diff --git a/apps/sim/app/api/files/utils.test.ts b/apps/sim/app/api/files/utils.test.ts
index b495df731d5..7a01716b04e 100644
--- a/apps/sim/app/api/files/utils.test.ts
+++ b/apps/sim/app/api/files/utils.test.ts
@@ -178,6 +178,15 @@ describe('extractFilename', () => {
         expect(response.headers.get('Content-Security-Policy')).toBeNull()
       })
 
+      it('appends the content-type extension to an extensionless download name', () => {
+        const response = createFileResponse({
+          buffer: Buffer.from('fake-image-data'),
+          contentType: 'image/png',
+          filename: 'navbar_2',
+        })
+        expect(response.headers.get('Content-Disposition')).toBe('inline; filename="navbar_2.png"')
+      })
+
       it('defaults to a PRIVATE cache so access-verified content is never shared-cached', () => {
         const response = createFileResponse({
           buffer: Buffer.from('fake-image-data'),
diff --git a/apps/sim/app/api/files/utils.ts b/apps/sim/app/api/files/utils.ts
index c74679197b0..c7bd642db8e 100644
--- a/apps/sim/app/api/files/utils.ts
+++ b/apps/sim/app/api/files/utils.ts
@@ -4,7 +4,7 @@ import {
   isPayloadSizeLimitError,
   readNodeStreamToBufferWithLimit,
 } from '@/lib/core/utils/stream-limits'
-import { sanitizeFileKey } from '@/lib/uploads/utils/file-utils'
+import { ensureFileNameExtension, sanitizeFileKey } from '@/lib/uploads/utils/file-utils'
 
 const logger = createLogger('FilesUtils')
 
@@ -240,16 +240,13 @@ export function encodeFilenameForHeader(storageKey: string): string {
   return `filename="${asciiSafe}"; filename*=UTF-8''${encodeExtValue(filename)}`
 }
 
+/**
+ * Derives the served filename from the CALLER's content type (`getSecureFileHeaders`
+ * downgrades `text/html`) before the header decision, so a derived `.html` name gets the
+ * same forced-attachment treatment a stored `.html` file gets.
+ */
 export function createFileResponse(file: FileResponse): NextResponse {
-  // Sim pages store an extensionless name and serve/download as compiled
-  // HTML — re-append the extension so the saved file opens in a browser.
-  // Decided from the CALLER's content type (getSecureFileHeaders downgrades
-  // text/html), and BEFORE the header decision, so the .html name gets the
-  // same forced-attachment treatment a legacy .html file gets.
-  const servedFilename =
-    file.contentType === 'text/html' && !/\.[A-Za-z0-9]{1,8}$/.test(file.filename)
-      ? `${file.filename}.html`
-      : file.filename
+  const servedFilename = ensureFileNameExtension(file.filename, file.contentType)
 
   const { contentType, disposition } = getSecureFileHeaders(servedFilename, file.contentType)
 
diff --git a/apps/sim/app/api/v2/files/bulk-download/route.ts b/apps/sim/app/api/v2/files/bulk-download/route.ts
index 06c7a9096af..b2d51b44d21 100644
--- a/apps/sim/app/api/v2/files/bulk-download/route.ts
+++ b/apps/sim/app/api/v2/files/bulk-download/route.ts
@@ -58,6 +58,7 @@ export const GET = defineV2BinaryRoute({
       filesToZip.map((file) => ({
         name: file.name,
         folderPath: file.folderId ? folderPaths.get(file.folderId) : null,
+        contentType: file.type,
       }))
     )
     const archive = new ZipArchive({ store: true })
diff --git a/apps/sim/app/api/workspaces/[id]/files/download/route.ts b/apps/sim/app/api/workspaces/[id]/files/download/route.ts
index 6d4220fd1a2..f1ccd1ce2bd 100644
--- a/apps/sim/app/api/workspaces/[id]/files/download/route.ts
+++ b/apps/sim/app/api/workspaces/[id]/files/download/route.ts
@@ -46,6 +46,7 @@ export const GET = defineInternalBinaryRoute({
       filesToZip.map((file) => ({
         name: file.name,
         folderPath: file.folderId ? folderPaths.get(file.folderId) : null,
+        contentType: file.type,
       }))
     )
     const archive = new ZipArchive({ store: true })
diff --git a/apps/sim/lib/internal/file/operations.ts b/apps/sim/lib/internal/file/operations.ts
index 1f432057b97..5ae07140097 100644
--- a/apps/sim/lib/internal/file/operations.ts
+++ b/apps/sim/lib/internal/file/operations.ts
@@ -1750,7 +1750,11 @@ export async function executeFileManageOperation(
         // Mirror the workspace folder layout, dropping the ancestor chain the whole
         // selection shares so archiving one folder does not nest it under its parents.
         const entryPaths = buildZipEntryPaths(
-          archiveEntries.map((entry) => ({ name: entry.file.name, folderPath: entry.folderPath })),
+          archiveEntries.map((entry) => ({
+            name: entry.file.name,
+            folderPath: entry.folderPath,
+            contentType: entry.file.type,
+          })),
           { rebaseOnCommonFolder: true }
         )
 
diff --git a/apps/sim/lib/uploads/contexts/workspace/fetch-external-url.test.ts b/apps/sim/lib/uploads/contexts/workspace/fetch-external-url.test.ts
index d00eceb0fae..e13fbefd7df 100644
--- a/apps/sim/lib/uploads/contexts/workspace/fetch-external-url.test.ts
+++ b/apps/sim/lib/uploads/contexts/workspace/fetch-external-url.test.ts
@@ -234,6 +234,25 @@ describe('fetchExternalUrlToWorkspace', () => {
     )
   })
 
+  it('names a bare download path by the response content type', async () => {
+    secureFetchWithPinnedIPSpy.mockResolvedValueOnce(makeResponse('jpeg bytes', 'image/jpeg'))
+
+    const result = await fetchExternalUrlToWorkspace({
+      url: 'https://cdn.example.com/assets/8f1c/download',
+      userId: 'user-1',
+      workspaceId: 'workspace-1',
+    })
+
+    expect(result.filename).toBe('download.jpg')
+    expect(uploadWorkspaceFileSpy).toHaveBeenCalledWith(
+      'workspace-1',
+      'user-1',
+      expect.any(Buffer),
+      'download.jpg',
+      'image/jpeg'
+    )
+  })
+
   it('forwards custom headers to the fetch', async () => {
     secureFetchWithPinnedIPSpy.mockResolvedValue(makeResponse('bytes', 'text/plain'))
 
diff --git a/apps/sim/lib/uploads/contexts/workspace/fetch-external-url.ts b/apps/sim/lib/uploads/contexts/workspace/fetch-external-url.ts
index 23b04edbd3c..b290b20b78b 100644
--- a/apps/sim/lib/uploads/contexts/workspace/fetch-external-url.ts
+++ b/apps/sim/lib/uploads/contexts/workspace/fetch-external-url.ts
@@ -12,7 +12,7 @@ import {
   readResponseToBufferWithLimit,
 } from '@/lib/core/utils/stream-limits'
 import { uploadWorkspaceFile } from '@/lib/uploads/contexts/workspace/workspace-file-manager'
-import { getMimeTypeFromExtension } from '@/lib/uploads/utils/file-utils'
+import { ensureFileNameExtension, getMimeTypeFromExtension } from '@/lib/uploads/utils/file-utils'
 import { getUserEntityPermissions } from '@/lib/workspaces/permissions/utils'
 import type { UserFile } from '@/executor/types'
 
@@ -92,8 +92,8 @@ export async function fetchExternalUrlToWorkspace(
     throw new ExternalUrlValidationError(urlValidation.error)
   }
 
-  const filename = new URL(url).pathname.split('/').pop() || 'download'
-  const extension = path.extname(filename).toLowerCase().substring(1)
+  const pathFilename = new URL(url).pathname.split('/').pop() || 'download'
+  const extension = path.extname(pathFilename).toLowerCase().substring(1)
 
   const response = await secureFetchWithPinnedIP(url, urlValidation.resolvedIP, {
     profile: 'contentFetch',
@@ -119,6 +119,7 @@ export async function fetchExternalUrlToWorkspace(
   })
 
   const mimeType = response.headers.get('content-type') || getMimeTypeFromExtension(extension)
+  const filename = ensureFileNameExtension(pathFilename, mimeType)
 
   let savedWorkspaceFile: UserFile | undefined
   if (workspaceId && saveToWorkspace) {
diff --git a/apps/sim/lib/uploads/utils/file-utils.test.ts b/apps/sim/lib/uploads/utils/file-utils.test.ts
index b51a2d78102..fbc7a69c376 100644
--- a/apps/sim/lib/uploads/utils/file-utils.test.ts
+++ b/apps/sim/lib/uploads/utils/file-utils.test.ts
@@ -4,8 +4,10 @@
 import { createLogger } from '@sim/logger'
 import { describe, expect, it } from 'vitest'
 import {
+  ensureFileNameExtension,
   extractStorageKey,
   extractWorkspaceIdFromStorageKey,
+  getExtensionFromMimeType,
   getMimeTypeFromExtension,
   inferContextFromKey,
   isAbortError,
@@ -311,3 +313,25 @@ describe('resolveMediaMimeType', () => {
     expect(resolveMediaMimeType(null, 'weird.bin', 'video')).toBe('video/mp4')
   })
 })
+
+describe('getExtensionFromMimeType', () => {
+  it('ignores content-type parameters', () => {
+    expect(getExtensionFromMimeType('image/png')).toBe('png')
+    expect(getExtensionFromMimeType('text/html; charset=utf-8')).toBe('html')
+    expect(getExtensionFromMimeType('application/octet-stream')).toBeNull()
+  })
+})
+
+describe('ensureFileNameExtension', () => {
+  it('appends the content-type extension only when the name has none', () => {
+    expect(ensureFileNameExtension('navbar_2', 'image/png')).toBe('navbar_2.png')
+    expect(ensureFileNameExtension('download (641)', 'image/jpeg; charset=binary')).toBe(
+      'download (641).jpg'
+    )
+    expect(ensureFileNameExtension('hero.png', 'image/jpeg')).toBe('hero.png')
+    expect(ensureFileNameExtension('site.webmanifest', 'application/json')).toBe('site.webmanifest')
+    expect(ensureFileNameExtension('Sim.ai <> RVTech', 'text/html')).toBe('Sim.ai <> RVTech.html')
+    expect(ensureFileNameExtension('blob', 'application/octet-stream')).toBe('blob')
+    expect(ensureFileNameExtension('blob', null)).toBe('blob')
+  })
+})
diff --git a/apps/sim/lib/uploads/utils/file-utils.ts b/apps/sim/lib/uploads/utils/file-utils.ts
index 3f0df1c73c8..b00ac1ab7ee 100644
--- a/apps/sim/lib/uploads/utils/file-utils.ts
+++ b/apps/sim/lib/uploads/utils/file-utils.ts
@@ -3,6 +3,7 @@ import { omit } from '@sim/utils/object'
 import type { StorageContext } from '@/lib/uploads'
 import {
   ACCEPTED_FILE_TYPES,
+  isAlphanumericExtension,
   SUPPORTED_ARCHIVE_EXTENSIONS,
   SUPPORTED_DOCUMENT_EXTENSIONS,
 } from '@/lib/uploads/utils/validation'
@@ -609,12 +610,25 @@ const MIME_TO_EXTENSION: Record<string, string> = {
 }
 
 /**
- * Get file extension from MIME type
+ * Get file extension from MIME type. Parameters such as `; charset=utf-8` are ignored.
  * @param mimeType - MIME type string
  * @returns File extension without dot, or null if not found
  */
 export function getExtensionFromMimeType(mimeType: string): string | null {
-  return MIME_TO_EXTENSION[mimeType.toLowerCase()] || null
+  return MIME_TO_EXTENSION[mimeType.split(';')[0].trim().toLowerCase()] || null
+}
+
+/**
+ * Appends the extension the content type implies when a file name carries none, so a
+ * saved copy opens in the right application.
+ */
+export function ensureFileNameExtension(
+  fileName: string,
+  contentType: string | null | undefined
+): string {
+  if (!contentType || isAlphanumericExtension(getFileExtension(fileName))) return fileName
+  const extension = getExtensionFromMimeType(contentType)
+  return extension ? `${fileName}.${extension}` : fileName
 }
 
 /**
diff --git a/apps/sim/lib/uploads/zip-entry-path.test.ts b/apps/sim/lib/uploads/zip-entry-path.test.ts
index c51d6080891..c8d8aae178c 100644
--- a/apps/sim/lib/uploads/zip-entry-path.test.ts
+++ b/apps/sim/lib/uploads/zip-entry-path.test.ts
@@ -19,6 +19,16 @@ describe('buildZipEntryPaths', () => {
     ])
   })
 
+  it('appends the content-type extension to an extensionless name', () => {
+    expect(
+      buildZipEntryPaths([
+        { name: 'navbar_2', folderPath: 'Screenshots', contentType: 'image/png' },
+        { name: 'navbar_2', folderPath: 'Screenshots', contentType: 'image/png' },
+        { name: 'readme', folderPath: null },
+      ])
+    ).toEqual(['Screenshots/navbar_2.png', 'Screenshots/navbar_2 (1).png', 'readme'])
+  })
+
   it('sanitizes a slash within one escaped folder name instead of nesting it', () => {
     expect(
       buildZipEntryPaths([{ name: 'contract.pdf', folderPath: 'Finance\\/Legal/Quarterly' }])
diff --git a/apps/sim/lib/uploads/zip-entry-path.ts b/apps/sim/lib/uploads/zip-entry-path.ts
index 5f7cc254f3b..d3f4e895abd 100644
--- a/apps/sim/lib/uploads/zip-entry-path.ts
+++ b/apps/sim/lib/uploads/zip-entry-path.ts
@@ -1,3 +1,4 @@
+import { ensureFileNameExtension } from '@/lib/uploads/utils/file-utils'
 import { parseWorkspaceFileFolderDisplayPath } from '@/lib/workspace-files/folder-display-path'
 
 /** Characters that are illegal in file names on common desktop platforms. */
@@ -9,6 +10,8 @@ export interface ZipEntrySource {
   name: string
   /** Workspace-root-relative folder path holding the file, or null when it sits at the root. */
   folderPath?: string | null
+  /** Stored content type; supplies the extension when the name carries none. */
+  contentType?: string | null
 }
 
 export interface BuildZipEntryPathsOptions {
@@ -109,7 +112,7 @@ export function buildZipEntryPaths(
   const usedPaths = new Set<string>()
 
   return sources.map((source) => {
-    const leafName = toLeafName(source.name)
+    const leafName = ensureFileNameExtension(toLeafName(source.name), source.contentType)
     const folderSegments = toSegments(source.folderPath).slice(rebaseLength)
     const basePath = safeEntryPath([...folderSegments, leafName]) || leafName