diff --git a/src/app/api/workers/resync-failed-files/route.ts b/src/app/api/workers/resync-failed-files/route.ts
new file mode 100644
index 0000000..18767af
--- /dev/null
+++ b/src/app/api/workers/resync-failed-files/route.ts
@@ -0,0 +1,6 @@
+import { resyncFailedFiles } from '@/features/workers/resync-failed-files/api/resync-failed-files.controller'
+import { withErrorHandler } from '@/utils/withErrorHandler'
+
+export const maxDuration = 300
+
+export const GET = withErrorHandler(resyncFailedFiles)
diff --git a/src/config/server.env.ts b/src/config/server.env.ts
index 44d0b7e..cd2d54d 100644
--- a/src/config/server.env.ts
+++ b/src/config/server.env.ts
@@ -12,6 +12,7 @@ const ServerEnvSchema = z.object({
   DROPBOX_SCOPES: z.string().min(1),
   DROPBOX_API_URL: z.url(),
   TRIGGER_MACHINE: TriggerMachineSchema,
+  CRON_SECRET: z.string().min(1),
 })
 
 const env = ServerEnvSchema.parse(process.env)
diff --git a/src/features/workers/resync-failed-files/api/resync-failed-files.controller.ts b/src/features/workers/resync-failed-files/api/resync-failed-files.controller.ts
new file mode 100644
index 0000000..a765f0f
--- /dev/null
+++ b/src/features/workers/resync-failed-files/api/resync-failed-files.controller.ts
@@ -0,0 +1,16 @@
+import httpStatus from 'http-status'
+import { type NextRequest, NextResponse } from 'next/server'
+import env from '@/config/server.env'
+import APIError from '@/errors/APIError'
+import { ResyncService } from '@/features/workers/resync-failed-files/lib/resync-failed-files.service'
+
+export const resyncFailedFiles = async (request: NextRequest) => {
+  const authHeader = request.headers.get('authorization')
+  if (authHeader !== `Bearer ${env.CRON_SECRET}`) {
+    throw new APIError('Unauthorized', httpStatus.UNAUTHORIZED)
+  }
+
+  const resyncService = new ResyncService()
+  await resyncService.resyncFailedFiles()
+  return NextResponse.json({ message: 'Succeslyfully trigger re syncing of files.' })
+}
diff --git a/src/features/workers/resync-failed-files/helper/resync-failed-files.helper.ts b/src/features/workers/resync-failed-files/helper/resync-failed-files.helper.ts
new file mode 100644
index 0000000..808aa1e
--- /dev/null
+++ b/src/features/workers/resync-failed-files/helper/resync-failed-files.helper.ts
@@ -0,0 +1,126 @@
+import { and, eq } from 'drizzle-orm'
+import z from 'zod'
+import env from '@/config/server.env'
+import db from '@/db'
+import { type FileSyncSelectType, fileFolderSync } from '@/db/schema/fileFolderSync.schema'
+import APIError from '@/errors/APIError'
+import { SyncService } from '@/features/sync/lib/Sync.service'
+import { DropboxFileListFolderSingleEntrySchema } from '@/features/sync/types'
+import { CopilotAPI } from '@/lib/copilot/CopilotAPI'
+import { generateToken } from '@/lib/copilot/generateToken'
+import User from '@/lib/copilot/models/User.model'
+import { DropboxClient } from '@/lib/dropbox/DropboxClient'
+
+export const syncFailedFilesToAssembly = async (
+  portalId: string,
+  failedSyncs: FileSyncSelectType[],
+) => {
+  const dropboxConnection = await getDropboxConnection(portalId)
+  if (!dropboxConnection) {
+    console.warn('Dropbox account not found for portal:', portalId)
+    return null
+  }
+
+  const { user, copilotApi, dbxClient, connectionToken, syncService } =
+    await initializeSyncDependencies(dropboxConnection, portalId)
+
+  for (const failedSync of failedSyncs) {
+    await processFailedSync(failedSync, copilotApi, dbxClient, syncService, user, connectionToken)
+  }
+}
+
+const getDropboxConnection = async (portalId: string) => {
+  const connection = await db.query.dropboxConnections.findFirst({
+    where: (dropboxConnections, { eq }) =>
+      and(eq(dropboxConnections.portalId, portalId), eq(dropboxConnections.status, true)),
+  })
+
+  if (!connection?.refreshToken || !connection?.accountId) {
+    console.error('⚠️ Dropbox connection not found for portal:', portalId)
+    return null
+  }
+
+  return connection
+}
+
+const initializeSyncDependencies = async (
+  dropboxConnection: NonNullable<Awaited<ReturnType<typeof getDropboxConnection>>>,
+  portalId: string,
+) => {
+  const { refreshToken, rootNamespaceId, accountId, initiatedBy } = dropboxConnection
+
+  if (!refreshToken || !accountId || !rootNamespaceId) {
+    throw new APIError(`Dropbox connection not found for portal: ${portalId}`, 404)
+  }
+
+  const token = generateToken(env.COPILOT_API_KEY, {
+    workspaceId: portalId,
+    internalUserId: initiatedBy,
+  })
+
+  const user = await User.authenticate(token)
+  const copilotApi = new CopilotAPI(token)
+  const dbxClient = new DropboxClient(refreshToken, rootNamespaceId)
+
+  const connectionToken = {
+    refreshToken,
+    accountId,
+    rootNamespaceId,
+  }
+
+  const syncService = new SyncService(user, connectionToken)
+
+  return { user, copilotApi, dbxClient, connectionToken, syncService }
+}
+
+const processFailedSync = async (
+  failedSync: FileSyncSelectType,
+  copilotApi: CopilotAPI,
+  dbxClient: DropboxClient,
+  syncService: SyncService,
+  user: Awaited<ReturnType<typeof User.authenticate>>,
+  connectionToken: { refreshToken: string; accountId: string; rootNamespaceId: string },
+) => {
+  const fileId = z.string().parse(failedSync.assemblyFileId)
+  const file = await copilotApi.retrieveFile(fileId)
+
+  // Only proceed if file is missing or pending in Assembly
+  if (file && file.status !== 'pending') return
+
+  const fileInDropbox = await getFileFromDropbox(dbxClient, failedSync.dbxFileId ?? '')
+  if (!fileInDropbox) return
+
+  const channelSync = await db.query.channelSync.findFirst({
+    where: (channelSync, { eq }) => eq(channelSync.id, failedSync.channelSyncId),
+  })
+
+  if (!channelSync) return
+
+  // Sync file from Dropbox to Assembly
+  const payload = {
+    entry: DropboxFileListFolderSingleEntrySchema.parse(fileInDropbox),
+    opts: {
+      dbxRootPath: channelSync.dbxRootPath,
+      assemblyChannelId: channelSync.assemblyChannelId,
+      channelSyncId: channelSync.id,
+      user,
+      connectionToken,
+    },
+  }
+
+  await syncService.syncDropboxFilesToAssembly(payload)
+  await db.delete(fileFolderSync).where(eq(fileFolderSync.id, failedSync.id))
+}
+
+const getFileFromDropbox = async (dbxClient: DropboxClient, dropboxFileId: string) => {
+  if (!dropboxFileId) return null
+
+  const dropboxClient = dbxClient.getDropboxClient()
+
+  try {
+    const fileMetadata = await dropboxClient.filesGetMetadata({ path: dropboxFileId })
+    return fileMetadata.result
+  } catch (_err) {
+    return null
+  }
+}
diff --git a/src/features/workers/resync-failed-files/lib/resync-failed-files.service.ts b/src/features/workers/resync-failed-files/lib/resync-failed-files.service.ts
new file mode 100644
index 0000000..7b5c839
--- /dev/null
+++ b/src/features/workers/resync-failed-files/lib/resync-failed-files.service.ts
@@ -0,0 +1,44 @@
+import { and, isNull } from 'drizzle-orm'
+import db from '@/db'
+import { ObjectType } from '@/db/constants'
+import { resyncFailedFilesInAssembly } from '@/trigger/processFileSync'
+import type { FailedSyncWorkspaceMap } from '../utils/types'
+
+export class ResyncService {
+  async resyncFailedFiles() {
+    const failedSyncs = await db.query.fileFolderSync.findMany({
+      where: (fileFolderSync, { eq }) =>
+        and(
+          isNull(fileFolderSync.contentHash),
+          eq(fileFolderSync.object, ObjectType.FILE),
+          isNull(fileFolderSync.deletedAt),
+        ),
+    })
+
+    console.info('Total number of failed syncs: ', failedSyncs.length)
+    const failedSyncWorkspaceMap: FailedSyncWorkspaceMap = failedSyncs.reduce(
+      (acc: FailedSyncWorkspaceMap, failedSync) => {
+        const portalId = failedSync.portalId
+
+        if (!acc[portalId]) {
+          acc[portalId] = []
+        }
+
+        acc[portalId].push(failedSync)
+        return acc
+      },
+      {},
+    )
+
+    for (const portalId in failedSyncWorkspaceMap) {
+      const failedSyncsForPortal = failedSyncWorkspaceMap[portalId]
+      resyncFailedFilesInAssembly.trigger({
+        portalId,
+        failedSyncs: failedSyncsForPortal,
+      })
+      console.info(
+        `Enqueued resync job for portal: ${portalId} with ${failedSyncsForPortal.length} files`,
+      )
+    }
+  }
+}
diff --git a/src/features/workers/resync-failed-files/utils/types.ts b/src/features/workers/resync-failed-files/utils/types.ts
new file mode 100644
index 0000000..fa68e84
--- /dev/null
+++ b/src/features/workers/resync-failed-files/utils/types.ts
@@ -0,0 +1,3 @@
+import type { FileSyncSelectType } from '@/db/schema/fileFolderSync.schema'
+
+export type FailedSyncWorkspaceMap = Record<string, FileSyncSelectType[]>
diff --git a/src/lib/copilot/CopilotAPI.ts b/src/lib/copilot/CopilotAPI.ts
index b43b31d..ac51919 100644
--- a/src/lib/copilot/CopilotAPI.ts
+++ b/src/lib/copilot/CopilotAPI.ts
@@ -23,6 +23,8 @@ import {
   CopilotFileCreateSchema,
   type CopilotFileList,
   CopilotFileListSchema,
+  CopilotFileRetrieve,
+  CopilotFileRetrieveSchema,
   type CopilotListArgs,
   type CopilotPrice,
   CopilotPriceSchema,
@@ -223,6 +225,11 @@ export class CopilotAPI {
     return CopilotFileListSchema.parse(list)
   }
 
+  async _retrieveFile(id: string): Promise<CopilotFileRetrieve> {
+    const file = await this.copilot.retrieveFile({ id })
+    return CopilotFileRetrieveSchema.parse(file)
+  }
+
   async _retrieveFileChannel(id: string) {
     const fileChannel = await this.copilot.retrieveFileChannel({ id })
     return CopilotFileChannelRetrieveSchema.parse(fileChannel)
@@ -260,6 +267,7 @@ export class CopilotAPI {
   uploadFile = this.wrapWithRetry(this._uploadFile)
   deleteFile = this.wrapWithRetry(this._deleteFile)
   listFiles = this.wrapWithRetry(this._listFiles)
+  retrieveFile = this.wrapWithRetry(this._retrieveFile)
   retrieveFileChannel = this.wrapWithRetry(this._retrieveFileChannel)
   listFileChannels = this.wrapWithRetry(this._listFileChannels)
 }
diff --git a/src/trigger/processFileSync.ts b/src/trigger/processFileSync.ts
index d3ea855..dadf47e 100644
--- a/src/trigger/processFileSync.ts
+++ b/src/trigger/processFileSync.ts
@@ -3,7 +3,7 @@ import { and, eq, isNotNull } from 'drizzle-orm'
 import z from 'zod'
 import env from '@/config/server.env'
 import type { DropboxConnectionTokens } from '@/db/schema/dropboxConnections.schema'
-import { fileFolderSync } from '@/db/schema/fileFolderSync.schema'
+import { type FileSyncSelectType, fileFolderSync } from '@/db/schema/fileFolderSync.schema'
 import { MAX_FILES_LIMIT } from '@/features/sync/constant'
 import { MapFilesService } from '@/features/sync/lib/MapFiles.service'
 import { SyncService } from '@/features/sync/lib/Sync.service'
@@ -15,6 +15,7 @@ import {
   type WhereClause,
 } from '@/features/sync/types'
 import { DropboxWebhook } from '@/features/webhook/dropbox/lib/webhook.service'
+import { syncFailedFilesToAssembly } from '@/features/workers/resync-failed-files/helper/resync-failed-files.helper'
 import { CopilotAPI } from '@/lib/copilot/CopilotAPI'
 import type User from '@/lib/copilot/models/User.model'
 import { DropboxAuthClient } from '@/lib/dropbox/DropboxAuthClient'
@@ -399,3 +400,19 @@ export const updateAssemblyFileInDropbox = task({
     await syncAssemblyFileToDropbox.trigger(payload)
   },
 })
+
+export const resyncFailedFilesInAssembly = task({
+  id: 'resync-failed-files-in-assembly',
+  machine,
+  queue: {
+    name: 'resync-failed-files-in-assembly',
+    concurrencyLimit: 5,
+  },
+  retry: {
+    maxAttempts: 3,
+  },
+  run: async (payload: { portalId: string; failedSyncs: FileSyncSelectType[] }) => {
+    const { portalId, failedSyncs } = payload
+    await syncFailedFilesToAssembly(portalId, failedSyncs)
+  },
+})
diff --git a/vercel.json b/vercel.json
new file mode 100644
index 0000000..de818b3
--- /dev/null
+++ b/vercel.json
@@ -0,0 +1,11 @@
+{
+  "$schema": "https://openapi.vercel.sh/vercel.json",
+  "regions": ["iad1", "pdx1"],
+  "buildCommand": "./scripts/build/build.sh",
+  "crons": [
+    {
+      "path": "/api/workers/resync-failed-files",
+      "schedule": "0 0 * * *"
+    }
+  ]
+}