simstudioai · waleedlatif1 · Aug 18, 2026 · Aug 17, 2026 · Aug 17, 2026 · Aug 17, 2026
diff --git a/apps/sim/app/api/tools/file/manage/route.ts b/apps/sim/app/api/tools/file/manage/route.ts
@@ -34,6 +34,7 @@ import {
   type DecompressResult,
   decompressArchiveBufferToWorkspaceFiles,
   MAX_ARCHIVE_BYTES,
+  statusForArchiveError,
 } from '@/lib/uploads/archive'
 import type { getWorkspaceFile } from '@/lib/uploads/contexts/workspace/workspace-file-manager'
 import {
@@ -1183,7 +1184,7 @@ export const POST = withRouteHandler(async (request: NextRequest) => {
           if (archiveError instanceof ArchiveError) {
             // The error message is single-sourced in ArchiveError (caps included);
             // only the HTTP status is mapped here.
-            const status = archiveError.reason === 'invalid' ? 400 : 413
+            const status = statusForArchiveError(archiveError)
             return NextResponse.json(
               { success: false, error: `"${archive.name}": ${archiveError.message}` },
               { status }

diff --git a/apps/sim/app/api/webhooks/outbox/process/route.ts b/apps/sim/app/api/webhooks/outbox/process/route.ts
@@ -10,6 +10,7 @@ import { processOutboxEvents } from '@/lib/core/outbox/service'
 import { generateRequestId } from '@/lib/core/utils/request'
 import { withRouteHandler } from '@/lib/core/utils/with-route-handler'
 import { knowledgeDocumentProcessingOutboxHandlers } from '@/lib/knowledge/documents/processing-outbox-handler'
+import { workspaceFileStorageCleanupOutboxHandlers } from '@/lib/uploads/contexts/workspace/workspace-file-storage-cleanup-outbox'
 import { workflowDeploymentOutboxHandlers } from '@/lib/workflows/deployment-outbox'
 import { invitationMigrationOutboxHandlers } from '@/lib/workspaces/admin-move'
 import { reapStaleBackgroundWork } from '@/ee/workspace-forking/lib/background-work/store'
@@ -25,6 +26,7 @@ const handlers = {
   ...enterpriseIssuanceOutboxHandlers,
   ...invitationMigrationOutboxHandlers,
   ...knowledgeDocumentProcessingOutboxHandlers,
+  ...workspaceFileStorageCleanupOutboxHandlers,
   ...workflowDeploymentOutboxHandlers,
 } as const
 

diff --git a/apps/sim/app/api/workspaces/[id]/files/[fileId]/extract/route.test.ts b/apps/sim/app/api/workspaces/[id]/files/[fileId]/extract/route.test.ts
@@ -0,0 +1,82 @@
+/**
+ * @vitest-environment node
+ */
+import { NextRequest } from 'next/server'
+import { beforeEach, describe, expect, it, vi } from 'vitest'
+
+const mocks = vi.hoisted(() => ({
+  getSession: vi.fn(),
+  extract: vi.fn(),
+}))
+
+vi.mock('@/lib/auth', () => ({ getSession: mocks.getSession }))
+
+vi.mock('@/lib/workspace-files/application/extract-workspace-file', () => ({
+  extractWorkspaceFile: {
+    operation: { id: 'files.extract_archive', minimumRole: 'write', workspaceApiKey: 'deny' },
+    execute: mocks.extract,
+  },
+}))
+
+import { ArchiveError } from '@/lib/uploads/archive'
+import { POST } from '@/app/api/workspaces/[id]/files/[fileId]/extract/route'
+
+const WORKSPACE_ID = 'workspace-1'
+const FILE_ID = 'wf_1'
+const context = { params: Promise.resolve({ id: WORKSPACE_ID, fileId: FILE_ID }) }
+
+function callExtract() {
+  return POST(
+    new NextRequest(
+      `http://localhost:3000/api/workspaces/${WORKSPACE_ID}/files/${FILE_ID}/extract`,
+      { method: 'POST' }
+    ),
+    context
+  )
+}
+
+describe('POST /api/workspaces/[id]/files/[fileId]/extract', () => {
+  beforeEach(() => {
+    vi.clearAllMocks()
+    mocks.getSession.mockResolvedValue({
+      user: { id: 'user-1' },
+      session: { id: 'session-1' },
+    })
+    mocks.extract.mockResolvedValue({ folderName: 'bundle', extractedCount: 2, skippedCount: 0 })
+  })
+
+  it('passes a session principal and canonical assertion to the extraction use case', async () => {
+    const response = await callExtract()
+
+    expect(response.status).toBe(200)
+    expect(await response.json()).toEqual({
+      success: true,
+      folderName: 'bundle',
+      extractedCount: 2,
+      skippedCount: 0,
+    })
+    expect(mocks.extract).toHaveBeenCalledWith({
+      principal: { kind: 'session', userId: 'user-1', sessionId: 'session-1' },
+      input: { fileId: FILE_ID, assertedWorkspaceId: WORKSPACE_ID },
+      request: expect.anything(),
+    })
+  })
+
+  it('authenticates before invoking extraction', async () => {
+    mocks.getSession.mockResolvedValue(null)
+
+    const response = await callExtract()
+
+    expect(response.status).toBe(401)
+    expect(mocks.extract).not.toHaveBeenCalled()
+  })
+
+  it('returns a caller-safe error for an invalid zip', async () => {
+    mocks.extract.mockRejectedValue(new ArchiveError('invalid', 'Not a valid .zip archive.'))
+
+    const response = await callExtract()
+
+    expect(response.status).toBe(400)
+    expect(await response.json()).toEqual({ error: 'Not a valid .zip archive.' })
+  })
+})
diff --git a/apps/sim/app/api/workspaces/[id]/files/[fileId]/extract/route.ts b/apps/sim/app/api/workspaces/[id]/files/[fileId]/extract/route.ts
@@ -0,0 +1,27 @@
+import { extractWorkspaceFileContract } from '@/lib/api/contracts/workspace-files'
+import {
+  defineInternalJsonRoute,
+  internalRateLimits,
+  internalSessionAuth,
+} from '@/lib/api/server/routes'
+import { internalFileErrorPolicies } from '@/lib/workspace-files/api'
+import { extractWorkspaceFile } from '@/lib/workspace-files/application/extract-workspace-file'
+import { fileOperations } from '@/lib/workspace-files/application/operations'
+
+export const dynamic = 'force-dynamic'
+export const maxDuration = 300
+
+/**
+ * POST /api/workspaces/[id]/files/[fileId]/extract
+ * Unzip an archive file into a new folder beside it (requires write permission)
+ */
+export const POST = defineInternalJsonRoute({
+  contract: extractWorkspaceFileContract,
+  auth: internalSessionAuth,
+  operation: fileOperations.extractArchive,
+  rateLimit: internalRateLimits.none({ reason: 'Preserve existing internal file behavior' }),
+  errorPolicy: internalFileErrorPolicies.extractArchive,
+  mapInput: ({ params }) => ({ fileId: params.fileId, assertedWorkspaceId: params.id }),
+  useCase: extractWorkspaceFile,
+  present: (result) => ({ success: true, ...result }),
+})
diff --git a/apps/sim/app/workspace/[workspaceId]/files/files.tsx b/apps/sim/app/workspace/[workspaceId]/files/files.tsx
@@ -33,12 +33,14 @@ import {
   formatFileSize,
   getFileExtension,
   getMimeTypeFromExtension,
+  isArchiveFileName,
   isAudioFileType,
   isVideoFileType,
   resolveEffectiveMimeType,
 } from '@/lib/uploads/utils/file-utils'
 import {
   isSupportedExtension,
+  SUPPORTED_ARCHIVE_EXTENSIONS,
   SUPPORTED_AUDIO_EXTENSIONS,
   SUPPORTED_CODE_EXTENSIONS,
   SUPPORTED_DOCUMENT_EXTENSIONS,
@@ -119,6 +121,7 @@ import { useWorkspaceMembersQuery, type WorkspaceMember } from '@/hooks/queries/
 import {
   useBulkArchiveWorkspaceFileItems,
   useCreateWorkspaceFileFolder,
+  useExtractWorkspaceFile,
   useMoveWorkspaceFileItems,
   useUpdateWorkspaceFileFolder,
   useWorkspaceFileFolders,
@@ -174,6 +177,7 @@ const SUPPORTED_EXTENSIONS = [
   ...SUPPORTED_AUDIO_EXTENSIONS,
   ...SUPPORTED_VIDEO_EXTENSIONS,
   ...SUPPORTED_IMAGE_EXTENSIONS,
+  ...SUPPORTED_ARCHIVE_EXTENSIONS,
 ] as const
 
 const ACCEPT_ATTR = SUPPORTED_EXTENSIONS.map((ext) => `.${ext}`).join(',')
@@ -189,6 +193,7 @@ const COLUMNS: ResourceColumn[] = [
 
 const MIME_TYPE_LABELS: Record<string, string> = {
   'application/pdf': 'PDF',
+  'application/zip': 'ZIP',
   'application/msword': 'Word',
   'application/vnd.openxmlformats-officedocument.wordprocessingml.document': 'Word',
   'application/vnd.ms-excel': 'Excel',
@@ -277,6 +282,7 @@ export function Files() {
   const deleteFile = useDeleteWorkspaceFile()
   const renameFile = useRenameWorkspaceFile()
   const createFolder = useCreateWorkspaceFileFolder()
+  const extractFile = useExtractWorkspaceFile()
   const updateFolder = useUpdateWorkspaceFileFolder()
   const moveItems = useMoveWorkspaceFileItems()
   const bulkArchiveItems = useBulkArchiveWorkspaceFileItems()
@@ -386,6 +392,8 @@ export function Files() {
   })
   const [showUnsavedChangesAlert, setShowUnsavedChangesAlert] = useState(false)
   const [showDeleteConfirm, setShowDeleteConfirm] = useState(false)
+  const [extractTargetId, setExtractTargetId] = useState<string | null>(null)
+  const extractTarget = extractTargetId ? (fileById.get(extractTargetId) ?? null) : null
   const contextMenuItemRef = useRef<FileResourceItem | null>(null)
   const [deleteTarget, setDeleteTarget] = useState<{
     fileIds: string[]
@@ -1430,6 +1438,11 @@ export function Files() {
           void setFilesParams({ folderId: parsed.id, new: null })
           return
         }
+        const file = fileByIdRef.current.get(parsed.id)
+        if (file && isArchiveFileName(file.name)) {
+          setExtractTargetId(file.id)
+          return
+        }
         router.push(
           currentFolderId
             ? `/workspace/${workspaceId}/files/${parsed.id}?folderId=${currentFolderId}`
@@ -1440,6 +1453,21 @@ export function Files() {
     [router, workspaceId, currentFolderId, setFilesParams]
   )
 
+  const handleExtract = async () => {
+    if (!extractTarget || !canEdit) return
+    try {
+      await extractFile.mutateAsync({
+        workspaceId,
+        fileId: extractTarget.id,
+        fileName: extractTarget.name,
+      })
+    } catch (error) {
+      logger.error('Failed to unzip archive:', error)
+    } finally {
+      setExtractTargetId(null)
+    }
+  }
+
   const handleUploadClick = useCallback(() => {
     if (!canEdit || uploading) return
     fileInputRef.current?.click()
@@ -1895,9 +1923,14 @@ export function Files() {
                 }
               />
               {isDraggingOver ? (
-                <div className='pointer-events-none absolute inset-0 z-10 flex flex-col items-center justify-center gap-2 border border-[var(--brand-secondary)] border-dashed bg-[var(--bg)]/80 transition-colors'>
+                <div className='pointer-events-none absolute inset-0 z-[var(--z-dropdown)] flex flex-col items-center justify-center gap-2 border border-[var(--brand-secondary)] border-dashed bg-[var(--white)] transition-colors dark:bg-[var(--surface-4)]'>
                   <Upload className='size-5 text-[var(--brand-secondary)]' />
-                  <p className='text-[var(--brand-secondary)] text-sm'>Drop to upload</p>
+                  <div className='flex flex-col gap-0.5 text-center'>
+                    <p className='text-[var(--brand-secondary)] text-sm'>Drop to upload</p>
+                    <p className='text-[var(--text-tertiary)] text-xs'>
+                      Release files here to add them to this workspace
+                    </p>
+                  </div>
                 </div>
               ) : null}
             </>
@@ -1944,6 +1977,25 @@ export function Files() {
         isPending={deleteFile.isPending || bulkArchiveItems.isPending}
       />
 
+      <ChipConfirmModal
+        open={Boolean(extractTarget)}
+        onOpenChange={(open) => !open && setExtractTargetId(null)}
+        title='Unzip archive?'
+        text={[
+          'This will unzip ',
+          { text: extractTarget?.name ?? 'this archive', bold: true },
+          ' into a new folder beside it.',
+        ]}
+        confirm={{
+          label: 'Unzip',
+          onClick: () => void handleExtract(),
+          variant: 'primary',
+          pending: extractFile.isPending,
+          pendingLabel: 'Unzipping...',
+          disabled: !canEdit,
+        }}
+      />
+
       {shareModal}
 
       <input

diff --git a/apps/sim/hooks/queries/workspace-file-folders.test.ts b/apps/sim/hooks/queries/workspace-file-folders.test.ts
@@ -0,0 +1,55 @@
+/**
+ * @vitest-environment node
+ */
+import { beforeEach, describe, expect, it, vi } from 'vitest'
+import { ApiClientError } from '@/lib/api/client/errors'
+import { useExtractWorkspaceFile } from '@/hooks/queries/workspace-file-folders'
+
+const { queryClient } = vi.hoisted(() => ({
+  queryClient: {
+    invalidateQueries: vi.fn(),
+  },
+}))
+
+vi.mock('@sim/emcn', () => ({
+  toast: { error: vi.fn(), success: vi.fn() },
+}))
+
+vi.mock('@tanstack/react-query', () => ({
+  keepPreviousData: {},
+  useMutation: vi.fn((options) => options),
+  useQuery: vi.fn(),
+  useQueryClient: vi.fn(() => queryClient),
+}))
+
+vi.mock('@/lib/api/client/request', () => ({ requestJson: vi.fn() }))
+
+const variables = { workspaceId: 'workspace-1', fileId: 'file-1', fileName: 'archive.zip' }
+
+describe('useExtractWorkspaceFile reconciliation', () => {
+  beforeEach(() => {
+    vi.clearAllMocks()
+  })
+
+  it('invalidates file browsers after success', () => {
+    const mutation = useExtractWorkspaceFile()
+
+    mutation.onSuccess(
+      { success: true, folderName: 'archive', extractedCount: 2, skippedCount: 0 },
+      variables
+    )
+    mutation.onSettled(undefined, undefined, variables)
+
+    expect(queryClient.invalidateQueries).toHaveBeenCalledTimes(3)
+  })
+
+  it('invalidates file browsers after an API error response', () => {
+    const mutation = useExtractWorkspaceFile()
+    const error = new ApiClientError({ status: 409, message: 'Folder exists', body: {} })
+
+    mutation.onError(error, variables)
+    mutation.onSettled(undefined, error, variables)
+
+    expect(queryClient.invalidateQueries).toHaveBeenCalledTimes(3)
+  })
+})
diff --git a/apps/sim/hooks/queries/workspace-file-folders.ts b/apps/sim/hooks/queries/workspace-file-folders.ts
@@ -11,6 +11,7 @@ import {
   updateWorkspaceFileFolderContract,
   type WorkspaceFileFolderApi,
 } from '@/lib/api/contracts/workspace-file-folders'
+import { extractWorkspaceFileContract } from '@/lib/api/contracts/workspace-files'
 import {
   buildWorkspaceFileFolderDisplayPath,
   parseWorkspaceFileFolderDisplayPath,
@@ -87,6 +88,25 @@ export function useCreateWorkspaceFileFolder() {
   })
 }
 
+export function useExtractWorkspaceFile() {
+  const queryClient = useQueryClient()
+  return useMutation({
+    mutationFn: async (variables: { workspaceId: string; fileId: string; fileName: string }) =>
+      requestJson(extractWorkspaceFileContract, {
+        params: { id: variables.workspaceId, fileId: variables.fileId },
+      }),
+    onSuccess: (data, variables) => {
+      toast.success(`Unzipped "${variables.fileName}" into "${data.folderName}"`)
+    },
+    onError: (error) => {
+      toast.error(toError(error).message)
+    },
+    onSettled: (_data, _error, variables) => {
+      invalidateWorkspaceFileBrowsers(queryClient, variables.workspaceId)
+    },
+  })
+}
+
 export function useUpdateWorkspaceFileFolder() {
   const queryClient = useQueryClient()
   return useMutation({

diff --git a/apps/sim/lib/api/contracts/workspace-files.ts b/apps/sim/lib/api/contracts/workspace-files.ts
@@ -145,6 +145,14 @@ const listWorkspaceFilesResponseSchema = workspaceFileSuccessSchema.extend({
 
 export type ListWorkspaceFilesResponse = z.output<typeof listWorkspaceFilesResponseSchema>
 
+export const extractWorkspaceFileResponseSchema = workspaceFileSuccessSchema.extend({
+  folderName: z.string(),
+  extractedCount: z.number().int().nonnegative(),
+  skippedCount: z.number().int().nonnegative(),
+})
+
+export type ExtractWorkspaceFileResponse = z.output<typeof extractWorkspaceFileResponseSchema>
+
 export const listWorkspaceFilesContract = defineRouteContract({
   method: 'GET',
   path: '/api/workspaces/[id]/files',
@@ -184,6 +192,16 @@ export const renameWorkspaceFileContract = defineRouteContract({
   error: renameWorkspaceFileErrorSchema,
 })
 
+export const extractWorkspaceFileContract = defineRouteContract({
+  method: 'POST',
+  path: '/api/workspaces/[id]/files/[fileId]/extract',
+  params: workspaceFileParamsSchema,
+  response: {
+    mode: 'json',
+    schema: extractWorkspaceFileResponseSchema,
+  },
+})
+
 export const updateWorkspaceFileDimensionsContract = defineRouteContract({
   method: 'PATCH',
   path: '/api/workspaces/[id]/files/[fileId]/dimensions',