diff --git a/package.json b/package.json
index dbab64b..840d111 100644
--- a/package.json
+++ b/package.json
@@ -13,6 +13,7 @@
     "clean": "pnpm -r exec rm -rf dist node_modules",
     "server:start": "pnpm --filter @ai-assistant/server start",
     "server:dev": "pnpm --filter @ai-assistant/server start:dev",
+    "web:dev": "pnpm --filter @ai-assistant/web dev",
     "desktop:dev": "pnpm --filter @ai-assistant/desktop dev",
     "desktop:build": "pnpm --filter @ai-assistant/desktop build"
   },
diff --git a/packages/web/src/App.tsx b/packages/web/src/App.tsx
index 935b0c3..d6284e3 100644
--- a/packages/web/src/App.tsx
+++ b/packages/web/src/App.tsx
@@ -4,7 +4,7 @@
  * 响应式布局：支持桌面端和移动端
  */
 
-import { useState, useEffect } from 'react';
+import { useState, useEffect, useCallback } from 'react';
 import { Sidebar } from './components/Sidebar';
 import { ChatPage } from './pages/Chat';
 import { FileBrowser } from './components/FileBrowser';
@@ -49,6 +49,16 @@ export function App() {
     setCurrentSessionId(session.id);
   };
 
+  // 会话不存在时自动创建新会话
+  const handleSessionNotFound = useCallback(async () => {
+    try {
+      const { data: newSession } = await createSession();
+      setCurrentSessionId(newSession.id);
+    } catch (error) {
+      console.error('Failed to create new session:', error);
+    }
+  }, []);
+
   if (isInitializing) {
     return (
       <div className="h-screen flex items-center justify-center bg-gray-900">
@@ -116,7 +126,7 @@ export function App() {
         {/* 聊天区域 */}
         <div className={`flex-1 min-w-0 ${showFileBrowser ? 'hidden md:block md:w-1/2' : 'w-full'}`}>
           {currentSessionId ? (
-            <ChatPage key={currentSessionId} sessionId={currentSessionId} />
+            <ChatPage key={currentSessionId} sessionId={currentSessionId} onSessionNotFound={handleSessionNotFound} />
           ) : (
             <div className="flex-1 flex items-center justify-center h-full">
               <p className="text-gray-400">Select or create a session</p>
diff --git a/packages/web/src/hooks/useChat.ts b/packages/web/src/hooks/useChat.ts
index 52a339f..548116e 100644
--- a/packages/web/src/hooks/useChat.ts
+++ b/packages/web/src/hooks/useChat.ts
@@ -10,6 +10,7 @@ import { createWebSocket, getMessages, type Message } from '../api/client';
 interface UseChatOptions {
   sessionId: string;
   onError?: (error: Error) => void;
+  onSessionNotFound?: () => void;
 }
 
 interface ChatState {
@@ -19,7 +20,7 @@ interface ChatState {
   streamingContent: string;
 }
 
-export function useChat({ sessionId, onError }: UseChatOptions) {
+export function useChat({ sessionId, onError, onSessionNotFound }: UseChatOptions) {
   const [state, setState] = useState<ChatState>({
     messages: [],
     isConnected: false,
@@ -29,6 +30,14 @@ export function useChat({ sessionId, onError }: UseChatOptions) {
 
   const wsRef = useRef<WebSocket | null>(null);
   const reconnectTimeoutRef = useRef<NodeJS.Timeout>();
+  const reconnectAttemptsRef = useRef(0);
+  const maxReconnectAttempts = 5;
+
+  // 用 ref 存储回调，避免依赖变化导致无限循环
+  const onErrorRef = useRef(onError);
+  const onSessionNotFoundRef = useRef(onSessionNotFound);
+  onErrorRef.current = onError;
+  onSessionNotFoundRef.current = onSessionNotFound;
 
   // 加载历史消息
   const loadMessages = useCallback(async () => {
@@ -36,9 +45,15 @@ export function useChat({ sessionId, onError }: UseChatOptions) {
       const { data } = await getMessages(sessionId);
       setState((prev) => ({ ...prev, messages: data }));
     } catch (error) {
-      onError?.(error instanceof Error ? error : new Error('Failed to load messages'));
+      // 会话不存在（404 或 "Session not found"），通知上层重新创建
+      const msg = error instanceof Error ? error.message : '';
+      if (msg.includes('404') || msg.toLowerCase().includes('not found')) {
+        onSessionNotFoundRef.current?.();
+        return;
+      }
+      onErrorRef.current?.(error instanceof Error ? error : new Error('Failed to load messages'));
     }
-  }, [sessionId, onError]);
+  }, [sessionId]);
 
   // 连接 WebSocket
   const connect = useCallback(() => {
@@ -47,17 +62,21 @@ export function useChat({ sessionId, onError }: UseChatOptions) {
     const ws = createWebSocket(sessionId);
 
     ws.onopen = () => {
+      reconnectAttemptsRef.current = 0; // 连接成功，重置重连次数
       setState((prev) => ({ ...prev, isConnected: true }));
     };
 
     ws.onclose = () => {
       setState((prev) => ({ ...prev, isConnected: false }));
-      // 自动重连
-      reconnectTimeoutRef.current = setTimeout(connect, 3000);
+      // 限制重连次数
+      if (reconnectAttemptsRef.current < maxReconnectAttempts) {
+        reconnectAttemptsRef.current++;
+        reconnectTimeoutRef.current = setTimeout(connect, 3000);
+      }
     };
 
     ws.onerror = () => {
-      onError?.(new Error('WebSocket connection error'));
+      onErrorRef.current?.(new Error('WebSocket connection error'));
     };
 
     ws.onmessage = (event) => {
@@ -98,7 +117,7 @@ export function useChat({ sessionId, onError }: UseChatOptions) {
             break;
 
           case 'error':
-            onError?.(new Error(message.payload?.message || 'Unknown error'));
+            onErrorRef.current?.(new Error(message.payload?.message || 'Unknown error'));
             setState((prev) => ({ ...prev, isLoading: false, streamingContent: '' }));
             break;
         }
@@ -108,13 +127,13 @@ export function useChat({ sessionId, onError }: UseChatOptions) {
     };
 
     wsRef.current = ws;
-  }, [sessionId, onError]);
+  }, [sessionId]);
 
   // 发送消息
   const sendMessage = useCallback(
     (content: string) => {
       if (!wsRef.current || wsRef.current.readyState !== WebSocket.OPEN) {
-        onError?.(new Error('WebSocket not connected'));
+        onErrorRef.current?.(new Error('WebSocket not connected'));
         return;
       }
 
@@ -128,7 +147,7 @@ export function useChat({ sessionId, onError }: UseChatOptions) {
         })
       );
     },
-    [sessionId, onError]
+    [sessionId]
   );
 
   // 取消处理
diff --git a/packages/web/src/pages/Chat.tsx b/packages/web/src/pages/Chat.tsx
index 14c18e5..b13524c 100644
--- a/packages/web/src/pages/Chat.tsx
+++ b/packages/web/src/pages/Chat.tsx
@@ -10,9 +10,10 @@ import { ChatInput } from '../components/ChatInput';
 
 interface ChatPageProps {
   sessionId: string;
+  onSessionNotFound?: () => void;
 }
 
-export function ChatPage({ sessionId }: ChatPageProps) {
+export function ChatPage({ sessionId, onSessionNotFound }: ChatPageProps) {
   const {
     messages,
     isConnected,
@@ -25,6 +26,7 @@ export function ChatPage({ sessionId }: ChatPageProps) {
     onError: (error) => {
       console.error('Chat error:', error);
     },
+    onSessionNotFound,
   });
 
   const messagesEndRef = useRef<HTMLDivElement>(null);