diff --git a/apps/sim/app/workspace/[workspaceId]/components/impersonation-banner/impersonation-expired.tsx b/apps/sim/app/workspace/[workspaceId]/components/impersonation-banner/impersonation-expired.tsx
new file mode 100644
index 00000000000..2702660d7ff
--- /dev/null
+++ b/apps/sim/app/workspace/[workspaceId]/components/impersonation-banner/impersonation-expired.tsx
@@ -0,0 +1,67 @@
+'use client'
+
+import { useCallback, useEffect, useRef, useState } from 'react'
+import { Chip } from '@sim/emcn'
+import { useSession } from '@/lib/auth/auth-client'
+import { recoverFromStaleSession } from '@/lib/auth/stale-session-recovery'
+
+/**
+ * Cleanly logs out when an impersonation session expires while the app is
+ * mounted.
+ *
+ * Detection keys off the transition: this only activates when the session
+ * query settles to `null` after a session that carried `impersonatedBy` (the
+ * expired session is deleted server-side, so the live session can't be used).
+ *
+ * Recovery goes through {@link recoverFromStaleSession}: the expired session's
+ * cookies are never cleared server-side (better-auth's customSession plugin
+ * swallows the deletion headers), and the login route bounces any request
+ * still carrying a session cookie back to /workspace. The helper signs out
+ * (which clears the cookies without requiring a live session), wipes per-user
+ * client state, and only navigates when the sign-out succeeded — navigating
+ * after a failed sign-out would recreate the redirect loop.
+ */
+export function ImpersonationExpired() {
+  const { data: session, isPending, error } = useSession()
+  const startedRef = useRef(false)
+  const [sawImpersonation, setSawImpersonation] = useState(false)
+  const [failed, setFailed] = useState(false)
+
+  if (!sawImpersonation && session?.session?.impersonatedBy) {
+    setSawImpersonation(true)
+  }
+
+  const expired = sawImpersonation && !isPending && !error && !session?.user
+
+  const attemptRecovery = useCallback(() => {
+    setFailed(false)
+    void recoverFromStaleSession().then((recovered) => {
+      if (!recovered) setFailed(true)
+    })
+  }, [])
+
+  useEffect(() => {
+    if (!expired || startedRef.current) return
+    startedRef.current = true
+    attemptRecovery()
+  }, [expired, attemptRecovery])
+
+  if (!expired) {
+    return null
+  }
+
+  return (
+    <main className='fixed inset-0 z-50 flex flex-col items-center justify-center gap-3 bg-[var(--surface-1)] p-6'>
+      <p className='text-[var(--text-muted)] text-sm'>
+        {failed
+          ? 'The impersonation session expired, but signing out failed.'
+          : 'The impersonation session expired. Signing you out…'}
+      </p>
+      {failed && (
+        <Chip variant='primary' onClick={attemptRecovery}>
+          Try again
+        </Chip>
+      )}
+    </main>
+  )
+}
diff --git a/apps/sim/app/workspace/[workspaceId]/components/impersonation-banner/index.ts b/apps/sim/app/workspace/[workspaceId]/components/impersonation-banner/index.ts
index dcfa353780c..1482b93081b 100644
--- a/apps/sim/app/workspace/[workspaceId]/components/impersonation-banner/index.ts
+++ b/apps/sim/app/workspace/[workspaceId]/components/impersonation-banner/index.ts
@@ -1 +1,2 @@
 export { ImpersonationBanner } from './impersonation-banner'
+export { ImpersonationExpired } from './impersonation-expired'
diff --git a/apps/sim/app/workspace/[workspaceId]/layout.test.tsx b/apps/sim/app/workspace/[workspaceId]/layout.test.tsx
index 33beae266a0..c2bd9879894 100644
--- a/apps/sim/app/workspace/[workspaceId]/layout.test.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/layout.test.tsx
@@ -59,6 +59,7 @@ vi.mock('@/ee/whitelabeling/components/branding-provider', () => ({
 
 vi.mock('@/app/workspace/[workspaceId]/components/impersonation-banner', () => ({
   ImpersonationBanner: () => null,
+  ImpersonationExpired: () => null,
 }))
 
 vi.mock('@/app/workspace/[workspaceId]/components/workspace-chrome', () => ({
diff --git a/apps/sim/app/workspace/[workspaceId]/layout.tsx b/apps/sim/app/workspace/[workspaceId]/layout.tsx
index 645496c18c9..f10df8f2883 100644
--- a/apps/sim/app/workspace/[workspaceId]/layout.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/layout.tsx
@@ -4,7 +4,10 @@ import { cookies } from 'next/headers'
 import { redirect } from 'next/navigation'
 import { getSession } from '@/lib/auth'
 import { getQueryClient } from '@/app/_shell/providers/get-query-client'
-import { ImpersonationBanner } from '@/app/workspace/[workspaceId]/components/impersonation-banner'
+import {
+  ImpersonationBanner,
+  ImpersonationExpired,
+} from '@/app/workspace/[workspaceId]/components/impersonation-banner'
 import { WorkspaceAccessDenied } from '@/app/workspace/[workspaceId]/components/workspace-access-denied'
 import { WorkspaceChrome } from '@/app/workspace/[workspaceId]/components/workspace-chrome'
 import {
@@ -66,6 +69,7 @@ export default async function WorkspaceLayout({
             <GlobalCommandsProvider>
               <div className='flex h-screen w-full flex-col overflow-hidden bg-[var(--surface-1)]'>
                 <ImpersonationBanner />
+                <ImpersonationExpired />
                 <WorkspacePermissionsProvider>
                   <WorkspaceScopeSync />
                   <WorkspaceChrome initialSidebarCollapsed={initialSidebarCollapsed}>
diff --git a/apps/sim/app/workspace/page.tsx b/apps/sim/app/workspace/page.tsx
index 5e277d699e3..6137b205d19 100644
--- a/apps/sim/app/workspace/page.tsx
+++ b/apps/sim/app/workspace/page.tsx
@@ -9,10 +9,10 @@ import { isApiClientError } from '@/lib/api/client/errors'
 import { requestJson } from '@/lib/api/client/request'
 import { getWorkflowStateContract } from '@/lib/api/contracts/workflows'
 import { createWorkspaceContract } from '@/lib/api/contracts/workspaces'
-import { signOut, useSession } from '@/lib/auth/auth-client'
+import { useSession } from '@/lib/auth/auth-client'
+import { recoverFromStaleSession } from '@/lib/auth/stale-session-recovery'
 import { WorkspaceRecencyStorage } from '@/lib/core/utils/browser-storage'
 import { useWorkspacesWithMetadata, type WorkspaceCreationPolicy } from '@/hooks/queries/workspace'
-import { clearUserData } from '@/stores'
 
 const logger = createLogger('WorkspacePage')
 
@@ -27,24 +27,6 @@ function isStaleSessionError(error: unknown): boolean {
   return isApiClientError(error) && error.status === 401
 }
 
-/**
- * Signs out (clearing every auth cookie server-side), wipes per-user client
- * state, and navigates to login. Returns false without navigating when the
- * sign-out request fails — the cookies are still set, so going to /login
- * would only get bounced back to /workspace by the middleware.
- */
-async function recoverFromStaleSession(): Promise<boolean> {
-  try {
-    await signOut()
-  } catch (error) {
-    logger.error('Failed to sign out while recovering from a stale session:', error)
-    return false
-  }
-  await clearUserData()
-  window.location.assign('/login')
-  return true
-}
-
 export default function WorkspacePage() {
   const router = useRouter()
   const { data: session, isPending: isSessionPending, error: sessionError } = useSession()
@@ -77,8 +59,17 @@ export default function WorkspacePage() {
       // Indeterminate auth (errored session query, no cached identity): show
       // the error card — /login would bounce back while a session cookie exists.
       if (sessionError) return
-      logger.info('User not authenticated, redirecting to login')
-      router.replace('/login')
+      // A clean null session can still have stale auth cookies behind it (an
+      // expired impersonation session's cookies are never cleared server-side),
+      // and the middleware bounces /login back here while any session cookie
+      // exists — a bare replace('/login') loops forever on the spinner. Recover
+      // the same way as the 401 path: sign out (clears the cookies without
+      // needing a live session), then navigate.
+      hasRedirectedRef.current = true
+      logger.info('User not authenticated, signing out stale cookies and redirecting to login')
+      void recoverFromStaleSession().then((recovered) => {
+        if (!recovered) setRecoveryFailed(true)
+      })
       return
     }
 
diff --git a/apps/sim/hooks/queries/session.ts b/apps/sim/hooks/queries/session.ts
index add45a08854..686a2447c7b 100644
--- a/apps/sim/hooks/queries/session.ts
+++ b/apps/sim/hooks/queries/session.ts
@@ -1,4 +1,4 @@
-import { type QueryClient, useQuery } from '@tanstack/react-query'
+import { type QueryClient, useQuery, useQueryClient } from '@tanstack/react-query'
 import { client } from '@/lib/auth/auth-client'
 import {
   type AppSession,
@@ -12,8 +12,14 @@ export const sessionKeys = {
   detail: () => [...sessionKeys.all, 'detail'] as const,
 }
 
-async function fetchSession(signal?: AbortSignal): Promise<AppSession> {
-  const res = await client.getSession({ fetchOptions: { signal } })
+async function fetchSession(
+  signal?: AbortSignal,
+  disableCookieCache?: boolean
+): Promise<AppSession> {
+  const res = await client.getSession({
+    ...(disableCookieCache ? { query: { disableCookieCache: true } } : {}),
+    fetchOptions: { signal },
+  })
   return extractSessionDataFromAuthClientResult(res) as AppSession
 }
 
@@ -35,6 +41,8 @@ export async function refreshSessionQuery(queryClient: QueryClient): Promise<App
   return fresh
 }
 
+export const IMPERSONATION_REFETCH_INTERVAL = 60 * 1000
+
 /**
  * Reads the current Better Auth session via the client SDK.
  *
@@ -44,12 +52,29 @@ export async function refreshSessionQuery(queryClient: QueryClient): Promise<App
  * `retry: false` preserves the prior fail-fast contract: an auth failure (expired
  * token, startup network partition) surfaces immediately rather than retrying a
  * request that won't succeed.
+ *
+ * While the session is an impersonation session, the query polls and refetches
+ * on focus (overriding the global `refetchOnWindowFocus: false`) so an expiry —
+ * including one slept through with the laptop closed — settles the query to
+ * `null` and surfaces the impersonation-expired recovery screen. Those
+ * refetches also bypass Better Auth's cookie cache: it can otherwise keep
+ * vouching for a session that was expired or revoked server-side, and the
+ * expiry detection shouldn't depend on the cache's own TTL details.
+ * Impersonation sessions are short-lived and admin-only, so none of these
+ * overrides affect normal sessions.
  */
 export function useSessionQuery() {
+  const queryClient = useQueryClient()
   return useQuery({
     queryKey: sessionKeys.detail(),
-    queryFn: ({ signal }) => fetchSession(signal),
+    queryFn: ({ signal }) => {
+      const cached = queryClient.getQueryData<AppSession>(sessionKeys.detail())
+      return fetchSession(signal, Boolean(cached?.session?.impersonatedBy))
+    },
     staleTime: SESSION_STALE_TIME,
     retry: false,
+    refetchInterval: (query) =>
+      query.state.data?.session?.impersonatedBy ? IMPERSONATION_REFETCH_INTERVAL : false,
+    refetchOnWindowFocus: (query) => Boolean(query.state.data?.session?.impersonatedBy),
   })
 }
diff --git a/apps/sim/lib/auth/stale-session-recovery.ts b/apps/sim/lib/auth/stale-session-recovery.ts
new file mode 100644
index 00000000000..a3b9b38f6a7
--- /dev/null
+++ b/apps/sim/lib/auth/stale-session-recovery.ts
@@ -0,0 +1,29 @@
+'use client'
+
+import { createLogger } from '@sim/logger'
+import { signOut } from '@/lib/auth/auth-client'
+import { clearUserData } from '@/stores'
+
+const logger = createLogger('StaleSessionRecovery')
+
+/**
+ * Signs out (clearing every auth cookie server-side), wipes per-user client
+ * state, and navigates to login. Returns false without navigating when the
+ * sign-out request fails — the cookies are still set, so going to /login
+ * would only get bounced back to /workspace by the middleware.
+ *
+ * Shared by the /workspace loader (stale-cookie 401s and clean-null sessions)
+ * and the impersonation-expired screen, so every identity-recovery path clears
+ * cookies and persisted client state the same way.
+ */
+export async function recoverFromStaleSession(): Promise<boolean> {
+  try {
+    await signOut()
+  } catch (error) {
+    logger.error('Failed to sign out while recovering from a stale session:', error)
+    return false
+  }
+  await clearUserData()
+  window.location.assign('/login')
+  return true
+}