diff --git a/apps/app-frontend/src/pages/instance/Files.vue b/apps/app-frontend/src/pages/instance/Files.vue
index 72d75cfceb..c64adee333 100644
--- a/apps/app-frontend/src/pages/instance/Files.vue
+++ b/apps/app-frontend/src/pages/instance/Files.vue
@@ -229,7 +229,6 @@ async function handleDownloadFile(path: string, _fileName: string) {
 const uploadState = ref<UploadState>({
 	isUploading: false,
 	currentFileName: null,
-	currentFileProgress: 0,
 	uploadedBytes: 0,
 	totalBytes: 0,
 	completedFiles: 0,
@@ -241,8 +240,7 @@ async function handleUploadFiles(files: File[]) {
 
 	uploadState.value = {
 		isUploading: true,
-		currentFileName: '',
-		currentFileProgress: 0,
+		currentFileName: files[0]?.name ?? null,
 		uploadedBytes: 0,
 		totalBytes: files.reduce((sum, f) => sum + f.size, 0),
 		completedFiles: 0,
@@ -258,7 +256,6 @@ async function handleUploadFiles(files: File[]) {
 			await writeFileBytes(targetPath, new Uint8Array(buffer))
 			uploadState.value.completedFiles++
 			uploadState.value.uploadedBytes += file.size
-			uploadState.value.currentFileProgress = 1
 		}
 	} catch (e) {
 		addNotification({
diff --git a/packages/api-client/src/platform/xhr-upload-client.ts b/packages/api-client/src/platform/xhr-upload-client.ts
index d16e765899..60d4e6b8f6 100644
--- a/packages/api-client/src/platform/xhr-upload-client.ts
+++ b/packages/api-client/src/platform/xhr-upload-client.ts
@@ -96,13 +96,16 @@ export abstract class XHRUploadClient extends AbstractModrinthClient {
 		return new Promise<T>((resolve, reject) => {
 			const xhr = new XMLHttpRequest()
 			const metadata = context.metadata as UploadMetadata
+			const fallbackTotal = this.getUploadPayloadSize(metadata)
 
 			xhr.upload.addEventListener('progress', (e) => {
-				if (e.lengthComputable) {
+				const total = e.lengthComputable ? e.total : fallbackTotal
+				if (total > 0) {
+					const loaded = Math.min(e.loaded, total)
 					const progress: UploadProgress = {
-						loaded: e.loaded,
-						total: e.total,
-						progress: e.loaded / e.total,
+						loaded,
+						total,
+						progress: loaded / total,
 					}
 					progressCallbacks.forEach((cb) => cb(progress))
 				}
@@ -146,6 +149,18 @@ export abstract class XHRUploadClient extends AbstractModrinthClient {
 		})
 	}
 
+	private getUploadPayloadSize(metadata: UploadMetadata): number {
+		if ('file' in metadata) {
+			return metadata.file.size
+		}
+
+		let total = 0
+		metadata.formData.forEach((value) => {
+			total += value instanceof Blob ? value.size : new Blob([value]).size
+		})
+		return total
+	}
+
 	protected createUploadError(xhr: XMLHttpRequest): ModrinthApiError {
 		let responseData: unknown
 		try {
diff --git a/packages/api-client/src/types/upload.ts b/packages/api-client/src/types/upload.ts
index 61e50dc94d..467faa9a28 100644
--- a/packages/api-client/src/types/upload.ts
+++ b/packages/api-client/src/types/upload.ts
@@ -93,7 +93,6 @@ export interface UploadHandle<T> {
 export interface UploadState {
 	isUploading: boolean
 	currentFileName: string | null
-	currentFileProgress: number
 	uploadedBytes: number
 	totalBytes: number
 	completedFiles: number
diff --git a/packages/ui/src/components/servers/admonitions/UploadAdmonition.vue b/packages/ui/src/components/servers/admonitions/UploadAdmonition.vue
index 7c0656d9ef..bd1e14cb74 100644
--- a/packages/ui/src/components/servers/admonitions/UploadAdmonition.vue
+++ b/packages/ui/src/components/servers/admonitions/UploadAdmonition.vue
@@ -1,18 +1,14 @@
 <template>
-	<Admonition type="info" :progress="overallProgress" progress-color="blue">
+	<Admonition type="info" :progress="displayProgress" progress-color="blue">
 		<template #icon>
 			<UploadIcon class="h-6 w-6 flex-none text-brand-blue" />
 		</template>
 		<template #header>
-			{{
-				state.currentFileName
-					? `Uploading ${state.currentFileName} (${state.completedFiles}/${state.totalFiles})`
-					: `Uploading files (${state.completedFiles}/${state.totalFiles})`
-			}}
+			{{ headerText }}
 		</template>
 		<span class="text-secondary">
-			{{ formatBytes(state.uploadedBytes) }} / {{ formatBytes(state.totalBytes) }} ({{
-				Math.round(overallProgress * 100)
+			{{ formatBytes(displayUploadedBytes) }} / {{ formatBytes(state.totalBytes) }} ({{
+				Math.round(displayProgress * 100)
 			}}%)
 		</span>
 		<template v-if="cancelUpload" #top-right-actions>
@@ -39,9 +35,32 @@ const ctx = injectModrinthServerContext()
 const state = computed(() => ctx.uploadState.value)
 const cancelUpload = computed(() => ctx.cancelUpload.value)
 
-const overallProgress = computed(() => {
+const headerText = computed(() => {
 	const s = state.value
-	if (!s.isUploading || s.totalFiles === 0) return 0
-	return Math.min((s.completedFiles + s.currentFileProgress) / s.totalFiles, 1)
+	if (s.currentFileName) {
+		return `Uploading ${s.currentFileName} (${currentFileNumber.value}/${s.totalFiles})`
+	}
+	return `Uploading files (${s.completedFiles}/${s.totalFiles})`
+})
+
+const currentFileNumber = computed(() => {
+	const s = state.value
+	if (s.totalFiles === 0) return 0
+	return Math.min(s.completedFiles + 1, s.totalFiles)
+})
+
+const displayUploadedBytes = computed(() => {
+	const s = state.value
+	if (s.totalBytes <= 0) return s.uploadedBytes
+	return Math.min(s.uploadedBytes, s.totalBytes)
+})
+
+const displayProgress = computed(() => {
+	const s = state.value
+	if (!s.isUploading) return 0
+	if (s.totalBytes > 0) {
+		return displayUploadedBytes.value / s.totalBytes
+	}
+	return 0
 })
 </script>
diff --git a/packages/ui/src/composables/server-manage-core-runtime.ts b/packages/ui/src/composables/server-manage-core-runtime.ts
index 4d6665ac40..73e8828f8e 100644
--- a/packages/ui/src/composables/server-manage-core-runtime.ts
+++ b/packages/ui/src/composables/server-manage-core-runtime.ts
@@ -349,7 +349,6 @@ export function useServerManageCoreRuntime(options: UseServerManageCoreRuntimeOp
 	const uploadState = ref<UploadState>({
 		isUploading: false,
 		currentFileName: null,
-		currentFileProgress: 0,
 		uploadedBytes: 0,
 		totalBytes: 0,
 		completedFiles: 0,
diff --git a/packages/ui/src/layouts/wrapped/hosting/manage/content.vue b/packages/ui/src/layouts/wrapped/hosting/manage/content.vue
index ab51b3f0e7..ad6a9fb289 100644
--- a/packages/ui/src/layouts/wrapped/hosting/manage/content.vue
+++ b/packages/ui/src/layouts/wrapped/hosting/manage/content.vue
@@ -702,31 +702,49 @@ function handleUploadFiles() {
 	input.onchange = async () => {
 		if (!input.files) return
 		const files = Array.from(input.files)
+		if (files.length === 0) return
 		const wid = worldId.value
 		if (!wid) return
 
+		const totalBytes = files.reduce((sum, f) => sum + f.size, 0)
 		uploadState.value = {
 			isUploading: true,
-			currentFileName: null,
-			currentFileProgress: 0,
+			currentFileName: files[0]?.name ?? null,
 			uploadedBytes: 0,
-			totalBytes: files.reduce((sum, f) => sum + f.size, 0),
+			totalBytes,
 			completedFiles: 0,
 			totalFiles: files.length,
 		}
 
+		const cumulativeFileBytes = files.reduce<number[]>((out, file) => {
+			out.push((out[out.length - 1] ?? 0) + file.size)
+			return out
+		}, [])
+
+		function updateUploadProgress(loaded: number, total: number) {
+			const uploadedBytes =
+				total > 0 ? Math.round((Math.min(loaded, total) / total) * totalBytes) : loaded
+			const clampedUploadedBytes = Math.min(uploadedBytes, totalBytes)
+			const completedFiles = cumulativeFileBytes.filter(
+				(bytes) => bytes <= clampedUploadedBytes,
+			).length
+			const currentFileIndex = Math.min(completedFiles, files.length - 1)
+
+			uploadState.value.uploadedBytes = clampedUploadedBytes
+			uploadState.value.completedFiles = completedFiles
+			uploadState.value.currentFileName = files[currentFileIndex]?.name ?? null
+		}
+
 		const handle = client.kyros.content_v1.uploadAddonFile(wid, files, {
-			onProgress: (p) => {
-				uploadState.value.currentFileProgress = p.progress
-				uploadState.value.uploadedBytes = p.loaded
-				uploadState.value.totalBytes = p.total
-			},
+			onProgress: ({ loaded, total }) => updateUploadProgress(loaded, total),
 		})
 		cancelUpload.value = () => handle.cancel()
 
 		try {
 			await handle.promise
+			uploadState.value.uploadedBytes = totalBytes
 			uploadState.value.completedFiles = files.length
+			uploadState.value.currentFileName = files[files.length - 1]?.name ?? null
 			await contentQuery.refetch()
 		} catch (err) {
 			if (err instanceof Error && err.message === 'Upload cancelled') return
@@ -740,7 +758,6 @@ function handleUploadFiles() {
 			uploadState.value = {
 				isUploading: false,
 				currentFileName: null,
-				currentFileProgress: 0,
 				uploadedBytes: 0,
 				totalBytes: 0,
 				completedFiles: 0,
diff --git a/packages/ui/src/layouts/wrapped/hosting/manage/files.vue b/packages/ui/src/layouts/wrapped/hosting/manage/files.vue
index 3ade290d9a..2fab7397d0 100644
--- a/packages/ui/src/layouts/wrapped/hosting/manage/files.vue
+++ b/packages/ui/src/layouts/wrapped/hosting/manage/files.vue
@@ -374,7 +374,6 @@ async function uploadFiles(files: File[]) {
 	uploadState.value = {
 		isUploading: true,
 		currentFileName: files[0].name,
-		currentFileProgress: 0,
 		uploadedBytes: 0,
 		totalBytes,
 		completedFiles: 0,
@@ -389,13 +388,11 @@ async function uploadFiles(files: File[]) {
 		const filePath = `${currentPath.value}/${file.name}`.replace('//', '/')
 
 		uploadState.value.currentFileName = file.name
-		uploadState.value.currentFileProgress = 0
 
 		try {
 			const uploader = client.kyros.files_v0.uploadFile(filePath, file, {
-				onProgress: ({ progress }) => {
-					uploadState.value.currentFileProgress = progress
-					uploadState.value.uploadedBytes = completedBytes + Math.round(file.size * progress)
+				onProgress: ({ loaded }) => {
+					uploadState.value.uploadedBytes = completedBytes + Math.min(loaded, file.size)
 				},
 			})
 			activeUploadCancel = () => uploader.cancel()
@@ -420,7 +417,6 @@ async function uploadFiles(files: File[]) {
 	uploadState.value = {
 		isUploading: false,
 		currentFileName: null,
-		currentFileProgress: 0,
 		uploadedBytes: 0,
 		totalBytes: 0,
 		completedFiles: 0,
diff --git a/packages/ui/src/stories/servers/EditServerIcon.stories.ts b/packages/ui/src/stories/servers/EditServerIcon.stories.ts
index a9b0bfdf6f..3a95bf10a4 100644
--- a/packages/ui/src/stories/servers/EditServerIcon.stories.ts
+++ b/packages/ui/src/stories/servers/EditServerIcon.stories.ts
@@ -46,7 +46,6 @@ const meta = {
 				const uploadState = ref<UploadState>({
 					isUploading: false,
 					currentFileName: null,
-					currentFileProgress: 0,
 					uploadedBytes: 0,
 					totalBytes: 0,
 					completedFiles: 0,
diff --git a/packages/ui/src/stories/servers/ServerPanelAdmonitions.stories.ts b/packages/ui/src/stories/servers/ServerPanelAdmonitions.stories.ts
index 9afdf5b429..84f905dd5e 100644
--- a/packages/ui/src/stories/servers/ServerPanelAdmonitions.stories.ts
+++ b/packages/ui/src/stories/servers/ServerPanelAdmonitions.stories.ts
@@ -52,7 +52,6 @@ const meta = {
 				const uploadState = ref<UploadState>({
 					isUploading: true,
 					currentFileName: 'resourcepack.zip',
-					currentFileProgress: 0.2,
 					uploadedBytes: 20_000,
 					totalBytes: 100_000,
 					completedFiles: 1,