claudia-orchestrator 0.1.5 → 0.1.7

package/README.md

@@ -1,107 +1,52 @@
-# Claudia Orchestrator
+# Claudia
 
-A cognitive telemetry dashboard for Claude Code sessions. Orchestrate multiple AI coding sessions with real-time streaming, AI-powered insights, and session analysis.
+A dashboard for orchestrating Claude Code sessions. Run multiple AI coding sessions in parallel with real-time streaming and AI-powered insights.
 
-## What This Is
-
-Claudia Orchestrator wraps Claude Code CLI sessions and adds:
-
-- **Live insight surfacing** — See what the model is doing: assumptions, uncertainties, scope drift, progress
-- **Multi-session management** — Run multiple Claude Code sessions in parallel from one dashboard
-- **Real-time streaming** — PTY-based process management with instant output
-- **Session persistence** — Sessions survive server restarts
-
-## Quick Start
-
-**Requirements:** Node.js 22+, Claude Code CLI installed and authenticated
+## Install
 
 ```bash
-# Run directly (no install needed)
 npx claudia-orchestrator
+```
 
-# Or install globally
+Or install globally:
+
+```bash
 npm install -g claudia-orchestrator
 claudia
 ```
 
-The dashboard runs at `http://localhost:3001`. Your auth token is displayed on first launch — open the URL shown in terminal.
+**Requirements:** Node.js 22+, Claude Code CLI installed and authenticated
 
 ## Features
 
-### Session Orchestration
-- Start new Claude Code sessions from the browser
-- Resume previous sessions
-- Run multiple sessions in parallel
-- Stream output in real-time
-
-### AI Insights (Beta)
-During beta, all users get access to AI-powered session insights:
-- **Current State** — What's happening right now
-- **Milestones** — Progress tracking with done/current/pending tasks
-- **Notable Events** — Errors, breakthroughs, decisions, course corrections
-- **Context Panels** — Key information extracted from the session
-
-Insights require your own Anthropic API key (set `ANTHROPIC_API_KEY` environment variable).
-
-### Voice Input
-Dictation powered by Gemini 2.5 Flash. Requires a Google API key (`GOOGLE_API_KEY`).
-
-### Push Notifications
-Get notified when sessions complete or need input. Supports web-push and ntfy.sh.
+- **Multi-session management** — Run multiple Claude Code sessions in parallel
+- **Real-time streaming** — PTY-based output with instant feedback
+- **AI insights** — See what the model is doing: assumptions, progress, uncertainties
+- **Session persistence** — Sessions survive server restarts
+- **Voice input** — Dictation powered by Gemini 2.5 Flash
+- **Push notifications** — Get notified when sessions complete or need input
 
-## Configuration
+## Setup
 
-Config lives in `~/.claudia/`:
-- `config.json` — Server settings, API keys, auth token
-- `session-info.db` — Session metadata and insights cache
+The dashboard runs at `http://localhost:3001`. Your auth token is displayed on first launch.
 
-### Environment Variables
+### API Keys
 
 | Variable | Purpose |
 |----------|---------|
 | `ANTHROPIC_API_KEY` | Required for AI insights |
 | `GOOGLE_API_KEY` | Optional for voice dictation |
 
+Set these in your environment or in `~/.claudia/config.json`.
+
 ### Remote Access
 
 1. Edit `~/.claudia/config.json`, set `server.host` to `0.0.0.0`
-2. Use HTTPS via reverse proxy (Caddy, nginx) for security
-3. Or use Tailscale Serve for secure access
-
-## System Requirements
-
-- **Node.js:** 22+ (native modules: node-pty, better-sqlite3, sharp)
-- **Claude Code:** Must be installed and authenticated (`claude` command available)
-- **Platform:** Linux, macOS, WSL2
-
-## Beta Status
-
-This is beta software. During beta:
-- All Pro features are enabled for everyone
-- AI insights require your own API key
-- Session limits are not enforced
-
-## Troubleshooting
-
-### "Module not found" or native module errors
-```bash
-# Rebuild native modules for your Node version
-rm -rf node_modules
-npm install
-```
-
-### Sessions not starting
-Ensure Claude Code CLI is working:
-```bash
-claude --version
-```
-
-### Insights not generating
-Check that `ANTHROPIC_API_KEY` is set in `~/.claudia/config.json` or as an environment variable.
+2. Use HTTPS via reverse proxy (Caddy, nginx) or Tailscale Serve
 
-## Credits
+## Status
 
-Forked from [cui](https://github.com/BMPixel/cui) by Wenbo Pan. Extended with cognitive telemetry and licensing infrastructure.
+Claudia is in beta. For feedback or support, email jason@liggi.dev.
 
 ## License
 

package/dist/cli-parser.d.ts

@@ -1,8 +1,6 @@
 export interface CLIConfig {
     port?: number;
     host?: string;
-    token?: string;
-    skipAuthToken?: boolean;
 }
 /**
  * Parse command line arguments

package/dist/cli-parser.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"cli-parser.d.ts","sourceRoot":"","sources":["../src/cli-parser.ts"],"names":[],"mappings":"AAEA,MAAM,WAAW,SAAS;IACxB,IAAI,CAAC,EAAE,MAAM,CAAC;IACd,IAAI,CAAC,EAAE,MAAM,CAAC;CACf;AAED;;GAEG;AACH,wBAAgB,SAAS,CAAC,IAAI,EAAE,MAAM,EAAE,GAAG,SAAS,CAyCnD"}

package/dist/cli-parser.js

@@ -34,21 +34,9 @@ export function parseArgs(argv) {
                     process.exit(1);
                 }
                 break;
-            case '--token':
-                if (i + 1 < args.length) {
-                    config.token = args[++i];
-                }
-                else {
-                    logger.error('--token requires a value');
-                    process.exit(1);
-                }
-                break;
-            case '--skip-auth-token':
-                config.skipAuthToken = true;
-                break;
             default:
                 logger.error(`Unknown argument: ${arg}`);
-                logger.info('Usage: claudia [--port <number>] [--host <string>] [--token <string>] [--skip-auth-token]');
+                logger.info('Usage: claudia [--port <number>] [--host <string>]');
                 process.exit(1);
         }
     }

package/dist/cli-parser.js.map

@@ -1 +1 @@
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package/dist/cui-server.d.ts

@@ -8,9 +8,9 @@ export declare class CUIServer {
     private processManager;
     private streamManager;
     private historyReader;
-    private statusTracker;
     private permissionTracker;
     private questionTracker;
+    private pendingQuestionService;
     private mcpConfigGenerator;
     private fileSystemService;
     private configService;
@@ -28,8 +28,6 @@ export declare class CUIServer {
     constructor(configOverrides?: {
         port?: number;
         host?: string;
-        token?: string;
-        skipAuthToken?: boolean;
     });
     /**
      * Get the Express app instance

package/dist/cui-server.d.ts.map

@@ -1 +1 @@
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package/dist/cui-server.js

@@ -11,6 +11,7 @@ import { StreamManager } from './services/stream-manager.js';
 import { ClaudeHistoryReader } from './services/claude-history-reader.js';
 import { PermissionTracker } from './services/permission-tracker.js';
 import { QuestionTracker } from './services/question-tracker.js';
+import { PendingQuestionService } from './services/pending-question-service.js';
 import { MCPConfigGenerator } from './services/mcp-config-generator.js';
 import { FileSystemService } from './services/file-system-service.js';
 import { ConfigService } from './services/config-service.js';
@@ -22,7 +23,6 @@ import { NotificationService } from './services/notification-service.js';
 import { WebPushService } from './services/web-push-service.js';
 import { geminiService } from './services/gemini-service.js';
 import { anthropicService } from './services/anthropic-service.js';
-import { SessionInsightsService } from './services/session-insights-service.js';
 import { ClaudeRouterService } from './services/claude-router-service.js';
 import { CUIError } from './types/index.js';
 import { createLogger } from './services/logger.js';
@@ -30,22 +30,22 @@ import { createConversationRoutes } from './routes/conversation.routes.js';
 import { createSystemRoutes } from './routes/system.routes.js';
 import { createPermissionRoutes } from './routes/permission.routes.js';
 import { createQuestionRoutes } from './routes/question.routes.js';
+import { createPendingQuestionRoutes } from './routes/pending-question.routes.js';
 import { createFileSystemRoutes } from './routes/filesystem.routes.js';
 import { createLogRoutes } from './routes/log.routes.js';
 import { createStreamingRoutes } from './routes/streaming.routes.js';
 import { createWorkingDirectoriesRoutes } from './routes/working-directories.routes.js';
 import { createConfigRoutes } from './routes/config.routes.js';
-import { createGeminiRoutes } from './routes/gemini.routes.js';
-import { createNotificationsRoutes } from './routes/notifications.routes.js';
 import { createInsightsRoutes } from './routes/insights.routes.js';
 import { createClaudiaRoutes } from './routes/claudia.routes.js';
 import { ClaudiaService } from './services/claudia-service.js';
 import { createLicenseRoutes } from './routes/license.routes.js';
+import { createAnalysisRoutes } from './routes/analysis.routes.js';
+import processEventsRouter from './routes/process-events.routes.js';
 import { errorHandler } from './middleware/error-handler.js';
 import { requestLogger } from './middleware/request-logger.js';
 import { createCorsMiddleware } from './middleware/cors-setup.js';
 import { queryParser } from './middleware/query-parser.js';
-import { authMiddleware, createAuthMiddleware } from './middleware/auth.js';
 // ViteExpress will be imported dynamically in initialize() if needed
 let ViteExpress;
 /**
@@ -57,9 +57,9 @@ export class CUIServer {
     processManager; // Initialized in initialize()
     streamManager;
     historyReader;
-    statusTracker;
     permissionTracker;
     questionTracker;
+    pendingQuestionService;
     mcpConfigGenerator;
     fileSystemService;
     configService;
@@ -94,15 +94,14 @@ export class CUIServer {
         // Use singleton to ensure event handlers get the same initialized instance
         this.sessionInfoService = SessionInfoService.getInstance();
         this.historyReader = new ClaudeHistoryReader(this.sessionInfoService);
-        // Create a single instance of ConversationStatusManager for both statusTracker and conversationStatusManager
         this.conversationStatusManager = new ConversationStatusManager();
-        this.statusTracker = this.conversationStatusManager; // Use the same instance for backward compatibility
         this.toolMetricsService = new ToolMetricsService();
         this.fileSystemService = new FileSystemService();
         // processManager is initialized in initialize() to support daemon mode
         this.streamManager = new StreamManager();
         this.permissionTracker = new PermissionTracker();
         this.questionTracker = new QuestionTracker();
+        this.pendingQuestionService = PendingQuestionService.getInstance();
         this.mcpConfigGenerator = new MCPConfigGenerator(this.fileSystemService);
         this.workingDirectoriesService = new WorkingDirectoriesService(this.historyReader, this.logger);
         this.notificationService = new NotificationService();
@@ -111,14 +110,11 @@ export class CUIServer {
         this.permissionTracker.setNotificationService(this.notificationService);
         this.permissionTracker.setConversationStatusManager(this.conversationStatusManager);
         this.permissionTracker.setHistoryReader(this.historyReader);
-        // Set up background insights computation when sessions end
-        const insightsService = new SessionInsightsService(this.historyReader, this.sessionInfoService);
-        this.conversationStatusManager.on('session-ended', ({ claudeSessionId }) => {
-            // Compute insights in background (fire and forget)
-            insightsService.computeInsights(claudeSessionId)
-                .then(insights => insightsService.cacheInsights(claudeSessionId, insights))
-                .catch(err => this.logger.debug('Background insights computation failed', { claudeSessionId, error: err }));
-        });
+        // NOTE: Session-ended insights computation was removed because it raced with
+        // the event-driven InsightsService. The session-ended handler would read the
+        // session file before all messages were flushed, caching insights with
+        // messageCount=1. The event-driven system (InsightsService) now handles all
+        // insight generation via file watching and action counting.
         this.logger.debug('Services initialized (processManager deferred to initialize())');
         this.setupMiddleware();
         // Routes and processManager integration are set up in initialize()
@@ -155,15 +151,24 @@ export class CUIServer {
             this.logger.debug('Initializing session info service');
             await this.sessionInfoService.initialize();
             this.logger.debug('Session info service initialized successfully');
-            // Initialize process manager
-            this.logger.debug('Initializing process manager');
-            this.processManager = await createProcessManager({
-                historyReader: this.historyReader,
-                statusTracker: this.statusTracker,
-                toolMetricsService: this.toolMetricsService,
-                sessionInfoService: this.sessionInfoService,
-                fileSystemService: this.fileSystemService
-            });
+            // Initialize pending question service (uses same DB as session info)
+            this.logger.debug('Initializing pending question service');
+            await this.pendingQuestionService.initialize();
+            this.logger.debug('Pending question service initialized successfully');
+            // Initialize process manager (skip if already set, e.g. by tests)
+            if (!this.processManager) {
+                this.logger.debug('Initializing process manager');
+                this.processManager = await createProcessManager({
+                    historyReader: this.historyReader,
+                    statusTracker: this.conversationStatusManager,
+                    toolMetricsService: this.toolMetricsService,
+                    sessionInfoService: this.sessionInfoService,
+                    fileSystemService: this.fileSystemService
+                });
+            }
+            else {
+                this.logger.debug('Process manager already set, skipping initialization');
+            }
             this.processManager.setNotificationService(this.notificationService);
             this.processManager.setConversationStatusManager(this.conversationStatusManager);
             // Set up event listeners now that processManager exists
@@ -184,8 +189,12 @@ export class CUIServer {
             this.logger.debug('Cost tracker initialized successfully');
             // Initialize insights service (unified event-driven system)
             this.logger.debug('Initializing insights service');
-            const { initializeInsightsService } = await import('./services/insights-service.js');
+            const { initializeInsightsService, getInsightsService } = await import('./services/insights-service.js');
             initializeInsightsService();
+            // Wire up session-ended to expedite insight patches
+            this.conversationStatusManager.on('session-ended', ({ claudeSessionId }) => {
+                getInsightsService().handleSessionEnded(claudeSessionId);
+            });
             this.logger.debug('Insights service initialized successfully');
             // Initialize router service if configured
             await this.initializeOrReloadRouter(config);
@@ -277,12 +286,9 @@ export class CUIServer {
                                 address: this.server?.address()
                             });
                             // Display startup info now that server is actually listening
-                            const config = this.configService.getConfig();
                             displayServerStartup({
                                 host: this.host,
                                 port: this.port,
-                                authToken: this.configOverrides?.token ?? config.authToken,
-                                skipAuthToken: this.configOverrides?.skipAuthToken,
                                 logger: this.logger
                             });
                             // Configure and bind ViteExpress AFTER server is listening
@@ -310,12 +316,9 @@ export class CUIServer {
                             mode: process.env.NODE_ENV || 'production'
                         });
                         // Display startup info now that server is actually listening
-                        const config = this.configService.getConfig();
                         displayServerStartup({
                             host: this.host,
                             port: this.port,
-                            authToken: this.configOverrides?.token ?? config.authToken,
-                            skipAuthToken: this.configOverrides?.skipAuthToken,
                             logger: this.logger
                         });
                         resolve();
@@ -461,38 +464,21 @@ export class CUIServer {
         // System routes (includes health check) - before auth
         this.app.use('/api/system', createSystemRoutes(this.processManager, this.historyReader));
         this.app.use('/', createSystemRoutes(this.processManager, this.historyReader)); // For /health at root
-        // Permission routes - before auth (needed for MCP server communication)
+        // Permission routes (needed for MCP server communication)
         this.app.use('/api/permissions', createPermissionRoutes(this.permissionTracker));
-        // Notifications routes - before auth (needed for service worker subscription on first load)
-        this.app.use('/api/notifications', createNotificationsRoutes(this.webPushService));
-        // Apply auth middleware to all other API routes unless skipAuthToken is set
-        if (!this.configOverrides?.skipAuthToken) {
-            if (this.configOverrides?.token) {
-                // Use custom auth middleware with token override
-                this.app.use('/api', createAuthMiddleware(this.configOverrides.token));
-                this.logger.info('Using custom authentication token from CLI');
-            }
-            else {
-                // Use default auth middleware
-                this.app.use('/api', authMiddleware);
-            }
-        }
-        else {
-            this.logger.warn('Authentication middleware is disabled - API endpoints are not protected!');
-        }
         // API routes
         // IMPORTANT: Insights routes must be registered BEFORE conversation routes
         // because conversation routes have a /:sessionId catch-all pattern that would
         // otherwise match paths like /activity-check
         this.app.use('/api/conversations', createInsightsRoutes(this.historyReader, this.sessionInfoService));
-        this.app.use('/api/conversations', createConversationRoutes(this.processManager, this.historyReader, this.statusTracker, this.sessionInfoService, this.conversationStatusManager, this.toolMetricsService));
+        this.app.use('/api/conversations', createConversationRoutes(this.processManager, this.historyReader, this.conversationStatusManager, this.sessionInfoService, this.toolMetricsService));
         this.app.use('/api/filesystem', createFileSystemRoutes(this.fileSystemService));
         this.app.use('/api/logs', createLogRoutes());
         this.app.use('/api/stream', createStreamingRoutes(this.streamManager));
         this.app.use('/api/working-directories', createWorkingDirectoriesRoutes(this.workingDirectoriesService));
         this.app.use('/api/config', createConfigRoutes(this.configService));
-        this.app.use('/api/gemini', createGeminiRoutes(geminiService));
         this.app.use('/api/questions', createQuestionRoutes(this.questionTracker, this.processManager));
+        this.app.use('/api/pending-questions', createPendingQuestionRoutes(this.pendingQuestionService, this.processManager, this.historyReader));
         // Claudia orchestrator routes
         const claudiaService = ClaudiaService.getInstance({
             processManager: this.processManager,
@@ -502,6 +488,10 @@ export class CUIServer {
         this.app.use('/api/claudia', createClaudiaRoutes(claudiaService));
         // License routes
         this.app.use('/api/license', createLicenseRoutes());
+        // Post-session analysis routes
+        this.app.use('/api/analysis', createAnalysisRoutes());
+        // Process event log routes (observability)
+        this.app.use('/api/process-events', processEventsRouter);
         // React Router catch-all - must be after all API routes
         const isDev = process.env.NODE_ENV === 'development';
         if (!isDev) {
@@ -518,6 +508,9 @@ export class CUIServer {
         this.logger.debug('Setting up ProcessManager integration with StreamManager');
         // Set up tool metrics service to listen to claude messages
         this.toolMetricsService.listenToClaudeMessages(this.processManager);
+        // Local map to track streamingId -> sessionId (populated from system_init messages)
+        // This is a simple, reliable source of truth that doesn't depend on external services
+        const streamingSessionMap = new Map();
         // Forward Claude messages to stream
         this.processManager.on('claude-message', ({ streamingId, message }) => {
             this.logger.debug('Received claude-message event', {
@@ -528,6 +521,15 @@ export class CUIServer {
                 contentLength: message?.content?.length || 0,
                 messageKeys: message ? Object.keys(message) : []
             });
+            // Capture sessionId from system init messages (this is our source of truth)
+            if (message && message.type === 'system' && message.subtype === 'init' && message.session_id) {
+                streamingSessionMap.set(streamingId, message.session_id);
+                this.logger.info('[SESSION-MAP] Captured sessionId from system_init', {
+                    streamingId: streamingId.slice(0, 8),
+                    sessionId: message.session_id.slice(0, 8),
+                    mapSize: streamingSessionMap.size
+                });
+            }
             // Skip broadcasting system init messages as they're now included in API response
             if (message && message.type === 'system' && message.subtype === 'init') {
                 this.logger.debug('Skipping broadcast of system init message (included in API response)', {
@@ -536,15 +538,83 @@ export class CUIServer {
                 });
                 return;
             }
-            // Detect AskUserQuestion tool_use and register with QuestionTracker
+            // Detect AskUserQuestion tool_use and register with QuestionTracker + persist to DB
+            // Debug: log all assistant messages to see what structure we're getting
+            if (message && message.type === 'assistant') {
+                this.logger.debug('Assistant message received', {
+                    streamingId,
+                    hasMessage: !!message.message,
+                    hasContent: !!message.message?.content,
+                    contentIsArray: Array.isArray(message.message?.content),
+                    contentLength: Array.isArray(message.message?.content) ? message.message.content.length : 0
+                });
+            }
             if (message && message.type === 'assistant' && message.message?.content) {
                 const content = message.message.content;
                 if (Array.isArray(content)) {
                     for (const block of content) {
+                        // Debug: log each block to see tool_use blocks
+                        if (block.type === 'tool_use') {
+                            this.logger.info('Tool use block detected', {
+                                streamingId,
+                                toolName: block.name,
+                                blockId: block.id
+                            });
+                        }
                         if (block.type === 'tool_use' && block.name === 'AskUserQuestion') {
+                            // Debug: log session state when AskUserQuestion arrives
+                            const activeSessions = this.conversationStatusManager.getActiveSessionIds();
+                            this.logger.info('AskUserQuestion detected - checking session state', {
+                                incomingStreamingId: streamingId,
+                                activeSessions,
+                                activeCount: activeSessions.length
+                            });
                             const input = block.input;
                             if (input.questions) {
-                                this.questionTracker.addQuestionRequest(block.id, input.questions, streamingId);
+                                // Add to in-memory tracker (for active session UI)
+                                const questionRequest = this.questionTracker.addQuestionRequest(block.id, input.questions, streamingId);
+                                // Persist to DB (for recovery after timeout/disconnect)
+                                // Use local streamingSessionMap as primary source (populated from system_init)
+                                // Fall back to other sources if needed
+                                let claudeSessionId = streamingSessionMap.get(streamingId);
+                                if (!claudeSessionId) {
+                                    claudeSessionId = this.conversationStatusManager.getSessionId(streamingId);
+                                    if (claudeSessionId) {
+                                        this.logger.debug('Using conversationStatusManager sessionId fallback', { streamingId, claudeSessionId });
+                                    }
+                                }
+                                if (!claudeSessionId) {
+                                    claudeSessionId = this.processManager.getClaudeSessionId(streamingId);
+                                    if (claudeSessionId) {
+                                        this.logger.debug('Using processManager sessionId fallback', { streamingId, claudeSessionId });
+                                    }
+                                }
+                                if (claudeSessionId) {
+                                    this.pendingQuestionService.addQuestion(questionRequest.id, claudeSessionId, streamingId, block.id, input.questions);
+                                    this.logger.info('AskUserQuestion persisted for recovery', {
+                                        questionId: questionRequest.id,
+                                        sessionId: claudeSessionId,
+                                        streamingId,
+                                        questionCount: input.questions.length
+                                    });
+                                    // Stop the session immediately to prevent Claude from continuing
+                                    // The session will be resumed when the user answers the question
+                                    this.logger.info('Stopping session to await user answer', { streamingId, claudeSessionId });
+                                    this.processManager.stopConversation(streamingId).catch((err) => {
+                                        this.logger.warn('Failed to stop session after AskUserQuestion', {
+                                            streamingId,
+                                            error: err instanceof Error ? err.message : String(err)
+                                        });
+                                    });
+                                }
+                                else {
+                                    this.logger.warn('AskUserQuestion NOT persisted - claudeSessionId not found for streamingId', {
+                                        questionId: questionRequest.id,
+                                        streamingId,
+                                        questionCount: input.questions.length,
+                                        activeSessionCount: this.conversationStatusManager.getActiveSessionIds().length
+                                    });
+                                }
                             }
                         }
                     }
@@ -566,9 +636,23 @@ export class CUIServer {
                 clientCount: this.streamManager.getClientCount(streamingId),
                 wasSuccessful: code === 0
             });
+            // Check for pending questions BEFORE unregistering (we need the sessionId mapping)
+            // If there are pending questions, this was likely an AskUserQuestion timeout
+            const pendingQuestions = this.pendingQuestionService.getPendingByStreamingId(streamingId);
+            if (pendingQuestions.length > 0) {
+                this.logger.info('Session closed with pending AskUserQuestion - questions preserved for later resume', {
+                    streamingId,
+                    pendingQuestionCount: pendingQuestions.length,
+                    questionIds: pendingQuestions.map(q => q.id)
+                });
+                // Questions remain in DB with status='pending' for later retrieval
+                // The in-memory tracker will be cleaned up below, but DB persists
+            }
+            // Clean up local session map
+            streamingSessionMap.delete(streamingId);
             // Unregister session from status tracker
             this.logger.debug('Unregistering session from status tracker', { streamingId });
-            this.statusTracker.unregisterActiveSession(streamingId);
+            this.conversationStatusManager.unregisterActiveSession(streamingId);
             // Clean up conversation context (handled automatically in unregisterActiveSession)
             // Clean up permissions for this streaming session
             const removedCount = this.permissionTracker.removePermissionsByStreamingId(streamingId);
@@ -578,14 +662,27 @@ export class CUIServer {
                     removedPermissions: removedCount
                 });
             }
-            // Clean up questions for this streaming session
-            const removedQuestions = this.questionTracker.removeQuestionsByStreamingId(streamingId);
-            if (removedQuestions > 0) {
-                this.logger.debug('Cleaned up questions for closed session', {
+            // Check for in-memory questions BEFORE removing them
+            // If there are pending questions, we need to keep them for error suppression
+            // They'll be cleaned up when answered or expired, not on session close
+            const inMemoryQuestions = this.questionTracker.getQuestionsByStreamingId(streamingId);
+            if (inMemoryQuestions.length > 0) {
+                this.logger.info('Preserving in-memory questions for error suppression (awaiting user answer)', {
                     streamingId,
-                    removedQuestions
+                    inMemoryQuestionCount: inMemoryQuestions.length,
+                    questionIds: inMemoryQuestions.map(q => q.id)
                 });
             }
+            else {
+                // No pending questions - safe to clean up
+                const removedQuestions = this.questionTracker.removeQuestionsByStreamingId(streamingId);
+                if (removedQuestions > 0) {
+                    this.logger.debug('Cleaned up in-memory questions for closed session', {
+                        streamingId,
+                        removedQuestions
+                    });
+                }
+            }
             if (code === 0) {
                 // Session completion notification removed
             }
@@ -593,15 +690,28 @@ export class CUIServer {
         });
         // Handle process errors
         this.processManager.on('process-error', ({ streamingId, error }) => {
-            this.logger.debug('Received process-error event, forwarding to StreamManager', {
+            this.logger.debug('Received process-error event', {
                 streamingId,
                 error,
                 errorLength: error?.toString().length || 0,
                 clientCount: this.streamManager.getClientCount(streamingId)
             });
+            // Check if there's a pending question for this streaming session
+            // If so, suppress the error - the session was intentionally stopped to wait for user answer
+            const pendingQuestions = this.questionTracker.getQuestionsByStreamingId(streamingId);
+            if (pendingQuestions.length > 0) {
+                this.logger.info('Suppressing process error due to pending AskUserQuestion', {
+                    streamingId,
+                    pendingQuestionCount: pendingQuestions.length,
+                    questionIds: pendingQuestions.map(q => q.id)
+                });
+                // Still unregister the session but don't broadcast the error
+                this.conversationStatusManager.unregisterActiveSession(streamingId);
+                return;
+            }
             // Unregister session from status tracker on error
             this.logger.debug('Unregistering session from status tracker due to error', { streamingId });
-            this.statusTracker.unregisterActiveSession(streamingId);
+            this.conversationStatusManager.unregisterActiveSession(streamingId);
             // Clean up conversation context on error (handled automatically in unregisterActiveSession)
             const errorEvent = {
                 type: 'error',
@@ -648,11 +758,13 @@ export class CUIServer {
         this.logger.debug('Setting up QuestionTracker integration');
         // Forward question events to stream
         this.questionTracker.on('question_request', (request) => {
-            this.logger.debug('Question request event received', {
+            // Log at info level to diagnose question flow issues
+            this.logger.info('Question request event received, broadcasting to stream', {
                 id: request.id,
                 toolUseId: request.toolUseId,
                 streamingId: request.streamingId,
-                questionCount: request.questions.length
+                questionCount: request.questions.length,
+                clientCount: this.streamManager.getClientCount(request.streamingId)
             });
             // Broadcast to the appropriate streaming session
             if (request.streamingId && request.streamingId !== 'unknown') {