diff --git a/apps/webclaw/src/screens/chat/chat-screen.tsx b/apps/webclaw/src/screens/chat/chat-screen.tsx
index 6c4fac7..bcebbbe 100644
--- a/apps/webclaw/src/screens/chat/chat-screen.tsx
+++ b/apps/webclaw/src/screens/chat/chat-screen.tsx
@@ -5,6 +5,7 @@ import { useQuery, useQueryClient } from '@tanstack/react-query'
 import {
   deriveFriendlyIdFromKey,
   isMissingGatewayAuth,
+  isSessionNotFound,
   readError,
 } from './utils'
 import { createOptimisticMessage } from './chat-screen-utils'
@@ -147,16 +148,17 @@ export function ChatScreen({
     navigate({ to: '/new', replace: true })
   }, [navigate])
   const stableContentStyle = useMemo<React.CSSProperties>(() => ({}), [])
+  const missingSessionError =
+    isSessionNotFound(historyError ?? '') ||
+    isSessionNotFound(sessionsError ?? '')
 
   const shouldRedirectToNew =
     !isNewChat &&
     !forcedSessionKey &&
     !isRecentSession(activeFriendlyId) &&
     sessionsQuery.isSuccess &&
-    sessions.length > 0 &&
     !sessions.some((session) => session.friendlyId === activeFriendlyId) &&
-    !historyQuery.isFetching &&
-    !historyQuery.isSuccess
+    (missingSessionError || (!historyQuery.isFetching && !historyQuery.isSuccess))
 
   const refreshHistory = useCallback(() => {
     void historyQuery.refetch()
@@ -520,7 +522,6 @@ export function ChatScreen({
     isRedirecting,
     shouldRedirectToNew,
     sessionsReady: sessionsQuery.isSuccess,
-    sessionsCount: sessions.length,
     sessionKeyForHistory,
     queryClient,
     setIsRedirecting,
diff --git a/apps/webclaw/src/screens/chat/hooks/use-chat-history.ts b/apps/webclaw/src/screens/chat/hooks/use-chat-history.ts
index 2c6dfdd..0a0aff7 100644
--- a/apps/webclaw/src/screens/chat/hooks/use-chat-history.ts
+++ b/apps/webclaw/src/screens/chat/hooks/use-chat-history.ts
@@ -27,8 +27,7 @@ export function useChatHistory({
   sessionsReady,
   queryClient,
 }: UseChatHistoryInput) {
-  const sessionKeyForHistory =
-    forcedSessionKey || activeSessionKey || activeFriendlyId
+  const sessionKeyForHistory = forcedSessionKey || activeSessionKey || ''
   const historyKey = chatQueryKeys.history(
     activeFriendlyId,
     sessionKeyForHistory,
@@ -77,6 +76,7 @@ export function useChatHistory({
       Boolean(activeFriendlyId) &&
       !isRedirecting &&
       (!sessionsReady || activeExists),
+    retry: false,
     placeholderData: function useCachedHistory(): HistoryResponse | undefined {
       return queryClient.getQueryData(historyKey)
     },
diff --git a/apps/webclaw/src/screens/chat/hooks/use-chat-redirect.ts b/apps/webclaw/src/screens/chat/hooks/use-chat-redirect.ts
index 6995dd9..9c4c736 100644
--- a/apps/webclaw/src/screens/chat/hooks/use-chat-redirect.ts
+++ b/apps/webclaw/src/screens/chat/hooks/use-chat-redirect.ts
@@ -11,7 +11,6 @@ type UseChatRedirectInput = {
   isRedirecting: boolean
   shouldRedirectToNew: boolean
   sessionsReady: boolean
-  sessionsCount: number
   sessionKeyForHistory: string
   queryClient: QueryClient
   setIsRedirecting: (value: boolean) => void
@@ -23,7 +22,6 @@ export function useChatRedirect({
   isRedirecting,
   shouldRedirectToNew,
   sessionsReady,
-  sessionsCount,
   sessionKeyForHistory,
   queryClient,
   setIsRedirecting,
@@ -43,7 +41,6 @@ export function useChatRedirect({
 
     if (isNewChat) return
     if (!sessionsReady) return
-    if (sessionsCount === 0) return
     if (!shouldRedirectToNew) return
     resetPendingSend()
     clearHistoryMessages(queryClient, activeFriendlyId, sessionKeyForHistory)
@@ -54,7 +51,6 @@ export function useChatRedirect({
     navigate,
     queryClient,
     sessionKeyForHistory,
-    sessionsCount,
     sessionsReady,
     setIsRedirecting,
     shouldRedirectToNew,
diff --git a/apps/webclaw/src/screens/chat/utils.ts b/apps/webclaw/src/screens/chat/utils.ts
index 48748c0..7fec5d4 100644
--- a/apps/webclaw/src/screens/chat/utils.ts
+++ b/apps/webclaw/src/screens/chat/utils.ts
@@ -130,3 +130,15 @@ export const missingGatewayAuthMessage =
 export function isMissingGatewayAuth(message: string): boolean {
   return message.includes(missingGatewayAuthMessage)
 }
+
+export function isSessionNotFound(message: string): boolean {
+  if (!message) return false
+  const normalized = message.toLowerCase()
+  if (normalized.includes('session not found')) return true
+  if (normalized.includes('unknown session')) return true
+  if (normalized.includes('chat not found')) return true
+  if (normalized.includes('not found') && normalized.includes('session')) {
+    return true
+  }
+  return false
+}