptionWrapperStyle(index)"
+							v-if="filteredActiveCategoryOptions.length === 0"
+							class="px-4 py-3.5 text-base font-medium text-secondary"
+						>
+							{{ activeCategoryEmptyStateLabel }}
+						</div>
+						<div
+							v-else
+							ref="activeCategoryOptionsListContainer"
+							:class="shouldVirtualizeActiveCategoryOptions ? 'relative' : 'flex flex-col'"
+							:style="activeCategoryOptionsListStyle"
 						>
 							<div
-								v-if="isDropdownFilterSectionHeader(item)"
-								class="flex items-center justify-between gap-3 border-0 px-4 py-2.5 text-sm font-semibold text-secondary"
-								:class="[
-									item.class,
-									item.dividerBefore && index > 0
-										? 'border-t border-solid border-surface-5'
-										: undefined,
-								]"
+								v-for="{ item, index } in renderedVisibleActiveCategoryOptions"
+								:key="getActiveCategoryItemKey(item, index)"
+								:class="
+									shouldVirtualizeActiveCategoryOptions ? 'absolute left-0 right-0' : undefined
+								"
+								:style="getActiveCategoryOptionWrapperStyle(index)"
 							>
-								<span class="flex min-w-0 items-center gap-2">
-									<component
-										:is="item.icon"
-										v-if="item.icon"
-										class="size-4 shrink-0"
-										aria-hidden="true"
-									/>
-									<span class="min-w-0 truncate">{{ item.label }}</span>
-								</span>
+								<div
+									v-if="isDropdownFilterSectionHeader(item)"
+									class="flex items-center justify-between gap-3 border-0 px-4 py-2.5 text-sm font-semibold text-secondary"
+									:class="[
+										item.class,
+										item.dividerBefore && index > 0
+											? 'border-t border-solid border-surface-5'
+											: undefined,
+									]"
+								>
+									<span class="flex min-w-0 items-center gap-2">
+										<component
+											:is="item.icon"
+											v-if="item.icon"
+											class="size-4 shrink-0"
+											aria-hidden="true"
+										/>
+										<span class="min-w-0 truncate">{{ item.label }}</span>
+									</span>
+									<button
+										v-if="hasSelectableSectionHeaderOptions(item)"
+										type="button"
+										class="border-0 bg-transparent p-0 text-sm font-semibold text-secondary shadow-none transition-colors hover:text-contrast"
+										@click="toggleSectionHeaderOptions(item)"
+									>
+										{{ areSectionHeaderOptionsSelected(item) ? 'Clear' : 'Select all' }}
+									</button>
+								</div>
 								<button
-									v-if="hasSelectableSectionHeaderOptions(item)"
+									v-else
 									type="button"
-									class="border-0 bg-transparent p-0 text-sm font-semibold text-secondary shadow-none transition-colors hover:text-contrast"
-									@click="toggleSectionHeaderOptions(item)"
+									class="flex w-full cursor-pointer items-center gap-2.5 border-0 px-4 py-3.5 text-left text-contrast shadow-none transition-all duration-150 bg-surface-4 hover:brightness-[115%] focus-visible:brightness-[115%] focus-visible:outline-none"
+									:class="[
+										shouldVirtualizeActiveCategoryOptions ? 'h-12' : undefined,
+										{
+											'brightness-[115%]': item.selected,
+											'pointer-events-none cursor-not-allowed opacity-50': item.disabled,
+										},
+									]"
+									:aria-disabled="item.disabled || undefined"
+									:aria-checked="item.selected"
+									role="checkbox"
+									@click="toggleFilterOption(activeCategory.key, item)"
 								>
-									{{ areSectionHeaderOptionsSelected(item) ? 'Clear' : 'Select all' }}
-								</button>
-							</div>
-							<button
-								v-else
-								type="button"
-								class="flex w-full cursor-pointer items-center gap-2.5 border-0 px-4 py-3.5 text-left text-contrast shadow-none transition-all duration-150 bg-surface-4 hover:brightness-[115%] focus-visible:brightness-[115%] focus-visible:outline-none"
-								:class="[
-									shouldVirtualizeActiveCategoryOptions ? 'h-12' : undefined,
-									{
-										'brightness-[115%]': item.selected,
-										'pointer-events-none cursor-not-allowed opacity-50': item.disabled,
-									},
-								]"
-								:aria-disabled="item.disabled || undefined"
-								:aria-checked="item.selected"
-								role="checkbox"
-								@click="toggleFilterOption(activeCategory.key, item)"
-							>
-								<span
-									v-if="checkboxPosition === 'left'"
-									class="checkbox-shadow flex h-5 w-5 shrink-0 items-center justify-center rounded-md border-[1px] border-solid"
-									:class="
-										item.selected
-											? 'border-button-border bg-brand text-brand-inverted'
-											: 'border-surface-5 bg-surface-2'
-									"
-								>
-									<CheckIcon v-if="item.selected" aria-hidden="true" stroke-width="3" />
-								</span>
-								<div class="flex min-w-0 flex-1 items-center justify-between gap-3">
-									<slot
-										v-if="$slots.option"
-										name="option"
-										:category="activeCategory"
-										:option="item"
-										:selected="item.selected"
-										:index="index"
-									></slot>
-									<template v-else>
-										<span
-											class="min-w-0 truncate font-semibold leading-tight"
-											:class="item.selected ? 'text-contrast' : 'text-primary'"
-										>
-											{{ item.label }}
-										</span>
+									<span
+										v-if="checkboxPosition === 'left'"
+										class="checkbox-shadow flex h-5 w-5 shrink-0 items-center justify-center rounded-md border-[1px] border-solid"
+										:class="
+											item.selected
+												? 'border-button-border bg-brand text-brand-inverted'
+												: 'border-surface-5 bg-surface-2'
+										"
+									>
+										<CheckIcon v-if="item.selected" aria-hidden="true" stroke-width="3" />
+									</span>
+									<div class="flex min-w-0 flex-1 items-center justify-between gap-3">
 										<slot
-											name="option-right"
+											v-if="$slots.option"
+											name="option"
 											:category="activeCategory"
 											:option="item"
 											:selected="item.selected"
+											:index="index"
 										></slot>
-									</template>
-								</div>
-								<span
-									v-if="checkboxPosition === 'right'"
-									class="flex shrink-0 items-center justify-center text-brand"
-								>
-									<CheckIcon v-if="item.selected" aria-hidden="true" class="size-5" />
-								</span>
-							</button>
+										<template v-else>
+											<span
+												class="min-w-0 truncate font-semibold leading-tight"
+												:class="item.selected ? 'text-contrast' : 'text-primary'"
+											>
+												{{ item.label }}
+											</span>
+											<slot
+												name="option-right"
+												:category="activeCategory"
+												:option="item"
+												:selected="item.selected"
+											></slot>
+										</template>
+									</div>
+									<span
+										v-if="checkboxPosition === 'right'"
+										class="flex shrink-0 items-center justify-center text-brand"
+									>
+										<CheckIcon v-if="item.selected" aria-hidden="true" class="size-5" />
+									</span>
+								</button>
+							</div>
 						</div>
 					</div>
 				</div>
+				<slot
+					name="category-footer"
+					:category="activeCategory"
+					:selected-values="activeCategorySelectedValues"
+					:set-selected-values="setActiveCategorySelectedValues"
+					:close-menu="closeAddMenu"
+				></slot>
 			</div>
-			<slot
-				name="category-footer"
-				:category="activeCategory"
-				:selected-values="activeCategorySelectedValues"
-				:set-selected-values="setActiveCategorySelectedValues"
-				:close-menu="closeAddMenu"
-			></slot>
-		</div>
+		</Transition>
 	</Teleport>
 </template>
 
@@ -726,12 +728,6 @@ const isMobileActiveSubmenu = computed(
 	() =>
 		isMobileAddMenuLayout.value && activeCategory.value !== undefined && hasSubmenuPosition.value,
 )
-const addMenuTransitionEnterActiveClass = computed(() =>
-	isMobileAddMenuLayout.value ? 'transition-none duration-0' : 'transition-opacity duration-150',
-)
-const addMenuTransitionEnterFromClass = computed(() =>
-	isMobileAddMenuLayout.value ? 'opacity-100' : 'opacity-0',
-)
 const addMenuTriggerElement = computed(() => addMenuTrigger.value?.element ?? null)
 const addMenuOutsideClickTarget = computed(() => menuContainer.value ?? submenu.value)
 const addMenuOutsideClickIgnore = computed(() => [addMenuTriggerElement, menuContainer, submenu])
diff --git a/packages/ui/src/components/base/DropzoneFileInput.vue b/packages/ui/src/components/base/DropzoneFileInput.vue
index a2023ef0cc..cac41e5e63 100644
--- a/packages/ui/src/components/base/DropzoneFileInput.vue
+++ b/packages/ui/src/components/base/DropzoneFileInput.vue
@@ -13,7 +13,7 @@
 	>
 		<div
 			:class="[
-				'grid place-content-center  text-brand border-brand border-solid border bg-highlight-green',
+				'grid place-content-center  text-brand border-brand border-solid border bg-brand-highlight',
 				size === 'small' ? 'w-10 h-10' : 'h-14 w-14',
 				size === 'small' ? 'rounded-xl' : 'rounded-2xl',
 			]"
diff --git a/packages/ui/src/components/base/FilterPills.vue b/packages/ui/src/components/base/FilterPills.vue
index fc0b0da539..4a5d052d98 100644
--- a/packages/ui/src/components/base/FilterPills.vue
+++ b/packages/ui/src/components/base/FilterPills.vue
@@ -38,7 +38,7 @@ function pillClass(active: boolean) {
 	return [
 		'cursor-pointer rounded-full border border-solid px-3 py-1.5 text-base font-semibold leading-5 transition-all duration-100 active:scale-[0.97]',
 		active
-			? 'border-green bg-brand-highlight text-brand'
+			? 'border-brand bg-brand-highlight text-brand'
 			: 'border-surface-5 bg-surface-4 text-primary hover:bg-surface-5',
 	]
 }
diff --git a/packages/ui/src/components/base/MultiSelect.vue b/packages/ui/src/components/base/MultiSelect.vue
index f765bd90e6..7d17408333 100644
--- a/packages/ui/src/components/base/MultiSelect.vue
+++ b/packages/ui/src/components/base/MultiSelect.vue
@@ -108,12 +108,7 @@
 		</component>
 
 		<Teleport to="#teleports">
-			<Transition
-				enter-active-class="transition-opacity duration-150"
-				leave-active-class="transition-opacity duration-150"
-				enter-from-class="opacity-0"
-				leave-to-class="opacity-0"
-			>
+			<Transition name="floating-expand">
 				<div
 					v-if="isOpen"
 					ref="dropdownRef"
diff --git a/packages/ui/src/components/base/buttons/TeleportOverflowMenu.vue b/packages/ui/src/components/base/buttons/TeleportOverflowMenu.vue
index f219a88910..8f0aec56f2 100644
--- a/packages/ui/src/components/base/buttons/TeleportOverflowMenu.vue
+++ b/packages/ui/src/components/base/buttons/TeleportOverflowMenu.vue
@@ -80,6 +80,19 @@ const { isOpen, panelStyle, anchorStyle, resolvedSide, open, close } = useAnchor
 	resolvedDistance,
 )
 
+const menuTransformOrigin = computed(() => {
+	switch (resolvedSide.value) {
+		case 'top':
+			return 'bottom center'
+		case 'left':
+			return 'right center'
+		case 'right':
+			return 'left center'
+		default:
+			return 'top center'
+	}
+})
+
 const menuItemClasses =
 	'overflow-menu-item flex min-h-10 w-full items-center gap-2 rounded-[10px] border-0 bg-transparent px-3 py-2 text-left text-base font-semibold leading-5 text-contrast no-underline ' +
 	'cursor-pointer whitespace-nowrap hover:bg-surface-4 focus-visible:bg-surface-4 focus-visible:outline-none ' +
@@ -294,20 +307,13 @@ defineExpose({ open: openMenu, close: closeMenu })
 	</component>
 
 	<Teleport to="body">
-		<Transition
-			enter-active-class="transition duration-125 ease-out"
-			enter-from-class="scale-95 opacity-0"
-			enter-to-class="scale-100 opacity-100"
-			leave-active-class="transition duration-100 ease-in"
-			leave-from-class="scale-100 opacity-100"
-			leave-to-class="scale-95 opacity-0"
-		>
+		<Transition name="floating-expand">
 			<div
 				v-if="isOpen"
 				:id="menuId"
 				ref="panelElement"
 				class="fixed isolate z-[9999] flex min-w-48 flex-col gap-1 rounded-[14px] bg-surface-3 p-2 shadow-lg ring-1 ring-surface-5"
-				:style="panelStyle"
+				:style="[panelStyle, { transformOrigin: menuTransformOrigin }]"
 				role="menu"
 				:aria-label="props.label"
 				@keydown="handleMenuKeydown"
diff --git a/packages/ui/src/components/base/buttons/TeleportPopoutMenu.vue b/packages/ui/src/components/base/buttons/TeleportPopoutMenu.vue
index 16574bfec9..8fc2ff4abb 100644
--- a/packages/ui/src/components/base/buttons/TeleportPopoutMenu.vue
+++ b/packages/ui/src/components/base/buttons/TeleportPopoutMenu.vue
@@ -123,14 +123,7 @@ defineExpose({ open: openMenu, close: closeMenu })
 	</component>
 
 	<Teleport to="body">
-		<Transition
-			enter-active-class="transition duration-125 ease-out"
-			enter-from-class="scale-95 opacity-0"
-			enter-to-class="scale-100 opacity-100"
-			leave-active-class="transition duration-100 ease-in"
-			leave-from-class="scale-100 opacity-100"
-			leave-to-class="scale-95 opacity-0"
-		>
+		<Transition name="floating-expand">
 			<div
 				v-if="isOpen"
 				:id="panelId"
diff --git a/packages/ui/src/components/base/index.ts b/packages/ui/src/components/base/index.ts
index 3f73e10c6e..4c74bf8dd0 100644
--- a/packages/ui/src/components/base/index.ts
+++ b/packages/ui/src/components/base/index.ts
@@ -122,6 +122,7 @@ export type { SortDirection, TableColumn } from './Table.vue'
 export { default as Table } from './Table.vue'
 export type { TabsTab, TabsValue } from './Tabs.vue'
 export { default as Tabs } from './Tabs.vue'
+export { default as TagIcon } from './TagIcon.vue'
 export { default as TagItem } from './TagItem.vue'
 export { default as TagTagItem } from './TagTagItem.vue'
 export type {
diff --git a/packages/ui/src/components/billing/PurchaseModal.vue b/packages/ui/src/components/billing/PurchaseModal.vue
index d1753d10a0..5c291fb92a 100644
--- a/packages/ui/src/components/billing/PurchaseModal.vue
+++ b/packages/ui/src/components/billing/PurchaseModal.vue
@@ -86,7 +86,7 @@
 							}"
 							@click="serverLoader = loader"
 						>
-							<LoaderIcon :loader="loader" class="!h-12 !w-12" />
+							<TagIcon :tag="loader" enforce-type="loader" class="!h-12 !w-12" />
 							<p class="text-lg font-bold m-0">{{ loader }}</p>
 						</button>
 					</div>
@@ -478,9 +478,9 @@ import Checkbox from '../base/Checkbox.vue'
 import Combobox from '../base/Combobox.vue'
 import Slider from '../base/Slider.vue'
 import StyledInput from '../base/StyledInput.vue'
+import TagIcon from '../base/TagIcon.vue'
 import AnimatedLogo from '../brand/AnimatedLogo.vue'
 import NewModal from '../modal/NewModal.vue'
-import LoaderIcon from '../servers/icons/LoaderIcon.vue'
 
 const { formatMessage } = useVIntl()
 const formatPrice = useFormatPrice()
diff --git a/packages/ui/src/components/billing/ServersPurchase0Plan.vue b/packages/ui/src/components/billing/ServersPurchase0Plan.vue
index 03ae8aaf7b..16d85c9fbb 100644
--- a/packages/ui/src/components/billing/ServersPurchase0Plan.vue
+++ b/packages/ui/src/components/billing/ServersPurchase0Plan.vue
@@ -246,9 +246,7 @@ function selectCustom() {
 			<div
 				class="z-10 -mb-3.5 rounded-full text-sm font-medium text-brand whitespace-nowrap absolute -top-3 right-4 bg-surface-3"
 			>
-				<div
-					class="bg-brand-highlight border border-solid border-highlight-green px-2.5 py-0.5 rounded-full"
-				>
+				<div class="bg-brand-highlight border border-solid border-brand px-2.5 py-0.5 rounded-full">
 					{{ formatMessage(messages.mostPopular) }}
 				</div>
 			</div>
diff --git a/packages/ui/src/components/project/ProjectSidebarCreators.vue b/packages/ui/src/components/project/ProjectSidebarCreators.vue
index 0e58d1b997..1eab4a2d36 100644
--- a/packages/ui/src/components/project/ProjectSidebarCreators.vue
+++ b/packages/ui/src/components/project/ProjectSidebarCreators.vue
@@ -2,45 +2,59 @@
 	<div class="flex flex-col gap-3">
 		<h2 class="text-lg font-semibold m-0">{{ formatMessage(messages.title) }}</h2>
 		<div class="flex flex-col gap-3 font-semibold">
-			<template v-if="organization">
+			<template v-if="loading">
+				<div v-for="i in 2" :key="`creator-skeleton-${i}`" class="flex gap-2 items-center">
+					<div class="size-[32px] rounded-full bg-surface-4 animate-pulse"></div>
+					<div class="flex flex-col gap-1.5">
+						<div class="w-24 h-4 rounded-full bg-surface-4 animate-pulse"></div>
+						<div class="w-16 h-3 rounded-full bg-surface-4 animate-pulse"></div>
+					</div>
+				</div>
+			</template>
+			<template v-else-if="isEmpty">
+				<span class="text-red"> Error: Project has no members. This shouldn't happen. </span>
+			</template>
+			<template v-else>
+				<template v-if="organization">
+					<AutoLink
+						class="flex gap-2 items-center w-fit text-primary leading-[1.2] group"
+						:to="orgLink(organization.slug)"
+						:target="linkTarget ?? null"
+					>
+						<Avatar :src="organization.icon_url" :alt="organization.name" size="32px" />
+						<div class="flex flex-col flex-nowrap justify-center">
+							<span class="group-hover:underline font-medium">
+								{{ organization.name }}
+							</span>
+							<span class="text-sm font-normal text-secondary flex items-center gap-1"
+								><OrganizationIcon /> {{ formatMessage(messages.organization) }}</span
+							>
+						</div>
+					</AutoLink>
+					<hr v-if="sortedMembers.length > 0" class="w-full border-button-border my-0.5" />
+				</template>
 				<AutoLink
+					v-for="member in sortedMembers"
+					:key="`member-${member.id}`"
 					class="flex gap-2 items-center w-fit text-primary leading-[1.2] group"
-					:to="orgLink(organization.slug)"
-					:target="linkTarget ?? null"
+					:to="userLink(member.user.username)"
+					:target="resolveLinkTarget(userLinkTarget)"
 				>
-					<Avatar :src="organization.icon_url" :alt="organization.name" size="32px" />
-					<div class="flex flex-col flex-nowrap justify-center">
-						<span class="group-hover:underline font-medium">
-							{{ organization.name }}
+					<Avatar :src="member.user.avatar_url" :alt="member.user.username" size="32px" circle />
+					<div class="flex flex-col">
+						<span class="flex w-full flex-nowrap items-center gap-1 group-hover:underline">
+							<span class="min-w-0 overflow-hidden truncate">{{ member.user.username }}</span>
+							<CrownIcon
+								v-if="member.is_owner"
+								v-tooltip="formatMessage(messages.owner)"
+								class="text-brand-orange"
+							/>
+							<ExternalIcon v-if="resolveLinkTarget(userLinkTarget) === '_blank'" />
 						</span>
-						<span class="text-sm font-normal text-secondary flex items-center gap-1"
-							><OrganizationIcon /> {{ formatMessage(messages.organization) }}</span
-						>
+						<span class="text-sm font-normal text-secondary">{{ member.role }}</span>
 					</div>
 				</AutoLink>
-				<hr v-if="sortedMembers.length > 0" class="w-full border-button-border my-0.5" />
 			</template>
-			<AutoLink
-				v-for="member in sortedMembers"
-				:key="`member-${member.id}`"
-				class="flex gap-2 items-center w-fit text-primary leading-[1.2] group"
-				:to="userLink(member.user.username)"
-				:target="resolveLinkTarget(userLinkTarget)"
-			>
-				<Avatar :src="member.user.avatar_url" :alt="member.user.username" size="32px" circle />
-				<div class="flex flex-col">
-					<span class="flex w-full flex-nowrap items-center gap-1 group-hover:underline">
-						<span class="min-w-0 overflow-hidden truncate">{{ member.user.username }}</span>
-						<CrownIcon
-							v-if="member.is_owner"
-							v-tooltip="formatMessage(messages.owner)"
-							class="text-brand-orange"
-						/>
-						<ExternalIcon v-if="resolveLinkTarget(userLinkTarget) === '_blank'" />
-					</span>
-					<span class="text-sm font-normal text-secondary">{{ member.role }}</span>
-				</div>
-			</AutoLink>
 		</div>
 	</div>
 </template>
@@ -80,6 +94,7 @@ const props = defineProps<{
 	userLink: (username: string) => string
 	linkTarget?: string
 	userLinkTarget?: string | null
+	loading?: boolean
 }>()
 
 function resolveLinkTarget(target: string | null | undefined): string | null {
@@ -113,6 +128,8 @@ const sortedMembers = computed(() => {
 	return owner ? [owner, ...rest] : rest
 })
 
+const isEmpty = computed(() => !props.organization && sortedMembers.value.length === 0)
+
 const messages = defineMessages({
 	title: {
 		id: 'project.about.creators.title',
diff --git a/packages/ui/src/components/project/ProjectSidebarServerInfo.vue b/packages/ui/src/components/project/ProjectSidebarServerInfo.vue
index f025f93afa..0c6767b788 100644
--- a/packages/ui/src/components/project/ProjectSidebarServerInfo.vue
+++ b/packages/ui/src/components/project/ProjectSidebarServerInfo.vue
@@ -1,5 +1,5 @@
 <template>
-	<div v-if="hasContent" class="flex flex-col gap-3">
+	<div v-if="loading || hasContent" class="flex flex-col gap-3">
 		<h2 class="text-lg m-0">{{ formatMessage(messages.title) }}</h2>
 
 		<div
@@ -15,6 +15,10 @@
 				<CopyIcon class="shrink-0" />
 			</div>
 		</div>
+		<div
+			v-else-if="loading && !projectV3"
+			class="h-12 rounded-2xl bg-surface-4 animate-pulse"
+		></div>
 
 		<section v-if="requiredContent" class="flex flex-col gap-2">
 			<h3 class="text-primary text-base m-0">{{ formatMessage(messages.requiredContent) }}</h3>
@@ -26,8 +30,13 @@
 				:onclick-version="requiredContent.onclickVersion"
 				:onclick-download="requiredContent.onclickDownload"
 				:show-custom-modpack-tooltip="requiredContent.showCustomModpackTooltip"
+				:loading-version="loading"
 			/>
 		</section>
+		<section v-else-if="loading" class="flex flex-col gap-2">
+			<h3 class="text-primary text-base m-0">{{ formatMessage(messages.requiredContent) }}</h3>
+			<div class="h-[52px] rounded-2xl bg-surface-4 animate-pulse"></div>
+		</section>
 		<section v-if="recommendedVersions.length" class="flex flex-col gap-2">
 			<h3 class="text-primary text-base m-0">{{ formatMessage(messages.minecraftJava) }}</h3>
 			<div class="flex flex-wrap gap-1.5">
@@ -57,6 +66,17 @@
 				</TagItem>
 			</div>
 		</section>
+		<section v-else-if="loading" class="flex flex-col gap-2">
+			<h3 class="text-primary text-base m-0">{{ formatMessage(messages.minecraftJava) }}</h3>
+			<div class="flex flex-wrap gap-1.5">
+				<div
+					v-for="width in ['w-16', 'w-20']"
+					:key="`version-skeleton-${width}`"
+					class="h-[26px] rounded-full bg-surface-4 animate-pulse"
+					:class="width"
+				></div>
+			</div>
+		</section>
 		<section v-if="props.ping !== undefined || region" class="flex flex-col gap-2">
 			<h3 class="text-primary text-base m-0">{{ formatMessage(messages.region) }}</h3>
 			<div class="flex flex-wrap gap-1.5 items-center">
@@ -115,6 +135,7 @@ interface Props {
 	loaders?: string[]
 	ping?: number
 	statusOnline?: boolean
+	loading?: boolean
 }
 
 const props = withDefaults(defineProps<Props>(), {
diff --git a/packages/ui/src/components/project/server/ServerModpackContentCard.vue b/packages/ui/src/components/project/server/ServerModpackContentCard.vue
index 1d25e4b6c0..e448286df5 100644
--- a/packages/ui/src/components/project/server/ServerModpackContentCard.vue
+++ b/packages/ui/src/components/project/server/ServerModpackContentCard.vue
@@ -27,6 +27,10 @@
 				>
 					{{ versionNumber }}
 				</div>
+				<div
+					v-else-if="loadingVersion"
+					class="w-16 h-4 my-0.5 rounded-full bg-surface-4 animate-pulse"
+				></div>
 			</div>
 		</div>
 		<IconButton
@@ -58,6 +62,7 @@ defineProps<{
 	onclickVersion?: () => void
 	onclickDownload?: () => void
 	showCustomModpackTooltip?: boolean
+	loadingVersion?: boolean
 }>()
 
 const { formatMessage } = useVIntl()
diff --git a/packages/ui/src/components/project/server/ServerPing.vue b/packages/ui/src/components/project/server/ServerPing.vue
index 43185cea63..1d2198b3aa 100644
--- a/packages/ui/src/components/project/server/ServerPing.vue
+++ b/packages/ui/src/components/project/server/ServerPing.vue
@@ -33,10 +33,10 @@ const { formatMessage } = useVIntl()
 
 const pingClass = computed(() => {
 	if (props.ping === undefined) {
-		return 'border-brand bg-highlight-green text-brand'
+		return 'border-green bg-highlight-green text-green'
 	}
 	if (props.ping < 150) {
-		return 'border-brand bg-highlight-green text-brand'
+		return 'border-green bg-highlight-green text-green'
 	}
 	if (props.ping < 250) {
 		return 'border-brand-orange bg-highlight-orange text-orange'
diff --git a/packages/ui/src/components/servers/access/AccessTable.vue b/packages/ui/src/components/servers/access/AccessTable.vue
index 2a88cd322a..6babe5b7ac 100644
--- a/packages/ui/src/components/servers/access/AccessTable.vue
+++ b/packages/ui/src/components/servers/access/AccessTable.vue
@@ -514,7 +514,7 @@ function roleClasses(role: ServerAccessRole): string {
 		case 'owner':
 			return 'border-orange !bg-highlight-orange !text-orange'
 		case 'editor':
-			return 'border-green !bg-highlight-green !text-brand'
+			return 'border-green !bg-highlight-green !text-green'
 		case 'viewer':
 			return 'border-blue !bg-highlight-blue !text-blue'
 	}
diff --git a/packages/ui/src/components/servers/access/RemoveAccessModal.vue b/packages/ui/src/components/servers/access/RemoveAccessModal.vue
index 77e397d051..6543740e00 100644
--- a/packages/ui/src/components/servers/access/RemoveAccessModal.vue
+++ b/packages/ui/src/components/servers/access/RemoveAccessModal.vue
@@ -300,7 +300,7 @@ function roleClasses(role: ServerAccessRole): string {
 		case 'owner':
 			return 'border-orange bg-highlight-orange text-orange'
 		case 'editor':
-			return 'border-green bg-highlight-green text-brand'
+			return 'border-green bg-highlight-green text-green'
 		case 'viewer':
 			return 'border-blue bg-highlight-blue text-blue'
 	}
diff --git a/packages/ui/src/components/servers/access/events/UserAccessEvent.vue b/packages/ui/src/components/servers/access/events/UserAccessEvent.vue
index 37ebd5b805..71a6a06ca5 100644
--- a/packages/ui/src/components/servers/access/events/UserAccessEvent.vue
+++ b/packages/ui/src/components/servers/access/events/UserAccessEvent.vue
@@ -115,7 +115,7 @@ function roleClasses(role: ServerAccessRole): string {
 		case 'owner':
 			return 'border-orange bg-highlight-orange text-orange'
 		case 'editor':
-			return 'border-green bg-highlight-green text-brand'
+			return 'border-green bg-highlight-green text-green'
 		case 'viewer':
 			return 'border-blue bg-highlight-blue text-blue'
 	}
diff --git a/packages/ui/src/components/servers/icons/LoaderIcon.vue b/packages/ui/src/components/servers/icons/LoaderIcon.vue
deleted file mode 100644
index b2e3e35f0f..0000000000
--- a/packages/ui/src/components/servers/icons/LoaderIcon.vue
+++ /dev/null
@@ -1,236 +0,0 @@
-<template>
-	<svg
-		v-if="normalizedLoader === 'Fabric'"
-		xmlns="http://www.w3.org/2000/svg"
-		xml:space="preserve"
-		fill-rule="evenodd"
-		stroke-linecap="round"
-		stroke-linejoin="round"
-		clip-rule="evenodd"
-		viewBox="0 0 24 24"
-	>
-		<path fill="none" d="M0 0h24v24H0z" />
-		<path
-			fill="none"
-			stroke="currentColor"
-			stroke-width="23"
-			d="m820 761-85.6-87.6c-4.6-4.7-10.4-9.6-25.9 1-19.9 13.6-8.4 21.9-5.2 25.4 8.2 9 84.1 89 97.2 104 2.5 2.8-20.3-22.5-6.5-39.7 5.4-7 18-12 26-3 6.5 7.3 10.7 18-3.4 29.7-24.7 20.4-102 82.4-127 103-12.5 10.3-28.5 2.3-35.8-6-7.5-8.9-30.6-34.6-51.3-58.2-5.5-6.3-4.1-19.6 2.3-25 35-30.3 91.9-73.8 111.9-90.8"
-			transform="matrix(.08671 0 0 .0867 -49.8 -56)"
-		/>
-	</svg>
-	<svg
-		v-else-if="normalizedLoader === 'Quilt'"
-		xmlns:xlink="http://www.w3.org/1999/xlink"
-		xml:space="preserve"
-		fill-rule="evenodd"
-		stroke-linecap="round"
-		stroke-linejoin="round"
-		stroke-miterlimit="2"
-		clip-rule="evenodd"
-		viewBox="0 0 24 24"
-	>
-		<defs>
-			<path
-				id="quilt"
-				fill="none"
-				stroke="currentColor"
-				stroke-width="65.6"
-				d="M442.5 233.9c0-6.4-5.2-11.6-11.6-11.6h-197c-6.4 0-11.6 5.2-11.6 11.6v197c0 6.4 5.2 11.6 11.6 11.6h197c6.4 0 11.6-5.2 11.6-11.7v-197Z"
-			></path>
-		</defs>
-		<path fill="none" d="M0 0h24v24H0z"></path>
-		<use
-			xlink:href="#quilt"
-			stroke-width="65.6"
-			transform="matrix(.03053 0 0 .03046 -3.2 -3.2)"
-		></use>
-		<use xlink:href="#quilt" stroke-width="65.6" transform="matrix(.03053 0 0 .03046 -3.2 7)"></use>
-		<use
-			xlink:href="#quilt"
-			stroke-width="65.6"
-			transform="matrix(.03053 0 0 .03046 6.9 -3.2)"
-		></use>
-		<path
-			fill="none"
-			stroke="currentColor"
-			stroke-width="70.4"
-			d="M442.5 234.8c0-7-5.6-12.5-12.5-12.5H234.7c-6.8 0-12.4 5.6-12.4 12.5V430c0 6.9 5.6 12.5 12.4 12.5H430c6.9 0 12.5-5.6 12.5-12.5V234.8Z"
-			transform="rotate(45 3.5 24) scale(.02843 .02835)"
-		></path>
-	</svg>
-	<svg
-		v-else-if="normalizedLoader === 'Forge'"
-		ml:space="preserve"
-		fill-rule="evenodd"
-		stroke-linecap="round"
-		stroke-linejoin="round"
-		stroke-miterlimit="1.5"
-		clip-rule="evenodd"
-		viewBox="0 0 24 24"
-	>
-		<path fill="none" d="M0 0h24v24H0z"></path>
-		<path
-			fill="none"
-			stroke="currentColor"
-			stroke-width="2"
-			d="M2 7.5h8v-2h12v2s-7 3.4-7 6 3.1 3.1 3.1 3.1l.9 3.9H5l1-4.1s3.8.1 4-2.9c.2-2.7-6.5-.7-8-6Z"
-		></path>
-	</svg>
-	<svg
-		v-else-if="normalizedLoader === 'NeoForge'"
-		enable-background="new 0 0 24 24"
-		version="1.1"
-		viewBox="0 0 24 24"
-		xml:space="preserve"
-		xmlns="http://www.w3.org/2000/svg"
-	>
-		<g
-			fill="none"
-			stroke="currentColor"
-			stroke-linecap="round"
-			stroke-linejoin="round"
-			stroke-width="2"
-		>
-			<path d="m12 19.2v2m0-2v2" />
-			<path
-				d="m8.4 1.3c0.5 1.5 0.7 3 0.1 4.6-0.2 0.5-0.9 1.5-1.6 1.5m8.7-6.1c-0.5 1.5-0.7 3-0.1 4.6 0.2 0.6 0.9 1.5 1.6 1.5"
-			/>
-			<path d="m3.6 15.8h-1.7m18.5 0h1.7" />
-			<path d="m3.2 12.1h-1.7m19.3 0h1.8" />
-			<path d="m8.1 12.7v1.6m7.8-1.6v1.6" />
-			<path d="m10.8 18h1.2m0 1.2-1.2-1.2m2.4 0h-1.2m0 1.2 1.2-1.2" />
-			<path
-				d="m4 9.7c-0.5 1.2-0.8 2.4-0.8 3.7 0 3.1 2.9 6.3 5.3 8.2 0.9 0.7 2.2 1.1 3.4 1.1m0.1-17.8c-1.1 0-2.1 0.2-3.2 0.7m11.2 4.1c0.5 1.2 0.8 2.4 0.8 3.7 0 3.1-2.9 6.3-5.3 8.2-0.9 0.7-2.2 1.1-3.4 1.1m-0.1-17.8c1.1 0 2.1 0.2 3.2 0.7"
-			/>
-			<path
-				d="m4 9.7c-0.2-1.8-0.3-3.7 0.5-5.5s2.2-2.6 3.9-3m11.6 8.5c0.2-1.9 0.3-3.7-0.5-5.5s-2.2-2.6-3.9-3"
-			/>
-			<path d="m12 21.2-2.4 0.4m2.4-0.4 2.4 0.4" />
-		</g>
-	</svg>
-	<svg
-		v-else-if="normalizedLoader === 'Paper'"
-		xml:space="preserve"
-		fill-rule="evenodd"
-		stroke-linecap="round"
-		stroke-linejoin="round"
-		stroke-miterlimit="1.5"
-		clip-rule="evenodd"
-		viewBox="0 0 24 24"
-	>
-		<path fill="none" d="M0 0h24v24H0z" />
-		<path fill="none" stroke="currentColor" stroke-width="2" d="m12 18 6 2 3-17L2 14l6 2" />
-		<path stroke="currentColor" stroke-width="2" d="m9 21-1-5 4 2-3 3Z" />
-		<path fill="currentColor" d="m12 18-4-2 10-9-6 11Z" />
-	</svg>
-	<svg
-		v-else-if="normalizedLoader === 'Spigot'"
-		viewBox="0 0 332 284"
-		style="
-			fill-rule: evenodd;
-			clip-rule: evenodd;
-			stroke-linejoin: round;
-			fill: none;
-			fill-rule: nonzero;
-			stroke-width: 24px;
-		"
-		stroke="currentColor"
-	>
-		<path
-			d="M147.5,27l27,-15l27.5,15l66.5,0l0,33.5l-73,-0.912l0,45.5l26,-0.088l0,31.5l-12.5,0l0,15.5l16,21.5l35,0l0,-21.5l35.5,0l0,21.5l24.5,0l0,55.5l-24.5,0l0,17l-35.5,0l0,-27l-35,0l-55.5,14.5l-67.5,-14.5l-15,14.5l18,12.5l-3,24.5l-41.5,1.5l-48.5,-19.5l6,-19l24.5,-4.5l16,-41l79,-36l-7,-15.5l0,-31.5l23.5,0l0,-45.5l-73.5,0l0,-32.5l67,0Z"
-		/>
-	</svg>
-	<svg
-		v-else-if="normalizedLoader === 'Bukkit'"
-		viewBox="0 0 292 319"
-		style="fill-rule: evenodd; clip-rule: evenodd; stroke-linecap: round; stroke-linejoin: round"
-		stroke="currentColor"
-	>
-		<g transform="matrix(1,0,0,1,0,-5)">
-			<path
-				d="M12,109.5L12,155L34.5,224L57.5,224L57.5,271L81,294L160,294L160,172L259.087,172L265,155L265,109.5M12,109.5L12,64L34.5,64L34.5,41L81,17L195.5,17L241,41L241,64L265,64L265,109.5M12,109.5L81,109.5L81,132L195.5,132L195.5,109.5L265,109.5M264.087,204L264.087,244M207.5,272L207.5,312M250,272L250,312L280,312L280,272L250,272ZM192.5,204L192.5,244L222.5,244L222.5,204L192.5,204Z"
-				style="fill: none; fill-rule: nonzero; stroke-width: 24px"
-			/>
-		</g>
-	</svg>
-	<svg
-		v-else-if="normalizedLoader === 'Purpur'"
-		xml:space="preserve"
-		fill-rule="evenodd"
-		stroke-linecap="round"
-		stroke-linejoin="round"
-		stroke-miterlimit="1.5"
-		clip-rule="evenodd"
-		viewBox="0 0 24 24"
-	>
-		<defs>
-			<path
-				id="purpur"
-				fill="none"
-				stroke="currentColor"
-				stroke-width="1.68"
-				d="m264 41.95 8-4v8l-8 4v-8Z"
-			></path>
-		</defs>
-		<path fill="none" d="M0 0h24v24H0z"></path>
-		<path
-			fill="none"
-			stroke="currentColor"
-			stroke-width="1.77"
-			d="m264 29.95-8 4 8 4.42 8-4.42-8-4Z"
-			transform="matrix(1.125 0 0 1.1372 -285 -31.69)"
-		></path>
-		<path
-			fill="none"
-			stroke="currentColor"
-			stroke-width="1.77"
-			d="m272 38.37-8 4.42-8-4.42"
-			transform="matrix(1.125 0 0 1.1372 -285 -31.69)"
-		></path>
-		<path
-			fill="none"
-			stroke="currentColor"
-			stroke-width="1.77"
-			d="m260 31.95 8 4.21V45"
-			transform="matrix(1.125 0 0 1.1372 -285 -31.69)"
-		></path>
-		<path
-			fill="none"
-			stroke="currentColor"
-			stroke-width="1.77"
-			d="M260 45v-8.84l8-4.21"
-			transform="matrix(1.125 0 0 1.1372 -285 -31.69)"
-		></path>
-		<use
-			xlink:href="#purpur"
-			stroke-width="1.68"
-			transform="matrix(1.125 0 0 1.2569 -285 -40.78)"
-		></use>
-		<use
-			xlink:href="#purpur"
-			stroke-width="1.68"
-			transform="matrix(-1.125 0 0 1.2569 309 -40.78)"
-		></use>
-	</svg>
-	<svg v-else-if="normalizedLoader === 'Vanilla'" viewBox="0 0 20 20" fill="currentColor">
-		<path
-			fill-rule="evenodd"
-			d="M9.504 1.132a1 1 0 01.992 0l1.75 1a1 1 0 11-.992 1.736L10 3.152l-1.254.716a1 1 0 11-.992-1.736l1.75-1zM5.618 4.504a1 1 0 01-.372 1.364L5.016 6l.23.132a1 1 0 11-.992 1.736L4 7.723V8a1 1 0 01-2 0V6a.996.996 0 01.52-.878l1.734-.99a1 1 0 011.364.372zm8.764 0a1 1 0 011.364-.372l1.733.99A1.002 1.002 0 0118 6v2a1 1 0 11-2 0v-.277l-.254.145a1 1 0 11-.992-1.736l.23-.132-.23-.132a1 1 0 01-.372-1.364zm-7 4a1 1 0 011.364-.372L10 8.848l1.254-.716a1 1 0 11.992 1.736L11 10.58V12a1 1 0 11-2 0v-1.42l-1.246-.712a1 1 0 01-.372-1.364zM3 11a1 1 0 011 1v1.42l1.246.712a1 1 0 11-.992 1.736l-1.75-1A1 1 0 012 14v-2a1 1 0 011-1zm14 0a1 1 0 011 1v2a1 1 0 01-.504.868l-1.75 1a1 1 0 11-.992-1.736L16 13.42V12a1 1 0 011-1zm-9.618 5.504a1 1 0 011.364-.372l.254.145V16a1 1 0 112 0v.277l.254-.145a1 1 0 11.992 1.736l-1.735.992a.995.995 0 01-1.022 0l-1.735-.992a1 1 0 01-.372-1.364z"
-			clip-rule="evenodd"
-		></path>
-	</svg>
-	<LoaderIcon v-else />
-</template>
-
-<script setup lang="ts">
-import { LoaderIcon } from '@modrinth/assets'
-import { computed } from 'vue'
-
-import { formatLoaderLabel, type ServerLoader } from '#ui/utils/loaders'
-
-const props = defineProps<{
-	loader: ServerLoader
-}>()
-
-const normalizedLoader = computed(() => formatLoaderLabel(props.loader))
-</script>
diff --git a/packages/ui/src/components/servers/icons/index.ts b/packages/ui/src/components/servers/icons/index.ts
index 71498d858d..4e635fb3f2 100644
--- a/packages/ui/src/components/servers/icons/index.ts
+++ b/packages/ui/src/components/servers/icons/index.ts
@@ -1,2 +1 @@
-export { default as LoaderIcon } from './LoaderIcon.vue'
 export { default as ServerIcon } from './ServerIcon.vue'
diff --git a/packages/ui/src/components/servers/labels/ServerLoaderLabel.vue b/packages/ui/src/components/servers/labels/ServerLoaderLabel.vue
index 9478a89a9e..8ad5a4e626 100644
--- a/packages/ui/src/components/servers/labels/ServerLoaderLabel.vue
+++ b/packages/ui/src/components/servers/labels/ServerLoaderLabel.vue
@@ -2,7 +2,7 @@
 	<div class="flex min-w-0 flex-row items-center gap-2 truncate">
 		<Separator v-if="!noSeparator" />
 		<div class="flex flex-row items-center gap-1.5">
-			<LoaderIcon v-if="loader" :loader="loader" />
+			<TagIcon v-if="loader" :tag="loader" enforce-type="loader" />
 			<div v-else class="size-5 shrink-0 animate-pulse rounded-full bg-button-border"></div>
 			<AutoLink
 				v-if="isLink"
@@ -41,7 +41,7 @@ import { injectServerSettingsModal } from '#ui/providers/server-settings-modal'
 import type { ServerLoader } from '#ui/utils/loaders'
 
 import AutoLink from '../../base/AutoLink.vue'
-import LoaderIcon from '../icons/LoaderIcon.vue'
+import TagIcon from '../../base/TagIcon.vue'
 import Separator from './Separator.vue'
 
 defineProps<{
diff --git a/packages/ui/src/components/sharing/invite-players-modal/index.vue b/packages/ui/src/components/sharing/invite-players-modal/index.vue
index 656459e741..1188a1fcd9 100644
--- a/packages/ui/src/components/sharing/invite-players-modal/index.vue
+++ b/packages/ui/src/components/sharing/invite-players-modal/index.vue
@@ -147,6 +147,7 @@ import { Button } from '#ui/components/base/buttons'
 
 import { defineMessages, useVIntl } from '../../../composables/i18n'
 import { injectNotificationManager } from '../../../providers'
+import { commonMessages } from '../../../utils/common-messages'
 import Avatar from '../../base/Avatar.vue'
 import Combobox from '../../base/Combobox.vue'
 import NewModal from '../../modal/NewModal.vue'
@@ -226,10 +227,6 @@ const messages = defineMessages({
 		id: 'sharing.invite-players-modal.added',
 		defaultMessage: 'Added',
 	},
-	cancelButton: {
-		id: 'sharing.invite-players-modal.cancel',
-		defaultMessage: 'Cancel',
-	},
 	requestedButton: {
 		id: 'sharing.invite-players-modal.requested',
 		defaultMessage: 'Request sent',
@@ -297,7 +294,9 @@ const searchPlaceholderLabel = computed(
 const addButtonLabel = computed(() => props.addLabel ?? formatMessage(messages.addButton))
 const inviteButtonLabel = computed(() => props.inviteLabel ?? formatMessage(messages.inviteButton))
 const addedButtonLabel = computed(() => props.addedLabel ?? formatMessage(messages.addedButton))
-const cancelButtonLabel = computed(() => props.cancelLabel ?? formatMessage(messages.cancelButton))
+const cancelButtonLabel = computed(
+	() => props.cancelLabel ?? formatMessage(commonMessages.cancelButton),
+)
 const requestedButtonLabel = computed(
 	() => props.requestedLabel ?? formatMessage(messages.requestedButton),
 )
diff --git a/packages/ui/src/components/sharing/invite-players-modal/invite-players-modal-invite-link-editor.vue b/packages/ui/src/components/sharing/invite-players-modal/invite-players-modal-invite-link-editor.vue
index e1caca8cd1..c59177c2fd 100644
--- a/packages/ui/src/components/sharing/invite-players-modal/invite-players-modal-invite-link-editor.vue
+++ b/packages/ui/src/components/sharing/invite-players-modal/invite-players-modal-invite-link-editor.vue
@@ -32,7 +32,7 @@
 							/>
 							<div class="flex justify-end gap-2 p-3 pt-1">
 								<Button type="outlined" native-type="button" @click="cancelCustomExpiry">
-									{{ formatMessage(messages.cancel) }}
+									{{ formatMessage(commonMessages.cancelButton) }}
 								</Button>
 								<Button
 									type="colored"
@@ -73,7 +73,7 @@
 			<div class="flex justify-end gap-2">
 				<Button :disabled="saving" @click="modal?.hide()">
 					<XIcon aria-hidden="true" />
-					{{ formatMessage(messages.cancel) }}
+					{{ formatMessage(commonMessages.cancelButton) }}
 				</Button>
 				<Button type="colored" color="brand" :disabled="!canSave" @click="save">
 					<SpinnerIcon v-if="saving" class="animate-spin" aria-hidden="true" />
@@ -94,6 +94,7 @@ import { Button } from '#ui/components/base/buttons'
 import { useFormatDateTime } from '../../../composables'
 import { defineMessages, useVIntl } from '../../../composables/i18n'
 import { injectNotificationManager } from '../../../providers'
+import { commonMessages } from '../../../utils/common-messages'
 import Combobox, { type ComboboxOption } from '../../base/Combobox.vue'
 import DatePicker from '../../base/DatePicker.vue'
 import StyledInput from '../../base/StyledInput.vue'
@@ -186,10 +187,6 @@ const messages = defineMessages({
 		id: 'sharing.invite-players-modal.custom-expiry-value',
 		defaultMessage: 'Custom: {date}',
 	},
-	cancel: {
-		id: 'sharing.invite-players-modal.cancel-button',
-		defaultMessage: 'Cancel',
-	},
 	apply: {
 		id: 'sharing.invite-players-modal.apply-button',
 		defaultMessage: 'Apply',
diff --git a/packages/ui/src/components/user/UserPageHeader.vue b/packages/ui/src/components/user/UserPageHeader.vue
index 5fd30e87db..a99f3eadaf 100644
--- a/packages/ui/src/components/user/UserPageHeader.vue
+++ b/packages/ui/src/components/user/UserPageHeader.vue
@@ -57,7 +57,15 @@
 
 		<template #actions>
 			<PageHeaderActions>
-				<ButtonLink v-if="isSelf" size="xl" :to="editProfileLink">
+				<Button
+					v-if="isSelf && typeof editProfileLink === 'function'"
+					size="xl"
+					@click="editProfileLink"
+				>
+					<EditIcon />
+					{{ formatMessage(commonMessages.editButton) }}
+				</Button>
+				<ButtonLink v-else-if="isSelf" size="xl" :to="editProfileLink">
 					<EditIcon />
 					{{ formatMessage(commonMessages.editButton) }}
 				</ButtonLink>
@@ -96,7 +104,7 @@ import { computed } from 'vue'
 
 import Avatar from '#ui/components/base/Avatar.vue'
 import type { OverflowMenuOption } from '#ui/components/base/buttons'
-import { ButtonLink, TeleportOverflowMenu } from '#ui/components/base/buttons'
+import { Button, ButtonLink, TeleportOverflowMenu } from '#ui/components/base/buttons'
 import PageHeader from '#ui/components/base/page-header/index.vue'
 import PageHeaderMetadata from '#ui/components/base/page-header/metadata/index.vue'
 import PageHeaderMetadataNumberItem from '#ui/components/base/page-header/metadata/page-header-metadata-number-item.vue'
@@ -128,10 +136,6 @@ const messages = defineMessages({
 		id: 'profile.button.unblock',
 		defaultMessage: 'Unblock',
 	},
-	editRoleButton: {
-		id: 'profile.button.edit-role',
-		defaultMessage: 'Edit role',
-	},
 	infoButton: {
 		id: 'profile.button.info',
 		defaultMessage: 'View user details',
@@ -212,7 +216,7 @@ const emit = defineEmits<{
 	toggleAffiliate: []
 	openInfo: []
 	openAnalytics: []
-	editRole: []
+	editUser: []
 }>()
 
 const { formatMessage } = useVIntl()
@@ -298,10 +302,10 @@ const moreActions = computed<OverflowMenuOption[]>(() => [
 		shown: props.showStaffActions && props.isAdmin,
 	},
 	{
-		id: 'edit-role',
-		label: formatMessage(messages.editRoleButton),
+		id: 'edit-user',
+		label: 'Edit user',
 		icon: EditIcon,
-		action: () => emit('editRole'),
+		action: () => emit('editUser'),
 		tone: 'orange',
 		shown: props.showStaffActions && props.isAdmin,
 	},
diff --git a/packages/ui/src/layouts/shared/browse-tab/header.vue b/packages/ui/src/layouts/shared/browse-tab/header.vue
index b2094e07fa..34ee71ef27 100644
--- a/packages/ui/src/layouts/shared/browse-tab/header.vue
+++ b/packages/ui/src/layouts/shared/browse-tab/header.vue
@@ -10,7 +10,7 @@ import { IconButton } from '#ui/components/base/buttons'
 import PageHeader from '#ui/components/base/page-header/index.vue'
 import PageHeaderMetadata from '#ui/components/base/page-header/metadata/index.vue'
 import PageHeaderMetadataItem from '#ui/components/base/page-header/metadata/page-header-metadata-item.vue'
-import LoaderIcon from '#ui/components/servers/icons/LoaderIcon.vue'
+import TagIcon from '#ui/components/base/TagIcon.vue'
 import { useServerImage } from '#ui/composables/use-server-image'
 import { formatLoaderLabel } from '#ui/utils/loaders'
 
@@ -77,8 +77,8 @@ const metadataItems = computed(() => {
 		items.push({
 			id: 'loader',
 			label: loaderLabel,
-			icon: LoaderIcon,
-			iconProps: { loader: loaderName },
+			icon: TagIcon,
+			iconProps: { tag: loaderName, enforceType: 'loader' },
 			class: '!text-primary',
 		})
 	}
diff --git a/packages/ui/src/layouts/shared/content-tab/components/ContentSelectionBar.vue b/packages/ui/src/layouts/shared/content-tab/components/ContentSelectionBar.vue
index bf2ec3f9c8..949f0c3e6b 100644
--- a/packages/ui/src/layouts/shared/content-tab/components/ContentSelectionBar.vue
+++ b/packages/ui/src/layouts/shared/content-tab/components/ContentSelectionBar.vue
@@ -295,7 +295,7 @@ const bulkProgressMessage = computed(() => {
 				:aria-valuenow="bulkWaiting ? undefined : bulkProgress"
 				:aria-valuemin="0"
 				:aria-valuemax="bulkTotal"
-				style="box-shadow: 0px -2px 4px 0px rgba(27, 217, 106, 0.1)"
+				style="box-shadow: 0px -2px 4px 0px color-mix(in srgb, var(--color-brand) 10%, transparent)"
 			/>
 		</div>
 	</FloatingActionBar>
diff --git a/packages/ui/src/layouts/shared/content-tab/components/modals/ModpackContentModal.vue b/packages/ui/src/layouts/shared/content-tab/components/modals/ModpackContentModal.vue
index 1dc3f4933a..2cdf830569 100644
--- a/packages/ui/src/layouts/shared/content-tab/components/modals/ModpackContentModal.vue
+++ b/packages/ui/src/layouts/shared/content-tab/components/modals/ModpackContentModal.vue
@@ -493,7 +493,7 @@ defineExpose({ show, showLoading, hide, getState, restore, updateItem, setItems
 							class="rounded-full border border-solid px-3 py-1.5 text-base font-semibold leading-5 transition-colors"
 							:class="
 								selectedFilters.length === 0
-									? 'border-green bg-brand-highlight text-brand'
+									? 'border-brand bg-brand-highlight text-brand'
 									: 'border-surface-5 bg-surface-4 text-primary hover:bg-surface-5'
 							"
 							@click="selectedFilters = []"
@@ -507,7 +507,7 @@ defineExpose({ show, showLoading, hide, getState, restore, updateItem, setItems
 							class="rounded-full border border-solid px-3 py-1.5 text-base font-semibold leading-5 transition-colors"
 							:class="
 								selectedFilters.includes(option.id)
-									? 'border-green bg-brand-highlight text-brand'
+									? 'border-brand bg-brand-highlight text-brand'
 									: 'border-surface-5 bg-surface-4 text-primary hover:bg-surface-5'
 							"
 							@click="toggleFilter(option.id)"
diff --git a/packages/ui/src/layouts/shared/content-tab/components/modals/content-updater-modal/index.vue b/packages/ui/src/layouts/shared/content-tab/components/modals/content-updater-modal/index.vue
index cee3fb48a2..a6d3c66943 100644
--- a/packages/ui/src/layouts/shared/content-tab/components/modals/content-updater-modal/index.vue
+++ b/packages/ui/src/layouts/shared/content-tab/components/modals/content-updater-modal/index.vue
@@ -566,7 +566,7 @@ function getBadgeClasses(version: Labrinth.Versions.v2.Version): string {
 	// Version type badges
 	switch (version.version_type) {
 		case 'release':
-			return 'bg-highlight-green border-brand text-brand'
+			return 'bg-highlight-green border-green text-green'
 		case 'beta':
 			return 'bg-highlight-blue border-brand-blue text-brand-blue'
 		case 'alpha':
@@ -579,7 +579,7 @@ function getBadgeClasses(version: Labrinth.Versions.v2.Version): string {
 function getVersionTypeBadgeClasses(version: Labrinth.Versions.v2.Version): string {
 	switch (version.version_type) {
 		case 'release':
-			return 'bg-highlight-green border-brand text-brand'
+			return 'bg-highlight-green border-green text-green'
 		case 'beta':
 			return 'bg-highlight-blue border-brand-blue text-brand-blue'
 		case 'alpha':
diff --git a/packages/ui/src/layouts/shared/content-tab/layout.vue b/packages/ui/src/layouts/shared/content-tab/layout.vue
index 5e7366cd24..2ec27bb643 100644
--- a/packages/ui/src/layouts/shared/content-tab/layout.vue
+++ b/packages/ui/src/layouts/shared/content-tab/layout.vue
@@ -854,7 +854,7 @@ const confirmUnlinkModal = ref<InstanceType<typeof ConfirmUnlinkModal>>()
 									class="cursor-pointer rounded-full border border-solid px-3 py-1.5 text-base font-semibold leading-5 transition-all duration-100 active:scale-[0.97]"
 									:class="
 										selectedFilters.length === 0
-											? 'border-green bg-brand-highlight text-brand'
+											? 'border-brand bg-brand-highlight text-brand'
 											: 'border-surface-5 bg-surface-4 text-primary hover:bg-surface-5'
 									"
 									:aria-pressed="selectedFilters.length === 0"
@@ -868,7 +868,7 @@ const confirmUnlinkModal = ref<InstanceType<typeof ConfirmUnlinkModal>>()
 									class="cursor-pointer rounded-full border border-solid px-3 py-1.5 text-base font-semibold leading-5 transition-all duration-100 active:scale-[0.97]"
 									:class="
 										selectedFilters.includes(option.id)
-											? 'border-green bg-brand-highlight text-brand'
+											? 'border-brand bg-brand-highlight text-brand'
 											: 'border-surface-5 bg-surface-4 text-primary hover:bg-surface-5'
 									"
 									:aria-pressed="selectedFilters.includes(option.id)"
diff --git a/packages/ui/src/layouts/shared/files-tab/components/FileContextMenu.vue b/packages/ui/src/layouts/shared/files-tab/components/FileContextMenu.vue
index 6bc8da0469..340c136540 100644
--- a/packages/ui/src/layouts/shared/files-tab/components/FileContextMenu.vue
+++ b/packages/ui/src/layouts/shared/files-tab/components/FileContextMenu.vue
@@ -1,18 +1,11 @@
 <template>
 	<Teleport to="#teleports">
-		<Transition
-			enter-active-class="transition duration-125 ease-out"
-			enter-from-class="transform scale-75 opacity-0"
-			enter-to-class="transform scale-100 opacity-100"
-			leave-active-class="transition duration-125 ease-in"
-			leave-from-class="transform scale-100 opacity-100"
-			leave-to-class="transform scale-75 opacity-0"
-		>
+		<Transition name="floating-expand">
 			<div
 				v-if="visible"
 				ref="menuRef"
 				class="fixed isolate z-[9999] flex w-fit min-w-[180px] flex-col gap-2 overflow-hidden rounded-2xl border border-solid border-surface-5 bg-bg-raised p-2 shadow-lg"
-				:style="{ left: `${position.x}px`, top: `${position.y}px` }"
+				:style="{ left: `${position.x}px`, top: `${position.y}px`, transformOrigin: 'top left' }"
 				role="menu"
 				tabindex="-1"
 				@mousedown.stop
diff --git a/packages/ui/src/layouts/shared/files-tab/components/editor/EditorFindReplace.vue b/packages/ui/src/layouts/shared/files-tab/components/editor/EditorFindReplace.vue
index 47a19ca752..4248691886 100644
--- a/packages/ui/src/layouts/shared/files-tab/components/editor/EditorFindReplace.vue
+++ b/packages/ui/src/layouts/shared/files-tab/components/editor/EditorFindReplace.vue
@@ -66,9 +66,9 @@
 				</IconButton>
 				<div class="mx-0.5 h-4 w-px bg-surface-5" />
 				<IconButton
-					v-tooltip="formatMessage(messages.closeFind)"
+					v-tooltip="formatMessage(commonMessages.closeButton)"
 					type="quiet"
-					:label="formatMessage(messages.closeFind)"
+					:label="formatMessage(commonMessages.closeButton)"
 					@click="close"
 				>
 					<XIcon />
@@ -118,6 +118,7 @@ import { nextTick, ref, watch } from 'vue'
 import { Button, IconButton } from '#ui/components/base/buttons'
 import StyledInput from '#ui/components/base/StyledInput.vue'
 import { defineMessages, useVIntl } from '#ui/composables/i18n'
+import { commonMessages } from '#ui/utils/common-messages'
 
 const props = defineProps<{
 	isFindOpen: boolean
@@ -161,10 +162,6 @@ const messages = defineMessages({
 		id: 'files.editor.find-next-match',
 		defaultMessage: 'Next match',
 	},
-	closeFind: {
-		id: 'files.editor.find-close',
-		defaultMessage: 'Close',
-	},
 	toggleReplace: {
 		id: 'files.editor.find-toggle-replace',
 		defaultMessage: 'Toggle replace',
diff --git a/packages/ui/src/layouts/shared/user-profile/components/edit-user-modal.vue b/packages/ui/src/layouts/shared/user-profile/components/edit-user-modal.vue
new file mode 100644
index 0000000000..64e3e27043
--- /dev/null
+++ b/packages/ui/src/layouts/shared/user-profile/components/edit-user-modal.vue
@@ -0,0 +1,310 @@
+<template>
+	<NewModal ref="modal" header="Edit user" :closable="!isSaving">
+		<div class="flex w-[28rem] flex-col gap-4">
+			<div class="flex flex-col gap-2.5">
+				<span class="text-lg font-semibold text-contrast">Profile picture</span>
+				<div class="flex items-center gap-4">
+					<Avatar
+						:src="displayedAvatarUrl"
+						size="md"
+						circle
+						:alt="form.username || user.username"
+					/>
+					<div class="flex flex-col gap-2">
+						<FileButton
+							:max-size="262144"
+							:prompt="formatMessage(commonMessages.uploadImageButton)"
+							accept="image/png,image/jpeg,image/gif,image/webp"
+							size="md"
+							:disabled="isSaving"
+							@change="showAvatarPreview"
+						>
+							<UploadIcon aria-hidden="true" />
+						</FileButton>
+						<Button
+							v-if="avatarUrl && !pendingAvatarDeletion"
+							native-type="button"
+							size="md"
+							:disabled="isSaving"
+							@click="removeAvatar"
+						>
+							<TrashIcon aria-hidden="true" />
+							{{ formatMessage(commonMessages.removeImageButton) }}
+						</Button>
+						<Button
+							v-if="avatarFile || pendingAvatarDeletion"
+							native-type="button"
+							size="md"
+							:disabled="isSaving"
+							@click="resetAvatar"
+						>
+							<UndoIcon aria-hidden="true" />
+							{{ formatMessage(commonMessages.resetButton) }}
+						</Button>
+					</div>
+				</div>
+			</div>
+
+			<div class="flex flex-col gap-2.5">
+				<label class="text-lg font-semibold text-contrast" for="admin-edit-username">
+					{{ formatMessage(commonMessages.usernameLabel) }}
+				</label>
+				<div class="flex items-center gap-2">
+					<StyledInput
+						id="admin-edit-username"
+						v-model="form.username"
+						class="w-full"
+						:error="form.username.length > 39"
+						:disabled="isSaving"
+					/>
+					<span
+						v-if="form.username.length >= 30"
+						class="shrink-0 text-secondary"
+						:class="{ 'text-red': form.username.length > 39 }"
+					>
+						{{ form.username.length }}/39
+					</span>
+				</div>
+			</div>
+
+			<div class="flex flex-col gap-2.5">
+				<label class="text-lg font-semibold text-contrast" for="admin-edit-bio">Bio</label>
+				<StyledInput
+					id="admin-edit-bio"
+					v-model="form.bio"
+					multiline
+					:error="form.bio.length > 160"
+					:disabled="isSaving"
+				/>
+				<div class="text-secondary" :class="{ 'text-red': form.bio.length > 160 }">
+					{{ form.bio.length }}/160
+				</div>
+			</div>
+
+			<div class="flex flex-col gap-2.5">
+				<span class="text-lg font-semibold text-contrast">Role</span>
+				<Combobox
+					v-model="form.role"
+					:options="roleOptions"
+					placeholder="Select a role"
+					:disabled="isSaving"
+				/>
+			</div>
+
+			<div class="flex justify-end gap-2">
+				<Button native-type="button" :disabled="isSaving" @click="cancel">
+					<XIcon />
+					{{ formatMessage(commonMessages.cancelButton) }}
+				</Button>
+				<Button
+					type="colored"
+					color="brand"
+					native-type="button"
+					:disabled="!canSave || isSaving"
+					@click="save"
+				>
+					<template v-if="isSaving">
+						<SpinnerIcon class="animate-spin" />
+						{{ formatMessage(commonMessages.savingButton) }}
+					</template>
+					<template v-else>
+						<SaveIcon />
+						{{ formatMessage(commonMessages.saveChangesButton) }}
+					</template>
+				</Button>
+			</div>
+		</div>
+	</NewModal>
+</template>
+
+<script setup lang="ts">
+import type { Labrinth } from '@modrinth/api-client'
+import { SaveIcon, SpinnerIcon, TrashIcon, UndoIcon, UploadIcon, XIcon } from '@modrinth/assets'
+import { useQueryClient } from '@tanstack/vue-query'
+import { computed, onBeforeUnmount, ref, shallowRef } from 'vue'
+import { useRouter } from 'vue-router'
+
+import Avatar from '#ui/components/base/Avatar.vue'
+import { Button, FileButton } from '#ui/components/base/buttons'
+import Combobox from '#ui/components/base/Combobox.vue'
+import StyledInput from '#ui/components/base/StyledInput.vue'
+import NewModal from '#ui/components/modal/NewModal.vue'
+import { useVIntl } from '#ui/composables'
+import { injectNotificationManager } from '#ui/providers'
+import { commonMessages } from '#ui/utils'
+
+import { injectUserProfile } from '../providers'
+
+const props = defineProps<{
+	user: Labrinth.Users.v3.User
+	userId: string
+}>()
+
+const userProfile = injectUserProfile()
+const notificationManager = injectNotificationManager()
+const queryClient = useQueryClient()
+const router = useRouter()
+const { formatMessage } = useVIntl()
+
+const modal = ref<InstanceType<typeof NewModal> | null>(null)
+const isSaving = ref(false)
+const form = ref<{
+	username: string
+	bio: string
+	role: Labrinth.Users.v3.Role | null
+}>({
+	username: '',
+	bio: '',
+	role: null,
+})
+const avatarUrl = ref<string | null>(null)
+const avatarFile = shallowRef<File | null>(null)
+const avatarPreviewUrl = ref<string | null>(null)
+const pendingAvatarDeletion = ref(false)
+
+const roleOptions = [
+	{ value: 'developer', label: 'None' },
+	{ value: 'moderator', label: 'Content Moderator' },
+	{ value: 'admin', label: 'Admin' },
+] satisfies { value: Labrinth.Users.v3.Role; label: string }[]
+
+const displayedAvatarUrl = computed(() => {
+	if (avatarPreviewUrl.value) {
+		return avatarPreviewUrl.value
+	}
+	if (pendingAvatarDeletion.value) {
+		return null
+	}
+	return avatarUrl.value
+})
+
+const hasChanges = computed(() => {
+	return (
+		form.value.username !== props.user.username ||
+		form.value.bio !== (props.user.bio ?? '') ||
+		form.value.role !== props.user.role ||
+		Boolean(avatarFile.value || pendingAvatarDeletion.value)
+	)
+})
+
+const canSave = computed(() => {
+	return (
+		hasChanges.value &&
+		form.value.username.length > 0 &&
+		form.value.username.length <= 39 &&
+		form.value.bio.length <= 160 &&
+		form.value.role !== null
+	)
+})
+
+function revokeAvatarPreview(): void {
+	if (avatarPreviewUrl.value) {
+		URL.revokeObjectURL(avatarPreviewUrl.value)
+		avatarPreviewUrl.value = null
+	}
+}
+
+function syncFromUser(): void {
+	revokeAvatarPreview()
+	form.value = {
+		username: props.user.username,
+		bio: props.user.bio ?? '',
+		role: props.user.role,
+	}
+	avatarUrl.value = props.user.avatar_url ?? null
+	avatarFile.value = null
+	pendingAvatarDeletion.value = false
+}
+
+function showAvatarPreview(files: File[]): void {
+	const file = files[0]
+	if (!file) {
+		return
+	}
+
+	revokeAvatarPreview()
+	avatarFile.value = file
+	avatarPreviewUrl.value = URL.createObjectURL(file)
+	pendingAvatarDeletion.value = false
+}
+
+function removeAvatar(): void {
+	revokeAvatarPreview()
+	avatarFile.value = null
+	pendingAvatarDeletion.value = true
+}
+
+function resetAvatar(): void {
+	revokeAvatarPreview()
+	avatarFile.value = null
+	pendingAvatarDeletion.value = false
+}
+
+function show(): void {
+	syncFromUser()
+	modal.value?.show()
+}
+
+function hide(): void {
+	modal.value?.hide()
+}
+
+function cancel(): void {
+	syncFromUser()
+	hide()
+}
+
+async function save(): Promise<void> {
+	if (!form.value.role || !canSave.value || isSaving.value) {
+		return
+	}
+	const nextUsername = form.value.username
+	const usernameChanged = nextUsername !== props.user.username
+	isSaving.value = true
+	try {
+		const patch: Partial<Pick<Labrinth.Users.v3.User, 'bio' | 'role' | 'username'>> = {}
+		if (usernameChanged) {
+			patch.username = nextUsername
+		}
+		if (form.value.bio !== (props.user.bio ?? '')) {
+			patch.bio = form.value.bio
+		}
+		if (form.value.role !== props.user.role) {
+			patch.role = form.value.role
+		}
+		if (Object.keys(patch).length > 0) {
+			await userProfile.patchUser(props.user.id, patch)
+		}
+
+		if (pendingAvatarDeletion.value) {
+			await userProfile.deleteAvatar(props.user.id)
+		} else if (avatarFile.value) {
+			const extension = avatarFile.value.type.split('/').at(-1)
+			if (!extension) throw new Error('The selected image does not have a valid file type.')
+			await userProfile.changeAvatar(props.user.id, avatarFile.value, extension)
+		}
+
+		await queryClient.invalidateQueries({ queryKey: ['user', props.userId] })
+		hide()
+
+		if (usernameChanged) {
+			await router.replace(`/user/${encodeURIComponent(nextUsername)}`)
+		}
+	} catch {
+		notificationManager.addNotification({
+			type: 'error',
+			title: 'Failed to update user',
+			text: 'An error occurred while updating this user. Please try again.',
+		})
+	} finally {
+		isSaving.value = false
+	}
+}
+
+onBeforeUnmount(revokeAvatarPreview)
+
+defineExpose({
+	show,
+	hide,
+})
+</script>
diff --git a/packages/ui/src/layouts/shared/user-profile/layout.vue b/packages/ui/src/layouts/shared/user-profile/layout.vue
index 608994520e..8ffe648c35 100644
--- a/packages/ui/src/layouts/shared/user-profile/layout.vue
+++ b/packages/ui/src/layouts/shared/user-profile/layout.vue
@@ -37,41 +37,7 @@
 			</template>
 		</NewModal>
 
-		<NewModal
-			v-if="variant === 'web'"
-			ref="editRoleModal"
-			:header="formatMessage(messages.editRoleButton)"
-		>
-			<div class="flex w-80 flex-col gap-4">
-				<Combobox
-					v-model="selectedRole"
-					:options="roleOptions"
-					:placeholder="formatMessage(messages.selectRolePlaceholder)"
-				/>
-				<div class="flex justify-end gap-2">
-					<Button native-type="button" @click="cancelRoleEdit">
-						<XIcon />
-						{{ formatMessage(commonMessages.cancelButton) }}
-					</Button>
-					<Button
-						type="colored"
-						color="brand"
-						native-type="button"
-						:disabled="!selectedRole || selectedRole === user.role || isSavingRole"
-						@click="saveRoleEdit"
-					>
-						<template v-if="isSavingRole">
-							<SpinnerIcon class="animate-spin" />
-							{{ formatMessage(messages.savingLabel) }}
-						</template>
-						<template v-else>
-							<SaveIcon />
-							{{ formatMessage(commonMessages.saveChangesButton) }}
-						</template>
-					</Button>
-				</div>
-			</div>
-		</NewModal>
+		<EditUserModal v-if="variant === 'web'" ref="editUserModal" :user="user" :user-id="userId" />
 
 		<NewModal
 			v-if="variant === 'web' && isStaffViewing"
@@ -226,7 +192,7 @@
 					@open-analytics="
 						openPath(`/dashboard/analytics?user=${encodeURIComponent(user.username)}`)
 					"
-					@edit-role="openRoleEditModal"
+					@edit-user="editUserModal?.show()"
 				>
 					<template v-if="isModrinthUser" #summary>
 						<IntlFormatted :message-id="messages.officialAccountBio">
@@ -460,7 +426,6 @@ import {
 	LibraryIcon,
 	LinkIcon,
 	LockIcon,
-	SaveIcon,
 	SpinnerIcon,
 	XIcon,
 } from '@modrinth/assets'
@@ -477,7 +442,6 @@ import Admonition from '#ui/components/base/Admonition.vue'
 import AutoLink from '#ui/components/base/AutoLink.vue'
 import Avatar from '#ui/components/base/Avatar.vue'
 import { Button } from '#ui/components/base/buttons'
-import Combobox from '#ui/components/base/Combobox.vue'
 import EmptyState from '#ui/components/base/EmptyState.vue'
 import IntlFormatted from '#ui/components/base/IntlFormatted.vue'
 import NavTabs from '#ui/components/base/NavTabs.vue'
@@ -496,8 +460,9 @@ import {
 	injectPageContext,
 	injectTags,
 } from '#ui/providers'
-import { commonMessages, getProjectTypeTitleMessage } from '#ui/utils'
+import { commonMessages, getProjectTypeTitleMessage, sortProjectTypes } from '#ui/utils'
 
+import EditUserModal from './components/edit-user-modal.vue'
 import { blockedUsersQueryKey, injectUserProfile } from './providers'
 import {
 	hasActivePride26Midas,
@@ -571,18 +536,6 @@ const messages = defineMessages({
 		id: 'profile.collection.projects-count',
 		defaultMessage: '{count, plural, one {# project} other {# projects}}',
 	},
-	savingLabel: {
-		id: 'profile.label.saving',
-		defaultMessage: 'Saving...',
-	},
-	editRoleButton: {
-		id: 'profile.button.edit-role',
-		defaultMessage: 'Edit role',
-	},
-	selectRolePlaceholder: {
-		id: 'profile.role.select-placeholder',
-		defaultMessage: 'Select a role',
-	},
 	userDetailsTitle: {
 		id: 'profile.details.title',
 		defaultMessage: 'User details',
@@ -692,14 +645,6 @@ const messages = defineMessages({
 		defaultMessage:
 			'The official user account of Modrinth. Get support at <support-link></support-link> or via email at <email></email>',
 	},
-	roleUpdateErrorTitle: {
-		id: 'profile.role.update-error-title',
-		defaultMessage: 'Failed to update role',
-	},
-	roleUpdateErrorDescription: {
-		id: 'profile.role.update-error-description',
-		defaultMessage: 'An error occurred while updating the user role. Please try again.',
-	},
 	blockButton: {
 		id: 'profile.button.block',
 		defaultMessage: 'Block',
@@ -840,7 +785,7 @@ const projectTypes = computed(() => {
 	const types = new Set(projects.value.map((project) => project.resolvedProjectType))
 	if (collections.value.length > 0) types.add('collection')
 	types.delete('project')
-	return [...types]
+	return sortProjectTypes(types)
 })
 
 const navLinks = computed(() => {
@@ -851,15 +796,13 @@ const navLinks = computed(() => {
 			label: formatMessage(commonMessages.allProjectType),
 			href: profilePath,
 		},
-		...projectTypes.value
-			.map((projectType) => ({
-				label:
-					projectType === 'collection'
-						? formatMessage(messages.collectionsLabel)
-						: formatMessage(getProjectTypeTitleMessage(projectType), { count: 2 }),
-				href: `${profilePath}/${projectType}s`,
-			}))
-			.sort((first, second) => first.label.localeCompare(second.label)),
+		...projectTypes.value.map((projectType) => ({
+			label:
+				projectType === 'collection'
+					? formatMessage(messages.collectionsLabel)
+					: formatMessage(getProjectTypeTitleMessage(projectType), { count: 2 }),
+			href: `${profilePath}/${projectType}s`,
+		})),
 	]
 })
 
@@ -1045,35 +988,15 @@ async function retryQueries(): Promise<void> {
 }
 
 const userDetailsModal = ref<ModalRef | null>(null)
-const editRoleModal = ref<ModalRef | null>(null)
+const editUserModal = ref<InstanceType<typeof EditUserModal> | null>(null)
 const blockUserModal = ref<ModalRef | null>(null)
-const selectedRole = ref<Labrinth.Users.v3.Role | null>(null)
-const isSavingRole = ref(false)
 const isBlockingUser = ref(false)
 const isUnblockingUser = ref(false)
-const roleOptions = [
-	{ value: 'developer', label: 'Developer' },
-	{ value: 'moderator', label: 'Moderator' },
-	{ value: 'admin', label: 'Admin' },
-] satisfies { value: Labrinth.Users.v3.Role; label: string }[]
-
-watch(
-	user,
-	(currentUser) => {
-		selectedRole.value = currentUser?.role ?? null
-	},
-	{ immediate: true },
-)
 
 function openUserDetails(): void {
 	userDetailsModal.value?.show()
 }
 
-function openRoleEditModal(): void {
-	selectedRole.value = user.value?.role ?? null
-	editRoleModal.value?.show()
-}
-
 async function handleBlockAction(): Promise<void> {
 	if (!auth.user.value) {
 		await auth.requestSignIn(route.fullPath)
@@ -1150,11 +1073,6 @@ async function unblockCurrentUser(): Promise<void> {
 	}
 }
 
-function cancelRoleEdit(): void {
-	selectedRole.value = user.value?.role ?? null
-	editRoleModal.value?.hide()
-}
-
 async function toggleAffiliate(): Promise<void> {
 	if (!user.value) return
 	await userProfile.patchUser(user.value.id, {
@@ -1162,23 +1080,4 @@ async function toggleAffiliate(): Promise<void> {
 	})
 	await queryClient.invalidateQueries({ queryKey: ['user', props.userId] })
 }
-
-async function saveRoleEdit(): Promise<void> {
-	if (!user.value || !selectedRole.value || selectedRole.value === user.value.role) return
-
-	isSavingRole.value = true
-	try {
-		await userProfile.patchUser(user.value.id, { role: selectedRole.value })
-		await queryClient.invalidateQueries({ queryKey: ['user', props.userId] })
-		editRoleModal.value?.hide()
-	} catch {
-		notificationManager.addNotification({
-			type: 'error',
-			title: formatMessage(messages.roleUpdateErrorTitle),
-			text: formatMessage(messages.roleUpdateErrorDescription),
-		})
-	} finally {
-		isSavingRole.value = false
-	}
-}
 </script>
diff --git a/packages/ui/src/layouts/shared/user-profile/providers/user-profile.ts b/packages/ui/src/layouts/shared/user-profile/providers/user-profile.ts
index 6314ece5c6..58270661bd 100644
--- a/packages/ui/src/layouts/shared/user-profile/providers/user-profile.ts
+++ b/packages/ui/src/layouts/shared/user-profile/providers/user-profile.ts
@@ -9,8 +9,10 @@ export interface UserProfileContext {
 	getCollections: (userId: string) => Promise<Labrinth.Collections.Collection[]>
 	patchUser: (
 		userId: string,
-		patch: Partial<Pick<Labrinth.Users.v3.User, 'badges' | 'role'>>,
+		patch: Partial<Pick<Labrinth.Users.v3.User, 'badges' | 'bio' | 'role' | 'username'>>,
 	) => Promise<void>
+	changeAvatar: (userId: string, file: Blob, extension: string) => Promise<void>
+	deleteAvatar: (userId: string) => Promise<void>
 	getBlockedUsers: () => Promise<Labrinth.BlockedUsers.v3.BlockedUserId[]>
 	blockUser: (userId: string) => Promise<void>
 	unblockUser: (userId: string) => Promise<void>
diff --git a/packages/ui/src/layouts/wrapped/hosting/manage/backups.vue b/packages/ui/src/layouts/wrapped/hosting/manage/backups.vue
index 2e313a3877..8733d59559 100644
--- a/packages/ui/src/layouts/wrapped/hosting/manage/backups.vue
+++ b/packages/ui/src/layouts/wrapped/hosting/manage/backups.vue
@@ -234,7 +234,9 @@
 							role="progressbar"
 							:aria-valuemin="0"
 							:aria-valuemax="bulkTotal"
-							style="box-shadow: 0px -2px 4px 0px rgba(27, 217, 106, 0.1)"
+							style="
+								box-shadow: 0px -2px 4px 0px color-mix(in srgb, var(--color-brand) 10%, transparent);
+							"
 						/>
 					</div>
 				</FloatingActionBar>
diff --git a/packages/ui/src/layouts/wrapped/hosting/manage/root.vue b/packages/ui/src/layouts/wrapped/hosting/manage/root.vue
index dbf56d1b69..978b6b6c49 100644
--- a/packages/ui/src/layouts/wrapped/hosting/manage/root.vue
+++ b/packages/ui/src/layouts/wrapped/hosting/manage/root.vue
@@ -142,8 +142,8 @@
 							<template v-else>
 								<PageHeaderMetadataItem
 									v-if="serverData.loader"
-									:icon="LoaderIcon"
-									:icon-props="{ loader: serverData.loader }"
+									:icon="TagIcon"
+									:icon-props="{ tag: serverData.loader, enforceType: 'loader' }"
 								>
 									{{ formatLoaderLabel(serverData.loader) }} {{ serverData.mc_version }}
 								</PageHeaderMetadataItem>
@@ -433,9 +433,9 @@ import PageHeaderMetadata from '#ui/components/base/page-header/metadata/index.v
 import PageHeaderMetadataItem from '#ui/components/base/page-header/metadata/page-header-metadata-item.vue'
 import PageHeaderActions from '#ui/components/base/page-header/page-header-actions.vue'
 import ServerNotice from '#ui/components/base/ServerNotice.vue'
+import TagIcon from '#ui/components/base/TagIcon.vue'
 import ConfirmLeaveModal from '#ui/components/modal/ConfirmLeaveModal.vue'
 import ServerPanelAdmonitions from '#ui/components/servers/admonitions/ServerPanelAdmonitions.vue'
-import LoaderIcon from '#ui/components/servers/icons/LoaderIcon.vue'
 import ServerIcon from '#ui/components/servers/icons/ServerIcon.vue'
 import MedalServerCountdown from '#ui/components/servers/marketing/MedalServerCountdown.vue'
 import { PanelServerActionButton } from '#ui/components/servers/server-header'
diff --git a/packages/ui/src/locales/cs-CZ/index.json b/packages/ui/src/locales/cs-CZ/index.json
index 6552d0fc48..56154cebc0 100644
--- a/packages/ui/src/locales/cs-CZ/index.json
+++ b/packages/ui/src/locales/cs-CZ/index.json
@@ -1130,9 +1130,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Soubor uložen"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Zavřít"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Najít"
   },
@@ -4557,4 +4554,3 @@
     "defaultMessage": "Typ"
   }
 }
-
diff --git a/packages/ui/src/locales/da-DK/index.json b/packages/ui/src/locales/da-DK/index.json
index 4e5043ceac..71381b8a42 100644
--- a/packages/ui/src/locales/da-DK/index.json
+++ b/packages/ui/src/locales/da-DK/index.json
@@ -557,9 +557,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Fil gemt"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Luk"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Find"
   },
@@ -2253,4 +2250,3 @@
     "defaultMessage": "Vanilla Shader"
   }
 }
-
diff --git a/packages/ui/src/locales/de-CH/index.json b/packages/ui/src/locales/de-CH/index.json
index 692f659b71..6e4905cadc 100644
--- a/packages/ui/src/locales/de-CH/index.json
+++ b/packages/ui/src/locales/de-CH/index.json
@@ -1304,9 +1304,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Datei gespeichert"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Schliessen"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Finden"
   },
@@ -2900,9 +2897,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Projekt erstellen"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Rolle bearbeiten"
-  },
   "profile.button.info": {
     "defaultMessage": "Nutzerdetails anzeigen"
   },
@@ -2984,24 +2978,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {Projekt} other {Projekte}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Speichert..."
-  },
   "profile.official-account": {
     "defaultMessage": "Offizielles Modrinth-Konto"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Das offizielle Benutzerkonto von Modrinth. Erhalte Hilfe unter <support-link></support-link> oder per E-Mail unter <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Eine Rolle auswählen"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Beim Aktualisieren dieser Nutzerrolle ist ein Fehler aufgetreten. Bitte versuche es erneut."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Rolle konnte nicht aktualisiert werden"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Beim Freigeben dieses Nutzers ist ein Fehler aufgetreten. Bitte versuche es erneut."
   },
@@ -5390,12 +5372,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Avatar von {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Abbrechen"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Abbrechen"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Benutzerdefiniert..."
   },
diff --git a/packages/ui/src/locales/de-DE/index.json b/packages/ui/src/locales/de-DE/index.json
index 059190f819..ae03ce5cf3 100644
--- a/packages/ui/src/locales/de-DE/index.json
+++ b/packages/ui/src/locales/de-DE/index.json
@@ -1304,9 +1304,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Datei gespeichert"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Schließen"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Finden"
   },
@@ -2900,9 +2897,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Projekt erstellen"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Rolle bearbeiten"
-  },
   "profile.button.info": {
     "defaultMessage": "Nutzerdetails anzeigen"
   },
@@ -2984,24 +2978,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {Projekt} other {Projekte}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Speichert..."
-  },
   "profile.official-account": {
     "defaultMessage": "Offizielles Modrinth-Konto"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Das offizielle Benutzerkonto von Modrinth. Erhalte Hilfe unter <support-link></support-link> oder per E-Mail unter <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Eine Rolle auswählen"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Beim Aktualisieren dieser Nutzerrolle ist ein Fehler aufgetreten. Bitte versuche es erneut."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Rolle konnte nicht aktualisiert werden"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Beim Freigeben dieses Nutzers ist ein Fehler aufgetreten. Bitte versuche es erneut."
   },
@@ -5390,12 +5372,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Avatar von {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Abbrechen"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Abbrechen"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Benutzerdefiniert..."
   },
diff --git a/packages/ui/src/locales/en-US/index.json b/packages/ui/src/locales/en-US/index.json
index 276afb94e4..586a423ac3 100644
--- a/packages/ui/src/locales/en-US/index.json
+++ b/packages/ui/src/locales/en-US/index.json
@@ -1307,9 +1307,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "File saved"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Close"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Find"
   },
@@ -2903,9 +2900,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Create a project"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Edit role"
-  },
   "profile.button.info": {
     "defaultMessage": "View user details"
   },
@@ -3002,24 +2996,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {project} other {projects}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Saving..."
-  },
   "profile.official-account": {
     "defaultMessage": "Official Modrinth account"
   },
   "profile.official-account.bio": {
     "defaultMessage": "The official user account of Modrinth. Get support at <support-link></support-link> or via email at <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Select a role"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "An error occurred while updating the user role. Please try again."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Failed to update role"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "An error occurred while unblocking this user. Please try again."
   },
@@ -5480,12 +5462,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "{username}'s avatar"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Cancel"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Cancel"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Custom..."
   },
diff --git a/packages/ui/src/locales/es-419/index.json b/packages/ui/src/locales/es-419/index.json
index 202a53ba1a..b3f20d36f3 100644
--- a/packages/ui/src/locales/es-419/index.json
+++ b/packages/ui/src/locales/es-419/index.json
@@ -1304,9 +1304,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Archivo guardado"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Cerrar"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Buscar"
   },
@@ -2900,9 +2897,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Crear un proyecto"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Editar rol"
-  },
   "profile.button.info": {
     "defaultMessage": "Ver detalles del usuario"
   },
@@ -2999,24 +2993,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {proyecto} other {proyectos}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Guardando..."
-  },
   "profile.official-account": {
     "defaultMessage": "Cuenta oficial de Modrinth"
   },
   "profile.official-account.bio": {
     "defaultMessage": "La cuenta oficial de Modrinth. Consigue ayuda en <support-link></support-link> o escríbenos a través de email: <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Selecciona un rol"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Ocurrió un error al actualizar el rol del usuario. Por favor inténtalo otra vez."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Error al actualizar el rol"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Ocurrió un error al desbloquear a este usuario. Por favor inténtalo otra vez."
   },
@@ -5405,12 +5387,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Avatar de {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Cancelar"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Cancelar"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Otro..."
   },
diff --git a/packages/ui/src/locales/es-ES/index.json b/packages/ui/src/locales/es-ES/index.json
index bfeabbbb50..d198fae97f 100644
--- a/packages/ui/src/locales/es-ES/index.json
+++ b/packages/ui/src/locales/es-ES/index.json
@@ -1187,9 +1187,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Archivo guardado"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Cerrar"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Encontrar"
   },
diff --git a/packages/ui/src/locales/fil-PH/index.json b/packages/ui/src/locales/fil-PH/index.json
index 330f5de707..643493b467 100644
--- a/packages/ui/src/locales/fil-PH/index.json
+++ b/packages/ui/src/locales/fil-PH/index.json
@@ -341,9 +341,6 @@
   "external-project-license-status.yes": {
     "defaultMessage": "Oo"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Isara"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Hahanapin"
   },
@@ -2766,4 +2763,3 @@
     "defaultMessage": "Uri"
   }
 }
-
diff --git a/packages/ui/src/locales/fr-FR/index.json b/packages/ui/src/locales/fr-FR/index.json
index fff669d8f5..7d4f4a73b9 100644
--- a/packages/ui/src/locales/fr-FR/index.json
+++ b/packages/ui/src/locales/fr-FR/index.json
@@ -1301,9 +1301,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Fichier sauvegardé"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Fermer"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Trouver"
   },
@@ -2894,9 +2891,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Créer un projet"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Modifier le rôle"
-  },
   "profile.button.info": {
     "defaultMessage": "Voir les détails de l'utilisateur"
   },
@@ -2978,24 +2972,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural,one {projet}other {projets}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Enregistrement..."
-  },
   "profile.official-account": {
     "defaultMessage": "Compte Modrinth officiel"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Le compte utilisateur officiel de Modrinth. Obtenez de l’aide via <support-link></support-link> ou par e-mail à <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Sélectionner un rôle"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Une erreur s'est produite lors de la mise à jour du rôle utilisateur. Veuillez réessayer."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Impossible de mettre à jour le rôle"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Une erreur s'est produite pendant le déblocage de cet utilisateur. Veuillez réessayer."
   },
@@ -5381,12 +5363,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Avatar de {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Annuler"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Annuler"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Personnaliser..."
   },
diff --git a/packages/ui/src/locales/hu-HU/index.json b/packages/ui/src/locales/hu-HU/index.json
index 3779af7ee2..5e9d85aa35 100644
--- a/packages/ui/src/locales/hu-HU/index.json
+++ b/packages/ui/src/locales/hu-HU/index.json
@@ -1028,9 +1028,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "A fájl mentve"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Bezárás"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Keresés"
   },
@@ -2537,9 +2534,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Projekt létrehozása"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Szerep szerkesztése"
-  },
   "profile.button.info": {
     "defaultMessage": "Felhasználói adatok megtekintése"
   },
@@ -2612,24 +2606,12 @@
   "profile.label.project-count": {
     "defaultMessage": "projekt"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Mentés..."
-  },
   "profile.official-account": {
     "defaultMessage": "Hivatalos Modrinth-fiók"
   },
   "profile.official-account.bio": {
     "defaultMessage": "A Modrinth hivatalos felhasználói fiókja. Támogatás a <support-link></support-link> oldalon kaphatsz vagy e-mailben a <email></email> címen."
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Válassz egy rangot"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Hiba történt a felhasználói szerepkör frissítése közben. Kérlek próbáld meg újra."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "A szerepkör frissítése nem sikerült"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Hiba történt a felhasználó letiltásának feloldása közben. Kérlek próbáld meg újra."
   },
@@ -4544,12 +4526,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "{username} avatárja"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Mégse"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Mégse"
-  },
   "sharing.invite-players-modal.edit-invite-link": {
     "defaultMessage": "Meghívólink szerkesztése."
   },
diff --git a/packages/ui/src/locales/id-ID/index.json b/packages/ui/src/locales/id-ID/index.json
index ea86cec49e..f813993ef3 100644
--- a/packages/ui/src/locales/id-ID/index.json
+++ b/packages/ui/src/locales/id-ID/index.json
@@ -824,9 +824,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Berkas disimpan"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Tutup"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Cari"
   },
@@ -2985,4 +2982,3 @@
     "defaultMessage": "Anda memiliki perubahan yang belum tersimpan."
   }
 }
-
diff --git a/packages/ui/src/locales/it-IT/index.json b/packages/ui/src/locales/it-IT/index.json
index f37274273a..1e68e2bed5 100644
--- a/packages/ui/src/locales/it-IT/index.json
+++ b/packages/ui/src/locales/it-IT/index.json
@@ -1274,9 +1274,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "File salvato"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Chiudi"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Trova"
   },
@@ -2858,9 +2855,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Crea un progetto"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Modifica ruolo"
-  },
   "profile.button.info": {
     "defaultMessage": "Mostra info utente"
   },
@@ -2957,24 +2951,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {progetto} other {progetti}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Salvataggio..."
-  },
   "profile.official-account": {
     "defaultMessage": "Account Modrinth ufficiale"
   },
   "profile.official-account.bio": {
     "defaultMessage": "L'account ufficiale di Modrinth. Ricevi assistenza presso <support-link></support-link> o tramite mail presso <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Seleziona il ruolo"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Sì è verificato un errore nel salvataggio del ruolo utente. Riprova più tardi."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Impossibile salvare il ruolo"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Sì è verificato un errore nello sbloccare l'utente. Riprova più tardi."
   },
@@ -5363,12 +5345,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Foto profilo di {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Annulla"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Annulla"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Personalizzata..."
   },
diff --git a/packages/ui/src/locales/ja-JP/index.json b/packages/ui/src/locales/ja-JP/index.json
index df940eeb9a..4aa329319f 100644
--- a/packages/ui/src/locales/ja-JP/index.json
+++ b/packages/ui/src/locales/ja-JP/index.json
@@ -1220,9 +1220,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "保存済み"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "閉じる"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "検索"
   },
diff --git a/packages/ui/src/locales/ko-KR/index.json b/packages/ui/src/locales/ko-KR/index.json
index 5fbdd8d469..7070a2cd32 100644
--- a/packages/ui/src/locales/ko-KR/index.json
+++ b/packages/ui/src/locales/ko-KR/index.json
@@ -1304,9 +1304,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "파일 저장됨"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "닫다"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "찾다"
   },
@@ -2900,9 +2897,6 @@
   "profile.button.create-project": {
     "defaultMessage": "프로젝트 만들기"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "역할 수정"
-  },
   "profile.button.info": {
     "defaultMessage": "사용자 상세 정보 보기"
   },
@@ -2984,24 +2978,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, other {프로젝트}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "저장 중..."
-  },
   "profile.official-account": {
     "defaultMessage": "공식 Modrinth 계정"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Modrinth의 공식 사용자 계정입니다. <support-link></support-link> 또는 <email></email> 을 통해 문의해 주세요"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "역할 선택"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "사용자 역할을 업데이트하는 동안 오류가 발생했습니다. 다시 시도해 주세요."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "역할 업데이트 실패"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "이 사용자의 차단을 해제하는 동안 오류가 발생했습니다. 다시 시도해 주세요."
   },
@@ -5387,12 +5369,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "{username} 님의 아바타"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "취소"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "취소"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "커스텀..."
   },
diff --git a/packages/ui/src/locales/ms-MY/index.json b/packages/ui/src/locales/ms-MY/index.json
index ac9fff9c1f..07a9a3002a 100644
--- a/packages/ui/src/locales/ms-MY/index.json
+++ b/packages/ui/src/locales/ms-MY/index.json
@@ -914,9 +914,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Fail disimpan"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Tutup"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Cari"
   },
@@ -5058,4 +5055,3 @@
     "defaultMessage": "Jenis"
   }
 }
-
diff --git a/packages/ui/src/locales/nl-NL/index.json b/packages/ui/src/locales/nl-NL/index.json
index 5d4b8101e9..17e3c1ba54 100644
--- a/packages/ui/src/locales/nl-NL/index.json
+++ b/packages/ui/src/locales/nl-NL/index.json
@@ -1301,9 +1301,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Bestand opgeslagen"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Sluiten"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Vind"
   },
@@ -2861,9 +2858,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Een project aanmaken"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Rol bewerken"
-  },
   "profile.button.info": {
     "defaultMessage": "Gebruikersgegevens bekijken"
   },
@@ -2942,9 +2936,6 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {project} other {projecten}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Opslaan..."
-  },
   "profile.official-account": {
     "defaultMessage": "Officieel Modrinth-account"
   },
@@ -5210,12 +5201,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Avatar van {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Annuleren"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Annuleren"
-  },
   "sharing.invite-players-modal.edit-invite-link": {
     "defaultMessage": "Uitnodigingslink bewerken."
   },
diff --git a/packages/ui/src/locales/pl-PL/index.json b/packages/ui/src/locales/pl-PL/index.json
index dfa9cbadee..3c2f2a39ba 100644
--- a/packages/ui/src/locales/pl-PL/index.json
+++ b/packages/ui/src/locales/pl-PL/index.json
@@ -1298,9 +1298,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Plik zapisany"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Zamknij"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Znajdź"
   },
@@ -2888,9 +2885,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Utwórz projekt"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Edytuj rolę"
-  },
   "profile.button.info": {
     "defaultMessage": "Otwórz szczegóły użytkownika"
   },
@@ -2963,24 +2957,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {projekt} few {projekty} other {projektów}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Zapisywanie..."
-  },
   "profile.official-account": {
     "defaultMessage": "Oficjalne konto Modrinth"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Oficjalne konto Modrinth. Otrzymaj wsparcie na stronie <support-link></support-link> lub poprzez e-mail <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Wybierz rolę"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Wystąpił błąd podczas ustawiania roli tego użytkownika. Spróbuj ponownie później."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Nie udało się zaktualizować roli"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Wystąpił błąd podczas odblokowywania tego użytkownika. Spróbuj ponownie później."
   },
@@ -5360,12 +5342,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Awatar użytkownika {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Anuluj"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Anuluj"
-  },
   "sharing.invite-players-modal.expiry-label": {
     "defaultMessage": "Data wygaśnięcia"
   },
diff --git a/packages/ui/src/locales/pt-BR/index.json b/packages/ui/src/locales/pt-BR/index.json
index cdd3b7480f..e2c43cbc28 100644
--- a/packages/ui/src/locales/pt-BR/index.json
+++ b/packages/ui/src/locales/pt-BR/index.json
@@ -1304,9 +1304,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Arquivo salvo"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Fechar"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Localizar"
   },
@@ -2900,9 +2897,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Criar projeto"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Editar cargo"
-  },
   "profile.button.info": {
     "defaultMessage": "Ver detalhes do usuário"
   },
@@ -2999,24 +2993,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {projeto} other {projetos}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Salvando..."
-  },
   "profile.official-account": {
     "defaultMessage": "Conta oficial do Modrinth"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Conta oficial do Modrinth. Obtenha suporte em<support-link></support-link> ou por e-mail via <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Selecione um cargo"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Ocorreu um erro ao atualizar o cargo do usuário. Tente novamente."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Falha ao atualizar cargo"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Ocorreu um erro ao desbloquear este usuário. Tente novamente."
   },
@@ -5405,12 +5387,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Avatar de {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Cancelar"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Cancelar"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Personalizado..."
   },
diff --git a/packages/ui/src/locales/pt-PT/index.json b/packages/ui/src/locales/pt-PT/index.json
index a0e28dd70f..3fae453a27 100644
--- a/packages/ui/src/locales/pt-PT/index.json
+++ b/packages/ui/src/locales/pt-PT/index.json
@@ -497,9 +497,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Ficheiro salvo"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Fechar"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Encontrar"
   },
@@ -2526,4 +2523,3 @@
     "defaultMessage": "Tens alterações por guardar."
   }
 }
-
diff --git a/packages/ui/src/locales/ro-RO/index.json b/packages/ui/src/locales/ro-RO/index.json
index 689a414b43..3fe8371574 100644
--- a/packages/ui/src/locales/ro-RO/index.json
+++ b/packages/ui/src/locales/ro-RO/index.json
@@ -551,9 +551,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Fișier salvat"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Închide"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Caută"
   },
diff --git a/packages/ui/src/locales/ru-RU/index.json b/packages/ui/src/locales/ru-RU/index.json
index 857e3b76a8..f2bb62d04f 100644
--- a/packages/ui/src/locales/ru-RU/index.json
+++ b/packages/ui/src/locales/ru-RU/index.json
@@ -1232,9 +1232,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Файл сохранён"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Закрыть"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Найти"
   },
@@ -2813,9 +2810,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Создать проект"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Настройка роли"
-  },
   "profile.button.info": {
     "defaultMessage": "Посмотреть подробности"
   },
@@ -2912,24 +2906,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {проект} few {проекта} other {проектов}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Сохранение..."
-  },
   "profile.official-account": {
     "defaultMessage": "Официальный аккаунт Modrinth"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Официальный аккаунт Modrinth. Связь с поддержкой: <support-link></support-link> или по почте <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Выберите роль"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Произошла ошибка при обновлении роли. Попробуйте снова."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Не удалось обновить роль"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Произошла ошибка при разблокировке пользователя. Попробуйте снова."
   },
@@ -5318,12 +5300,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Аватар {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Отозвать"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Отмена"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Другое..."
   },
diff --git a/packages/ui/src/locales/sr-CS/index.json b/packages/ui/src/locales/sr-CS/index.json
index da75b36663..4b8b811f0f 100644
--- a/packages/ui/src/locales/sr-CS/index.json
+++ b/packages/ui/src/locales/sr-CS/index.json
@@ -1253,9 +1253,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Datoteka sačuvana"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Zatvori"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Pronađi"
   },
diff --git a/packages/ui/src/locales/sv-SE/index.json b/packages/ui/src/locales/sv-SE/index.json
index a85eed24fb..59a8d96bde 100644
--- a/packages/ui/src/locales/sv-SE/index.json
+++ b/packages/ui/src/locales/sv-SE/index.json
@@ -1142,9 +1142,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Filen sparades"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Stäng"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Hitta"
   },
@@ -2561,9 +2558,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Skapa ett projekt"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Ändra roll"
-  },
   "profile.button.info": {
     "defaultMessage": "Visa användardetaljer"
   },
@@ -2630,21 +2624,9 @@
   "profile.label.project-count": {
     "defaultMessage": "Projekt"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Sparar..."
-  },
   "profile.official-account": {
     "defaultMessage": "Officiellt Modrinth-konto"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Välj en roll"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Ett fel inträffade medan användarrollen uppdaterades. Vänligen försök igen."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Misslyckades att uppdatera rollen"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Ett fel inträffade under avblockeringen av den här användaren. Vänligen försök igen."
   },
@@ -4754,12 +4736,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "{username}s avatar"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Avbryt"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Avbryt"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Anpassat..."
   },
diff --git a/packages/ui/src/locales/tr-TR/index.json b/packages/ui/src/locales/tr-TR/index.json
index d5e5821e31..ea5220b0ee 100644
--- a/packages/ui/src/locales/tr-TR/index.json
+++ b/packages/ui/src/locales/tr-TR/index.json
@@ -1274,9 +1274,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Dosya kaydedildi"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Kapat"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Bul"
   },
diff --git a/packages/ui/src/locales/uk-UA/index.json b/packages/ui/src/locales/uk-UA/index.json
index f8ee8d05c6..198e64e748 100644
--- a/packages/ui/src/locales/uk-UA/index.json
+++ b/packages/ui/src/locales/uk-UA/index.json
@@ -1259,9 +1259,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Файл збережено"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Закрити"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Знайти"
   },
@@ -2855,9 +2852,6 @@
   "profile.button.create-project": {
     "defaultMessage": "Створити проєкт"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "Зміна ролі"
-  },
   "profile.button.info": {
     "defaultMessage": "Деталі про користувача"
   },
@@ -2948,24 +2942,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, one {проєкт} few {проєкти} many {проєктів} other {проєктів}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "Збереження..."
-  },
   "profile.official-account": {
     "defaultMessage": "Офіційний обліковий запис Modrinth"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Офіційний обліковий запис Modrinth. Зв'язатися з підтримкою можна за <support-link></support-link> або через електронну пошту за <email></email>"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "Виберіть роль"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "Виникла помилка під час оновлення ролі користувача. Спробуйте знову."
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "Не вдалося оновити роль"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "Виникла помилка під час розблокування користувача. Спробуйте знову."
   },
@@ -5354,12 +5336,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "Аватар користувача {username}"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "Скасувати"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "Скасувати"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "Власна…"
   },
diff --git a/packages/ui/src/locales/vi-VN/index.json b/packages/ui/src/locales/vi-VN/index.json
index b356f09f22..96044097c8 100644
--- a/packages/ui/src/locales/vi-VN/index.json
+++ b/packages/ui/src/locales/vi-VN/index.json
@@ -935,9 +935,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "Tệp đã được lưu"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "Đóng"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "Tìm"
   },
@@ -5082,4 +5079,3 @@
     "defaultMessage": "Đội ngũ Modrinth"
   }
 }
-
diff --git a/packages/ui/src/locales/zh-CN/index.json b/packages/ui/src/locales/zh-CN/index.json
index 93095a14f1..e3b69f652a 100644
--- a/packages/ui/src/locales/zh-CN/index.json
+++ b/packages/ui/src/locales/zh-CN/index.json
@@ -1304,9 +1304,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "文件已保存"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "关闭"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "查找"
   },
@@ -2900,9 +2897,6 @@
   "profile.button.create-project": {
     "defaultMessage": "创建项目"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "编辑角色"
-  },
   "profile.button.info": {
     "defaultMessage": "查看用户详情"
   },
@@ -2999,24 +2993,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, other {项目}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "正在保存……"
-  },
   "profile.official-account": {
     "defaultMessage": "官方 Modrinth 账户"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Modrinth 的官方用户账号。可通过 <support-link></support-link> 或电子邮件 <email></email> 获取支持"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "选择角色"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "更新用户角色时发生了错误。请重试。"
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "更新角色失败"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "解除屏蔽该用户时发生了错误。请重试。"
   },
@@ -5405,12 +5387,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "{username} 的头像"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "取消"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "取消"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "自定义……"
   },
diff --git a/packages/ui/src/locales/zh-TW/index.json b/packages/ui/src/locales/zh-TW/index.json
index eec7c7f511..959891bdf4 100644
--- a/packages/ui/src/locales/zh-TW/index.json
+++ b/packages/ui/src/locales/zh-TW/index.json
@@ -1304,9 +1304,6 @@
   "files.editor.file-saved-title": {
     "defaultMessage": "已儲存檔案"
   },
-  "files.editor.find-close": {
-    "defaultMessage": "關閉"
-  },
   "files.editor.find-in-file": {
     "defaultMessage": "尋找"
   },
@@ -2900,9 +2897,6 @@
   "profile.button.create-project": {
     "defaultMessage": "建立專案"
   },
-  "profile.button.edit-role": {
-    "defaultMessage": "編輯身分"
-  },
   "profile.button.info": {
     "defaultMessage": "檢視使用者詳細資訊"
   },
@@ -2999,24 +2993,12 @@
   "profile.label.project-count": {
     "defaultMessage": "{count, plural, other {個專案}}"
   },
-  "profile.label.saving": {
-    "defaultMessage": "正在儲存..."
-  },
   "profile.official-account": {
     "defaultMessage": "Modrinth 官方帳號"
   },
   "profile.official-account.bio": {
     "defaultMessage": "Modrinth 的官方使用者帳號。請至 <support-link></support-link> 取得支援，或透過電子郵件 <email></email> 聯絡客服團隊"
   },
-  "profile.role.select-placeholder": {
-    "defaultMessage": "選擇身分"
-  },
-  "profile.role.update-error-description": {
-    "defaultMessage": "更新使用者身分時發生錯誤，請再試一次。"
-  },
-  "profile.role.update-error-title": {
-    "defaultMessage": "無法更新身分"
-  },
   "profile.unblock-user.error-description": {
     "defaultMessage": "解除封鎖使用者時發生錯誤，請再試一次。"
   },
@@ -5405,12 +5387,6 @@
   "sharing.invite-players-modal.avatar-alt": {
     "defaultMessage": "{username} 的顯示圖片"
   },
-  "sharing.invite-players-modal.cancel": {
-    "defaultMessage": "取消"
-  },
-  "sharing.invite-players-modal.cancel-button": {
-    "defaultMessage": "取消"
-  },
   "sharing.invite-players-modal.custom-expiry": {
     "defaultMessage": "自訂..."
   },
diff --git a/packages/ui/src/stories/base/PageHeader.stories.ts b/packages/ui/src/stories/base/PageHeader.stories.ts
index d2e569ae6b..a8344567da 100644
--- a/packages/ui/src/stories/base/PageHeader.stories.ts
+++ b/packages/ui/src/stories/base/PageHeader.stories.ts
@@ -35,8 +35,8 @@ import PageHeaderMetadataTagsItem from '../../components/base/page-header/metada
 import PageHeaderMetadataTimeItem from '../../components/base/page-header/metadata/page-header-metadata-time-item.vue'
 import PageHeaderActions from '../../components/base/page-header/page-header-actions.vue'
 import PageHeaderBadgeItem from '../../components/base/page-header/page-header-badge-item.vue'
+import TagIcon from '../../components/base/TagIcon.vue'
 import TagItem from '../../components/base/TagItem.vue'
-import LoaderIcon from '../../components/servers/icons/LoaderIcon.vue'
 import ServerIcon from '../../components/servers/icons/ServerIcon.vue'
 
 const noop = () => undefined
@@ -220,11 +220,11 @@ export const CreatorHeader: Story = {
 
 export const AppInstanceHeader: Story = {
 	render: () => ({
-		components: { ...pageHeaderComponents, LoaderIcon, TeleportOverflowMenu },
+		components: { ...pageHeaderComponents, TagIcon, TeleportOverflowMenu },
 		setup() {
 			return {
 				...pageHeaderIcons,
-				LoaderIcon,
+				TagIcon,
 				menuActions,
 				noop,
 			}
@@ -238,7 +238,7 @@ export const AppInstanceHeader: Story = {
 				<template #metadata>
 					<PageHeaderMetadata>
 						<PageHeaderMetadataItem :icon="Gamepad2Icon" tooltip="Minecraft version">Minecraft 1.20.1</PageHeaderMetadataItem>
-						<PageHeaderMetadataItem :icon="LoaderIcon" :icon-props="{ loader: 'Fabric' }" tooltip="Mod loader">
+						<PageHeaderMetadataItem :icon="TagIcon" :icon-props="{ tag: 'Fabric', enforceType: 'loader' }" tooltip="Mod loader">
 							Fabric 0.16.14
 						</PageHeaderMetadataItem>
 						<PageHeaderMetadataItem :icon="TimerIcon" tooltip="Total playtime">12 hours</PageHeaderMetadataItem>
@@ -266,11 +266,11 @@ export const AppInstanceHeader: Story = {
 
 export const BrowseHeader: Story = {
 	render: () => ({
-		components: { ...pageHeaderComponents, LoaderIcon, TeleportOverflowMenu },
+		components: { ...pageHeaderComponents, TagIcon, TeleportOverflowMenu },
 		setup() {
 			return {
 				...pageHeaderIcons,
-				LoaderIcon,
+				TagIcon,
 				noop,
 			}
 		},
@@ -289,7 +289,7 @@ export const BrowseHeader: Story = {
 						<PageHeaderMetadataItem class="!text-primary" :icon="Gamepad2Icon" tooltip="Minecraft version">
 							Minecraft 1.20.1
 						</PageHeaderMetadataItem>
-						<PageHeaderMetadataItem class="!text-primary" :icon="LoaderIcon" :icon-props="{ loader: 'Fabric' }" tooltip="Mod loader">
+						<PageHeaderMetadataItem class="!text-primary" :icon="TagIcon" :icon-props="{ tag: 'Fabric', enforceType: 'loader' }" tooltip="Mod loader">
 							Fabric
 						</PageHeaderMetadataItem>
 					</PageHeaderMetadata>
@@ -343,12 +343,12 @@ export const ServerPanelRootHeader: Story = {
 
 export const ServerPanelInstanceHeader: Story = {
 	render: () => ({
-		components: { ...pageHeaderComponents, LoaderIcon, TeleportOverflowMenu },
+		components: { ...pageHeaderComponents, TagIcon, TeleportOverflowMenu },
 		setup() {
 			return {
 				...pageHeaderIcons,
 				joinedActions,
-				LoaderIcon,
+				TagIcon,
 				noop,
 			}
 		},
@@ -363,7 +363,7 @@ export const ServerPanelInstanceHeader: Story = {
 				<template #metadata>
 					<PageHeaderMetadata>
 						<PageHeaderMetadataItem :icon="Gamepad2Icon" tooltip="Minecraft version">Minecraft 1.20.1</PageHeaderMetadataItem>
-						<PageHeaderMetadataItem :icon="LoaderIcon" :icon-props="{ loader: 'Fabric' }" tooltip="Mod loader">
+						<PageHeaderMetadataItem :icon="TagIcon" :icon-props="{ tag: 'Fabric', enforceType: 'loader' }" tooltip="Mod loader">
 							Fabric 0.19.2
 						</PageHeaderMetadataItem>
 						<PageHeaderMetadataItem :icon="TimerIcon" tooltip="Last activity">Last active 2 weeks ago</PageHeaderMetadataItem>
diff --git a/packages/ui/src/styles/tailwind-utilities.css b/packages/ui/src/styles/tailwind-utilities.css
index adc17e4fd2..c32ef00996 100644
--- a/packages/ui/src/styles/tailwind-utilities.css
+++ b/packages/ui/src/styles/tailwind-utilities.css
@@ -1,3 +1,26 @@
+:root {
+	--ease-out-expo: cubic-bezier(0.16, 1, 0.3, 1);
+}
+
+.floating-expand-enter-from,
+.floating-expand-leave-to {
+	opacity: 0;
+	scale: 0.9 0.3;
+}
+
+.floating-expand-enter-to,
+.floating-expand-leave-from {
+	opacity: 1;
+}
+
+.floating-expand-enter-active,
+.floating-expand-leave-active {
+	transition:
+		opacity 0.125s var(--ease-out-expo),
+		scale 0.125s var(--ease-out-expo);
+	transform-origin: top;
+}
+
 @layer utilities {
 	.heading-xl {
 		@apply m-0 text-xl font-semibold leading-none text-contrast;
diff --git a/packages/ui/src/utils/index.ts b/packages/ui/src/utils/index.ts
index 6aeb20c1a9..217dd867e4 100644
--- a/packages/ui/src/utils/index.ts
+++ b/packages/ui/src/utils/index.ts
@@ -6,6 +6,7 @@ export * from './file-extensions'
 export * from './game-modes'
 export * from './loaders'
 export * from './notices'
+export * from './project-types'
 export * from './savable'
 export * from './search'
 export * from './server-content-installing'
diff --git a/packages/ui/src/utils/project-types.ts b/packages/ui/src/utils/project-types.ts
new file mode 100644
index 0000000000..447532156a
--- /dev/null
+++ b/packages/ui/src/utils/project-types.ts
@@ -0,0 +1,31 @@
+export const PROJECT_TYPE_ORDER = [
+	'mod',
+	'resourcepack',
+	'datapack',
+	'shader',
+	'modpack',
+	'plugin',
+	'server',
+	'collection',
+] as const
+
+export type OrderedProjectType = (typeof PROJECT_TYPE_ORDER)[number]
+
+const PROJECT_TYPE_SORT_ALIASES: Record<string, string> = {
+	minecraft_java_server: 'server',
+	shaderpack: 'shader',
+}
+
+export function getProjectTypeSortIndex(type: string): number {
+	const normalized = PROJECT_TYPE_SORT_ALIASES[type] ?? type
+	const index = (PROJECT_TYPE_ORDER as readonly string[]).indexOf(normalized)
+	return index === -1 ? PROJECT_TYPE_ORDER.length : index
+}
+
+export function compareProjectTypes(a: string, b: string): number {
+	return getProjectTypeSortIndex(a) - getProjectTypeSortIndex(b)
+}
+
+export function sortProjectTypes<T extends string>(types: Iterable<T>): T[] {
+	return [...types].sort(compareProjectTypes)
+}
diff --git a/packages/ui/src/utils/search.ts b/packages/ui/src/utils/search.ts
index cce30fa434..7aa23bb799 100644
--- a/packages/ui/src/utils/search.ts
+++ b/packages/ui/src/utils/search.ts
@@ -108,10 +108,10 @@ export type ProjectType =
 
 const ALL_PROJECT_TYPES: ProjectType[] = [
 	'mod',
-	'modpack',
 	'resourcepack',
-	'shader',
 	'datapack',
+	'shader',
+	'modpack',
 	'plugin',
 	'server',
 ]
diff --git a/packages/ui/src/utils/use-anchored-teleport.ts b/packages/ui/src/utils/use-anchored-teleport.ts
index 453de58fb6..304fc4601e 100644
--- a/packages/ui/src/utils/use-anchored-teleport.ts
+++ b/packages/ui/src/utils/use-anchored-teleport.ts
@@ -37,7 +37,8 @@ export function useAnchoredTeleport(
 		if (!isOpen.value || !trigger.value || !panel.value) return
 
 		const triggerRect = trigger.value.getBoundingClientRect()
-		const panelRect = panel.value.getBoundingClientRect()
+		const panelWidth = panel.value.offsetWidth
+		const panelHeight = panel.value.offsetHeight
 		const offset = distance.value
 		const alignsEnd = placement.value.endsWith('end')
 		const isHorizontal = placement.value.startsWith('right') || placement.value.startsWith('left')
@@ -49,34 +50,27 @@ export function useAnchoredTeleport(
 			const spaceRight = window.innerWidth - triggerRect.right - viewportPadding
 			const spaceLeft = triggerRect.left - viewportPadding
 			const opensRight = prefersRight
-				? panelRect.width + offset <= spaceRight || spaceRight > spaceLeft
-				: panelRect.width + offset > spaceLeft && spaceRight > spaceLeft
+				? panelWidth + offset <= spaceRight || spaceRight > spaceLeft
+				: panelWidth + offset > spaceLeft && spaceRight > spaceLeft
 
 			resolvedSide.value = opensRight ? 'right' : 'left'
-			idealTop = alignsEnd ? triggerRect.bottom - panelRect.height : triggerRect.top
-			idealLeft = opensRight
-				? triggerRect.right + offset
-				: triggerRect.left - panelRect.width - offset
+			idealTop = alignsEnd ? triggerRect.bottom - panelHeight : triggerRect.top
+			idealLeft = opensRight ? triggerRect.right + offset : triggerRect.left - panelWidth - offset
 		} else {
 			const prefersTop = placement.value.startsWith('top')
 			const spaceBelow = window.innerHeight - triggerRect.bottom - viewportPadding
 			const spaceAbove = triggerRect.top - viewportPadding
 			const opensAbove = prefersTop
-				? panelRect.height + offset <= spaceAbove || spaceAbove > spaceBelow
-				: panelRect.height + offset > spaceBelow && spaceAbove > spaceBelow
+				? panelHeight + offset <= spaceAbove || spaceAbove > spaceBelow
+				: panelHeight + offset > spaceBelow && spaceAbove > spaceBelow
 
 			resolvedSide.value = opensAbove ? 'top' : 'bottom'
-			idealTop = opensAbove
-				? triggerRect.top - panelRect.height - offset
-				: triggerRect.bottom + offset
-			idealLeft = alignsEnd ? triggerRect.right - panelRect.width : triggerRect.left
+			idealTop = opensAbove ? triggerRect.top - panelHeight - offset : triggerRect.bottom + offset
+			idealLeft = alignsEnd ? triggerRect.right - panelWidth : triggerRect.left
 		}
 
-		const maxTop = Math.max(
-			viewportPadding,
-			window.innerHeight - panelRect.height - viewportPadding,
-		)
-		const maxLeft = Math.max(viewportPadding, window.innerWidth - panelRect.width - viewportPadding)
+		const maxTop = Math.max(viewportPadding, window.innerHeight - panelHeight - viewportPadding)
+		const maxLeft = Math.max(viewportPadding, window.innerWidth - panelWidth - viewportPadding)
 		const panelTop = Math.min(Math.max(idealTop, viewportPadding), maxTop)
 		const panelLeft = Math.min(Math.max(idealLeft, viewportPadding), maxLeft)
 
@@ -89,13 +83,13 @@ export function useAnchoredTeleport(
 			? {
 					top: `${Math.min(
 						Math.max(triggerRect.top + triggerRect.height / 2 - panelTop, anchorPadding),
-						Math.max(anchorPadding, panelRect.height - anchorPadding),
+						Math.max(anchorPadding, panelHeight - anchorPadding),
 					)}px`,
 				}
 			: {
 					left: `${Math.min(
 						Math.max(triggerRect.left + triggerRect.width / 2 - panelLeft, anchorPadding),
-						Math.max(anchorPadding, panelRect.width - anchorPadding),
+						Math.max(anchorPadding, panelWidth - anchorPadding),
 					)}px`,
 				}
 	}