diff --git a/packages/vscode-ide-companion/src/cli/cliDetector.ts b/packages/vscode-ide-companion/src/cli/cliDetector.ts
index 875c2858..c1de868a 100644
--- a/packages/vscode-ide-companion/src/cli/cliDetector.ts
+++ b/packages/vscode-ide-companion/src/cli/cliDetector.ts
@@ -24,6 +24,125 @@ export class CliDetector {
   private static lastCheckTime: number = 0;
   private static readonly CACHE_DURATION_MS = 30000; // 30 seconds
 
+  /**
+   * Lightweight check if the Qwen Code CLI is installed
+   * This version only checks for CLI existence without getting version info for faster performance
+   * @param forceRefresh - Force a new check, ignoring cache
+   * @returns Detection result with installation status and path
+   */
+  static async detectQwenCliLightweight(
+    forceRefresh = false,
+  ): Promise<CliDetectionResult> {
+    const now = Date.now();
+
+    // Return cached result if available and not expired
+    if (
+      !forceRefresh &&
+      this.cachedResult &&
+      now - this.lastCheckTime < this.CACHE_DURATION_MS
+    ) {
+      console.log('[CliDetector] Returning cached result');
+      return this.cachedResult;
+    }
+
+    console.log(
+      '[CliDetector] Starting lightweight CLI detection, current PATH:',
+      process.env.PATH,
+    );
+
+    try {
+      const isWindows = process.platform === 'win32';
+      const whichCommand = isWindows ? 'where' : 'which';
+
+      // Check if qwen command exists
+      try {
+        // Use simpler detection without NVM for speed
+        const detectionCommand = isWindows
+          ? `${whichCommand} qwen`
+          : `${whichCommand} qwen`;
+
+        console.log(
+          '[CliDetector] Detecting CLI with lightweight command:',
+          detectionCommand,
+        );
+
+        const { stdout } = await execAsync(detectionCommand, {
+          timeout: 3000, // Reduced timeout for faster detection
+          shell: isWindows ? undefined : '/bin/bash',
+        });
+
+        // The output may contain multiple lines
+        // We want the first line which should be the actual path
+        const lines = stdout
+          .trim()
+          .split('\n')
+          .filter((line) => line.trim());
+        const cliPath = lines[0]; // Just take the first path
+
+        console.log('[CliDetector] Found CLI at:', cliPath);
+
+        this.cachedResult = {
+          isInstalled: true,
+          cliPath,
+          // Version is not retrieved in lightweight detection
+        };
+        this.lastCheckTime = now;
+        return this.cachedResult;
+      } catch (detectionError) {
+        console.log('[CliDetector] CLI not found, error:', detectionError);
+        // CLI not found
+        let error = `Qwen Code CLI not found in PATH. Please install it using: npm install -g @qwen-code/qwen-code@latest`;
+
+        // Provide specific guidance for permission errors
+        if (detectionError instanceof Error) {
+          const errorMessage = detectionError.message;
+          if (
+            errorMessage.includes('EACCES') ||
+            errorMessage.includes('Permission denied')
+          ) {
+            error += `\n\nThis may be due to permission issues. Possible solutions:
+              \n1. Reinstall the CLI without sudo: npm install -g @qwen-code/qwen-code@latest
+              \n2. If previously installed with sudo, fix ownership: sudo chown -R $(whoami) $(npm config get prefix)/lib/node_modules/@qwen-code/qwen-code
+              \n3. Use nvm for Node.js version management to avoid permission issues
+              \n4. Check your PATH environment variable includes npm's global bin directory`;
+          }
+        }
+
+        this.cachedResult = {
+          isInstalled: false,
+          error,
+        };
+        this.lastCheckTime = now;
+        return this.cachedResult;
+      }
+    } catch (error) {
+      console.log('[CliDetector] General detection error:', error);
+      const errorMessage =
+        error instanceof Error ? error.message : String(error);
+
+      let userFriendlyError = `Failed to detect Qwen Code CLI: ${errorMessage}`;
+
+      // Provide specific guidance for permission errors
+      if (
+        errorMessage.includes('EACCES') ||
+        errorMessage.includes('Permission denied')
+      ) {
+        userFriendlyError += `\n\nThis may be due to permission issues. Possible solutions:
+          \n1. Reinstall the CLI without sudo: npm install -g @qwen-code/qwen-code@latest
+          \n2. If previously installed with sudo, fix ownership: sudo chown -R $(whoami) $(npm config get prefix)/lib/node_modules/@qwen-code/qwen-code
+          \n3. Use nvm for Node.js version management to avoid permission issues
+          \n4. Check your PATH environment variable includes npm's global bin directory`;
+      }
+
+      this.cachedResult = {
+        isInstalled: false,
+        error: userFriendlyError,
+      };
+      this.lastCheckTime = now;
+      return this.cachedResult;
+    }
+  }
+
   /**
    * Checks if the Qwen Code CLI is installed
    * @param forceRefresh - Force a new check, ignoring cache
diff --git a/packages/vscode-ide-companion/src/services/acpConnection.ts b/packages/vscode-ide-companion/src/services/acpConnection.ts
index f4c95948..f999c602 100644
--- a/packages/vscode-ide-companion/src/services/acpConnection.ts
+++ b/packages/vscode-ide-companion/src/services/acpConnection.ts
@@ -42,7 +42,9 @@ export class AcpConnection {
   onPermissionRequest: (data: AcpPermissionRequest) => Promise<{
     optionId: string;
   }> = () => Promise.resolve({ optionId: 'allow' });
-  onEndTurn: () => void = () => {};
+  onEndTurn: (reason?: string) => void = (reason?: string | undefined) => {
+    console.log('[ACP] onEndTurn__________ reason:', reason || 'unknown');
+  };
   // Called after successful initialize() with the initialize result
   onInitialized: (init: unknown) => void = () => {};
 
diff --git a/packages/vscode-ide-companion/src/services/acpMessageHandler.ts b/packages/vscode-ide-companion/src/services/acpMessageHandler.ts
index db7802ce..e07cedfb 100644
--- a/packages/vscode-ide-companion/src/services/acpMessageHandler.ts
+++ b/packages/vscode-ide-companion/src/services/acpMessageHandler.ts
@@ -110,13 +110,30 @@ export class AcpMessageHandler {
         // JSON.stringify(message.result).substring(0, 200),
         message.result,
       );
-      if (
+
+      console.log(
+        '[ACP] Response for message.result:',
+        message.result,
         message.result &&
-        typeof message.result === 'object' &&
-        'stopReason' in message.result &&
-        message.result.stopReason === 'end_turn'
-      ) {
-        callbacks.onEndTurn();
+          typeof message.result === 'object' &&
+          'stopReason' in message.result,
+
+        !!callbacks.onEndTurn,
+      );
+
+      if (message.result && typeof message.result === 'object') {
+        const stopReasonValue =
+          (message.result as { stopReason?: unknown }).stopReason ??
+          (message.result as { stop_reason?: unknown }).stop_reason;
+        if (typeof stopReasonValue === 'string') {
+          callbacks.onEndTurn(stopReasonValue);
+        } else if (
+          'stopReason' in message.result ||
+          'stop_reason' in message.result
+        ) {
+          // stop_reason present but not a string (e.g., null) -> still emit
+          callbacks.onEndTurn();
+        }
       }
       resolve(message.result);
     } else if ('error' in message) {
diff --git a/packages/vscode-ide-companion/src/services/qwenAgentManager.ts b/packages/vscode-ide-companion/src/services/qwenAgentManager.ts
index 5ddd5612..3c701331 100644
--- a/packages/vscode-ide-companion/src/services/qwenAgentManager.ts
+++ b/packages/vscode-ide-companion/src/services/qwenAgentManager.ts
@@ -17,11 +17,18 @@ import type {
   ToolCallUpdateData,
   QwenAgentCallbacks,
 } from '../types/chatTypes.js';
-import { QwenConnectionHandler } from '../services/qwenConnectionHandler.js';
+import {
+  QwenConnectionHandler,
+  type QwenConnectionResult,
+} from '../services/qwenConnectionHandler.js';
 import { QwenSessionUpdateHandler } from './qwenSessionUpdateHandler.js';
 import { CliContextManager } from '../cli/cliContextManager.js';
 import { authMethod } from '../types/acpTypes.js';
-import { MIN_CLI_VERSION_FOR_SESSION_METHODS } from '../cli/cliVersionManager.js';
+import {
+  MIN_CLI_VERSION_FOR_SESSION_METHODS,
+  type CliVersionInfo,
+} from '../cli/cliVersionManager.js';
+import { isAuthenticationRequiredError } from '../utils/authErrors.js';
 
 export type { ChatMessage, PlanEntry, ToolCallUpdateData };
 
@@ -30,6 +37,13 @@ export type { ChatMessage, PlanEntry, ToolCallUpdateData };
  *
  * Coordinates various modules and provides unified interface
  */
+interface AgentConnectOptions {
+  autoAuthenticate?: boolean;
+}
+interface AgentSessionOptions {
+  autoAuthenticate?: boolean;
+}
+
 export class QwenAgentManager {
   private connection: AcpConnection;
   private sessionReader: QwenSessionReader;
@@ -119,10 +133,10 @@ export class QwenAgentManager {
       return { optionId: 'allow_once' };
     };
 
-    this.connection.onEndTurn = () => {
+    this.connection.onEndTurn = (reason?: string) => {
       try {
         if (this.callbacks.onEndTurn) {
-          this.callbacks.onEndTurn();
+          this.callbacks.onEndTurn(reason);
         } else if (this.callbacks.onStreamChunk) {
           // Fallback: send a zero-length chunk then rely on streamEnd elsewhere
           this.callbacks.onStreamChunk('');
@@ -136,6 +150,36 @@ export class QwenAgentManager {
     this.connection.onInitialized = (init: unknown) => {
       try {
         const obj = (init || {}) as Record<string, unknown>;
+
+        // Extract version information from initialize response
+        const serverVersion =
+          obj['version'] || obj['serverVersion'] || obj['cliVersion'];
+        if (serverVersion) {
+          console.log(
+            '[QwenAgentManager] Server version from initialize response:',
+            serverVersion,
+          );
+
+          // Update CLI context with version info from server
+          const cliContextManager = CliContextManager.getInstance();
+
+          // Create version info directly without async call
+          const versionInfo: CliVersionInfo = {
+            version: String(serverVersion),
+            isSupported: true, // Assume supported for now
+            features: {
+              supportsSessionList: true,
+              supportsSessionLoad: true,
+            },
+            detectionResult: {
+              isInstalled: true,
+              version: String(serverVersion),
+            },
+          };
+
+          cliContextManager.setCurrentVersionInfo(versionInfo);
+        }
+
         const modes = obj['modes'] as
           | {
               currentModeId?: 'plan' | 'default' | 'auto-edit' | 'yolo';
@@ -164,13 +208,18 @@ export class QwenAgentManager {
    * @param workingDir - Working directory
    * @param cliPath - CLI path (optional, if provided will override the path in configuration)
    */
-  async connect(workingDir: string, _cliPath?: string): Promise<void> {
+  async connect(
+    workingDir: string,
+    _cliPath?: string,
+    options?: AgentConnectOptions,
+  ): Promise<QwenConnectionResult> {
     this.currentWorkingDir = workingDir;
-    await this.connectionHandler.connect(
+    return this.connectionHandler.connect(
       this.connection,
       this.sessionReader,
       workingDir,
       _cliPath,
+      options,
     );
   }
 
@@ -1170,7 +1219,11 @@ export class QwenAgentManager {
    * @param workingDir - Working directory
    * @returns Newly created session ID
    */
-  async createNewSession(workingDir: string): Promise<string | null> {
+  async createNewSession(
+    workingDir: string,
+    options?: AgentSessionOptions,
+  ): Promise<string | null> {
+    const autoAuthenticate = options?.autoAuthenticate ?? true;
     // Reuse existing session if present
     if (this.connection.currentSessionId) {
       return this.connection.currentSessionId;
@@ -1188,12 +1241,15 @@ export class QwenAgentManager {
         try {
           await this.connection.newSession(workingDir);
         } catch (err) {
-          const msg = err instanceof Error ? err.message : String(err);
-          const requiresAuth =
-            msg.includes('Authentication required') ||
-            msg.includes('(code: -32000)');
+          const requiresAuth = isAuthenticationRequiredError(err);
 
           if (requiresAuth) {
+            if (!autoAuthenticate) {
+              console.warn(
+                '[QwenAgentManager] session/new requires authentication but auto-auth is disabled. Deferring until user logs in.',
+              );
+              throw err;
+            }
             console.warn(
               '[QwenAgentManager] session/new requires authentication. Retrying with authenticate...',
             );
@@ -1310,9 +1366,10 @@ export class QwenAgentManager {
   /**
    * Register end-of-turn callback
    *
-   * @param callback - Called when ACP stopReason === 'end_turn'
+   * @param callback - Called when ACP stopReason is reported
    */
-  onEndTurn(callback: () => void): void {
+  onEndTurn(callback: (reason?: string) => void): void {
+    console.log('[QwenAgentManager] onEndTurn__________ callback:', callback);
     this.callbacks.onEndTurn = callback;
     this.sessionUpdateHandler.updateCallbacks(this.callbacks);
   }
diff --git a/packages/vscode-ide-companion/src/services/qwenConnectionHandler.ts b/packages/vscode-ide-companion/src/services/qwenConnectionHandler.ts
index 6a74cd56..e35ce64c 100644
--- a/packages/vscode-ide-companion/src/services/qwenConnectionHandler.ts
+++ b/packages/vscode-ide-companion/src/services/qwenConnectionHandler.ts
@@ -10,15 +10,17 @@
  * Handles Qwen Agent connection establishment, authentication, and session creation
  */
 
-import * as vscode from 'vscode';
+// import * as vscode from 'vscode';
 import type { AcpConnection } from './acpConnection.js';
 import type { QwenSessionReader } from '../services/qwenSessionReader.js';
-import {
-  CliVersionManager,
-  MIN_CLI_VERSION_FOR_SESSION_METHODS,
-} from '../cli/cliVersionManager.js';
-import { CliContextManager } from '../cli/cliContextManager.js';
+import { CliDetector } from '../cli/cliDetector.js';
 import { authMethod } from '../types/acpTypes.js';
+import { isAuthenticationRequiredError } from '../utils/authErrors.js';
+
+export interface QwenConnectionResult {
+  sessionCreated: boolean;
+  requiresAuth: boolean;
+}
 
 /**
  * Qwen Connection Handler class
@@ -38,36 +40,39 @@ export class QwenConnectionHandler {
     sessionReader: QwenSessionReader,
     workingDir: string,
     cliPath?: string,
-  ): Promise<void> {
+    options?: {
+      autoAuthenticate?: boolean;
+    },
+  ): Promise<QwenConnectionResult> {
     const connectId = Date.now();
     console.log(`[QwenAgentManager] 🚀 CONNECT() CALLED - ID: ${connectId}`);
+    const autoAuthenticate = options?.autoAuthenticate ?? true;
+    let sessionCreated = false;
+    let requiresAuth = false;
 
-    // Check CLI version and features
-    const cliVersionManager = CliVersionManager.getInstance();
-    const versionInfo = await cliVersionManager.detectCliVersion();
-    console.log('[QwenAgentManager] CLI version info:', versionInfo);
-
-    // Store CLI context
-    const cliContextManager = CliContextManager.getInstance();
-    cliContextManager.setCurrentVersionInfo(versionInfo);
-
-    // Show warning if CLI version is below minimum requirement
-    if (!versionInfo.isSupported) {
-      // Wait to determine release version number
-      vscode.window.showWarningMessage(
-        `Qwen Code CLI version ${versionInfo.version} is below the minimum required version. Some features may not work properly. Please upgrade to version ${MIN_CLI_VERSION_FOR_SESSION_METHODS} or later.`,
-      );
+    // Lightweight check if CLI exists (without version info for faster performance)
+    const detectionResult = await CliDetector.detectQwenCliLightweight(
+      /* forceRefresh */ true,
+    );
+    if (!detectionResult.isInstalled) {
+      throw new Error(detectionResult.error || 'Qwen CLI not found');
     }
+    console.log('[QwenAgentManager] CLI detected at:', detectionResult.cliPath);
 
-    const config = vscode.workspace.getConfiguration('qwenCode');
-    // Use the provided CLI path if available, otherwise use the configured path
-    const effectiveCliPath =
-      cliPath || config.get<string>('qwen.cliPath', 'qwen');
+    // TODO: @yiliang114. closed temporarily
+    // Show warning if CLI version is below minimum requirement
+    // if (!versionInfo.isSupported) {
+    //   // Wait to determine release version number
+    //   vscode.window.showWarningMessage(
+    //     `Qwen Code CLI version ${versionInfo.version} is below the minimum required version. Some features may not work properly. Please upgrade to version ${MIN_CLI_VERSION_FOR_SESSION_METHODS} or later.`,
+    //   );
+    // }
 
     // Build extra CLI arguments (only essential parameters)
     const extraArgs: string[] = [];
 
-    await connection.connect(effectiveCliPath, workingDir, extraArgs);
+    // TODO:
+    await connection.connect(cliPath!, workingDir, extraArgs);
 
     // Try to restore existing session or create new session
     // Note: Auto-restore on connect is disabled to avoid surprising loads
@@ -85,18 +90,40 @@ export class QwenConnectionHandler {
         console.log(
           '[QwenAgentManager] Creating new session (letting CLI handle authentication)...',
         );
-        await this.newSessionWithRetry(connection, workingDir, 3, authMethod);
+        await this.newSessionWithRetry(
+          connection,
+          workingDir,
+          3,
+          authMethod,
+          autoAuthenticate,
+        );
         console.log('[QwenAgentManager] New session created successfully');
+        sessionCreated = true;
       } catch (sessionError) {
-        console.log(`\n⚠️ [SESSION FAILED] newSessionWithRetry threw error\n`);
-        console.log(`[QwenAgentManager] Error details:`, sessionError);
-        throw sessionError;
+        const needsAuth =
+          autoAuthenticate === false &&
+          isAuthenticationRequiredError(sessionError);
+        if (needsAuth) {
+          requiresAuth = true;
+          console.log(
+            '[QwenAgentManager] Session creation requires authentication; waiting for user-triggered login.',
+          );
+        } else {
+          console.log(
+            `\n⚠️ [SESSION FAILED] newSessionWithRetry threw error\n`,
+          );
+          console.log(`[QwenAgentManager] Error details:`, sessionError);
+          throw sessionError;
+        }
       }
+    } else {
+      sessionCreated = true;
     }
 
     console.log(`\n========================================`);
     console.log(`[QwenAgentManager] ✅ CONNECT() COMPLETED SUCCESSFULLY`);
     console.log(`========================================\n`);
+    return { sessionCreated, requiresAuth };
   }
 
   /**
@@ -111,6 +138,7 @@ export class QwenConnectionHandler {
     workingDir: string,
     maxRetries: number,
     authMethod: string,
+    autoAuthenticate: boolean,
   ): Promise<void> {
     for (let attempt = 1; attempt <= maxRetries; attempt++) {
       try {
@@ -130,10 +158,14 @@ export class QwenConnectionHandler {
 
         // If Qwen reports that authentication is required, try to
         // authenticate on-the-fly once and retry without waiting.
-        const requiresAuth =
-          errorMessage.includes('Authentication required') ||
-          errorMessage.includes('(code: -32000)');
+        const requiresAuth = isAuthenticationRequiredError(error);
         if (requiresAuth) {
+          if (!autoAuthenticate) {
+            console.log(
+              '[QwenAgentManager] Authentication required but auto-authentication is disabled. Propagating error.',
+            );
+            throw error;
+          }
           console.log(
             '[QwenAgentManager] Qwen requires authentication. Authenticating and retrying session/new...',
           );
diff --git a/packages/vscode-ide-companion/src/types/chatTypes.ts b/packages/vscode-ide-companion/src/types/chatTypes.ts
index 90ebbb87..57ec8504 100644
--- a/packages/vscode-ide-companion/src/types/chatTypes.ts
+++ b/packages/vscode-ide-companion/src/types/chatTypes.ts
@@ -34,7 +34,7 @@ export interface QwenAgentCallbacks {
   onToolCall?: (update: ToolCallUpdateData) => void;
   onPlan?: (entries: PlanEntry[]) => void;
   onPermissionRequest?: (request: AcpPermissionRequest) => Promise<string>;
-  onEndTurn?: () => void;
+  onEndTurn?: (reason?: string) => void;
   onModeInfo?: (info: {
     currentModeId?: ApprovalModeValue;
     availableModes?: Array<{
diff --git a/packages/vscode-ide-companion/src/types/connectionTypes.ts b/packages/vscode-ide-companion/src/types/connectionTypes.ts
index b49bd027..258ea798 100644
--- a/packages/vscode-ide-companion/src/types/connectionTypes.ts
+++ b/packages/vscode-ide-companion/src/types/connectionTypes.ts
@@ -19,7 +19,7 @@ export interface AcpConnectionCallbacks {
   onPermissionRequest: (data: AcpPermissionRequest) => Promise<{
     optionId: string;
   }>;
-  onEndTurn: () => void;
+  onEndTurn: (reason?: string) => void;
 }
 
 export interface AcpConnectionState {
diff --git a/packages/vscode-ide-companion/src/utils/authErrors.ts b/packages/vscode-ide-companion/src/utils/authErrors.ts
new file mode 100644
index 00000000..4b7de266
--- /dev/null
+++ b/packages/vscode-ide-companion/src/utils/authErrors.ts
@@ -0,0 +1,26 @@
+/**
+ * @license
+ * Copyright 2025 Qwen Team
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+const AUTH_ERROR_PATTERNS = [
+  'Authentication required',
+  '(code: -32000)',
+  'Unauthorized',
+  'Invalid token',
+  'Session expired',
+];
+
+export const isAuthenticationRequiredError = (error: unknown): boolean => {
+  if (!error) {
+    return false;
+  }
+  const message =
+    error instanceof Error
+      ? error.message
+      : typeof error === 'string'
+        ? error
+        : String(error);
+  return AUTH_ERROR_PATTERNS.some((pattern) => message.includes(pattern));
+};
diff --git a/packages/vscode-ide-companion/src/webview/App.tsx b/packages/vscode-ide-companion/src/webview/App.tsx
index 4bdf6622..d083740c 100644
--- a/packages/vscode-ide-companion/src/webview/App.tsx
+++ b/packages/vscode-ide-companion/src/webview/App.tsx
@@ -29,6 +29,7 @@ import { PermissionDrawer } from './components/PermissionDrawer/PermissionDrawer
 import { ToolCall } from './components/messages/toolcalls/ToolCall.js';
 import { hasToolCallOutput } from './components/messages/toolcalls/shared/utils.js';
 import { EmptyState } from './components/layout/EmptyState.js';
+import { OnboardingPage } from './components/layout/OnboardingPage.js';
 import { type CompletionItem } from '../types/completionItemTypes.js';
 import { useCompletionTrigger } from './hooks/useCompletionTrigger.js';
 import { ChatHeader } from './components/layout/ChatHeader.js';
@@ -67,6 +68,7 @@ export const App: React.FC = () => {
     toolCall: PermissionToolCall;
   } | null>(null);
   const [planEntries, setPlanEntries] = useState<PlanEntry[]>([]);
+  const [isAuthenticated, setIsAuthenticated] = useState<boolean | null>(null);
   const messagesEndRef = useRef<HTMLDivElement>(
     null,
   ) as React.RefObject<HTMLDivElement>;
@@ -176,6 +178,7 @@ export const App: React.FC = () => {
     vscode,
     inputFieldRef,
     isStreaming: messageHandling.isStreaming,
+    isWaitingForResponse: messageHandling.isWaitingForResponse,
   });
 
   // Handle cancel/stop from the input bar
@@ -218,6 +221,7 @@ export const App: React.FC = () => {
     inputFieldRef,
     setInputText,
     setEditMode,
+    setIsAuthenticated,
   });
 
   // Auto-scroll handling: keep the view pinned to bottom when new content arrives,
@@ -662,26 +666,37 @@ export const App: React.FC = () => {
 
       <div
         ref={messagesContainerRef}
-        className="chat-messages messages-container flex-1 overflow-y-auto overflow-x-hidden pt-5 pr-5 pl-5 pb-[120px] flex flex-col relative min-w-0 focus:outline-none [&::-webkit-scrollbar]:w-2 [&::-webkit-scrollbar-track]:bg-transparent [&::-webkit-scrollbar-thumb]:bg-white/20 [&::-webkit-scrollbar-thumb]:rounded-sm [&::-webkit-scrollbar-thumb]:hover:bg-white/30 [&>*]:flex [&>*]:gap-0 [&>*]:items-start [&>*]:text-left [&>*]:py-2 [&>*:not(:last-child)]:pb-[8px] [&>*]:flex-col [&>*]:relative [&>*]:animate-[fadeIn_0.2s_ease-in]"
+        className="chat-messages messages-container flex-1 overflow-y-auto overflow-x-hidden pt-5 pr-5 pl-5 pb-[140px] flex flex-col relative min-w-0 focus:outline-none [&::-webkit-scrollbar]:w-2 [&::-webkit-scrollbar-track]:bg-transparent [&::-webkit-scrollbar-thumb]:bg-white/20 [&::-webkit-scrollbar-thumb]:rounded-sm [&::-webkit-scrollbar-thumb]:hover:bg-white/30 [&>*]:flex [&>*]:gap-0 [&>*]:items-start [&>*]:text-left [&>*]:py-2 [&>*:not(:last-child)]:pb-[8px] [&>*]:flex-col [&>*]:relative [&>*]:animate-[fadeIn_0.2s_ease-in]"
       >
         {!hasContent ? (
-          <EmptyState />
+          isAuthenticated === false ? (
+            <OnboardingPage
+              onLogin={() => {
+                vscode.postMessage({ type: 'login', data: {} });
+                messageHandling.setWaitingForResponse(
+                  'Logging in to Qwen Code...',
+                );
+              }}
+            />
+          ) : isAuthenticated === null ? (
+            <EmptyState loadingMessage="Checking login status…" />
+          ) : (
+            <EmptyState isAuthenticated />
+          )
         ) : (
           <>
             {/* Render all messages and tool calls */}
             {renderMessages()}
-            {/* Flow-in persistent slot: keeps a small constant height so toggling */}
-            {/* the waiting message doesn't change list height to zero. When */}
-            {/* active, render the waiting message inline (not fixed). */}
-            <div className="waiting-message-slot min-h-[28px]">
-              {messageHandling.isWaitingForResponse &&
-                messageHandling.loadingMessage && (
+
+            {/* Waiting message positioned fixed above the input form to avoid layout shifts */}
+            {messageHandling.isWaitingForResponse &&
+              messageHandling.loadingMessage && (
+                <div className="waiting-message-slot min-h-[28px]">
                   <WaitingMessage
                     loadingMessage={messageHandling.loadingMessage}
                   />
-                )}
-            </div>
-
+                </div>
+              )}
             <div ref={messagesEndRef} />
           </>
         )}
diff --git a/packages/vscode-ide-companion/src/webview/WebViewProvider.ts b/packages/vscode-ide-companion/src/webview/WebViewProvider.ts
index b4da60ab..34e6d24f 100644
--- a/packages/vscode-ide-companion/src/webview/WebViewProvider.ts
+++ b/packages/vscode-ide-companion/src/webview/WebViewProvider.ts
@@ -15,6 +15,7 @@ import { WebViewContent } from '../webview/WebViewContent.js';
 import { CliInstaller } from '../cli/cliInstaller.js';
 import { getFileName } from './utils/webviewUtils.js';
 import { type ApprovalModeValue } from '../types/acpTypes.js';
+import { isAuthenticationRequiredError } from '../utils/authErrors.js';
 
 export class WebViewProvider {
   private panelManager: PanelManager;
@@ -119,12 +120,16 @@ export class WebViewProvider {
       });
     });
 
-    // Setup end-turn handler from ACP stopReason=end_turn
-    this.agentManager.onEndTurn(() => {
+    // Setup end-turn handler from ACP stopReason notifications
+    this.agentManager.onEndTurn((reason) => {
+      console.log(' ============== ', reason);
       // Ensure WebView exits streaming state even if no explicit streamEnd was emitted elsewhere
       this.sendMessageToWebView({
         type: 'streamEnd',
-        data: { timestamp: Date.now(), reason: 'end_turn' },
+        data: {
+          timestamp: Date.now(),
+          reason: reason || 'end_turn',
+        },
       });
     });
 
@@ -520,10 +525,10 @@ export class WebViewProvider {
   private async attemptAuthStateRestoration(): Promise<void> {
     try {
       console.log(
-        '[WebViewProvider] Attempting connection (CLI handle authentication)...',
+        '[WebViewProvider] Attempting connection (without auto-auth)...',
       );
-      //always attempt connection and let CLI handle authentication
-      await this.initializeAgentConnection();
+      // Attempt a lightweight connection to detect prior auth without forcing login
+      await this.initializeAgentConnection({ autoAuthenticate: false });
     } catch (error) {
       console.error(
         '[WebViewProvider] Error in attemptAuthStateRestoration:',
@@ -537,14 +542,19 @@ export class WebViewProvider {
    * Initialize agent connection and session
    * Can be called from show() or via /login command
    */
-  async initializeAgentConnection(): Promise<void> {
-    return this.doInitializeAgentConnection();
+  async initializeAgentConnection(options?: {
+    autoAuthenticate?: boolean;
+  }): Promise<void> {
+    return this.doInitializeAgentConnection(options);
   }
 
   /**
    * Internal: perform actual connection/initialization (no auth locking).
    */
-  private async doInitializeAgentConnection(): Promise<void> {
+  private async doInitializeAgentConnection(options?: {
+    autoAuthenticate?: boolean;
+  }): Promise<void> {
+    const autoAuthenticate = options?.autoAuthenticate ?? true;
     const run = async () => {
       const workspaceFolder = vscode.workspace.workspaceFolders?.[0];
       const workingDir = workspaceFolder?.uri.fsPath || process.cwd();
@@ -553,7 +563,9 @@ export class WebViewProvider {
         '[WebViewProvider] Starting initialization, workingDir:',
         workingDir,
       );
-      console.log('[WebViewProvider] Using CLI-managed authentication');
+      console.log(
+        `[WebViewProvider] Using CLI-managed authentication (autoAuth=${autoAuthenticate})`,
+      );
 
       // Check if CLI is installed before attempting to connect
       const cliDetection = await CliDetector.detectQwenCli();
@@ -583,18 +595,34 @@ export class WebViewProvider {
           console.log('[WebViewProvider] Connecting to agent...');
 
           // Pass the detected CLI path to ensure we use the correct installation
-          await this.agentManager.connect(workingDir, cliDetection.cliPath);
+          const connectResult = await this.agentManager.connect(
+            workingDir,
+            cliDetection.cliPath,
+            options,
+          );
           console.log('[WebViewProvider] Agent connected successfully');
           this.agentInitialized = true;
+          if (connectResult.requiresAuth) {
+            this.sendMessageToWebView({
+              type: 'authState',
+              data: { authenticated: false },
+            });
+          }
 
           // Load messages from the current Qwen session
-          await this.loadCurrentSessionMessages();
+          const sessionReady = await this.loadCurrentSessionMessages(options);
 
-          // Notify webview that agent is connected
-          this.sendMessageToWebView({
-            type: 'agentConnected',
-            data: {},
-          });
+          if (sessionReady) {
+            // Notify webview that agent is connected
+            this.sendMessageToWebView({
+              type: 'agentConnected',
+              data: {},
+            });
+          } else {
+            console.log(
+              '[WebViewProvider] Session creation deferred until user logs in.',
+            );
+          }
         } catch (_error) {
           console.error('[WebViewProvider] Agent connection error:', _error);
           vscode.window.showWarningMessage(
@@ -654,7 +682,7 @@ export class WebViewProvider {
           });
 
           // Reinitialize connection (will trigger fresh authentication)
-          await this.doInitializeAgentConnection();
+          await this.doInitializeAgentConnection({ autoAuthenticate: true });
           console.log(
             '[WebViewProvider] Force re-login completed successfully',
           );
@@ -737,7 +765,11 @@ export class WebViewProvider {
    * Load messages from current Qwen session
    * Skips session restoration and creates a new session directly
    */
-  private async loadCurrentSessionMessages(): Promise<void> {
+  private async loadCurrentSessionMessages(options?: {
+    autoAuthenticate?: boolean;
+  }): Promise<boolean> {
+    const autoAuthenticate = options?.autoAuthenticate ?? true;
+    let sessionReady = false;
     try {
       console.log(
         '[WebViewProvider] Initializing with new session (skipping restoration)',
@@ -748,22 +780,47 @@ export class WebViewProvider {
 
       // avoid creating another session if connect() already created one.
       if (!this.agentManager.currentSessionId) {
-        try {
-          await this.agentManager.createNewSession(workingDir);
-          console.log('[WebViewProvider] ACP session created successfully');
-        } catch (sessionError) {
-          console.error(
-            '[WebViewProvider] Failed to create ACP session:',
-            sessionError,
-          );
-          vscode.window.showWarningMessage(
-            `Failed to create ACP session: ${sessionError}. You may need to authenticate first.`,
+        if (!autoAuthenticate) {
+          console.log(
+            '[WebViewProvider] Skipping ACP session creation until user logs in.',
           );
+          this.sendMessageToWebView({
+            type: 'authState',
+            data: { authenticated: false },
+          });
+        } else {
+          try {
+            await this.agentManager.createNewSession(workingDir, {
+              autoAuthenticate,
+            });
+            console.log('[WebViewProvider] ACP session created successfully');
+            sessionReady = true;
+          } catch (sessionError) {
+            const requiresAuth = isAuthenticationRequiredError(sessionError);
+            if (requiresAuth && !autoAuthenticate) {
+              console.log(
+                '[WebViewProvider] ACP session requires authentication; waiting for explicit login.',
+              );
+              this.sendMessageToWebView({
+                type: 'authState',
+                data: { authenticated: false },
+              });
+            } else {
+              console.error(
+                '[WebViewProvider] Failed to create ACP session:',
+                sessionError,
+              );
+              vscode.window.showWarningMessage(
+                `Failed to create ACP session: ${sessionError}. You may need to authenticate first.`,
+              );
+            }
+          }
         }
       } else {
         console.log(
           '[WebViewProvider] Existing ACP session detected, skipping new session creation',
         );
+        sessionReady = true;
       }
 
       await this.initializeEmptyConversation();
@@ -776,7 +833,10 @@ export class WebViewProvider {
         `Failed to load session messages: ${_error}`,
       );
       await this.initializeEmptyConversation();
+      return false;
     }
+
+    return sessionReady;
   }
 
   /**
diff --git a/packages/vscode-ide-companion/src/webview/components/layout/EmptyState.tsx b/packages/vscode-ide-companion/src/webview/components/layout/EmptyState.tsx
index 081352b8..f1b15c4c 100644
--- a/packages/vscode-ide-companion/src/webview/components/layout/EmptyState.tsx
+++ b/packages/vscode-ide-companion/src/webview/components/layout/EmptyState.tsx
@@ -7,10 +7,24 @@
 import type React from 'react';
 import { generateIconUrl } from '../../utils/resourceUrl.js';
 
-export const EmptyState: React.FC = () => {
+interface EmptyStateProps {
+  isAuthenticated?: boolean;
+  loadingMessage?: string;
+}
+
+export const EmptyState: React.FC<EmptyStateProps> = ({
+  isAuthenticated = false,
+  loadingMessage,
+}) => {
   // Generate icon URL using the utility function
   const iconUri = generateIconUrl('icon.png');
 
+  const description = loadingMessage
+    ? 'Preparing Qwen Code…'
+    : isAuthenticated
+      ? 'What would you like to do? Ask about this codebase or we can start writing code.'
+      : 'Welcome! Please log in to start using Qwen Code.';
+
   return (
     <div className="flex flex-col items-center justify-center h-full p-5 md:p-10">
       <div className="flex flex-col items-center gap-8 w-full">
@@ -23,9 +37,14 @@ export const EmptyState: React.FC = () => {
           />
           <div className="text-center">
             <div className="text-[15px] text-app-primary-foreground leading-normal font-normal max-w-[400px]">
-              What to do first? Ask about this codebase or we can start writing
-              code.
+              {description}
             </div>
+            {loadingMessage && (
+              <div className="flex items-center justify-center gap-2 mt-4 text-sm text-app-secondary-foreground">
+                <span className="inline-block h-3 w-3 rounded-full border-2 border-app-secondary-foreground/40 border-t-app-primary-foreground animate-spin" />
+                <span>{loadingMessage}</span>
+              </div>
+            )}
           </div>
         </div>
       </div>
diff --git a/packages/vscode-ide-companion/src/webview/components/layout/InputForm.tsx b/packages/vscode-ide-companion/src/webview/components/layout/InputForm.tsx
index fe86ea99..997c3f9a 100644
--- a/packages/vscode-ide-companion/src/webview/components/layout/InputForm.tsx
+++ b/packages/vscode-ide-companion/src/webview/components/layout/InputForm.tsx
@@ -113,6 +113,7 @@ export const InputForm: React.FC<InputFormProps> = ({
   onCompletionClose,
 }) => {
   const editModeInfo = getEditModeInfo(editMode);
+  const composerDisabled = isStreaming || isWaitingForResponse;
 
   const handleKeyDown = (e: React.KeyboardEvent) => {
     // ESC should cancel the current interaction (stop generation)
@@ -144,7 +145,7 @@ export const InputForm: React.FC<InputFormProps> = ({
 
   return (
     <div
-      className="p-1 px-4 pb-4"
+      className="p-1 px-4 pb-4 absolute bottom-0 left-0 right-0"
       style={{ backgroundColor: 'var(--app-primary-background)' }}
     >
       <div className="block">
@@ -171,7 +172,7 @@ export const InputForm: React.FC<InputFormProps> = ({
 
             <div
               ref={inputFieldRef}
-              contentEditable="plaintext-only"
+              contentEditable={'plaintext-only'}
               className="composer-input"
               role="textbox"
               aria-label="Message input"
@@ -179,10 +180,19 @@ export const InputForm: React.FC<InputFormProps> = ({
               data-placeholder="Ask Qwen Code …"
               // Use a data flag so CSS can show placeholder even if the browser
               // inserts an invisible <br> into contentEditable (so :empty no longer matches)
-              data-empty={inputText.trim().length === 0 ? 'true' : 'false'}
+              data-empty={
+                inputText.replace(/\u200B/g, '').trim().length === 0
+                  ? 'true'
+                  : 'false'
+              }
               onInput={(e) => {
+                if (composerDisabled) {
+                  return;
+                }
                 const target = e.target as HTMLDivElement;
-                onInputChange(target.textContent || '');
+                // Filter out zero-width space that we use to maintain height
+                const text = target.textContent?.replace(/\u200B/g, '') || '';
+                onInputChange(text);
               }}
               onCompositionStart={onCompositionStart}
               onCompositionEnd={onCompositionEnd}
@@ -280,7 +290,7 @@ export const InputForm: React.FC<InputFormProps> = ({
               <button
                 type="submit"
                 className="btn-send-compact [&>svg]:w-5 [&>svg]:h-5"
-                disabled={!inputText.trim()}
+                disabled={composerDisabled || !inputText.trim()}
               >
                 <ArrowUpIcon />
               </button>
diff --git a/packages/vscode-ide-companion/src/webview/components/layout/OnboardingPage.tsx b/packages/vscode-ide-companion/src/webview/components/layout/OnboardingPage.tsx
new file mode 100644
index 00000000..945f86a4
--- /dev/null
+++ b/packages/vscode-ide-companion/src/webview/components/layout/OnboardingPage.tsx
@@ -0,0 +1,81 @@
+import type React from 'react';
+import { generateIconUrl } from '../../utils/resourceUrl.js';
+
+interface OnboardingPageProps {
+  onLogin: () => void;
+}
+
+export const OnboardingPage: React.FC<OnboardingPageProps> = ({ onLogin }) => {
+  const iconUri = generateIconUrl('icon.png');
+
+  return (
+    <div className="flex flex-col items-center justify-center h-full p-5 md:p-10">
+      <div className="flex flex-col items-center gap-8 w-full max-w-md">
+        <div className="flex flex-col items-center gap-6">
+          <div className="relative">
+            <img
+              src={iconUri}
+              alt="Qwen Code Logo"
+              className="w-[80px] h-[80px] object-contain"
+            />
+            <div className="absolute -top-2 -right-2 w-6 h-6 bg-[#4f46e5] rounded-full flex items-center justify-center">
+              <svg width="12" height="12" viewBox="0 0 12 12" fill="white">
+                <path
+                  d="M2.5 1.5L9.5 8.5M9.5 1.5L2.5 8.5"
+                  stroke="white"
+                  strokeWidth="1.5"
+                  strokeLinecap="round"
+                />
+              </svg>
+            </div>
+          </div>
+
+          <div className="text-center">
+            <h1 className="text-2xl font-bold text-app-primary-foreground mb-2">
+              Welcome to Qwen Code
+            </h1>
+            <p className="text-app-secondary-foreground max-w-sm">
+              Qwen Code helps you understand, navigate, and transform your
+              codebase with AI assistance.
+            </p>
+          </div>
+
+          {/* <div className="flex flex-col gap-5 w-full">
+            <div className="bg-app-secondary-background rounded-xl p-5 border border-app-primary-border-color shadow-sm">
+              <h2 className="font-semibold text-app-primary-foreground mb-3">Get Started</h2>
+              <ul className="space-y-2">
+                <li className="flex items-start gap-2">
+                  <div className="mt-1 w-1.5 h-1.5 rounded-full bg-[#4f46e5] flex-shrink-0"></div>
+                  <span className="text-sm text-app-secondary-foreground">Understand complex codebases faster</span>
+                </li>
+                <li className="flex items-start gap-2">
+                  <div className="mt-1 w-1.5 h-1.5 rounded-full bg-[#4f46e5] flex-shrink-0"></div>
+                  <span className="text-sm text-app-secondary-foreground">Navigate with AI-powered suggestions</span>
+                </li>
+                <li className="flex items-start gap-2">
+                  <div className="mt-1 w-1.5 h-1.5 rounded-full bg-[#4f46e5] flex-shrink-0"></div>
+                  <span className="text-sm text-app-secondary-foreground">Transform code with confidence</span>
+                </li>
+              </ul>
+            </div>
+
+          </div> */}
+
+          <button
+            onClick={onLogin}
+            className="w-full px-4 py-3 bg-[#4f46e5] text-white font-medium rounded-lg shadow-sm"
+          >
+            Log in to Qwen Code
+          </button>
+
+          {/* <div className="text-center">
+            <p className="text-xs text-app-secondary-foreground">
+              By logging in, you agree to the Terms of Service and Privacy
+              Policy.
+            </p>
+          </div> */}
+        </div>
+      </div>
+    </div>
+  );
+};
diff --git a/packages/vscode-ide-companion/src/webview/hooks/useMessageSubmit.ts b/packages/vscode-ide-companion/src/webview/hooks/useMessageSubmit.ts
index 9f67bcc8..a91594c0 100644
--- a/packages/vscode-ide-companion/src/webview/hooks/useMessageSubmit.ts
+++ b/packages/vscode-ide-companion/src/webview/hooks/useMessageSubmit.ts
@@ -14,6 +14,7 @@ interface UseMessageSubmitProps {
   setInputText: (text: string) => void;
   inputFieldRef: React.RefObject<HTMLDivElement>;
   isStreaming: boolean;
+  isWaitingForResponse: boolean;
   // When true, do NOT auto-attach the active editor file/selection to context
   skipAutoActiveContext?: boolean;
 
@@ -40,6 +41,7 @@ export const useMessageSubmit = ({
   setInputText,
   inputFieldRef,
   isStreaming,
+  isWaitingForResponse,
   skipAutoActiveContext = false,
   fileContext,
   messageHandling,
@@ -48,7 +50,7 @@ export const useMessageSubmit = ({
     (e: React.FormEvent) => {
       e.preventDefault();
 
-      if (!inputText.trim() || isStreaming) {
+      if (!inputText.trim() || isStreaming || isWaitingForResponse) {
         return;
       }
 
@@ -56,7 +58,10 @@ export const useMessageSubmit = ({
       if (inputText.trim() === '/login') {
         setInputText('');
         if (inputFieldRef.current) {
-          inputFieldRef.current.textContent = '';
+          // Use a zero-width space to maintain the height of the contentEditable element
+          inputFieldRef.current.textContent = '\u200B';
+          // Set the data-empty attribute to show the placeholder
+          inputFieldRef.current.setAttribute('data-empty', 'true');
         }
         vscode.postMessage({
           type: 'login',
@@ -142,7 +147,10 @@ export const useMessageSubmit = ({
 
       setInputText('');
       if (inputFieldRef.current) {
-        inputFieldRef.current.textContent = '';
+        // Use a zero-width space to maintain the height of the contentEditable element
+        inputFieldRef.current.textContent = '\u200B';
+        // Set the data-empty attribute to show the placeholder
+        inputFieldRef.current.setAttribute('data-empty', 'true');
       }
       fileContext.clearFileReferences();
     },
@@ -154,6 +162,7 @@ export const useMessageSubmit = ({
       vscode,
       fileContext,
       skipAutoActiveContext,
+      isWaitingForResponse,
       messageHandling,
     ],
   );
diff --git a/packages/vscode-ide-companion/src/webview/hooks/useWebViewMessages.ts b/packages/vscode-ide-companion/src/webview/hooks/useWebViewMessages.ts
index 7a3f7e06..a227e470 100644
--- a/packages/vscode-ide-companion/src/webview/hooks/useWebViewMessages.ts
+++ b/packages/vscode-ide-companion/src/webview/hooks/useWebViewMessages.ts
@@ -109,6 +109,8 @@ interface UseWebViewMessagesProps {
   setInputText: (text: string) => void;
   // Edit mode setter (maps ACP modes to UI modes)
   setEditMode?: (mode: ApprovalModeValue) => void;
+  // Authentication state setter
+  setIsAuthenticated?: (authenticated: boolean | null) => void;
 }
 
 /**
@@ -126,6 +128,7 @@ export const useWebViewMessages = ({
   inputFieldRef,
   setInputText,
   setEditMode,
+  setIsAuthenticated,
 }: UseWebViewMessagesProps) => {
   // VS Code API for posting messages back to the extension host
   const vscode = useVSCode();
@@ -141,6 +144,7 @@ export const useWebViewMessages = ({
     clearToolCalls,
     setPlanEntries,
     handlePermissionRequest,
+    setIsAuthenticated,
   });
 
   // Track last "Updated Plan" snapshot toolcall to support merge/dedupe
@@ -185,6 +189,7 @@ export const useWebViewMessages = ({
       clearToolCalls,
       setPlanEntries,
       handlePermissionRequest,
+      setIsAuthenticated,
     };
   });
 
@@ -216,6 +221,7 @@ export const useWebViewMessages = ({
           }
           break;
         }
+
         case 'loginSuccess': {
           // Clear loading state and show a short assistant notice
           handlers.messageHandling.clearWaitingForResponse();
@@ -224,12 +230,16 @@ export const useWebViewMessages = ({
             content: 'Successfully logged in. You can continue chatting.',
             timestamp: Date.now(),
           });
+          // Set authentication state to true
+          handlers.setIsAuthenticated?.(true);
           break;
         }
 
         case 'agentConnected': {
           // Agent connected successfully; clear any pending spinner
           handlers.messageHandling.clearWaitingForResponse();
+          // Set authentication state to true
+          handlers.setIsAuthenticated?.(true);
           break;
         }
 
@@ -245,6 +255,8 @@ export const useWebViewMessages = ({
             content: `Failed to connect to Qwen agent: ${errorMsg}\nYou can still use the chat UI, but messages won't be sent to AI.`,
             timestamp: Date.now(),
           });
+          // Set authentication state to false
+          handlers.setIsAuthenticated?.(false);
           break;
         }
 
@@ -259,6 +271,20 @@ export const useWebViewMessages = ({
             content: errorMsg,
             timestamp: Date.now(),
           });
+          // Set authentication state to false
+          handlers.setIsAuthenticated?.(false);
+          break;
+        }
+
+        case 'authState': {
+          const state = (
+            message?.data as { authenticated?: boolean | null } | undefined
+          )?.authenticated;
+          if (typeof state === 'boolean') {
+            handlers.setIsAuthenticated?.(state);
+          } else {
+            handlers.setIsAuthenticated?.(null);
+          }
           break;
         }
 
@@ -303,6 +329,7 @@ export const useWebViewMessages = ({
               }
             }
           }
+          console.log('[useWebViewMessages1111]__________ other message:', msg);
           break;
         }
 
@@ -336,7 +363,7 @@ export const useWebViewMessages = ({
             const reason = (
               (message.data as { reason?: string } | undefined)?.reason || ''
             ).toLowerCase();
-            if (reason === 'user_cancelled') {
+            if (reason === 'user_cancelled' || reason === 'cancelled') {
               activeExecToolCallsRef.current.clear();
               handlers.messageHandling.clearWaitingForResponse();
               break;
diff --git a/packages/vscode-ide-companion/src/webview/styles/tailwind.css b/packages/vscode-ide-companion/src/webview/styles/tailwind.css
index 4c4b5e08..46d803d5 100644
--- a/packages/vscode-ide-companion/src/webview/styles/tailwind.css
+++ b/packages/vscode-ide-companion/src/webview/styles/tailwind.css
@@ -51,8 +51,7 @@
   .composer-form:focus-within {
     /* match existing highlight behavior */
     border-color: var(--app-input-highlight);
-    box-shadow: 0 1px 2px
-      color-mix(in srgb, var(--app-input-highlight), transparent 80%);
+    box-shadow: 0 1px 2px color-mix(in srgb, var(--app-input-highlight), transparent 80%);
   }
 
   /* Composer: input editable area */
@@ -67,7 +66,7 @@
      The data attribute is needed because some browsers insert a <br> in
      contentEditable, which breaks :empty matching. */
   .composer-input:empty:before,
-  .composer-input[data-empty='true']::before {
+  .composer-input[data-empty="true"]::before {
     content: attr(data-placeholder);
     color: var(--app-input-placeholder-foreground);
     pointer-events: none;
@@ -81,7 +80,7 @@
     outline: none;
   }
   .composer-input:disabled,
-  .composer-input[contenteditable='false'] {
+  .composer-input[contenteditable="false"] {
     color: #999;
     cursor: not-allowed;
   }
@@ -111,7 +110,7 @@
   }
   .btn-text-compact > svg {
     height: 1em;
-    width: 1em; 
+    width: 1em;
     flex-shrink: 0;
   }
   .btn-text-compact > span {
diff --git a/packages/vscode-ide-companion/src/webview/styles/timeline.css b/packages/vscode-ide-companion/src/webview/styles/timeline.css
index 25d5cc85..033e82d2 100644
--- a/packages/vscode-ide-companion/src/webview/styles/timeline.css
+++ b/packages/vscode-ide-companion/src/webview/styles/timeline.css
@@ -88,6 +88,22 @@
   z-index: 0;
 }
 
+/* Single-item AI sequence (both a start and an end): hide the connector entirely */
+.qwen-message.message-item:not(.user-message-container):is(
+    :first-child,
+    .user-message-container
+      + .qwen-message.message-item:not(.user-message-container),
+    .chat-messages
+      > :not(.qwen-message.message-item)
+      + .qwen-message.message-item:not(.user-message-container)
+  ):is(
+    :has(+ .user-message-container),
+    :has(+ :not(.qwen-message.message-item)),
+    :last-child
+  )::after {
+  display: none;
+}
+
 /* Handle the start of each AI message sequence - includes the first AI message in the entire message list and new AI messages interrupted by user messages */
 .qwen-message.message-item:not(.user-message-container):first-child::after,
 .user-message-container + .qwen-message.message-item:not(.user-message-container)::after,
@@ -123,4 +139,4 @@
   position: relative;
   padding-top: 8px;
   padding-bottom: 8px;
-}
\ No newline at end of file
+}