📝 Add docstrings to main

Docstrings generation was requested by @amoscicki.

* https://github.com/AutoMaker-Org/automaker/pull/290#issuecomment-3694458998

The following files were modified:

* `apps/server/src/routes/updates/common.ts`
* `apps/server/src/routes/updates/index.ts`
* `apps/server/src/routes/updates/routes/check.ts`
* `apps/server/src/routes/updates/routes/info.ts`
* `apps/server/src/routes/updates/routes/pull.ts`
* `apps/ui/src/components/updates/update-notifier.tsx`
* `apps/ui/src/components/views/settings-view.tsx`
* `apps/ui/src/components/views/settings-view/updates/updates-section.tsx`
* `apps/ui/src/hooks/use-settings-migration.ts`
* `apps/ui/src/hooks/use-update-polling.ts`
* `apps/ui/src/lib/utils.ts`
* `apps/ui/src/routes/__root.tsx`

.gitignore

@@ -79,4 +79,5 @@ blob-report/
 # Misc
 *.pem
 
-docker-compose.override.yml
+docker-compose.override.yml
+.claude/

README.md

@@ -19,7 +19,7 @@
 
 - [What Makes Automaker Different?](#what-makes-automaker-different)
   - [The Workflow](#the-workflow)
-  - [Powered by Claude Code](#powered-by-claude-code)
+  - [Powered by Claude Agent SDK](#powered-by-claude-agent-sdk)
   - [Why This Matters](#why-this-matters)
 - [Security Disclaimer](#security-disclaimer)
 - [Community & Support](#community--support)
@@ -28,22 +28,36 @@
   - [Quick Start](#quick-start)
 - [How to Run](#how-to-run)
   - [Development Mode](#development-mode)
-    - [Electron Desktop App (Recommended)](#electron-desktop-app-recommended)
-    - [Web Browser Mode](#web-browser-mode)
   - [Building for Production](#building-for-production)
-  - [Running Production Build](#running-production-build)
   - [Testing](#testing)
   - [Linting](#linting)
-  - [Authentication Options](#authentication-options)
-  - [Persistent Setup (Optional)](#persistent-setup-optional)
+  - [Environment Configuration](#environment-configuration)
+  - [Authentication Setup](#authentication-setup)
 - [Features](#features)
+  - [Core Workflow](#core-workflow)
+  - [AI & Planning](#ai--planning)
+  - [Project Management](#project-management)
+  - [Collaboration & Review](#collaboration--review)
+  - [Developer Tools](#developer-tools)
+  - [Advanced Features](#advanced-features)
 - [Tech Stack](#tech-stack)
+  - [Frontend](#frontend)
+  - [Backend](#backend)
+  - [Testing & Quality](#testing--quality)
+  - [Shared Libraries](#shared-libraries)
+- [Available Views](#available-views)
+- [Architecture](#architecture)
+  - [Monorepo Structure](#monorepo-structure)
+  - [How It Works](#how-it-works)
+  - [Key Architectural Patterns](#key-architectural-patterns)
+  - [Security & Isolation](#security--isolation)
+  - [Data Storage](#data-storage)
 - [Learn More](#learn-more)
 - [License](#license)
 
 </details>
 
-Automaker is an autonomous AI development studio that transforms how you build software. Instead of manually writing every line of code, you describe features on a Kanban board and watch as AI agents powered by Claude Code automatically implement them.
+Automaker is an autonomous AI development studio that transforms how you build software. Instead of manually writing every line of code, you describe features on a Kanban board and watch as AI agents powered by Claude Agent SDK automatically implement them. Built with React, Vite, Electron, and Express, Automaker provides a complete workflow for managing AI agents through a desktop application (or web browser), with features like real-time streaming, git worktree isolation, plan approval, and multi-agent task execution.
 
 ![Automaker UI](https://i.imgur.com/jdwKydM.png)
 
@@ -59,9 +73,9 @@ Traditional development tools help you write code. Automaker helps you **orchest
 4. **Review & Verify** - Review the changes, run tests, and approve when ready
 5. **Ship Faster** - Build entire applications in days, not weeks
 
-### Powered by Claude Code
+### Powered by Claude Agent SDK
 
-Automaker leverages the [Claude Agent SDK](https://docs.anthropic.com/en/docs/claude-code) to give AI agents full access to your codebase. Agents can read files, write code, execute commands, run tests, and make git commits—all while working in isolated git worktrees to keep your main branch safe.
+Automaker leverages the [Claude Agent SDK](https://www.npmjs.com/package/@anthropic-ai/claude-agent-sdk) to give AI agents full access to your codebase. Agents can read files, write code, execute commands, run tests, and make git commits—all while working in isolated git worktrees to keep your main branch safe. The SDK provides autonomous AI agents that can use tools, make decisions, and complete complex multi-step tasks without constant human intervention.
 
 ### Why This Matters
 
@@ -95,8 +109,7 @@ In the Discord, you can:
 - 🚀 Show off projects built with AI agents
 - 🤝 Collaborate with other developers and contributors
 
-👉 **Join the Discord:**  
-https://discord.gg/jjem7aEDKU
+👉 **Join the Discord:** [Agentic Jumpstart Discord](https://discord.gg/jjem7aEDKU)
 
 ---
 
@@ -104,28 +117,49 @@ https://discord.gg/jjem7aEDKU
 
 ### Prerequisites
 
-- Node.js 18+
-- npm
-- [Claude Code CLI](https://docs.anthropic.com/en/docs/claude-code) installed and authenticated
+- **Node.js 18+** (tested with Node.js 22)
+- **npm** (comes with Node.js)
+- **Authentication** (choose one):
+  - **[Claude Code CLI](https://code.claude.com/docs/en/overview)** (recommended) - Install and authenticate, credentials used automatically
+  - **Anthropic API Key** - Direct API key for Claude Agent SDK ([get one here](https://console.anthropic.com/))
 
 ### Quick Start
 
 ```bash
-# 1. Clone the repo
+# 1. Clone the repository
 git clone https://github.com/AutoMaker-Org/automaker.git
 cd automaker
 
 # 2. Install dependencies
 npm install
 
-# 3. Build local shared packages
+# 3. Build shared packages (Now can be skipped npm install / run dev does it automaticly)
 npm run build:packages
 
-# 4. Run Automaker (pick your mode)
+# 4. Set up authentication (skip if using Claude Code CLI)
+# If using Claude Code CLI: credentials are detected automatically
+# If using API key directly, choose one method:
+
+# Option A: Environment variable
+export ANTHROPIC_API_KEY="sk-ant-..."
+
+# Option B: Create .env file in project root
+echo "ANTHROPIC_API_KEY=sk-ant-..." > .env
+
+# 5. Start Automaker (interactive launcher)
 npm run dev
-# Then choose your run mode when prompted, or use specific commands below
+# Choose between:
+#   1. Web Application (browser at localhost:3007)
+#   2. Desktop Application (Electron - recommended)
 ```
 
+**Note:** The `npm run dev` command will:
+
+- Check for dependencies and install if needed
+- Install Playwright browsers for E2E tests
+- Kill any processes on ports 3007/3008
+- Present an interactive menu to choose your run mode
+
 ## How to Run
 
 ### Development Mode
@@ -163,31 +197,65 @@ npm run dev:web
 
 ### Building for Production
 
+#### Web Application
+
 ```bash
-# Build Next.js app
+# Build for web deployment (uses Vite)
 npm run build
 
-# Build Electron app for distribution
-npm run build:electron
+# Run production build
+npm run start
 ```
 
-### Running Production Build
+#### Desktop Application
 
 ```bash
-# Start production Next.js server
-npm run start
+# Build for current platform (macOS/Windows/Linux)
+npm run build:electron
+
+# Platform-specific builds
+npm run build:electron:mac     # macOS (DMG + ZIP, x64 + arm64)
+npm run build:electron:win     # Windows (NSIS installer, x64)
+npm run build:electron:linux   # Linux (AppImage + DEB, x64)
+
+# Output directory: apps/ui/release/
+```
+
+#### Docker Deployment
+
+```bash
+# Build and run with Docker Compose (recommended for security)
+docker-compose up -d
+
+# Access at http://localhost:3007
+# API at http://localhost:3008
 ```
 
 ### Testing
 
-```bash
-# Run tests headless
-npm run test
+#### End-to-End Tests (Playwright)
 
-# Run tests with browser visible
-npm run test:headed
+```bash
+npm run test            # Headless E2E tests
+npm run test:headed     # Browser visible E2E tests
 ```
 
+#### Unit Tests (Vitest)
+
+```bash
+npm run test:server              # Server unit tests
+npm run test:server:coverage     # Server tests with coverage
+npm run test:packages            # All shared package tests
+npm run test:all                 # Packages + server tests
+```
+
+#### Test Configuration
+
+- E2E tests run on ports 3007 (UI) and 3008 (server)
+- Automatically starts test servers before running
+- Uses Chromium browser via Playwright
+- Mock agent mode available in CI with `AUTOMAKER_MOCK_AGENT=true`
+
 ### Linting
 
 ```bash
@@ -195,59 +263,283 @@ npm run test:headed
 npm run lint
 ```
 
-### Authentication Options
+### Environment Configuration
 
-Automaker supports multiple authentication methods (in order of priority):
+#### Authentication (if not using Claude Code CLI)
 
-| Method           | Environment Variable | Description                     |
-| ---------------- | -------------------- | ------------------------------- |
-| API Key (env)    | `ANTHROPIC_API_KEY`  | Anthropic API key               |
-| API Key (stored) | —                    | Anthropic API key stored in app |
+- `ANTHROPIC_API_KEY` - Your Anthropic API key for Claude Agent SDK (not needed if using Claude Code CLI)
 
-### Persistent Setup (Optional)
+#### Optional - Server
+
+- `PORT` - Server port (default: 3008)
+- `DATA_DIR` - Data storage directory (default: ./data)
+- `ENABLE_REQUEST_LOGGING` - HTTP request logging (default: true)
+
+#### Optional - Security
+
+- `AUTOMAKER_API_KEY` - Optional API authentication for the server
+- `ALLOWED_ROOT_DIRECTORY` - Restrict file operations to specific directory
+- `CORS_ORIGIN` - CORS policy (default: \*)
+
+#### Optional - Development
+
+- `VITE_SKIP_ELECTRON` - Skip Electron in dev mode
+- `OPEN_DEVTOOLS` - Auto-open DevTools in Electron
+
+### Authentication Setup
+
+#### Option 1: Claude Code CLI (Recommended)
+
+Install and authenticate the Claude Code CLI following the [official quickstart guide](https://code.claude.com/docs/en/quickstart).
+
+Once authenticated, Automaker will automatically detect and use your CLI credentials. No additional configuration needed!
+
+#### Option 2: Direct API Key
+
+If you prefer not to use the CLI, you can provide an Anthropic API key directly using one of these methods:
+
+##### 2a. Shell Configuration
 
 Add to your `~/.bashrc` or `~/.zshrc`:
 
 ```bash
-export ANTHROPIC_API_KEY="YOUR_API_KEY_HERE"
+export ANTHROPIC_API_KEY="sk-ant-..."
 ```
 
-Then restart your terminal or run `source ~/.bashrc`.
+Then restart your terminal or run `source ~/.bashrc` (or `source ~/.zshrc`).
+
+##### 2b. .env File
+
+Create a `.env` file in the project root (gitignored):
+
+```bash
+ANTHROPIC_API_KEY=sk-ant-...
+PORT=3008
+DATA_DIR=./data
+```
+
+##### 2c. In-App Storage
+
+The application can store your API key securely in the settings UI. The key is persisted in the `DATA_DIR` directory.
 
 ## Features
 
+### Core Workflow
+
 - 📋 **Kanban Board** - Visual drag-and-drop board to manage features through backlog, in progress, waiting approval, and verified stages
 - 🤖 **AI Agent Integration** - Automatic AI agent assignment to implement features when moved to "In Progress"
-- 🧠 **Multi-Model Support** - Choose from multiple AI models including Claude Opus, Sonnet, and more
-- 💭 **Extended Thinking** - Enable extended thinking modes for complex problem-solving
-- 📡 **Real-time Agent Output** - View live agent output, logs, and file diffs as features are being implemented
-- 🔍 **Project Analysis** - AI-powered project structure analysis to understand your codebase
-- 📁 **Context Management** - Add context files to help AI agents understand your project better
-- 💡 **Feature Suggestions** - AI-generated feature suggestions based on your project
-- 🖼️ **Image Support** - Attach images and screenshots to feature descriptions
-- ⚡ **Concurrent Processing** - Configure concurrency to process multiple features simultaneously
-- 🧪 **Test Integration** - Automatic test running and verification for implemented features
-- 🔀 **Git Integration** - View git diffs and track changes made by AI agents
-- 👤 **AI Profiles** - Create and manage different AI agent profiles for various tasks
-- 💬 **Chat History** - Keep track of conversations and interactions with AI agents
-- ⌨️ **Keyboard Shortcuts** - Efficient navigation and actions via keyboard shortcuts
-- 🎨 **Dark/Light Theme** - Beautiful UI with theme support
-- 🖥️ **Cross-Platform** - Desktop application built with Electron for Windows, macOS, and Linux
+- 🔀 **Git Worktree Isolation** - Each feature executes in isolated git worktrees to protect your main branch
+- 📡 **Real-time Streaming** - Watch AI agents work in real-time with live tool usage, progress updates, and task completion
+- 🔄 **Follow-up Instructions** - Send additional instructions to running agents without stopping them
+
+### AI & Planning
+
+- 🧠 **Multi-Model Support** - Choose from Claude Opus, Sonnet, and Haiku per feature
+- 💭 **Extended Thinking** - Enable thinking modes (none, medium, deep, ultra) for complex problem-solving
+- 📝 **Planning Modes** - Four planning levels: skip (direct implementation), lite (quick plan), spec (task breakdown), full (phased execution)
+- ✅ **Plan Approval** - Review and approve AI-generated plans before implementation begins
+- 📊 **Multi-Agent Task Execution** - Spec mode spawns dedicated agents per task for focused implementation
+
+### Project Management
+
+- 🔍 **Project Analysis** - AI-powered codebase analysis to understand your project structure
+- 💡 **Feature Suggestions** - AI-generated feature suggestions based on project analysis
+- 📁 **Context Management** - Add markdown, images, and documentation files that agents automatically reference
+- 🔗 **Dependency Blocking** - Features can depend on other features, enforcing execution order
+- 🌳 **Graph View** - Visualize feature dependencies with interactive graph visualization
+- 📋 **GitHub Integration** - Import issues, validate feasibility, and convert to tasks automatically
+
+### Collaboration & Review
+
+- 🧪 **Verification Workflow** - Features move to "Waiting Approval" for review and testing
+- 💬 **Agent Chat** - Interactive chat sessions with AI agents for exploratory work
+- 👤 **AI Profiles** - Create custom agent configurations with different prompts, models, and settings
+- 📜 **Session History** - Persistent chat sessions across restarts with full conversation history
+- 🔍 **Git Diff Viewer** - Review changes made by agents before approving
+
+### Developer Tools
+
+- 🖥️ **Integrated Terminal** - Full terminal access with tabs, splits, and persistent sessions
+- 🖼️ **Image Support** - Attach screenshots and diagrams to feature descriptions for visual context
+- ⚡ **Concurrent Execution** - Configure how many features can run simultaneously (default: 3)
+- ⌨️ **Keyboard Shortcuts** - Fully customizable shortcuts for navigation and actions
+- 🎨 **Theme System** - 25+ themes including Dark, Light, Dracula, Nord, Catppuccin, and more
+- 🖥️ **Cross-Platform** - Desktop app for macOS (x64, arm64), Windows (x64), and Linux (x64)
+- 🌐 **Web Mode** - Run in browser or as Electron desktop app
+
+### Advanced Features
+
+- 🔐 **Docker Isolation** - Security-focused Docker deployment with no host filesystem access
+- 🎯 **Worktree Management** - Create, switch, commit, and create PRs from worktrees
+- 📊 **Usage Tracking** - Monitor Claude API usage with detailed metrics
+- 🔊 **Audio Notifications** - Optional completion sounds (mutable in settings)
+- 💾 **Auto-save** - All work automatically persisted to `.automaker/` directory
 
 ## Tech Stack
 
-- [Next.js](https://nextjs.org) - React framework
-- [Electron](https://www.electronjs.org/) - Desktop application framework
-- [Tailwind CSS](https://tailwindcss.com/) - Styling
-- [Zustand](https://zustand-demo.pmnd.rs/) - State management
-- [dnd-kit](https://dndkit.com/) - Drag and drop functionality
+### Frontend
+
+- **React 19** - UI framework
+- **Vite 7** - Build tool and development server
+- **Electron 39** - Desktop application framework
+- **TypeScript 5.9** - Type safety
+- **TanStack Router** - File-based routing
+- **Zustand 5** - State management with persistence
+- **Tailwind CSS 4** - Utility-first styling with 25+ themes
+- **Radix UI** - Accessible component primitives
+- **dnd-kit** - Drag and drop for Kanban board
+- **@xyflow/react** - Graph visualization for dependencies
+- **xterm.js** - Integrated terminal emulator
+- **CodeMirror 6** - Code editor for XML/syntax highlighting
+- **Lucide Icons** - Icon library
+
+### Backend
+
+- **Node.js** - JavaScript runtime with ES modules
+- **Express 5** - HTTP server framework
+- **TypeScript 5.9** - Type safety
+- **Claude Agent SDK** - AI agent integration (@anthropic-ai/claude-agent-sdk)
+- **WebSocket (ws)** - Real-time event streaming
+- **node-pty** - PTY terminal sessions
+
+### Testing & Quality
+
+- **Playwright** - End-to-end testing
+- **Vitest** - Unit testing framework
+- **ESLint 9** - Code linting
+- **Prettier 3** - Code formatting
+- **Husky** - Git hooks for pre-commit formatting
+
+### Shared Libraries
+
+- **@automaker/types** - Shared TypeScript definitions
+- **@automaker/utils** - Logging, error handling, image processing
+- **@automaker/prompts** - AI prompt templates
+- **@automaker/platform** - Path management and security
+- **@automaker/model-resolver** - Claude model alias resolution
+- **@automaker/dependency-resolver** - Feature dependency ordering
+- **@automaker/git-utils** - Git operations and worktree management
+
+## Available Views
+
+Automaker provides several specialized views accessible via the sidebar or keyboard shortcuts:
+
+| View               | Shortcut | Description                                                                                      |
+| ------------------ | -------- | ------------------------------------------------------------------------------------------------ |
+| **Board**          | `K`      | Kanban board for managing feature workflow (Backlog → In Progress → Waiting Approval → Verified) |
+| **Agent**          | `A`      | Interactive chat sessions with AI agents for exploratory work and questions                      |
+| **Spec**           | `D`      | Project specification editor with AI-powered generation and feature suggestions                  |
+| **Context**        | `C`      | Manage context files (markdown, images) that AI agents automatically reference                   |
+| **Profiles**       | `M`      | Create and manage AI agent profiles with custom prompts and configurations                       |
+| **Settings**       | `S`      | Configure themes, shortcuts, defaults, authentication, and more                                  |
+| **Terminal**       | `T`      | Integrated terminal with tabs, splits, and persistent sessions                                   |
+| **GitHub Issues**  | -        | Import and validate GitHub issues, convert to tasks                                              |
+| **Running Agents** | -        | View all active agents across projects with status and progress                                  |
+
+### Keyboard Navigation
+
+All shortcuts are customizable in Settings. Default shortcuts:
+
+- **Navigation:** `K` (Board), `A` (Agent), `D` (Spec), `C` (Context), `S` (Settings), `M` (Profiles), `T` (Terminal)
+- **UI:** `` ` `` (Toggle sidebar)
+- **Actions:** `N` (New item in current view), `G` (Start next features), `O` (Open project), `P` (Project picker)
+- **Projects:** `Q`/`E` (Cycle previous/next project)
+
+## Architecture
+
+### Monorepo Structure
+
+Automaker is built as an npm workspace monorepo with two main applications and seven shared packages:
+
+```text
+automaker/
+├── apps/
+│   ├── ui/          # React + Vite + Electron frontend
+│   └── server/      # Express + WebSocket backend
+└── libs/            # Shared packages
+    ├── types/                  # Core TypeScript definitions
+    ├── utils/                  # Logging, errors, utilities
+    ├── prompts/                # AI prompt templates
+    ├── platform/               # Path management, security
+    ├── model-resolver/         # Claude model aliasing
+    ├── dependency-resolver/    # Feature dependency ordering
+    └── git-utils/              # Git operations & worktree management
+```
+
+### How It Works
+
+1. **Feature Definition** - Users create feature cards on the Kanban board with descriptions, images, and configuration
+2. **Git Worktree Creation** - When a feature starts, a git worktree is created for isolated development
+3. **Agent Execution** - Claude Agent SDK executes in the worktree with full file system and command access
+4. **Real-time Streaming** - Agent output streams via WebSocket to the frontend for live monitoring
+5. **Plan Approval** (optional) - For spec/full planning modes, agents generate plans that require user approval
+6. **Multi-Agent Tasks** (spec mode) - Each task in the spec gets a dedicated agent for focused implementation
+7. **Verification** - Features move to "Waiting Approval" where changes can be reviewed via git diff
+8. **Integration** - After approval, changes can be committed and PRs created from the worktree
+
+### Key Architectural Patterns
+
+- **Event-Driven Architecture** - All server operations emit events that stream to the frontend
+- **Provider Pattern** - Extensible AI provider system (currently Claude, designed for future providers)
+- **Service-Oriented Backend** - Modular services for agent management, features, terminals, settings
+- **State Management** - Zustand with persistence for frontend state across restarts
+- **File-Based Storage** - No database; features stored as JSON files in `.automaker/` directory
+
+### Security & Isolation
+
+- **Git Worktrees** - Each feature executes in an isolated git worktree, protecting your main branch
+- **Path Sandboxing** - Optional `ALLOWED_ROOT_DIRECTORY` restricts file access
+- **Docker Isolation** - Recommended deployment uses Docker with no host filesystem access
+- **Plan Approval** - Optional plan review before implementation prevents unwanted changes
+
+### Data Storage
+
+Automaker uses a file-based storage system (no database required):
+
+#### Per-Project Data
+
+Stored in `{projectPath}/.automaker/`:
+
+```text
+.automaker/
+├── features/              # Feature JSON files and images
+│   └── {featureId}/
+│       ├── feature.json   # Feature metadata
+│       ├── agent-output.md # AI agent output log
+│       └── images/        # Attached images
+├── context/               # Context files for AI agents
+├── settings.json          # Project-specific settings
+├── spec.md               # Project specification
+├── analysis.json         # Project structure analysis
+└── feature-suggestions.json # AI-generated suggestions
+```
+
+#### Global Data
+
+Stored in `DATA_DIR` (default `./data`):
+
+```text
+data/
+├── settings.json          # Global settings, profiles, shortcuts
+├── credentials.json       # API keys (encrypted)
+├── sessions-metadata.json # Chat session metadata
+└── agent-sessions/        # Conversation histories
+    └── {sessionId}.json
+```
 
 ## Learn More
 
-To learn more about Next.js, take a look at the following resources:
+### Documentation
 
-- [Next.js Documentation](https://nextjs.org/docs) - learn about Next.js features and API.
-- [Learn Next.js](https://nextjs.org/learn) - an interactive Next.js tutorial.
+- [Project Documentation](./docs/) - Architecture guides, patterns, and developer docs
+- [Docker Isolation Guide](./docs/docker-isolation.md) - Security-focused Docker deployment
+- [Shared Packages Guide](./docs/llm-shared-packages.md) - Using monorepo packages
+
+### Community
+
+Join the **Agentic Jumpstart** Discord to connect with other builders exploring **agentic coding**:
+
+👉 [Agentic Jumpstart Discord](https://discord.gg/jjem7aEDKU)
 
 ## License
 

apps/app/server-bundle/package.json

@@ -1,15 +0,0 @@
-{
-  "name": "@automaker/server-bundle",
-  "version": "0.1.0",
-  "type": "module",
-  "main": "dist/index.js",
-  "dependencies": {
-    "@anthropic-ai/claude-agent-sdk": "^0.1.61",
-    "cors": "^2.8.5",
-    "dotenv": "^17.2.3",
-    "express": "^5.1.0",
-    "morgan": "^1.10.1",
-    "node-pty": "1.1.0-beta41",
-    "ws": "^8.18.0"
-  }
-}

apps/server/src/index.ts

@@ -48,6 +48,8 @@ import { createClaudeRoutes } from './routes/claude/index.js';
 import { ClaudeUsageService } from './services/claude-usage-service.js';
 import { createGitHubRoutes } from './routes/github/index.js';
 import { createContextRoutes } from './routes/context/index.js';
+import { createBacklogPlanRoutes } from './routes/backlog-plan/index.js';
+import { cleanupStaleValidations } from './routes/github/routes/validation-common.js';
 
 // Load environment variables
 dotenv.config();
@@ -111,10 +113,11 @@ app.use(express.json({ limit: '50mb' }));
 const events: EventEmitter = createEventEmitter();
 
 // Create services
-const agentService = new AgentService(DATA_DIR, events);
-const featureLoader = new FeatureLoader();
-const autoModeService = new AutoModeService(events);
+// Note: settingsService is created first so it can be injected into other services
 const settingsService = new SettingsService(DATA_DIR);
+const agentService = new AgentService(DATA_DIR, events, settingsService);
+const featureLoader = new FeatureLoader();
+const autoModeService = new AutoModeService(events, settingsService);
 const claudeUsageService = new ClaudeUsageService();
 
 // Initialize services
@@ -123,6 +126,15 @@ const claudeUsageService = new ClaudeUsageService();
   console.log('[Server] Agent service initialized');
 })();
 
+// Run stale validation cleanup every hour to prevent memory leaks from crashed validations
+const VALIDATION_CLEANUP_INTERVAL_MS = 60 * 60 * 1000; // 1 hour
+setInterval(() => {
+  const cleaned = cleanupStaleValidations();
+  if (cleaned > 0) {
+    console.log(`[Server] Cleaned up ${cleaned} stale validation entries`);
+  }
+}, VALIDATION_CLEANUP_INTERVAL_MS);
+
 // Mount API routes - health is unauthenticated for monitoring
 app.use('/api/health', createHealthRoutes());
 
@@ -138,17 +150,18 @@ app.use('/api/enhance-prompt', createEnhancePromptRoutes());
 app.use('/api/worktree', createWorktreeRoutes());
 app.use('/api/git', createGitRoutes());
 app.use('/api/setup', createSetupRoutes());
-app.use('/api/suggestions', createSuggestionsRoutes(events));
+app.use('/api/suggestions', createSuggestionsRoutes(events, settingsService));
 app.use('/api/models', createModelsRoutes());
-app.use('/api/spec-regeneration', createSpecRegenerationRoutes(events));
+app.use('/api/spec-regeneration', createSpecRegenerationRoutes(events, settingsService));
 app.use('/api/running-agents', createRunningAgentsRoutes(autoModeService));
 app.use('/api/workspace', createWorkspaceRoutes());
 app.use('/api/templates', createTemplatesRoutes());
 app.use('/api/terminal', createTerminalRoutes());
 app.use('/api/settings', createSettingsRoutes(settingsService));
 app.use('/api/claude', createClaudeRoutes(claudeUsageService));
-app.use('/api/github', createGitHubRoutes());
-app.use('/api/context', createContextRoutes());
+app.use('/api/github', createGitHubRoutes(events, settingsService));
+app.use('/api/context', createContextRoutes(settingsService));
+app.use('/api/backlog-plan', createBacklogPlanRoutes(events, settingsService));
 
 // Create HTTP server
 const server = createServer(app);
@@ -177,12 +190,31 @@ server.on('upgrade', (request, socket, head) => {
 
 // Events WebSocket connection handler
 wss.on('connection', (ws: WebSocket) => {
-  console.log('[WebSocket] Client connected');
+  console.log('[WebSocket] Client connected, ready state:', ws.readyState);
 
   // Subscribe to all events and forward to this client
   const unsubscribe = events.subscribe((type, payload) => {
+    console.log('[WebSocket] Event received:', {
+      type,
+      hasPayload: !!payload,
+      payloadKeys: payload ? Object.keys(payload) : [],
+      wsReadyState: ws.readyState,
+      wsOpen: ws.readyState === WebSocket.OPEN,
+    });
+
     if (ws.readyState === WebSocket.OPEN) {
-      ws.send(JSON.stringify({ type, payload }));
+      const message = JSON.stringify({ type, payload });
+      console.log('[WebSocket] Sending event to client:', {
+        type,
+        messageLength: message.length,
+        sessionId: (payload as any)?.sessionId,
+      });
+      ws.send(message);
+    } else {
+      console.log(
+        '[WebSocket] WARNING: Cannot send event, WebSocket not open. ReadyState:',
+        ws.readyState
+      );
     }
   });
 
@@ -192,7 +224,7 @@ wss.on('connection', (ws: WebSocket) => {
   });
 
   ws.on('error', (error) => {
-    console.error('[WebSocket] Error:', error);
+    console.error('[WebSocket] ERROR:', error);
     unsubscribe();
   });
 });

apps/server/src/lib/sdk-options.ts

@@ -136,6 +136,59 @@ function getBaseOptions(): Partial<Options> {
   };
 }
 
+/**
+ * Build system prompt configuration based on autoLoadClaudeMd setting.
+ * When autoLoadClaudeMd is true:
+ * - Uses preset mode with 'claude_code' to enable CLAUDE.md auto-loading
+ * - If there's a custom systemPrompt, appends it to the preset
+ * - Sets settingSources to ['project'] for SDK to load CLAUDE.md files
+ *
+ * @param config - The SDK options config
+ * @returns Object with systemPrompt and settingSources for SDK options
+ */
+function buildClaudeMdOptions(config: CreateSdkOptionsConfig): {
+  systemPrompt?: string | SystemPromptConfig;
+  settingSources?: Array<'user' | 'project' | 'local'>;
+} {
+  if (!config.autoLoadClaudeMd) {
+    // Standard mode - just pass through the system prompt as-is
+    return config.systemPrompt ? { systemPrompt: config.systemPrompt } : {};
+  }
+
+  // Auto-load CLAUDE.md mode - use preset with settingSources
+  const result: {
+    systemPrompt: SystemPromptConfig;
+    settingSources: Array<'user' | 'project' | 'local'>;
+  } = {
+    systemPrompt: {
+      type: 'preset',
+      preset: 'claude_code',
+    },
+    // Load both user (~/.claude/CLAUDE.md) and project (.claude/CLAUDE.md) settings
+    settingSources: ['user', 'project'],
+  };
+
+  // If there's a custom system prompt, append it to the preset
+  if (config.systemPrompt) {
+    result.systemPrompt.append = config.systemPrompt;
+  }
+
+  return result;
+}
+
+/**
+ * System prompt configuration for SDK options
+ * When using preset mode with claude_code, CLAUDE.md files are automatically loaded
+ */
+export interface SystemPromptConfig {
+  /** Use preset mode with claude_code to enable CLAUDE.md auto-loading */
+  type: 'preset';
+  /** The preset to use - 'claude_code' enables CLAUDE.md loading */
+  preset: 'claude_code';
+  /** Optional additional prompt to append to the preset */
+  append?: string;
+}
+
 /**
  * Options configuration for creating SDK options
  */
@@ -160,6 +213,12 @@ export interface CreateSdkOptionsConfig {
     type: 'json_schema';
     schema: Record<string, unknown>;
   };
+
+  /** Enable auto-loading of CLAUDE.md files via SDK's settingSources */
+  autoLoadClaudeMd?: boolean;
+
+  /** Enable sandbox mode for bash command isolation */
+  enableSandboxMode?: boolean;
 }
 
 /**
@@ -169,11 +228,15 @@ export interface CreateSdkOptionsConfig {
  * - Uses read-only tools for codebase analysis
  * - Extended turns for thorough exploration
  * - Opus model by default (can be overridden)
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createSpecGenerationOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     // Override permissionMode - spec generation only needs read-only tools
@@ -184,7 +247,7 @@ export function createSpecGenerationOptions(config: CreateSdkOptionsConfig): Opt
     maxTurns: MAX_TURNS.maximum,
     cwd: config.cwd,
     allowedTools: [...TOOL_PRESETS.specGeneration],
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
     ...(config.outputFormat && { outputFormat: config.outputFormat }),
   };
@@ -197,11 +260,15 @@ export function createSpecGenerationOptions(config: CreateSdkOptionsConfig): Opt
  * - Uses read-only tools (just needs to read the spec)
  * - Quick turns since it's mostly JSON generation
  * - Sonnet model by default for speed
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createFeatureGenerationOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     // Override permissionMode - feature generation only needs read-only tools
@@ -210,7 +277,7 @@ export function createFeatureGenerationOptions(config: CreateSdkOptionsConfig):
     maxTurns: MAX_TURNS.quick,
     cwd: config.cwd,
     allowedTools: [...TOOL_PRESETS.readOnly],
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
   };
 }
@@ -222,18 +289,22 @@ export function createFeatureGenerationOptions(config: CreateSdkOptionsConfig):
  * - Uses read-only tools for analysis
  * - Standard turns to allow thorough codebase exploration and structured output generation
  * - Opus model by default for thorough analysis
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createSuggestionsOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     model: getModelForUseCase('suggestions', config.model),
     maxTurns: MAX_TURNS.extended,
     cwd: config.cwd,
     allowedTools: [...TOOL_PRESETS.readOnly],
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
     ...(config.outputFormat && { outputFormat: config.outputFormat }),
   };
@@ -246,7 +317,8 @@ export function createSuggestionsOptions(config: CreateSdkOptionsConfig): Option
  * - Full tool access for code modification
  * - Standard turns for interactive sessions
  * - Model priority: explicit model > session model > chat default
- * - Sandbox enabled for bash safety
+ * - Sandbox mode controlled by enableSandboxMode setting
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createChatOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
@@ -255,17 +327,22 @@ export function createChatOptions(config: CreateSdkOptionsConfig): Options {
   // Model priority: explicit model > session model > chat default
   const effectiveModel = config.model || config.sessionModel;
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     model: getModelForUseCase('chat', effectiveModel),
     maxTurns: MAX_TURNS.standard,
     cwd: config.cwd,
     allowedTools: [...TOOL_PRESETS.chat],
-    sandbox: {
-      enabled: true,
-      autoAllowBashIfSandboxed: true,
-    },
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...(config.enableSandboxMode && {
+      sandbox: {
+        enabled: true,
+        autoAllowBashIfSandboxed: true,
+      },
+    }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
   };
 }
@@ -277,23 +354,29 @@ export function createChatOptions(config: CreateSdkOptionsConfig): Options {
  * - Full tool access for code modification and implementation
  * - Extended turns for thorough feature implementation
  * - Uses default model (can be overridden)
- * - Sandbox enabled for bash safety
+ * - Sandbox mode controlled by enableSandboxMode setting
+ * - When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createAutoModeOptions(config: CreateSdkOptionsConfig): Options {
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     model: getModelForUseCase('auto', config.model),
     maxTurns: MAX_TURNS.maximum,
     cwd: config.cwd,
     allowedTools: [...TOOL_PRESETS.fullAccess],
-    sandbox: {
-      enabled: true,
-      autoAllowBashIfSandboxed: true,
-    },
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...(config.enableSandboxMode && {
+      sandbox: {
+        enabled: true,
+        autoAllowBashIfSandboxed: true,
+      },
+    }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
   };
 }
@@ -302,6 +385,7 @@ export function createAutoModeOptions(config: CreateSdkOptionsConfig): Options {
  * Create custom SDK options with explicit configuration
  *
  * Use this when the preset options don't fit your use case.
+ * When autoLoadClaudeMd is true, uses preset mode and settingSources for CLAUDE.md loading
  */
 export function createCustomOptions(
   config: CreateSdkOptionsConfig & {
@@ -313,6 +397,9 @@ export function createCustomOptions(
   // Validate working directory before creating options
   validateWorkingDirectory(config.cwd);
 
+  // Build CLAUDE.md auto-loading options if enabled
+  const claudeMdOptions = buildClaudeMdOptions(config);
+
   return {
     ...getBaseOptions(),
     model: getModelForUseCase('default', config.model),
@@ -320,7 +407,7 @@ export function createCustomOptions(
     cwd: config.cwd,
     allowedTools: config.allowedTools ? [...config.allowedTools] : [...TOOL_PRESETS.readOnly],
     ...(config.sandbox && { sandbox: config.sandbox }),
-    ...(config.systemPrompt && { systemPrompt: config.systemPrompt }),
+    ...claudeMdOptions,
     ...(config.abortController && { abortController: config.abortController }),
   };
 }

apps/server/src/lib/secure-fs.ts

@@ -20,4 +20,9 @@ export const {
   lstat,
   joinPath,
   resolvePath,
+  // Throttling configuration and monitoring
+  configureThrottling,
+  getThrottlingConfig,
+  getPendingOperations,
+  getActiveOperations,
 } = secureFs;

apps/server/src/lib/settings-helpers.ts

@@ -0,0 +1,138 @@
+/**
+ * Helper utilities for loading settings and context file handling across different parts of the server
+ */
+
+import type { SettingsService } from '../services/settings-service.js';
+import type { ContextFilesResult, ContextFileInfo } from '@automaker/utils';
+
+/**
+ * Get the autoLoadClaudeMd setting, with project settings taking precedence over global.
+ * Returns false if settings service is not available.
+ *
+ * @param projectPath - Path to the project
+ * @param settingsService - Optional settings service instance
+ * @param logPrefix - Prefix for log messages (e.g., '[DescribeImage]')
+ * @returns Promise resolving to the autoLoadClaudeMd setting value
+ */
+export async function getAutoLoadClaudeMdSetting(
+  projectPath: string,
+  settingsService?: SettingsService | null,
+  logPrefix = '[SettingsHelper]'
+): Promise<boolean> {
+  if (!settingsService) {
+    console.log(`${logPrefix} SettingsService not available, autoLoadClaudeMd disabled`);
+    return false;
+  }
+
+  try {
+    // Check project settings first (takes precedence)
+    const projectSettings = await settingsService.getProjectSettings(projectPath);
+    if (projectSettings.autoLoadClaudeMd !== undefined) {
+      console.log(
+        `${logPrefix} autoLoadClaudeMd from project settings: ${projectSettings.autoLoadClaudeMd}`
+      );
+      return projectSettings.autoLoadClaudeMd;
+    }
+
+    // Fall back to global settings
+    const globalSettings = await settingsService.getGlobalSettings();
+    const result = globalSettings.autoLoadClaudeMd ?? false;
+    console.log(`${logPrefix} autoLoadClaudeMd from global settings: ${result}`);
+    return result;
+  } catch (error) {
+    console.error(`${logPrefix} Failed to load autoLoadClaudeMd setting:`, error);
+    throw error;
+  }
+}
+
+/**
+ * Get the enableSandboxMode setting from global settings.
+ * Returns false if settings service is not available.
+ *
+ * @param settingsService - Optional settings service instance
+ * @param logPrefix - Prefix for log messages (e.g., '[AgentService]')
+ * @returns Promise resolving to the enableSandboxMode setting value
+ */
+export async function getEnableSandboxModeSetting(
+  settingsService?: SettingsService | null,
+  logPrefix = '[SettingsHelper]'
+): Promise<boolean> {
+  if (!settingsService) {
+    console.log(`${logPrefix} SettingsService not available, sandbox mode disabled`);
+    return false;
+  }
+
+  try {
+    const globalSettings = await settingsService.getGlobalSettings();
+    const result = globalSettings.enableSandboxMode ?? true;
+    console.log(`${logPrefix} enableSandboxMode from global settings: ${result}`);
+    return result;
+  } catch (error) {
+    console.error(`${logPrefix} Failed to load enableSandboxMode setting:`, error);
+    throw error;
+  }
+}
+
+/**
+ * Filters out CLAUDE.md from context files when autoLoadClaudeMd is enabled
+ * and rebuilds the formatted prompt without it.
+ *
+ * When autoLoadClaudeMd is true, the SDK handles CLAUDE.md loading via settingSources,
+ * so we need to exclude it from the manual context loading to avoid duplication.
+ * Other context files (CODE_QUALITY.md, CONVENTIONS.md, etc.) are preserved.
+ *
+ * @param contextResult - Result from loadContextFiles
+ * @param autoLoadClaudeMd - Whether SDK auto-loading is enabled
+ * @returns Filtered context prompt (empty string if no non-CLAUDE.md files)
+ */
+export function filterClaudeMdFromContext(
+  contextResult: ContextFilesResult,
+  autoLoadClaudeMd: boolean
+): string {
+  // If autoLoadClaudeMd is disabled, return the original prompt unchanged
+  if (!autoLoadClaudeMd || contextResult.files.length === 0) {
+    return contextResult.formattedPrompt;
+  }
+
+  // Filter out CLAUDE.md (case-insensitive)
+  const nonClaudeFiles = contextResult.files.filter((f) => f.name.toLowerCase() !== 'claude.md');
+
+  // If all files were CLAUDE.md, return empty string
+  if (nonClaudeFiles.length === 0) {
+    return '';
+  }
+
+  // Rebuild prompt without CLAUDE.md using the same format as loadContextFiles
+  const formattedFiles = nonClaudeFiles.map((file) => formatContextFileEntry(file));
+
+  return `# Project Context Files
+
+The following context files provide project-specific rules, conventions, and guidelines.
+Each file serves a specific purpose - use the description to understand when to reference it.
+If you need more details about a context file, you can read the full file at the path provided.
+
+**IMPORTANT**: You MUST follow the rules and conventions specified in these files.
+- Follow ALL commands exactly as shown (e.g., if the project uses \`pnpm\`, NEVER use \`npm\` or \`npx\`)
+- Follow ALL coding conventions, commit message formats, and architectural patterns specified
+- Reference these rules before running ANY shell commands or making commits
+
+---
+
+${formattedFiles.join('\n\n---\n\n')}
+
+---
+
+**REMINDER**: Before taking any action, verify you are following the conventions specified above.
+`;
+}
+
+/**
+ * Format a single context file entry for the prompt
+ * (Matches the format used in @automaker/utils/context-loader.ts)
+ */
+function formatContextFileEntry(file: ContextFileInfo): string {
+  const header = `## ${file.name}`;
+  const pathInfo = `**Path:** \`${file.path}\``;
+  const descriptionInfo = file.description ? `\n**Purpose:** ${file.description}` : '';
+  return `${header}\n${pathInfo}${descriptionInfo}\n\n${file.content}`;
+}

apps/server/src/lib/validation-storage.ts

@@ -0,0 +1,181 @@
+/**
+ * Validation Storage - CRUD operations for GitHub issue validation results
+ *
+ * Stores validation results in .automaker/validations/{issueNumber}/validation.json
+ * Results include the validation verdict, metadata, and timestamp for cache invalidation.
+ */
+
+import * as secureFs from './secure-fs.js';
+import { getValidationsDir, getValidationDir, getValidationPath } from '@automaker/platform';
+import type { StoredValidation } from '@automaker/types';
+
+// Re-export StoredValidation for convenience
+export type { StoredValidation };
+
+/** Number of hours before a validation is considered stale */
+const VALIDATION_CACHE_TTL_HOURS = 24;
+
+/**
+ * Write validation result to storage
+ *
+ * Creates the validation directory if needed and stores the result as JSON.
+ *
+ * @param projectPath - Absolute path to project directory
+ * @param issueNumber - GitHub issue number
+ * @param data - Validation data to store
+ */
+export async function writeValidation(
+  projectPath: string,
+  issueNumber: number,
+  data: StoredValidation
+): Promise<void> {
+  const validationDir = getValidationDir(projectPath, issueNumber);
+  const validationPath = getValidationPath(projectPath, issueNumber);
+
+  // Ensure directory exists
+  await secureFs.mkdir(validationDir, { recursive: true });
+
+  // Write validation result
+  await secureFs.writeFile(validationPath, JSON.stringify(data, null, 2), 'utf-8');
+}
+
+/**
+ * Read validation result from storage
+ *
+ * @param projectPath - Absolute path to project directory
+ * @param issueNumber - GitHub issue number
+ * @returns Stored validation or null if not found
+ */
+export async function readValidation(
+  projectPath: string,
+  issueNumber: number
+): Promise<StoredValidation | null> {
+  try {
+    const validationPath = getValidationPath(projectPath, issueNumber);
+    const content = (await secureFs.readFile(validationPath, 'utf-8')) as string;
+    return JSON.parse(content) as StoredValidation;
+  } catch {
+    // File doesn't exist or can't be read
+    return null;
+  }
+}
+
+/**
+ * Get all stored validations for a project
+ *
+ * @param projectPath - Absolute path to project directory
+ * @returns Array of stored validations
+ */
+export async function getAllValidations(projectPath: string): Promise<StoredValidation[]> {
+  const validationsDir = getValidationsDir(projectPath);
+
+  try {
+    const dirs = await secureFs.readdir(validationsDir, { withFileTypes: true });
+
+    // Read all validation files in parallel for better performance
+    const promises = dirs
+      .filter((dir) => dir.isDirectory())
+      .map((dir) => {
+        const issueNumber = parseInt(dir.name, 10);
+        if (!isNaN(issueNumber)) {
+          return readValidation(projectPath, issueNumber);
+        }
+        return Promise.resolve(null);
+      });
+
+    const results = await Promise.all(promises);
+    const validations = results.filter((v): v is StoredValidation => v !== null);
+
+    // Sort by issue number
+    validations.sort((a, b) => a.issueNumber - b.issueNumber);
+
+    return validations;
+  } catch {
+    // Directory doesn't exist
+    return [];
+  }
+}
+
+/**
+ * Delete a validation from storage
+ *
+ * @param projectPath - Absolute path to project directory
+ * @param issueNumber - GitHub issue number
+ * @returns true if validation was deleted, false if not found
+ */
+export async function deleteValidation(projectPath: string, issueNumber: number): Promise<boolean> {
+  try {
+    const validationDir = getValidationDir(projectPath, issueNumber);
+    await secureFs.rm(validationDir, { recursive: true, force: true });
+    return true;
+  } catch {
+    return false;
+  }
+}
+
+/**
+ * Check if a validation is stale (older than TTL)
+ *
+ * @param validation - Stored validation to check
+ * @returns true if validation is older than 24 hours
+ */
+export function isValidationStale(validation: StoredValidation): boolean {
+  const validatedAt = new Date(validation.validatedAt);
+  const now = new Date();
+  const hoursDiff = (now.getTime() - validatedAt.getTime()) / (1000 * 60 * 60);
+  return hoursDiff > VALIDATION_CACHE_TTL_HOURS;
+}
+
+/**
+ * Get validation with freshness info
+ *
+ * @param projectPath - Absolute path to project directory
+ * @param issueNumber - GitHub issue number
+ * @returns Object with validation and isStale flag, or null if not found
+ */
+export async function getValidationWithFreshness(
+  projectPath: string,
+  issueNumber: number
+): Promise<{ validation: StoredValidation; isStale: boolean } | null> {
+  const validation = await readValidation(projectPath, issueNumber);
+  if (!validation) {
+    return null;
+  }
+
+  return {
+    validation,
+    isStale: isValidationStale(validation),
+  };
+}
+
+/**
+ * Mark a validation as viewed by the user
+ *
+ * @param projectPath - Absolute path to project directory
+ * @param issueNumber - GitHub issue number
+ * @returns true if validation was marked as viewed, false if not found
+ */
+export async function markValidationViewed(
+  projectPath: string,
+  issueNumber: number
+): Promise<boolean> {
+  const validation = await readValidation(projectPath, issueNumber);
+  if (!validation) {
+    return false;
+  }
+
+  validation.viewedAt = new Date().toISOString();
+  await writeValidation(projectPath, issueNumber, validation);
+  return true;
+}
+
+/**
+ * Get count of unviewed, non-stale validations for a project
+ *
+ * @param projectPath - Absolute path to project directory
+ * @returns Number of unviewed validations
+ */
+export async function getUnviewedValidationsCount(projectPath: string): Promise<number> {
+  const validations = await getAllValidations(projectPath);
+  return validations.filter((v) => !v.viewedAt && !isValidationStale(v)).length;
+}

apps/server/src/providers/claude-provider.ts

@@ -45,16 +45,16 @@ export class ClaudeProvider extends BaseProvider {
       maxTurns,
       cwd,
       allowedTools: toolsToUse,
-      permissionMode: 'acceptEdits',
-      sandbox: {
-        enabled: true,
-        autoAllowBashIfSandboxed: true,
-      },
+      permissionMode: 'default',
       abortController,
       // Resume existing SDK session if we have a session ID
       ...(sdkSessionId && conversationHistory && conversationHistory.length > 0
         ? { resume: sdkSessionId }
         : {}),
+      // Forward settingSources for CLAUDE.md file loading
+      ...(options.settingSources && { settingSources: options.settingSources }),
+      // Forward sandbox configuration
+      ...(options.sandbox && { sandbox: options.sandbox }),
     };
 
     // Build prompt payload
@@ -88,7 +88,8 @@ export class ClaudeProvider extends BaseProvider {
         yield msg as ProviderMessage;
       }
     } catch (error) {
-      console.error('[ClaudeProvider] executeQuery() error during execution:', error);
+      console.error('[ClaudeProvider] ERROR: executeQuery() error during execution:', error);
+      console.error('[ClaudeProvider] ERROR stack:', (error as Error).stack);
       throw error;
     }
   }

apps/server/src/providers/types.ts

@@ -26,13 +26,15 @@ export interface ExecuteOptions {
   prompt: string | Array<{ type: string; text?: string; source?: object }>;
   model: string;
   cwd: string;
-  systemPrompt?: string;
+  systemPrompt?: string | { type: 'preset'; preset: 'claude_code'; append?: string };
   maxTurns?: number;
   allowedTools?: string[];
   mcpServers?: Record<string, unknown>;
   abortController?: AbortController;
   conversationHistory?: ConversationMessage[]; // Previous messages for context
   sdkSessionId?: string; // Claude SDK session ID for resuming conversations
+  settingSources?: Array<'user' | 'project' | 'local'>; // Claude filesystem settings to load
+  sandbox?: { enabled: boolean; autoAllowBashIfSandboxed?: boolean }; // Sandbox configuration
 }
 
 /**

apps/server/src/routes/agent/index.ts

@@ -12,6 +12,10 @@ import { createHistoryHandler } from './routes/history.js';
 import { createStopHandler } from './routes/stop.js';
 import { createClearHandler } from './routes/clear.js';
 import { createModelHandler } from './routes/model.js';
+import { createQueueAddHandler } from './routes/queue-add.js';
+import { createQueueListHandler } from './routes/queue-list.js';
+import { createQueueRemoveHandler } from './routes/queue-remove.js';
+import { createQueueClearHandler } from './routes/queue-clear.js';
 
 export function createAgentRoutes(agentService: AgentService, _events: EventEmitter): Router {
   const router = Router();
@@ -27,5 +31,15 @@ export function createAgentRoutes(agentService: AgentService, _events: EventEmit
   router.post('/clear', createClearHandler(agentService));
   router.post('/model', createModelHandler(agentService));
 
+  // Queue routes
+  router.post(
+    '/queue/add',
+    validatePathParams('imagePaths[]'),
+    createQueueAddHandler(agentService)
+  );
+  router.post('/queue/list', createQueueListHandler(agentService));
+  router.post('/queue/remove', createQueueRemoveHandler(agentService));
+  router.post('/queue/clear', createQueueClearHandler(agentService));
+
   return router;
 }

apps/server/src/routes/agent/routes/queue-add.ts

@@ -0,0 +1,34 @@
+/**
+ * POST /queue/add endpoint - Add a prompt to the queue
+ */
+
+import type { Request, Response } from 'express';
+import { AgentService } from '../../../services/agent-service.js';
+import { getErrorMessage, logError } from '../common.js';
+
+export function createQueueAddHandler(agentService: AgentService) {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { sessionId, message, imagePaths, model } = req.body as {
+        sessionId: string;
+        message: string;
+        imagePaths?: string[];
+        model?: string;
+      };
+
+      if (!sessionId || !message) {
+        res.status(400).json({
+          success: false,
+          error: 'sessionId and message are required',
+        });
+        return;
+      }
+
+      const result = await agentService.addToQueue(sessionId, { message, imagePaths, model });
+      res.json(result);
+    } catch (error) {
+      logError(error, 'Add to queue failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/agent/routes/queue-clear.ts

@@ -0,0 +1,29 @@
+/**
+ * POST /queue/clear endpoint - Clear all prompts from the queue
+ */
+
+import type { Request, Response } from 'express';
+import { AgentService } from '../../../services/agent-service.js';
+import { getErrorMessage, logError } from '../common.js';
+
+export function createQueueClearHandler(agentService: AgentService) {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { sessionId } = req.body as { sessionId: string };
+
+      if (!sessionId) {
+        res.status(400).json({
+          success: false,
+          error: 'sessionId is required',
+        });
+        return;
+      }
+
+      const result = await agentService.clearQueue(sessionId);
+      res.json(result);
+    } catch (error) {
+      logError(error, 'Clear queue failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/agent/routes/queue-list.ts

@@ -0,0 +1,29 @@
+/**
+ * POST /queue/list endpoint - List queued prompts
+ */
+
+import type { Request, Response } from 'express';
+import { AgentService } from '../../../services/agent-service.js';
+import { getErrorMessage, logError } from '../common.js';
+
+export function createQueueListHandler(agentService: AgentService) {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { sessionId } = req.body as { sessionId: string };
+
+      if (!sessionId) {
+        res.status(400).json({
+          success: false,
+          error: 'sessionId is required',
+        });
+        return;
+      }
+
+      const result = agentService.getQueue(sessionId);
+      res.json(result);
+    } catch (error) {
+      logError(error, 'List queue failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/agent/routes/queue-remove.ts

@@ -0,0 +1,32 @@
+/**
+ * POST /queue/remove endpoint - Remove a prompt from the queue
+ */
+
+import type { Request, Response } from 'express';
+import { AgentService } from '../../../services/agent-service.js';
+import { getErrorMessage, logError } from '../common.js';
+
+export function createQueueRemoveHandler(agentService: AgentService) {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { sessionId, promptId } = req.body as {
+        sessionId: string;
+        promptId: string;
+      };
+
+      if (!sessionId || !promptId) {
+        res.status(400).json({
+          success: false,
+          error: 'sessionId and promptId are required',
+        });
+        return;
+      }
+
+      const result = await agentService.removeFromQueue(sessionId, promptId);
+      res.json(result);
+    } catch (error) {
+      logError(error, 'Remove from queue failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/agent/routes/send.ts

@@ -19,7 +19,16 @@ export function createSendHandler(agentService: AgentService) {
         model?: string;
       };
 
+      console.log('[Send Handler] Received request:', {
+        sessionId,
+        messageLength: message?.length,
+        workingDirectory,
+        imageCount: imagePaths?.length || 0,
+        model,
+      });
+
       if (!sessionId || !message) {
+        console.log('[Send Handler] ERROR: Validation failed - missing sessionId or message');
         res.status(400).json({
           success: false,
           error: 'sessionId and message are required',
@@ -27,6 +36,8 @@ export function createSendHandler(agentService: AgentService) {
         return;
       }
 
+      console.log('[Send Handler] Validation passed, calling agentService.sendMessage()');
+
       // Start the message processing (don't await - it streams via WebSocket)
       agentService
         .sendMessage({
@@ -37,12 +48,16 @@ export function createSendHandler(agentService: AgentService) {
           model,
         })
         .catch((error) => {
+          console.error('[Send Handler] ERROR: Background error in sendMessage():', error);
           logError(error, 'Send message failed (background)');
         });
 
+      console.log('[Send Handler] Returning immediate response to client');
+
       // Return immediately - responses come via WebSocket
       res.json({ success: true, message: 'Message sent' });
     } catch (error) {
+      console.error('[Send Handler] ERROR: Synchronous error:', error);
       logError(error, 'Send message failed');
       res.status(500).json({ success: false, error: getErrorMessage(error) });
     }

apps/server/src/routes/app-spec/generate-features-from-spec.ts

@@ -10,6 +10,8 @@ import { createFeatureGenerationOptions } from '../../lib/sdk-options.js';
 import { logAuthStatus } from './common.js';
 import { parseAndCreateFeatures } from './parse-and-create-features.js';
 import { getAppSpecPath } from '@automaker/platform';
+import type { SettingsService } from '../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../lib/settings-helpers.js';
 
 const logger = createLogger('SpecRegeneration');
 
@@ -19,7 +21,8 @@ export async function generateFeaturesFromSpec(
   projectPath: string,
   events: EventEmitter,
   abortController: AbortController,
-  maxFeatures?: number
+  maxFeatures?: number,
+  settingsService?: SettingsService
 ): Promise<void> {
   const featureCount = maxFeatures ?? DEFAULT_MAX_FEATURES;
   logger.debug('========== generateFeaturesFromSpec() started ==========');
@@ -91,9 +94,17 @@ IMPORTANT: Do not ask for clarification. The specification is provided above. Ge
     projectPath: projectPath,
   });
 
+  // Load autoLoadClaudeMd setting
+  const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+    projectPath,
+    settingsService,
+    '[FeatureGeneration]'
+  );
+
   const options = createFeatureGenerationOptions({
     cwd: projectPath,
     abortController,
+    autoLoadClaudeMd,
   });
 
   logger.debug('SDK Options:', JSON.stringify(options, null, 2));

apps/server/src/routes/app-spec/generate-spec.ts

@@ -17,6 +17,8 @@ import { createSpecGenerationOptions } from '../../lib/sdk-options.js';
 import { logAuthStatus } from './common.js';
 import { generateFeaturesFromSpec } from './generate-features-from-spec.js';
 import { ensureAutomakerDir, getAppSpecPath } from '@automaker/platform';
+import type { SettingsService } from '../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../lib/settings-helpers.js';
 
 const logger = createLogger('SpecRegeneration');
 
@@ -27,7 +29,8 @@ export async function generateSpec(
   abortController: AbortController,
   generateFeatures?: boolean,
   analyzeProject?: boolean,
-  maxFeatures?: number
+  maxFeatures?: number,
+  settingsService?: SettingsService
 ): Promise<void> {
   logger.info('========== generateSpec() started ==========');
   logger.info('projectPath:', projectPath);
@@ -83,9 +86,17 @@ ${getStructuredSpecPromptInstruction()}`;
     content: 'Starting spec generation...\n',
   });
 
+  // Load autoLoadClaudeMd setting
+  const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+    projectPath,
+    settingsService,
+    '[SpecRegeneration]'
+  );
+
   const options = createSpecGenerationOptions({
     cwd: projectPath,
     abortController,
+    autoLoadClaudeMd,
     outputFormat: {
       type: 'json_schema',
       schema: specOutputSchema,
@@ -269,7 +280,13 @@ ${getStructuredSpecPromptInstruction()}`;
     // Create a new abort controller for feature generation
     const featureAbortController = new AbortController();
     try {
-      await generateFeaturesFromSpec(projectPath, events, featureAbortController, maxFeatures);
+      await generateFeaturesFromSpec(
+        projectPath,
+        events,
+        featureAbortController,
+        maxFeatures,
+        settingsService
+      );
       // Final completion will be emitted by generateFeaturesFromSpec -> parseAndCreateFeatures
     } catch (featureError) {
       logger.error('Feature generation failed:', featureError);

apps/server/src/routes/app-spec/index.ts

@@ -9,13 +9,17 @@ import { createGenerateHandler } from './routes/generate.js';
 import { createGenerateFeaturesHandler } from './routes/generate-features.js';
 import { createStopHandler } from './routes/stop.js';
 import { createStatusHandler } from './routes/status.js';
+import type { SettingsService } from '../../services/settings-service.js';
 
-export function createSpecRegenerationRoutes(events: EventEmitter): Router {
+export function createSpecRegenerationRoutes(
+  events: EventEmitter,
+  settingsService?: SettingsService
+): Router {
   const router = Router();
 
   router.post('/create', createCreateHandler(events));
-  router.post('/generate', createGenerateHandler(events));
-  router.post('/generate-features', createGenerateFeaturesHandler(events));
+  router.post('/generate', createGenerateHandler(events, settingsService));
+  router.post('/generate-features', createGenerateFeaturesHandler(events, settingsService));
   router.post('/stop', createStopHandler());
   router.get('/status', createStatusHandler());
 

apps/server/src/routes/app-spec/routes/generate-features.ts

@@ -13,10 +13,14 @@ import {
   getErrorMessage,
 } from '../common.js';
 import { generateFeaturesFromSpec } from '../generate-features-from-spec.js';
+import type { SettingsService } from '../../../services/settings-service.js';
 
 const logger = createLogger('SpecRegeneration');
 
-export function createGenerateFeaturesHandler(events: EventEmitter) {
+export function createGenerateFeaturesHandler(
+  events: EventEmitter,
+  settingsService?: SettingsService
+) {
   return async (req: Request, res: Response): Promise<void> => {
     logger.info('========== /generate-features endpoint called ==========');
     logger.debug('Request body:', JSON.stringify(req.body, null, 2));
@@ -49,7 +53,7 @@ export function createGenerateFeaturesHandler(events: EventEmitter) {
       setRunningState(true, abortController);
       logger.info('Starting background feature generation task...');
 
-      generateFeaturesFromSpec(projectPath, events, abortController, maxFeatures)
+      generateFeaturesFromSpec(projectPath, events, abortController, maxFeatures, settingsService)
         .catch((error) => {
           logError(error, 'Feature generation failed with error');
           events.emit('spec-regeneration:event', {

apps/server/src/routes/app-spec/routes/generate.ts

@@ -13,10 +13,11 @@ import {
   getErrorMessage,
 } from '../common.js';
 import { generateSpec } from '../generate-spec.js';
+import type { SettingsService } from '../../../services/settings-service.js';
 
 const logger = createLogger('SpecRegeneration');
 
-export function createGenerateHandler(events: EventEmitter) {
+export function createGenerateHandler(events: EventEmitter, settingsService?: SettingsService) {
   return async (req: Request, res: Response): Promise<void> => {
     logger.info('========== /generate endpoint called ==========');
     logger.debug('Request body:', JSON.stringify(req.body, null, 2));
@@ -67,7 +68,8 @@ export function createGenerateHandler(events: EventEmitter) {
         abortController,
         generateFeatures,
         analyzeProject,
-        maxFeatures
+        maxFeatures,
+        settingsService
       )
         .catch((error) => {
           logError(error, 'Generation failed with error');

apps/server/src/routes/backlog-plan/common.ts

@@ -0,0 +1,39 @@
+/**
+ * Common utilities for backlog plan routes
+ */
+
+import { createLogger } from '@automaker/utils';
+
+const logger = createLogger('BacklogPlan');
+
+// State for tracking running generation
+let isRunning = false;
+let currentAbortController: AbortController | null = null;
+
+export function getBacklogPlanStatus(): { isRunning: boolean } {
+  return { isRunning };
+}
+
+export function setRunningState(running: boolean, abortController?: AbortController | null): void {
+  isRunning = running;
+  if (abortController !== undefined) {
+    currentAbortController = abortController;
+  }
+}
+
+export function getAbortController(): AbortController | null {
+  return currentAbortController;
+}
+
+export function getErrorMessage(error: unknown): string {
+  if (error instanceof Error) {
+    return error.message;
+  }
+  return String(error);
+}
+
+export function logError(error: unknown, context: string): void {
+  logger.error(`[BacklogPlan] ${context}:`, getErrorMessage(error));
+}
+
+export { logger };

apps/server/src/routes/backlog-plan/generate-plan.ts

@@ -0,0 +1,217 @@
+/**
+ * Generate backlog plan using Claude AI
+ */
+
+import type { EventEmitter } from '../../lib/events.js';
+import type { Feature, BacklogPlanResult, BacklogChange, DependencyUpdate } from '@automaker/types';
+import { FeatureLoader } from '../../services/feature-loader.js';
+import { ProviderFactory } from '../../providers/provider-factory.js';
+import { logger, setRunningState, getErrorMessage } from './common.js';
+import type { SettingsService } from '../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../lib/settings-helpers.js';
+
+const featureLoader = new FeatureLoader();
+
+/**
+ * Format features for the AI prompt
+ */
+function formatFeaturesForPrompt(features: Feature[]): string {
+  if (features.length === 0) {
+    return 'No features in backlog yet.';
+  }
+
+  return features
+    .map((f) => {
+      const deps = f.dependencies?.length ? `Dependencies: [${f.dependencies.join(', ')}]` : '';
+      const priority = f.priority !== undefined ? `Priority: ${f.priority}` : '';
+      return `- ID: ${f.id}
+  Title: ${f.title || 'Untitled'}
+  Description: ${f.description}
+  Category: ${f.category}
+  Status: ${f.status || 'backlog'}
+  ${priority}
+  ${deps}`.trim();
+    })
+    .join('\n\n');
+}
+
+/**
+ * Parse the AI response into a BacklogPlanResult
+ */
+function parsePlanResponse(response: string): BacklogPlanResult {
+  try {
+    // Try to extract JSON from the response
+    const jsonMatch = response.match(/```json\n?([\s\S]*?)\n?```/);
+    if (jsonMatch) {
+      return JSON.parse(jsonMatch[1]);
+    }
+
+    // Try to parse the whole response as JSON
+    return JSON.parse(response);
+  } catch {
+    // If parsing fails, return an empty result
+    logger.warn('[BacklogPlan] Failed to parse AI response as JSON');
+    return {
+      changes: [],
+      summary: 'Failed to parse AI response',
+      dependencyUpdates: [],
+    };
+  }
+}
+
+/**
+ * Generate a backlog modification plan based on user prompt
+ */
+export async function generateBacklogPlan(
+  projectPath: string,
+  prompt: string,
+  events: EventEmitter,
+  abortController: AbortController,
+  settingsService?: SettingsService,
+  model?: string
+): Promise<BacklogPlanResult> {
+  try {
+    // Load current features
+    const features = await featureLoader.getAll(projectPath);
+
+    events.emit('backlog-plan:event', {
+      type: 'backlog_plan_progress',
+      content: `Loaded ${features.length} features from backlog`,
+    });
+
+    // Build the system prompt
+    const systemPrompt = `You are an AI assistant helping to modify a software project's feature backlog.
+You will be given the current list of features and a user request to modify the backlog.
+
+IMPORTANT CONTEXT (automatically injected):
+- Remember to update the dependency graph if deleting existing features
+- Remember to define dependencies on new features hooked into relevant existing ones
+- Maintain dependency graph integrity (no orphaned dependencies)
+- When deleting a feature, identify which other features depend on it
+
+Your task is to analyze the request and produce a structured JSON plan with:
+1. Features to ADD (include title, description, category, and dependencies)
+2. Features to UPDATE (specify featureId and the updates)
+3. Features to DELETE (specify featureId)
+4. A summary of the changes
+5. Any dependency updates needed (removed dependencies due to deletions, new dependencies for new features)
+
+Respond with ONLY a JSON object in this exact format:
+\`\`\`json
+{
+  "changes": [
+    {
+      "type": "add",
+      "feature": {
+        "title": "Feature title",
+        "description": "Feature description",
+        "category": "Category name",
+        "dependencies": ["existing-feature-id"],
+        "priority": 1
+      },
+      "reason": "Why this feature should be added"
+    },
+    {
+      "type": "update",
+      "featureId": "existing-feature-id",
+      "feature": {
+        "title": "Updated title"
+      },
+      "reason": "Why this feature should be updated"
+    },
+    {
+      "type": "delete",
+      "featureId": "feature-id-to-delete",
+      "reason": "Why this feature should be deleted"
+    }
+  ],
+  "summary": "Brief overview of all proposed changes",
+  "dependencyUpdates": [
+    {
+      "featureId": "feature-that-depended-on-deleted",
+      "removedDependencies": ["deleted-feature-id"],
+      "addedDependencies": []
+    }
+  ]
+}
+\`\`\``;
+
+    // Build the user prompt
+    const userPrompt = `Current Features in Backlog:
+${formatFeaturesForPrompt(features)}
+
+---
+
+User Request: ${prompt}
+
+Please analyze the current backlog and the user's request, then provide a JSON plan for the modifications.`;
+
+    events.emit('backlog-plan:event', {
+      type: 'backlog_plan_progress',
+      content: 'Generating plan with AI...',
+    });
+
+    // Get the model to use
+    const effectiveModel = model || 'sonnet';
+    const provider = ProviderFactory.getProviderForModel(effectiveModel);
+
+    // Get autoLoadClaudeMd setting
+    const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+      projectPath,
+      settingsService,
+      '[BacklogPlan]'
+    );
+
+    // Execute the query
+    const stream = provider.executeQuery({
+      prompt: userPrompt,
+      model: effectiveModel,
+      cwd: projectPath,
+      systemPrompt,
+      maxTurns: 1,
+      allowedTools: [], // No tools needed for this
+      abortController,
+      settingSources: autoLoadClaudeMd ? ['user', 'project'] : undefined,
+    });
+
+    let responseText = '';
+
+    for await (const msg of stream) {
+      if (abortController.signal.aborted) {
+        throw new Error('Generation aborted');
+      }
+
+      if (msg.type === 'assistant') {
+        if (msg.message?.content) {
+          for (const block of msg.message.content) {
+            if (block.type === 'text') {
+              responseText += block.text;
+            }
+          }
+        }
+      }
+    }
+
+    // Parse the response
+    const result = parsePlanResponse(responseText);
+
+    events.emit('backlog-plan:event', {
+      type: 'backlog_plan_complete',
+      result,
+    });
+
+    return result;
+  } catch (error) {
+    const errorMessage = getErrorMessage(error);
+    logger.error('[BacklogPlan] Generation failed:', errorMessage);
+
+    events.emit('backlog-plan:event', {
+      type: 'backlog_plan_error',
+      error: errorMessage,
+    });
+
+    throw error;
+  } finally {
+    setRunningState(false, null);
+  }
+}

apps/server/src/routes/backlog-plan/index.ts

@@ -0,0 +1,30 @@
+/**
+ * Backlog Plan routes - HTTP API for AI-assisted backlog modification
+ */
+
+import { Router } from 'express';
+import type { EventEmitter } from '../../lib/events.js';
+import { validatePathParams } from '../../middleware/validate-paths.js';
+import { createGenerateHandler } from './routes/generate.js';
+import { createStopHandler } from './routes/stop.js';
+import { createStatusHandler } from './routes/status.js';
+import { createApplyHandler } from './routes/apply.js';
+import type { SettingsService } from '../../services/settings-service.js';
+
+export function createBacklogPlanRoutes(
+  events: EventEmitter,
+  settingsService?: SettingsService
+): Router {
+  const router = Router();
+
+  router.post(
+    '/generate',
+    validatePathParams('projectPath'),
+    createGenerateHandler(events, settingsService)
+  );
+  router.post('/stop', createStopHandler());
+  router.get('/status', createStatusHandler());
+  router.post('/apply', validatePathParams('projectPath'), createApplyHandler());
+
+  return router;
+}

apps/server/src/routes/backlog-plan/routes/apply.ts

@@ -0,0 +1,147 @@
+/**
+ * POST /apply endpoint - Apply a backlog plan
+ */
+
+import type { Request, Response } from 'express';
+import type { BacklogPlanResult, BacklogChange, Feature } from '@automaker/types';
+import { FeatureLoader } from '../../../services/feature-loader.js';
+import { getErrorMessage, logError, logger } from '../common.js';
+
+const featureLoader = new FeatureLoader();
+
+export function createApplyHandler() {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { projectPath, plan } = req.body as {
+        projectPath: string;
+        plan: BacklogPlanResult;
+      };
+
+      if (!projectPath) {
+        res.status(400).json({ success: false, error: 'projectPath required' });
+        return;
+      }
+
+      if (!plan || !plan.changes) {
+        res.status(400).json({ success: false, error: 'plan with changes required' });
+        return;
+      }
+
+      const appliedChanges: string[] = [];
+
+      // Load current features for dependency validation
+      const allFeatures = await featureLoader.getAll(projectPath);
+      const featureMap = new Map(allFeatures.map((f) => [f.id, f]));
+
+      // Process changes in order: deletes first, then adds, then updates
+      // This ensures we can remove dependencies before they cause issues
+
+      // 1. First pass: Handle deletes
+      const deletions = plan.changes.filter((c) => c.type === 'delete');
+      for (const change of deletions) {
+        if (!change.featureId) continue;
+
+        try {
+          // Before deleting, update any features that depend on this one
+          for (const feature of allFeatures) {
+            if (feature.dependencies?.includes(change.featureId)) {
+              const newDeps = feature.dependencies.filter((d) => d !== change.featureId);
+              await featureLoader.update(projectPath, feature.id, { dependencies: newDeps });
+              logger.info(
+                `[BacklogPlan] Removed dependency ${change.featureId} from ${feature.id}`
+              );
+            }
+          }
+
+          // Now delete the feature
+          const deleted = await featureLoader.delete(projectPath, change.featureId);
+          if (deleted) {
+            appliedChanges.push(`deleted:${change.featureId}`);
+            featureMap.delete(change.featureId);
+            logger.info(`[BacklogPlan] Deleted feature ${change.featureId}`);
+          }
+        } catch (error) {
+          logger.error(
+            `[BacklogPlan] Failed to delete ${change.featureId}:`,
+            getErrorMessage(error)
+          );
+        }
+      }
+
+      // 2. Second pass: Handle adds
+      const additions = plan.changes.filter((c) => c.type === 'add');
+      for (const change of additions) {
+        if (!change.feature) continue;
+
+        try {
+          // Create the new feature
+          const newFeature = await featureLoader.create(projectPath, {
+            title: change.feature.title,
+            description: change.feature.description || '',
+            category: change.feature.category || 'Uncategorized',
+            dependencies: change.feature.dependencies,
+            priority: change.feature.priority,
+            status: 'backlog',
+          });
+
+          appliedChanges.push(`added:${newFeature.id}`);
+          featureMap.set(newFeature.id, newFeature);
+          logger.info(`[BacklogPlan] Created feature ${newFeature.id}: ${newFeature.title}`);
+        } catch (error) {
+          logger.error(`[BacklogPlan] Failed to add feature:`, getErrorMessage(error));
+        }
+      }
+
+      // 3. Third pass: Handle updates
+      const updates = plan.changes.filter((c) => c.type === 'update');
+      for (const change of updates) {
+        if (!change.featureId || !change.feature) continue;
+
+        try {
+          const updated = await featureLoader.update(projectPath, change.featureId, change.feature);
+          appliedChanges.push(`updated:${change.featureId}`);
+          featureMap.set(change.featureId, updated);
+          logger.info(`[BacklogPlan] Updated feature ${change.featureId}`);
+        } catch (error) {
+          logger.error(
+            `[BacklogPlan] Failed to update ${change.featureId}:`,
+            getErrorMessage(error)
+          );
+        }
+      }
+
+      // 4. Apply dependency updates from the plan
+      if (plan.dependencyUpdates) {
+        for (const depUpdate of plan.dependencyUpdates) {
+          try {
+            const feature = featureMap.get(depUpdate.featureId);
+            if (feature) {
+              const currentDeps = feature.dependencies || [];
+              const newDeps = currentDeps
+                .filter((d) => !depUpdate.removedDependencies.includes(d))
+                .concat(depUpdate.addedDependencies.filter((d) => !currentDeps.includes(d)));
+
+              await featureLoader.update(projectPath, depUpdate.featureId, {
+                dependencies: newDeps,
+              });
+              logger.info(`[BacklogPlan] Updated dependencies for ${depUpdate.featureId}`);
+            }
+          } catch (error) {
+            logger.error(
+              `[BacklogPlan] Failed to update dependencies for ${depUpdate.featureId}:`,
+              getErrorMessage(error)
+            );
+          }
+        }
+      }
+
+      res.json({
+        success: true,
+        appliedChanges,
+      });
+    } catch (error) {
+      logError(error, 'Apply backlog plan failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/backlog-plan/routes/generate.ts

@@ -0,0 +1,62 @@
+/**
+ * POST /generate endpoint - Generate a backlog plan
+ */
+
+import type { Request, Response } from 'express';
+import type { EventEmitter } from '../../../lib/events.js';
+import { getBacklogPlanStatus, setRunningState, getErrorMessage, logError } from '../common.js';
+import { generateBacklogPlan } from '../generate-plan.js';
+import type { SettingsService } from '../../../services/settings-service.js';
+
+export function createGenerateHandler(events: EventEmitter, settingsService?: SettingsService) {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { projectPath, prompt, model } = req.body as {
+        projectPath: string;
+        prompt: string;
+        model?: string;
+      };
+
+      if (!projectPath) {
+        res.status(400).json({ success: false, error: 'projectPath required' });
+        return;
+      }
+
+      if (!prompt) {
+        res.status(400).json({ success: false, error: 'prompt required' });
+        return;
+      }
+
+      const { isRunning } = getBacklogPlanStatus();
+      if (isRunning) {
+        res.json({
+          success: false,
+          error: 'Backlog plan generation is already running',
+        });
+        return;
+      }
+
+      setRunningState(true);
+      const abortController = new AbortController();
+      setRunningState(true, abortController);
+
+      // Start generation in background
+      generateBacklogPlan(projectPath, prompt, events, abortController, settingsService, model)
+        .catch((error) => {
+          logError(error, 'Generate backlog plan failed (background)');
+          events.emit('backlog-plan:event', {
+            type: 'backlog_plan_error',
+            error: getErrorMessage(error),
+          });
+        })
+        .finally(() => {
+          setRunningState(false, null);
+        });
+
+      res.json({ success: true });
+    } catch (error) {
+      logError(error, 'Generate backlog plan failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/backlog-plan/routes/status.ts

@@ -0,0 +1,18 @@
+/**
+ * GET /status endpoint - Get backlog plan generation status
+ */
+
+import type { Request, Response } from 'express';
+import { getBacklogPlanStatus, getErrorMessage, logError } from '../common.js';
+
+export function createStatusHandler() {
+  return async (_req: Request, res: Response): Promise<void> => {
+    try {
+      const status = getBacklogPlanStatus();
+      res.json({ success: true, ...status });
+    } catch (error) {
+      logError(error, 'Get backlog plan status failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/backlog-plan/routes/stop.ts

@@ -0,0 +1,22 @@
+/**
+ * POST /stop endpoint - Stop the current backlog plan generation
+ */
+
+import type { Request, Response } from 'express';
+import { getAbortController, setRunningState, getErrorMessage, logError } from '../common.js';
+
+export function createStopHandler() {
+  return async (_req: Request, res: Response): Promise<void> => {
+    try {
+      const abortController = getAbortController();
+      if (abortController) {
+        abortController.abort();
+        setRunningState(false, null);
+      }
+      res.json({ success: true });
+    } catch (error) {
+      logError(error, 'Stop backlog plan failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/context/index.ts

@@ -8,17 +8,19 @@
 import { Router } from 'express';
 import { createDescribeImageHandler } from './routes/describe-image.js';
 import { createDescribeFileHandler } from './routes/describe-file.js';
+import type { SettingsService } from '../../services/settings-service.js';
 
 /**
  * Create the context router
  *
+ * @param settingsService - Optional settings service for loading autoLoadClaudeMd setting
  * @returns Express router with context endpoints
  */
-export function createContextRoutes(): Router {
+export function createContextRoutes(settingsService?: SettingsService): Router {
   const router = Router();
 
-  router.post('/describe-image', createDescribeImageHandler());
-  router.post('/describe-file', createDescribeFileHandler());
+  router.post('/describe-image', createDescribeImageHandler(settingsService));
+  router.post('/describe-file', createDescribeFileHandler(settingsService));
 
   return router;
 }

apps/server/src/routes/context/routes/describe-file.ts

@@ -17,6 +17,8 @@ import { PathNotAllowedError } from '@automaker/platform';
 import { createCustomOptions } from '../../../lib/sdk-options.js';
 import * as secureFs from '../../../lib/secure-fs.js';
 import * as path from 'path';
+import type { SettingsService } from '../../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../../lib/settings-helpers.js';
 
 const logger = createLogger('DescribeFile');
 
@@ -72,9 +74,12 @@ async function extractTextFromStream(
 /**
  * Create the describe-file request handler
  *
+ * @param settingsService - Optional settings service for loading autoLoadClaudeMd setting
  * @returns Express request handler for file description
  */
-export function createDescribeFileHandler(): (req: Request, res: Response) => Promise<void> {
+export function createDescribeFileHandler(
+  settingsService?: SettingsService
+): (req: Request, res: Response) => Promise<void> {
   return async (req: Request, res: Response): Promise<void> => {
     try {
       const { filePath } = req.body as DescribeFileRequestBody;
@@ -165,6 +170,13 @@ File: ${fileName}${truncated ? ' (truncated)' : ''}`;
       // Use the file's directory as the working directory
       const cwd = path.dirname(resolvedPath);
 
+      // Load autoLoadClaudeMd setting
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        cwd,
+        settingsService,
+        '[DescribeFile]'
+      );
+
       // Use centralized SDK options with proper cwd validation
       // No tools needed since we're passing file content directly
       const sdkOptions = createCustomOptions({
@@ -172,6 +184,7 @@ File: ${fileName}${truncated ? ' (truncated)' : ''}`;
         model: CLAUDE_MODEL_MAP.haiku,
         maxTurns: 1,
         allowedTools: [],
+        autoLoadClaudeMd,
         sandbox: { enabled: true, autoAllowBashIfSandboxed: true },
       });
 

apps/server/src/routes/context/routes/describe-image.ts

@@ -17,6 +17,8 @@ import { CLAUDE_MODEL_MAP } from '@automaker/types';
 import { createCustomOptions } from '../../../lib/sdk-options.js';
 import * as fs from 'fs';
 import * as path from 'path';
+import type { SettingsService } from '../../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../../lib/settings-helpers.js';
 
 const logger = createLogger('DescribeImage');
 
@@ -226,9 +228,12 @@ async function extractTextFromStream(
  * Uses Claude SDK query with multi-part content blocks to include the image (base64),
  * matching the agent runner behavior.
  *
+ * @param settingsService - Optional settings service for loading autoLoadClaudeMd setting
  * @returns Express request handler for image description
  */
-export function createDescribeImageHandler(): (req: Request, res: Response) => Promise<void> {
+export function createDescribeImageHandler(
+  settingsService?: SettingsService
+): (req: Request, res: Response) => Promise<void> {
   return async (req: Request, res: Response): Promise<void> => {
     const requestId = `describe-image-${Date.now()}-${Math.random().toString(36).slice(2, 9)}`;
     const startedAt = Date.now();
@@ -325,12 +330,20 @@ export function createDescribeImageHandler(): (req: Request, res: Response) => P
       const cwd = path.dirname(actualPath);
       logger.info(`[${requestId}] Using cwd=${cwd}`);
 
+      // Load autoLoadClaudeMd setting
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        cwd,
+        settingsService,
+        '[DescribeImage]'
+      );
+
       // Use the same centralized option builder used across the server (validates cwd)
       const sdkOptions = createCustomOptions({
         cwd,
         model: CLAUDE_MODEL_MAP.haiku,
         maxTurns: 1,
         allowedTools: [],
+        autoLoadClaudeMd,
         sandbox: { enabled: true, autoAllowBashIfSandboxed: true },
       });
 

apps/server/src/routes/github/index.ts

@@ -3,16 +3,54 @@
  */
 
 import { Router } from 'express';
+import type { EventEmitter } from '../../lib/events.js';
+import { validatePathParams } from '../../middleware/validate-paths.js';
 import { createCheckGitHubRemoteHandler } from './routes/check-github-remote.js';
 import { createListIssuesHandler } from './routes/list-issues.js';
 import { createListPRsHandler } from './routes/list-prs.js';
+import { createValidateIssueHandler } from './routes/validate-issue.js';
+import {
+  createValidationStatusHandler,
+  createValidationStopHandler,
+  createGetValidationsHandler,
+  createDeleteValidationHandler,
+  createMarkViewedHandler,
+} from './routes/validation-endpoints.js';
+import type { SettingsService } from '../../services/settings-service.js';
 
-export function createGitHubRoutes(): Router {
+export function createGitHubRoutes(
+  events: EventEmitter,
+  settingsService?: SettingsService
+): Router {
   const router = Router();
 
-  router.post('/check-remote', createCheckGitHubRemoteHandler());
-  router.post('/issues', createListIssuesHandler());
-  router.post('/prs', createListPRsHandler());
+  router.post('/check-remote', validatePathParams('projectPath'), createCheckGitHubRemoteHandler());
+  router.post('/issues', validatePathParams('projectPath'), createListIssuesHandler());
+  router.post('/prs', validatePathParams('projectPath'), createListPRsHandler());
+  router.post(
+    '/validate-issue',
+    validatePathParams('projectPath'),
+    createValidateIssueHandler(events, settingsService)
+  );
+
+  // Validation management endpoints
+  router.post(
+    '/validation-status',
+    validatePathParams('projectPath'),
+    createValidationStatusHandler()
+  );
+  router.post('/validation-stop', validatePathParams('projectPath'), createValidationStopHandler());
+  router.post('/validations', validatePathParams('projectPath'), createGetValidationsHandler());
+  router.post(
+    '/validation-delete',
+    validatePathParams('projectPath'),
+    createDeleteValidationHandler()
+  );
+  router.post(
+    '/validation-mark-viewed',
+    validatePathParams('projectPath'),
+    createMarkViewedHandler(events)
+  );
 
   return router;
 }

apps/server/src/routes/github/routes/list-issues.ts

@@ -2,6 +2,7 @@
  * POST /list-issues endpoint - List GitHub issues for a project
  */
 
+import { spawn } from 'child_process';
 import type { Request, Response } from 'express';
 import { execAsync, execEnv, getErrorMessage, logError } from './common.js';
 import { checkGitHubRemote } from './check-github-remote.js';
@@ -13,6 +14,19 @@ export interface GitHubLabel {
 
 export interface GitHubAuthor {
   login: string;
+  avatarUrl?: string;
+}
+
+export interface GitHubAssignee {
+  login: string;
+  avatarUrl?: string;
+}
+
+export interface LinkedPullRequest {
+  number: number;
+  title: string;
+  state: string;
+  url: string;
 }
 
 export interface GitHubIssue {
@@ -24,6 +38,8 @@ export interface GitHubIssue {
   labels: GitHubLabel[];
   url: string;
   body: string;
+  assignees: GitHubAssignee[];
+  linkedPRs?: LinkedPullRequest[];
 }
 
 export interface ListIssuesResult {
@@ -33,6 +49,146 @@ export interface ListIssuesResult {
   error?: string;
 }
 
+/**
+ * Fetch linked PRs for a list of issues using GitHub GraphQL API
+ */
+async function fetchLinkedPRs(
+  projectPath: string,
+  owner: string,
+  repo: string,
+  issueNumbers: number[]
+): Promise<Map<number, LinkedPullRequest[]>> {
+  const linkedPRsMap = new Map<number, LinkedPullRequest[]>();
+
+  if (issueNumbers.length === 0) {
+    return linkedPRsMap;
+  }
+
+  // Build GraphQL query for batch fetching linked PRs
+  // We fetch up to 20 issues at a time to avoid query limits
+  const batchSize = 20;
+  for (let i = 0; i < issueNumbers.length; i += batchSize) {
+    const batch = issueNumbers.slice(i, i + batchSize);
+
+    const issueQueries = batch
+      .map(
+        (num, idx) => `
+        issue${idx}: issue(number: ${num}) {
+          number
+          timelineItems(first: 10, itemTypes: [CROSS_REFERENCED_EVENT, CONNECTED_EVENT]) {
+            nodes {
+              ... on CrossReferencedEvent {
+                source {
+                  ... on PullRequest {
+                    number
+                    title
+                    state
+                    url
+                  }
+                }
+              }
+              ... on ConnectedEvent {
+                subject {
+                  ... on PullRequest {
+                    number
+                    title
+                    state
+                    url
+                  }
+                }
+              }
+            }
+          }
+        }`
+      )
+      .join('\n');
+
+    const query = `{
+      repository(owner: "${owner}", name: "${repo}") {
+        ${issueQueries}
+      }
+    }`;
+
+    try {
+      // Use spawn with stdin to avoid shell injection vulnerabilities
+      // --input - reads the JSON request body from stdin
+      const requestBody = JSON.stringify({ query });
+      const response = await new Promise<Record<string, unknown>>((resolve, reject) => {
+        const gh = spawn('gh', ['api', 'graphql', '--input', '-'], {
+          cwd: projectPath,
+          env: execEnv,
+        });
+
+        let stdout = '';
+        let stderr = '';
+        gh.stdout.on('data', (data: Buffer) => (stdout += data.toString()));
+        gh.stderr.on('data', (data: Buffer) => (stderr += data.toString()));
+
+        gh.on('close', (code) => {
+          if (code !== 0) {
+            return reject(new Error(`gh process exited with code ${code}: ${stderr}`));
+          }
+          try {
+            resolve(JSON.parse(stdout));
+          } catch (e) {
+            reject(e);
+          }
+        });
+
+        gh.stdin.write(requestBody);
+        gh.stdin.end();
+      });
+
+      const repoData = (response?.data as Record<string, unknown>)?.repository as Record<
+        string,
+        unknown
+      > | null;
+
+      if (repoData) {
+        batch.forEach((issueNum, idx) => {
+          const issueData = repoData[`issue${idx}`] as {
+            timelineItems?: {
+              nodes?: Array<{
+                source?: { number?: number; title?: string; state?: string; url?: string };
+                subject?: { number?: number; title?: string; state?: string; url?: string };
+              }>;
+            };
+          } | null;
+          if (issueData?.timelineItems?.nodes) {
+            const linkedPRs: LinkedPullRequest[] = [];
+            const seenPRs = new Set<number>();
+
+            for (const node of issueData.timelineItems.nodes) {
+              const pr = node?.source || node?.subject;
+              if (pr?.number && !seenPRs.has(pr.number)) {
+                seenPRs.add(pr.number);
+                linkedPRs.push({
+                  number: pr.number,
+                  title: pr.title || '',
+                  state: (pr.state || '').toLowerCase(),
+                  url: pr.url || '',
+                });
+              }
+            }
+
+            if (linkedPRs.length > 0) {
+              linkedPRsMap.set(issueNum, linkedPRs);
+            }
+          }
+        });
+      }
+    } catch (error) {
+      // If GraphQL fails, continue without linked PRs
+      console.warn(
+        'Failed to fetch linked PRs via GraphQL:',
+        error instanceof Error ? error.message : error
+      );
+    }
+  }
+
+  return linkedPRsMap;
+}
+
 export function createListIssuesHandler() {
   return async (req: Request, res: Response): Promise<void> => {
     try {
@@ -53,17 +209,17 @@ export function createListIssuesHandler() {
         return;
       }
 
-      // Fetch open and closed issues in parallel
+      // Fetch open and closed issues in parallel (now including assignees)
       const [openResult, closedResult] = await Promise.all([
         execAsync(
-          'gh issue list --state open --json number,title,state,author,createdAt,labels,url,body --limit 100',
+          'gh issue list --state open --json number,title,state,author,createdAt,labels,url,body,assignees --limit 100',
           {
             cwd: projectPath,
             env: execEnv,
           }
         ),
         execAsync(
-          'gh issue list --state closed --json number,title,state,author,createdAt,labels,url,body --limit 50',
+          'gh issue list --state closed --json number,title,state,author,createdAt,labels,url,body,assignees --limit 50',
           {
             cwd: projectPath,
             env: execEnv,
@@ -77,6 +233,24 @@ export function createListIssuesHandler() {
       const openIssues: GitHubIssue[] = JSON.parse(openStdout || '[]');
       const closedIssues: GitHubIssue[] = JSON.parse(closedStdout || '[]');
 
+      // Fetch linked PRs for open issues (more relevant for active work)
+      if (remoteStatus.owner && remoteStatus.repo && openIssues.length > 0) {
+        const linkedPRsMap = await fetchLinkedPRs(
+          projectPath,
+          remoteStatus.owner,
+          remoteStatus.repo,
+          openIssues.map((i) => i.number)
+        );
+
+        // Attach linked PRs to issues
+        for (const issue of openIssues) {
+          const linkedPRs = linkedPRsMap.get(issue.number);
+          if (linkedPRs) {
+            issue.linkedPRs = linkedPRs;
+          }
+        }
+      }
+
       res.json({
         success: true,
         openIssues,

apps/server/src/routes/github/routes/validate-issue.ts

@@ -0,0 +1,302 @@
+/**
+ * POST /validate-issue endpoint - Validate a GitHub issue using Claude SDK (async)
+ *
+ * Scans the codebase to determine if an issue is valid, invalid, or needs clarification.
+ * Runs asynchronously and emits events for progress and completion.
+ */
+
+import type { Request, Response } from 'express';
+import { query } from '@anthropic-ai/claude-agent-sdk';
+import type { EventEmitter } from '../../../lib/events.js';
+import type { IssueValidationResult, IssueValidationEvent, AgentModel } from '@automaker/types';
+import { createSuggestionsOptions } from '../../../lib/sdk-options.js';
+import { writeValidation } from '../../../lib/validation-storage.js';
+import {
+  issueValidationSchema,
+  ISSUE_VALIDATION_SYSTEM_PROMPT,
+  buildValidationPrompt,
+} from './validation-schema.js';
+import {
+  trySetValidationRunning,
+  clearValidationStatus,
+  getErrorMessage,
+  logError,
+  logger,
+} from './validation-common.js';
+import type { SettingsService } from '../../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../../lib/settings-helpers.js';
+
+/** Valid model values for validation */
+const VALID_MODELS: readonly AgentModel[] = ['opus', 'sonnet', 'haiku'] as const;
+
+/**
+ * Request body for issue validation
+ */
+interface ValidateIssueRequestBody {
+  projectPath: string;
+  issueNumber: number;
+  issueTitle: string;
+  issueBody: string;
+  issueLabels?: string[];
+  /** Model to use for validation (opus, sonnet, haiku) */
+  model?: AgentModel;
+}
+
+/**
+ * Run the validation asynchronously
+ *
+ * Emits events for start, progress, complete, and error.
+ * Stores result on completion.
+ */
+async function runValidation(
+  projectPath: string,
+  issueNumber: number,
+  issueTitle: string,
+  issueBody: string,
+  issueLabels: string[] | undefined,
+  model: AgentModel,
+  events: EventEmitter,
+  abortController: AbortController,
+  settingsService?: SettingsService
+): Promise<void> {
+  // Emit start event
+  const startEvent: IssueValidationEvent = {
+    type: 'issue_validation_start',
+    issueNumber,
+    issueTitle,
+    projectPath,
+  };
+  events.emit('issue-validation:event', startEvent);
+
+  // Set up timeout (6 minutes)
+  const VALIDATION_TIMEOUT_MS = 360000;
+  const timeoutId = setTimeout(() => {
+    logger.warn(`Validation timeout reached after ${VALIDATION_TIMEOUT_MS}ms`);
+    abortController.abort();
+  }, VALIDATION_TIMEOUT_MS);
+
+  try {
+    // Build the prompt
+    const prompt = buildValidationPrompt(issueNumber, issueTitle, issueBody, issueLabels);
+
+    // Load autoLoadClaudeMd setting
+    const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+      projectPath,
+      settingsService,
+      '[ValidateIssue]'
+    );
+
+    // Create SDK options with structured output and abort controller
+    const options = createSuggestionsOptions({
+      cwd: projectPath,
+      model,
+      systemPrompt: ISSUE_VALIDATION_SYSTEM_PROMPT,
+      abortController,
+      autoLoadClaudeMd,
+      outputFormat: {
+        type: 'json_schema',
+        schema: issueValidationSchema as Record<string, unknown>,
+      },
+    });
+
+    // Execute the query
+    const stream = query({ prompt, options });
+    let validationResult: IssueValidationResult | null = null;
+    let responseText = '';
+
+    for await (const msg of stream) {
+      // Collect assistant text for debugging and emit progress
+      if (msg.type === 'assistant' && msg.message?.content) {
+        for (const block of msg.message.content) {
+          if (block.type === 'text') {
+            responseText += block.text;
+
+            // Emit progress event
+            const progressEvent: IssueValidationEvent = {
+              type: 'issue_validation_progress',
+              issueNumber,
+              content: block.text,
+              projectPath,
+            };
+            events.emit('issue-validation:event', progressEvent);
+          }
+        }
+      }
+
+      // Extract structured output on success
+      if (msg.type === 'result' && msg.subtype === 'success') {
+        const resultMsg = msg as { structured_output?: IssueValidationResult };
+        if (resultMsg.structured_output) {
+          validationResult = resultMsg.structured_output;
+          logger.debug('Received structured output:', validationResult);
+        }
+      }
+
+      // Handle errors
+      if (msg.type === 'result') {
+        const resultMsg = msg as { subtype?: string };
+        if (resultMsg.subtype === 'error_max_structured_output_retries') {
+          logger.error('Failed to produce valid structured output after retries');
+          throw new Error('Could not produce valid validation output');
+        }
+      }
+    }
+
+    // Clear timeout
+    clearTimeout(timeoutId);
+
+    // Require structured output
+    if (!validationResult) {
+      logger.error('No structured output received from Claude SDK');
+      logger.debug('Raw response text:', responseText);
+      throw new Error('Validation failed: no structured output received');
+    }
+
+    logger.info(`Issue #${issueNumber} validation complete: ${validationResult.verdict}`);
+
+    // Store the result
+    await writeValidation(projectPath, issueNumber, {
+      issueNumber,
+      issueTitle,
+      validatedAt: new Date().toISOString(),
+      model,
+      result: validationResult,
+    });
+
+    // Emit completion event
+    const completeEvent: IssueValidationEvent = {
+      type: 'issue_validation_complete',
+      issueNumber,
+      issueTitle,
+      result: validationResult,
+      projectPath,
+      model,
+    };
+    events.emit('issue-validation:event', completeEvent);
+  } catch (error) {
+    clearTimeout(timeoutId);
+
+    const errorMessage = getErrorMessage(error);
+    logError(error, `Issue #${issueNumber} validation failed`);
+
+    // Emit error event
+    const errorEvent: IssueValidationEvent = {
+      type: 'issue_validation_error',
+      issueNumber,
+      error: errorMessage,
+      projectPath,
+    };
+    events.emit('issue-validation:event', errorEvent);
+
+    throw error;
+  }
+}
+
+/**
+ * Creates the handler for validating GitHub issues against the codebase.
+ *
+ * Uses Claude SDK with:
+ * - Read-only tools (Read, Glob, Grep) for codebase analysis
+ * - JSON schema structured output for reliable parsing
+ * - System prompt guiding the validation process
+ * - Async execution with event emission
+ */
+export function createValidateIssueHandler(
+  events: EventEmitter,
+  settingsService?: SettingsService
+) {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const {
+        projectPath,
+        issueNumber,
+        issueTitle,
+        issueBody,
+        issueLabels,
+        model = 'opus',
+      } = req.body as ValidateIssueRequestBody;
+
+      // Validate required fields
+      if (!projectPath) {
+        res.status(400).json({ success: false, error: 'projectPath is required' });
+        return;
+      }
+
+      if (!issueNumber || typeof issueNumber !== 'number') {
+        res
+          .status(400)
+          .json({ success: false, error: 'issueNumber is required and must be a number' });
+        return;
+      }
+
+      if (!issueTitle || typeof issueTitle !== 'string') {
+        res.status(400).json({ success: false, error: 'issueTitle is required' });
+        return;
+      }
+
+      if (typeof issueBody !== 'string') {
+        res.status(400).json({ success: false, error: 'issueBody must be a string' });
+        return;
+      }
+
+      // Validate model parameter at runtime
+      if (!VALID_MODELS.includes(model)) {
+        res.status(400).json({
+          success: false,
+          error: `Invalid model. Must be one of: ${VALID_MODELS.join(', ')}`,
+        });
+        return;
+      }
+
+      logger.info(`Starting async validation for issue #${issueNumber}: ${issueTitle}`);
+
+      // Create abort controller and atomically try to claim validation slot
+      // This prevents TOCTOU race conditions
+      const abortController = new AbortController();
+      if (!trySetValidationRunning(projectPath, issueNumber, abortController)) {
+        res.json({
+          success: false,
+          error: `Validation is already running for issue #${issueNumber}`,
+        });
+        return;
+      }
+
+      // Start validation in background (fire-and-forget)
+      runValidation(
+        projectPath,
+        issueNumber,
+        issueTitle,
+        issueBody,
+        issueLabels,
+        model,
+        events,
+        abortController,
+        settingsService
+      )
+        .catch((error) => {
+          // Error is already handled inside runValidation (event emitted)
+          logger.debug('Validation error caught in background handler:', error);
+        })
+        .finally(() => {
+          clearValidationStatus(projectPath, issueNumber);
+        });
+
+      // Return immediately
+      res.json({
+        success: true,
+        message: `Validation started for issue #${issueNumber}`,
+        issueNumber,
+      });
+    } catch (error) {
+      logError(error, `Issue validation failed`);
+      logger.error('Issue validation error:', error);
+
+      if (!res.headersSent) {
+        res.status(500).json({
+          success: false,
+          error: getErrorMessage(error),
+        });
+      }
+    }
+  };
+}

apps/server/src/routes/github/routes/validation-common.ts

@@ -0,0 +1,174 @@
+/**
+ * Common utilities and state for issue validation routes
+ *
+ * Tracks running validation status per issue to support:
+ * - Checking if a validation is in progress
+ * - Cancelling a running validation
+ * - Preventing duplicate validations for the same issue
+ */
+
+import { createLogger } from '@automaker/utils';
+import { getErrorMessage as getErrorMessageShared, createLogError } from '../../common.js';
+
+const logger = createLogger('IssueValidation');
+
+/**
+ * Status of a validation in progress
+ */
+interface ValidationStatus {
+  isRunning: boolean;
+  abortController: AbortController;
+  startedAt: Date;
+}
+
+/**
+ * Map of issue number to validation status
+ * Key format: `${projectPath}||${issueNumber}` to support multiple projects
+ * Note: Using `||` as delimiter since `:` appears in Windows paths (e.g., C:\)
+ */
+const validationStatusMap = new Map<string, ValidationStatus>();
+
+/** Maximum age for stale validation entries before cleanup (1 hour) */
+const MAX_VALIDATION_AGE_MS = 60 * 60 * 1000;
+
+/**
+ * Create a unique key for a validation
+ * Uses `||` as delimiter since `:` appears in Windows paths
+ */
+function getValidationKey(projectPath: string, issueNumber: number): string {
+  return `${projectPath}||${issueNumber}`;
+}
+
+/**
+ * Check if a validation is currently running for an issue
+ */
+export function isValidationRunning(projectPath: string, issueNumber: number): boolean {
+  const key = getValidationKey(projectPath, issueNumber);
+  const status = validationStatusMap.get(key);
+  return status?.isRunning ?? false;
+}
+
+/**
+ * Get validation status for an issue
+ */
+export function getValidationStatus(
+  projectPath: string,
+  issueNumber: number
+): { isRunning: boolean; startedAt?: Date } | null {
+  const key = getValidationKey(projectPath, issueNumber);
+  const status = validationStatusMap.get(key);
+  if (!status) {
+    return null;
+  }
+  return {
+    isRunning: status.isRunning,
+    startedAt: status.startedAt,
+  };
+}
+
+/**
+ * Get all running validations for a project
+ */
+export function getRunningValidations(projectPath: string): number[] {
+  const runningIssues: number[] = [];
+  const prefix = `${projectPath}||`;
+  for (const [key, status] of validationStatusMap.entries()) {
+    if (status.isRunning && key.startsWith(prefix)) {
+      const issueNumber = parseInt(key.slice(prefix.length), 10);
+      if (!isNaN(issueNumber)) {
+        runningIssues.push(issueNumber);
+      }
+    }
+  }
+  return runningIssues;
+}
+
+/**
+ * Set a validation as running
+ */
+export function setValidationRunning(
+  projectPath: string,
+  issueNumber: number,
+  abortController: AbortController
+): void {
+  const key = getValidationKey(projectPath, issueNumber);
+  validationStatusMap.set(key, {
+    isRunning: true,
+    abortController,
+    startedAt: new Date(),
+  });
+}
+
+/**
+ * Atomically try to set a validation as running (check-and-set)
+ * Prevents TOCTOU race conditions when starting validations
+ *
+ * @returns true if successfully claimed, false if already running
+ */
+export function trySetValidationRunning(
+  projectPath: string,
+  issueNumber: number,
+  abortController: AbortController
+): boolean {
+  const key = getValidationKey(projectPath, issueNumber);
+  if (validationStatusMap.has(key)) {
+    return false; // Already running
+  }
+  validationStatusMap.set(key, {
+    isRunning: true,
+    abortController,
+    startedAt: new Date(),
+  });
+  return true; // Successfully claimed
+}
+
+/**
+ * Cleanup stale validation entries (e.g., from crashed validations)
+ * Should be called periodically to prevent memory leaks
+ */
+export function cleanupStaleValidations(): number {
+  const now = Date.now();
+  let cleanedCount = 0;
+  for (const [key, status] of validationStatusMap.entries()) {
+    if (now - status.startedAt.getTime() > MAX_VALIDATION_AGE_MS) {
+      status.abortController.abort();
+      validationStatusMap.delete(key);
+      cleanedCount++;
+    }
+  }
+  if (cleanedCount > 0) {
+    logger.info(`Cleaned up ${cleanedCount} stale validation entries`);
+  }
+  return cleanedCount;
+}
+
+/**
+ * Clear validation status (call when validation completes or errors)
+ */
+export function clearValidationStatus(projectPath: string, issueNumber: number): void {
+  const key = getValidationKey(projectPath, issueNumber);
+  validationStatusMap.delete(key);
+}
+
+/**
+ * Abort a running validation
+ *
+ * @returns true if validation was aborted, false if not running
+ */
+export function abortValidation(projectPath: string, issueNumber: number): boolean {
+  const key = getValidationKey(projectPath, issueNumber);
+  const status = validationStatusMap.get(key);
+
+  if (!status || !status.isRunning) {
+    return false;
+  }
+
+  status.abortController.abort();
+  validationStatusMap.delete(key);
+  return true;
+}
+
+// Re-export shared utilities
+export { getErrorMessageShared as getErrorMessage };
+export const logError = createLogError(logger);
+export { logger };

apps/server/src/routes/github/routes/validation-endpoints.ts

@@ -0,0 +1,236 @@
+/**
+ * Additional validation endpoints for status, stop, and retrieving stored validations
+ */
+
+import type { Request, Response } from 'express';
+import type { EventEmitter } from '../../../lib/events.js';
+import type { IssueValidationEvent } from '@automaker/types';
+import {
+  isValidationRunning,
+  getValidationStatus,
+  getRunningValidations,
+  abortValidation,
+  getErrorMessage,
+  logError,
+  logger,
+} from './validation-common.js';
+import {
+  readValidation,
+  getAllValidations,
+  getValidationWithFreshness,
+  deleteValidation,
+  markValidationViewed,
+} from '../../../lib/validation-storage.js';
+
+/**
+ * POST /validation-status - Check if validation is running for an issue
+ */
+export function createValidationStatusHandler() {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { projectPath, issueNumber } = req.body as {
+        projectPath: string;
+        issueNumber?: number;
+      };
+
+      if (!projectPath) {
+        res.status(400).json({ success: false, error: 'projectPath is required' });
+        return;
+      }
+
+      // If issueNumber provided, check specific issue
+      if (issueNumber !== undefined) {
+        const status = getValidationStatus(projectPath, issueNumber);
+        res.json({
+          success: true,
+          isRunning: status?.isRunning ?? false,
+          startedAt: status?.startedAt?.toISOString(),
+        });
+        return;
+      }
+
+      // Otherwise, return all running validations for the project
+      const runningIssues = getRunningValidations(projectPath);
+      res.json({
+        success: true,
+        runningIssues,
+      });
+    } catch (error) {
+      logError(error, 'Validation status check failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}
+
+/**
+ * POST /validation-stop - Cancel a running validation
+ */
+export function createValidationStopHandler() {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { projectPath, issueNumber } = req.body as {
+        projectPath: string;
+        issueNumber: number;
+      };
+
+      if (!projectPath) {
+        res.status(400).json({ success: false, error: 'projectPath is required' });
+        return;
+      }
+
+      if (!issueNumber || typeof issueNumber !== 'number') {
+        res
+          .status(400)
+          .json({ success: false, error: 'issueNumber is required and must be a number' });
+        return;
+      }
+
+      const wasAborted = abortValidation(projectPath, issueNumber);
+
+      if (wasAborted) {
+        logger.info(`Validation for issue #${issueNumber} was stopped`);
+        res.json({
+          success: true,
+          message: `Validation for issue #${issueNumber} has been stopped`,
+        });
+      } else {
+        res.json({
+          success: false,
+          error: `No validation is running for issue #${issueNumber}`,
+        });
+      }
+    } catch (error) {
+      logError(error, 'Validation stop failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}
+
+/**
+ * POST /validations - Get stored validations for a project
+ */
+export function createGetValidationsHandler() {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { projectPath, issueNumber } = req.body as {
+        projectPath: string;
+        issueNumber?: number;
+      };
+
+      if (!projectPath) {
+        res.status(400).json({ success: false, error: 'projectPath is required' });
+        return;
+      }
+
+      // If issueNumber provided, get specific validation with freshness info
+      if (issueNumber !== undefined) {
+        const result = await getValidationWithFreshness(projectPath, issueNumber);
+
+        if (!result) {
+          res.json({
+            success: true,
+            validation: null,
+          });
+          return;
+        }
+
+        res.json({
+          success: true,
+          validation: result.validation,
+          isStale: result.isStale,
+        });
+        return;
+      }
+
+      // Otherwise, get all validations for the project
+      const validations = await getAllValidations(projectPath);
+
+      res.json({
+        success: true,
+        validations,
+      });
+    } catch (error) {
+      logError(error, 'Get validations failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}
+
+/**
+ * POST /validation-delete - Delete a stored validation
+ */
+export function createDeleteValidationHandler() {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { projectPath, issueNumber } = req.body as {
+        projectPath: string;
+        issueNumber: number;
+      };
+
+      if (!projectPath) {
+        res.status(400).json({ success: false, error: 'projectPath is required' });
+        return;
+      }
+
+      if (!issueNumber || typeof issueNumber !== 'number') {
+        res
+          .status(400)
+          .json({ success: false, error: 'issueNumber is required and must be a number' });
+        return;
+      }
+
+      const deleted = await deleteValidation(projectPath, issueNumber);
+
+      res.json({
+        success: true,
+        deleted,
+      });
+    } catch (error) {
+      logError(error, 'Delete validation failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}
+
+/**
+ * POST /validation-mark-viewed - Mark a validation as viewed by the user
+ */
+export function createMarkViewedHandler(events: EventEmitter) {
+  return async (req: Request, res: Response): Promise<void> => {
+    try {
+      const { projectPath, issueNumber } = req.body as {
+        projectPath: string;
+        issueNumber: number;
+      };
+
+      if (!projectPath) {
+        res.status(400).json({ success: false, error: 'projectPath is required' });
+        return;
+      }
+
+      if (!issueNumber || typeof issueNumber !== 'number') {
+        res
+          .status(400)
+          .json({ success: false, error: 'issueNumber is required and must be a number' });
+        return;
+      }
+
+      const success = await markValidationViewed(projectPath, issueNumber);
+
+      if (success) {
+        // Emit event so UI can update the unviewed count
+        const viewedEvent: IssueValidationEvent = {
+          type: 'issue_validation_viewed',
+          issueNumber,
+          projectPath,
+        };
+        events.emit('issue-validation:event', viewedEvent);
+      }
+
+      res.json({ success });
+    } catch (error) {
+      logError(error, 'Mark validation viewed failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/github/routes/validation-schema.ts

@@ -0,0 +1,138 @@
+/**
+ * Issue Validation Schema and System Prompt
+ *
+ * Defines the JSON schema for Claude's structured output and
+ * the system prompt that guides the validation process.
+ */
+
+/**
+ * JSON Schema for issue validation structured output.
+ * Used with Claude SDK's outputFormat option to ensure reliable parsing.
+ */
+export const issueValidationSchema = {
+  type: 'object',
+  properties: {
+    verdict: {
+      type: 'string',
+      enum: ['valid', 'invalid', 'needs_clarification'],
+      description: 'The validation verdict for the issue',
+    },
+    confidence: {
+      type: 'string',
+      enum: ['high', 'medium', 'low'],
+      description: 'How confident the AI is in its assessment',
+    },
+    reasoning: {
+      type: 'string',
+      description: 'Detailed explanation of the verdict',
+    },
+    bugConfirmed: {
+      type: 'boolean',
+      description: 'For bug reports: whether the bug was confirmed in the codebase',
+    },
+    relatedFiles: {
+      type: 'array',
+      items: { type: 'string' },
+      description: 'Files related to the issue found during analysis',
+    },
+    suggestedFix: {
+      type: 'string',
+      description: 'Suggested approach to fix or implement the issue',
+    },
+    missingInfo: {
+      type: 'array',
+      items: { type: 'string' },
+      description: 'Information needed when verdict is needs_clarification',
+    },
+    estimatedComplexity: {
+      type: 'string',
+      enum: ['trivial', 'simple', 'moderate', 'complex', 'very_complex'],
+      description: 'Estimated effort to address the issue',
+    },
+  },
+  required: ['verdict', 'confidence', 'reasoning'],
+  additionalProperties: false,
+} as const;
+
+/**
+ * System prompt that guides Claude in validating GitHub issues.
+ * Instructs the model to use read-only tools to analyze the codebase.
+ */
+export const ISSUE_VALIDATION_SYSTEM_PROMPT = `You are an expert code analyst validating GitHub issues against a codebase.
+
+Your task is to analyze a GitHub issue and determine if it's valid by scanning the codebase.
+
+## Validation Process
+
+1. **Read the issue carefully** - Understand what is being reported or requested
+2. **Search the codebase** - Use Glob to find relevant files by pattern, Grep to search for keywords
+3. **Examine the code** - Use Read to look at the actual implementation in relevant files
+4. **Form your verdict** - Based on your analysis, determine if the issue is valid
+
+## Verdicts
+
+- **valid**: The issue describes a real problem that exists in the codebase, or a clear feature request that can be implemented. The referenced files/components exist and the issue is actionable.
+
+- **invalid**: The issue describes behavior that doesn't exist, references non-existent files or components, is based on a misunderstanding of the code, or the described "bug" is actually expected behavior.
+
+- **needs_clarification**: The issue lacks sufficient detail to verify. Specify what additional information is needed in the missingInfo field.
+
+## For Bug Reports, Check:
+- Do the referenced files/components exist?
+- Does the code match what the issue describes?
+- Is the described behavior actually a bug or expected?
+- Can you locate the code that would cause the reported issue?
+
+## For Feature Requests, Check:
+- Does the feature already exist?
+- Is the implementation location clear?
+- Is the request technically feasible given the codebase structure?
+
+## Response Guidelines
+
+- **Always include relatedFiles** when you find relevant code
+- **Set bugConfirmed to true** only if you can definitively confirm a bug exists in the code
+- **Provide a suggestedFix** when you have a clear idea of how to address the issue
+- **Use missingInfo** when the verdict is needs_clarification to list what's needed
+- **Set estimatedComplexity** to help prioritize:
+  - trivial: Simple text changes, one-line fixes
+  - simple: Small changes to one file
+  - moderate: Changes to multiple files or moderate logic changes
+  - complex: Significant refactoring or new feature implementation
+  - very_complex: Major architectural changes or cross-cutting concerns
+
+Be thorough in your analysis but focus on files that are directly relevant to the issue.`;
+
+/**
+ * Build the user prompt for issue validation.
+ *
+ * Creates a structured prompt that includes the issue details for Claude
+ * to analyze against the codebase.
+ *
+ * @param issueNumber - The GitHub issue number
+ * @param issueTitle - The issue title
+ * @param issueBody - The issue body/description
+ * @param issueLabels - Optional array of label names
+ * @returns Formatted prompt string for the validation request
+ */
+export function buildValidationPrompt(
+  issueNumber: number,
+  issueTitle: string,
+  issueBody: string,
+  issueLabels?: string[]
+): string {
+  const labelsSection = issueLabels?.length ? `\n\n**Labels:** ${issueLabels.join(', ')}` : '';
+
+  return `Please validate the following GitHub issue by analyzing the codebase:
+
+## Issue #${issueNumber}: ${issueTitle}
+${labelsSection}
+
+### Description
+
+${issueBody || '(No description provided)'}
+
+---
+
+Scan the codebase to verify this issue. Look for the files, components, or functionality mentioned. Determine if this issue is valid, invalid, or needs clarification.`;
+}

apps/server/src/routes/suggestions/generate-suggestions.ts

@@ -6,9 +6,94 @@ import { query } from '@anthropic-ai/claude-agent-sdk';
 import type { EventEmitter } from '../../lib/events.js';
 import { createLogger } from '@automaker/utils';
 import { createSuggestionsOptions } from '../../lib/sdk-options.js';
+import { FeatureLoader } from '../../services/feature-loader.js';
+import { getAppSpecPath } from '@automaker/platform';
+import * as secureFs from '../../lib/secure-fs.js';
+import type { SettingsService } from '../../services/settings-service.js';
+import { getAutoLoadClaudeMdSetting } from '../../lib/settings-helpers.js';
 
 const logger = createLogger('Suggestions');
 
+/**
+ * Extract implemented features from app_spec.txt XML content
+ *
+ * Note: This uses regex-based parsing which is sufficient for our controlled
+ * XML structure. If more complex XML parsing is needed in the future, consider
+ * using a library like 'fast-xml-parser' or 'xml2js'.
+ */
+function extractImplementedFeatures(specContent: string): string[] {
+  const features: string[] = [];
+
+  // Match <implemented_features>...</implemented_features> section
+  const implementedMatch = specContent.match(
+    /<implemented_features>([\s\S]*?)<\/implemented_features>/
+  );
+
+  if (implementedMatch) {
+    const implementedSection = implementedMatch[1];
+
+    // Extract feature names from <name>...</name> tags using matchAll
+    const nameRegex = /<name>(.*?)<\/name>/g;
+    const matches = implementedSection.matchAll(nameRegex);
+
+    for (const match of matches) {
+      features.push(match[1].trim());
+    }
+  }
+
+  return features;
+}
+
+/**
+ * Load existing context (app spec and backlog features) to avoid duplicates
+ */
+async function loadExistingContext(projectPath: string): Promise<string> {
+  let context = '';
+
+  // 1. Read app_spec.txt for implemented features
+  try {
+    const appSpecPath = getAppSpecPath(projectPath);
+    const specContent = (await secureFs.readFile(appSpecPath, 'utf-8')) as string;
+
+    if (specContent && specContent.trim().length > 0) {
+      const implementedFeatures = extractImplementedFeatures(specContent);
+
+      if (implementedFeatures.length > 0) {
+        context += '\n\n=== ALREADY IMPLEMENTED FEATURES ===\n';
+        context += 'These features are already implemented in the codebase:\n';
+        context += implementedFeatures.map((feature) => `- ${feature}`).join('\n') + '\n';
+      }
+    }
+  } catch (error) {
+    // app_spec.txt doesn't exist or can't be read - that's okay
+    logger.debug('No app_spec.txt found or error reading it:', error);
+  }
+
+  // 2. Load existing features from backlog
+  try {
+    const featureLoader = new FeatureLoader();
+    const features = await featureLoader.getAll(projectPath);
+
+    if (features.length > 0) {
+      context += '\n\n=== EXISTING FEATURES IN BACKLOG ===\n';
+      context += 'These features are already planned or in progress:\n';
+      context +=
+        features
+          .map((feature) => {
+            const status = feature.status || 'pending';
+            const title = feature.title || feature.description?.substring(0, 50) || 'Untitled';
+            return `- ${title} (${status})`;
+          })
+          .join('\n') + '\n';
+    }
+  } catch (error) {
+    // Features directory doesn't exist or can't be read - that's okay
+    logger.debug('No features found or error loading them:', error);
+  }
+
+  return context;
+}
+
 /**
  * JSON Schema for suggestions output
  */
@@ -42,7 +127,8 @@ export async function generateSuggestions(
   projectPath: string,
   suggestionType: string,
   events: EventEmitter,
-  abortController: AbortController
+  abortController: AbortController,
+  settingsService?: SettingsService
 ): Promise<void> {
   const typePrompts: Record<string, string> = {
     features: 'Analyze this project and suggest new features that would add value.',
@@ -51,8 +137,13 @@ export async function generateSuggestions(
     performance: 'Analyze this project for performance issues and suggest optimizations.',
   };
 
-  const prompt = `${typePrompts[suggestionType] || typePrompts.features}
+  // Load existing context to avoid duplicates
+  const existingContext = await loadExistingContext(projectPath);
 
+  const prompt = `${typePrompts[suggestionType] || typePrompts.features}
+${existingContext}
+
+${existingContext ? '\nIMPORTANT: Do NOT suggest features that are already implemented or already in the backlog above. Focus on NEW ideas that complement what already exists.\n' : ''}
 Look at the codebase and provide 3-5 concrete suggestions.
 
 For each suggestion, provide:
@@ -63,14 +154,20 @@ For each suggestion, provide:
 
 The response will be automatically formatted as structured JSON.`;
 
-  events.emit('suggestions:event', {
-    type: 'suggestions_progress',
-    content: `Starting ${suggestionType} analysis...\n`,
-  });
+  // Don't send initial message - let the agent output speak for itself
+  // The first agent message will be captured as an info entry
+
+  // Load autoLoadClaudeMd setting
+  const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+    projectPath,
+    settingsService,
+    '[Suggestions]'
+  );
 
   const options = createSuggestionsOptions({
     cwd: projectPath,
     abortController,
+    autoLoadClaudeMd,
     outputFormat: {
       type: 'json_schema',
       schema: suggestionsSchema,

apps/server/src/routes/suggestions/index.ts

@@ -8,11 +8,19 @@ import { validatePathParams } from '../../middleware/validate-paths.js';
 import { createGenerateHandler } from './routes/generate.js';
 import { createStopHandler } from './routes/stop.js';
 import { createStatusHandler } from './routes/status.js';
+import type { SettingsService } from '../../services/settings-service.js';
 
-export function createSuggestionsRoutes(events: EventEmitter): Router {
+export function createSuggestionsRoutes(
+  events: EventEmitter,
+  settingsService?: SettingsService
+): Router {
   const router = Router();
 
-  router.post('/generate', validatePathParams('projectPath'), createGenerateHandler(events));
+  router.post(
+    '/generate',
+    validatePathParams('projectPath'),
+    createGenerateHandler(events, settingsService)
+  );
   router.post('/stop', createStopHandler());
   router.get('/status', createStatusHandler());
 

apps/server/src/routes/suggestions/routes/generate.ts

@@ -7,10 +7,11 @@ import type { EventEmitter } from '../../../lib/events.js';
 import { createLogger } from '@automaker/utils';
 import { getSuggestionsStatus, setRunningState, getErrorMessage, logError } from '../common.js';
 import { generateSuggestions } from '../generate-suggestions.js';
+import type { SettingsService } from '../../../services/settings-service.js';
 
 const logger = createLogger('Suggestions');
 
-export function createGenerateHandler(events: EventEmitter) {
+export function createGenerateHandler(events: EventEmitter, settingsService?: SettingsService) {
   return async (req: Request, res: Response): Promise<void> => {
     try {
       const { projectPath, suggestionType = 'features' } = req.body as {
@@ -37,7 +38,7 @@ export function createGenerateHandler(events: EventEmitter) {
       setRunningState(true, abortController);
 
       // Start generation in background
-      generateSuggestions(projectPath, suggestionType, events, abortController)
+      generateSuggestions(projectPath, suggestionType, events, abortController, settingsService)
         .catch((error) => {
           logError(error, 'Generate suggestions failed (background)');
           events.emit('suggestions:event', {

apps/server/src/routes/updates/common.ts

@@ -0,0 +1,162 @@
+/**
+ * Common utilities for update routes
+ */
+
+import { createLogger } from '@automaker/utils';
+import { exec } from 'child_process';
+import { promisify } from 'util';
+import path from 'path';
+import { fileURLToPath } from 'url';
+import { getErrorMessage as getErrorMessageShared, createLogError } from '../common.js';
+
+const logger = createLogger('Updates');
+export const execAsync = promisify(exec);
+
+// Re-export shared utilities
+export { getErrorMessageShared as getErrorMessage };
+export const logError = createLogError(logger);
+
+// ============================================================================
+// Extended PATH configuration for Electron apps
+// ============================================================================
+
+const pathSeparator = process.platform === 'win32' ? ';' : ':';
+const additionalPaths: string[] = [];
+
+if (process.platform === 'win32') {
+  // Windows paths
+  if (process.env.LOCALAPPDATA) {
+    additionalPaths.push(`${process.env.LOCALAPPDATA}\\Programs\\Git\\cmd`);
+  }
+  if (process.env.PROGRAMFILES) {
+    additionalPaths.push(`${process.env.PROGRAMFILES}\\Git\\cmd`);
+  }
+  if (process.env['ProgramFiles(x86)']) {
+    additionalPaths.push(`${process.env['ProgramFiles(x86)']}\\Git\\cmd`);
+  }
+} else {
+  // Unix/Mac paths
+  additionalPaths.push(
+    '/opt/homebrew/bin', // Homebrew on Apple Silicon
+    '/usr/local/bin', // Homebrew on Intel Mac, common Linux location
+    '/home/linuxbrew/.linuxbrew/bin' // Linuxbrew
+  );
+  // pipx, other user installs - only add if HOME is defined
+  if (process.env.HOME) {
+    additionalPaths.push(`${process.env.HOME}/.local/bin`);
+  }
+}
+
+const extendedPath = [process.env.PATH, ...additionalPaths.filter(Boolean)]
+  .filter(Boolean)
+  .join(pathSeparator);
+
+/**
+ * Environment variables with extended PATH for executing shell commands.
+ */
+export const execEnv = {
+  ...process.env,
+  PATH: extendedPath,
+};
+
+// ============================================================================
+// Automaker installation path
+// ============================================================================
+
+/**
+ * Locate the Automaker monorepo root directory.
+ *
+ * @returns Absolute path to the monorepo root directory (the directory containing the top-level `package.json`)
+ */
+export function getAutomakerRoot(): string {
+  // In ESM, we use import.meta.url to get the current file path
+  // This file is at: apps/server/src/routes/updates/common.ts
+  // So we need to go up 5 levels to get to the monorepo root
+  const __filename = fileURLToPath(import.meta.url);
+  const __dirname = path.dirname(__filename);
+
+  // Go up from: updates -> routes -> src -> server -> apps -> root
+  return path.resolve(__dirname, '..', '..', '..', '..', '..');
+}
+
+/**
+ * Determines whether Git is available on the system.
+ *
+ * @returns `true` if the `git` command is executable in the current environment, `false` otherwise.
+ */
+export async function isGitAvailable(): Promise<boolean> {
+  try {
+    await execAsync('git --version', { env: execEnv });
+    return true;
+  } catch {
+    return false;
+  }
+}
+
+/**
+ * Determine whether the given filesystem path is a Git repository.
+ *
+ * @param repoPath - Filesystem path to check
+ * @returns `true` if the path is inside a Git working tree, `false` otherwise.
+ */
+export async function isGitRepo(repoPath: string): Promise<boolean> {
+  try {
+    await execAsync('git rev-parse --is-inside-work-tree', { cwd: repoPath, env: execEnv });
+    return true;
+  } catch {
+    return false;
+  }
+}
+
+/**
+ * Retrieves the full commit hash pointed to by HEAD in the given repository.
+ *
+ * @param repoPath - Filesystem path of the Git repository to query
+ * @returns The full commit hash for HEAD as a trimmed string
+ */
+export async function getCurrentCommit(repoPath: string): Promise<string> {
+  const { stdout } = await execAsync('git rev-parse HEAD', { cwd: repoPath, env: execEnv });
+  return stdout.trim();
+}
+
+/**
+ * Retrieve the short commit hash of HEAD for the repository at the given path.
+ *
+ * @param repoPath - Filesystem path to the git repository
+ * @returns The short commit hash for `HEAD`
+ */
+export async function getShortCommit(repoPath: string): Promise<string> {
+  const { stdout } = await execAsync('git rev-parse --short HEAD', { cwd: repoPath, env: execEnv });
+  return stdout.trim();
+}
+
+/**
+ * Determine whether the repository contains uncommitted local changes.
+ *
+ * @param repoPath - Filesystem path to the Git repository to check
+ * @returns `true` if the repository has any uncommitted changes, `false` otherwise
+ */
+export async function hasLocalChanges(repoPath: string): Promise<boolean> {
+  const { stdout } = await execAsync('git status --porcelain', { cwd: repoPath, env: execEnv });
+  return stdout.trim().length > 0;
+}
+
+/**
+ * Determine whether a string is a well-formed git remote URL and contains no shell metacharacters.
+ *
+ * @param url - The URL to validate
+ * @returns `true` if `url` starts with a common git protocol (`https://`, `git@`, `git://`, `ssh://`) and does not contain shell metacharacters, `false` otherwise.
+ */
+export function isValidGitUrl(url: string): boolean {
+  // Allow HTTPS, SSH, and git protocols
+  const startsWithValidProtocol =
+    url.startsWith('https://') ||
+    url.startsWith('git@') ||
+    url.startsWith('git://') ||
+    url.startsWith('ssh://');
+
+  // Block shell metacharacters to prevent command injection
+  const hasShellChars = /[;`|&<>()$!\\[\] ]/.test(url);
+
+  return startsWithValidProtocol && !hasShellChars;
+}

apps/server/src/routes/updates/index.ts

@@ -0,0 +1,37 @@
+/**
+ * Update routes - HTTP API for checking and applying updates
+ *
+ * Provides endpoints for:
+ * - Checking if updates are available from upstream
+ * - Pulling updates from upstream
+ * - Getting current installation info
+ */
+
+import { Router } from 'express';
+import type { SettingsService } from '../../services/settings-service.js';
+import { createCheckHandler } from './routes/check.js';
+import { createPullHandler } from './routes/pull.js';
+import { createInfoHandler } from './routes/info.js';
+
+/**
+ * Create an Express Router that exposes API endpoints for update operations.
+ *
+ * @returns An Express Router with the routes:
+ * - GET `/check` — checks for available updates
+ * - POST `/pull` — pulls updates from upstream
+ * - GET `/info` — returns current installation info
+ */
+export function createUpdatesRoutes(settingsService: SettingsService): Router {
+  const router = Router();
+
+  // GET /api/updates/check - Check if updates are available
+  router.get('/check', createCheckHandler(settingsService));
+
+  // POST /api/updates/pull - Pull updates from upstream
+  router.post('/pull', createPullHandler(settingsService));
+
+  // GET /api/updates/info - Get current installation info
+  router.get('/info', createInfoHandler(settingsService));
+
+  return router;
+}

apps/server/src/routes/updates/routes/check.ts

@@ -0,0 +1,177 @@
+/**
+ * GET /check endpoint - Check if updates are available
+ *
+ * Compares local version with the remote upstream version.
+ */
+
+import type { Request, Response } from 'express';
+import type { SettingsService } from '../../../services/settings-service.js';
+import type { UpdateCheckResult } from '@automaker/types';
+import crypto from 'crypto';
+import {
+  execAsync,
+  execEnv,
+  getAutomakerRoot,
+  getCurrentCommit,
+  getShortCommit,
+  isGitRepo,
+  isGitAvailable,
+  isValidGitUrl,
+  getErrorMessage,
+  logError,
+} from '../common.js';
+
+/**
+ * Create an Express handler for the update check endpoint that compares the local Git commit
+ * against a configured upstream to determine whether an update is available.
+ *
+ * The handler validates Git availability and repository state, reads the upstream URL from
+ * global settings (with a default), attempts to fetch the upstream main branch using a
+ * temporary remote, and returns a structured result describing local and remote commits and
+ * whether the remote is ahead.
+ *
+ * @param settingsService - Service used to read global settings (used to obtain `autoUpdate.upstreamUrl`)
+ * @returns An Express request handler that responds with JSON. On success the response is
+ *   `{ success: true, result }` where `result` is an `UpdateCheckResult`. On error the response
+ *   is `{ success: false, error }`. If fetching the upstream fails the handler still responds
+ *   with `{ success: true, result }` where `result` indicates no update and includes an `error` message.
+ */
+export function createCheckHandler(settingsService: SettingsService) {
+  return async (_req: Request, res: Response): Promise<void> => {
+    try {
+      const installPath = getAutomakerRoot();
+
+      // Check if git is available
+      if (!(await isGitAvailable())) {
+        res.status(500).json({
+          success: false,
+          error: 'Git is not installed or not available in PATH',
+        });
+        return;
+      }
+
+      // Check if automaker directory is a git repo
+      if (!(await isGitRepo(installPath))) {
+        res.status(500).json({
+          success: false,
+          error: 'Automaker installation is not a git repository',
+        });
+        return;
+      }
+
+      // Get settings for upstream URL
+      const settings = await settingsService.getGlobalSettings();
+      const sourceUrl =
+        settings.autoUpdate?.upstreamUrl || 'https://github.com/AutoMaker-Org/automaker.git';
+
+      // Validate URL to prevent command injection
+      if (!isValidGitUrl(sourceUrl)) {
+        res.status(400).json({
+          success: false,
+          error: 'Invalid upstream URL format',
+        });
+        return;
+      }
+
+      // Get local version
+      const localVersion = await getCurrentCommit(installPath);
+      const localVersionShort = await getShortCommit(installPath);
+
+      // Use a random remote name to avoid conflicts with concurrent checks
+      const tempRemoteName = `automaker-update-check-${crypto.randomBytes(8).toString('hex')}`;
+
+      try {
+        // Add temporary remote
+        await execAsync(`git remote add ${tempRemoteName} "${sourceUrl}"`, {
+          cwd: installPath,
+          env: execEnv,
+        });
+
+        // Fetch from the temporary remote
+        await execAsync(`git fetch ${tempRemoteName} main`, {
+          cwd: installPath,
+          env: execEnv,
+        });
+
+        // Get remote version
+        const { stdout: remoteVersionOutput } = await execAsync(
+          `git rev-parse ${tempRemoteName}/main`,
+          { cwd: installPath, env: execEnv }
+        );
+        const remoteVersion = remoteVersionOutput.trim();
+
+        // Get short remote version
+        const { stdout: remoteVersionShortOutput } = await execAsync(
+          `git rev-parse --short ${tempRemoteName}/main`,
+          { cwd: installPath, env: execEnv }
+        );
+        const remoteVersionShort = remoteVersionShortOutput.trim();
+
+        // Check if remote is ahead of local (update available)
+        // git merge-base --is-ancestor <commit1> <commit2> returns 0 if commit1 is ancestor of commit2
+        let updateAvailable = false;
+        if (localVersion !== remoteVersion) {
+          try {
+            // Check if local is already an ancestor of remote (remote is ahead)
+            await execAsync(`git merge-base --is-ancestor ${localVersion} ${remoteVersion}`, {
+              cwd: installPath,
+              env: execEnv,
+            });
+            // If we get here (exit code 0), local is ancestor of remote, so update is available
+            updateAvailable = true;
+          } catch {
+            // Exit code 1 means local is NOT an ancestor of remote
+            // This means either local is ahead, or branches have diverged
+            // In either case, we don't show "update available"
+            updateAvailable = false;
+          }
+        }
+
+        const result: UpdateCheckResult = {
+          updateAvailable,
+          localVersion,
+          localVersionShort,
+          remoteVersion,
+          remoteVersionShort,
+          sourceUrl,
+          installPath,
+        };
+
+        res.json({
+          success: true,
+          result,
+        });
+      } catch (fetchError) {
+        const errorMsg = getErrorMessage(fetchError);
+        logError(fetchError, 'Failed to fetch from upstream');
+
+        res.json({
+          success: true,
+          result: {
+            updateAvailable: false,
+            localVersion,
+            localVersionShort,
+            remoteVersion: null,
+            remoteVersionShort: null,
+            sourceUrl,
+            installPath,
+            error: `Could not fetch from upstream: ${errorMsg}`,
+          } satisfies UpdateCheckResult,
+        });
+      } finally {
+        // Always clean up temp remote
+        try {
+          await execAsync(`git remote remove ${tempRemoteName}`, {
+            cwd: installPath,
+            env: execEnv,
+          });
+        } catch {
+          // Ignore cleanup errors
+        }
+      }
+    } catch (error) {
+      logError(error, 'Update check failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/updates/routes/info.ts

@@ -0,0 +1,136 @@
+/**
+ * GET /info endpoint - Get current installation info
+ *
+ * Returns current version, branch, and configuration info.
+ */
+
+import type { Request, Response } from 'express';
+import type { SettingsService } from '../../../services/settings-service.js';
+import { DEFAULT_AUTO_UPDATE_SETTINGS, type UpdateInfo } from '@automaker/types';
+import {
+  execAsync,
+  execEnv,
+  getAutomakerRoot,
+  getCurrentCommit,
+  getShortCommit,
+  isGitRepo,
+  isGitAvailable,
+  hasLocalChanges,
+  getErrorMessage,
+  logError,
+} from '../common.js';
+
+/**
+ * Creates an Express handler that returns update information for the application installation.
+ *
+ * The produced handler responds with a JSON payload containing an UpdateInfo result describing
+ * installation path, git-based version and branch data (when available), local change status,
+ * and configured auto-update settings. On failure the handler responds with HTTP 500 and a JSON
+ * error message.
+ *
+ * @returns An Express request handler that sends `{ success: true, result: UpdateInfo }` on success
+ *          or `{ success: false, error: string }` with HTTP 500 on error.
+ */
+export function createInfoHandler(settingsService: SettingsService) {
+  return async (_req: Request, res: Response): Promise<void> => {
+    try {
+      const installPath = getAutomakerRoot();
+
+      // Get settings
+      const settings = await settingsService.getGlobalSettings();
+      const autoUpdateSettings = settings.autoUpdate || DEFAULT_AUTO_UPDATE_SETTINGS;
+
+      // Check if git is available
+      const gitAvailable = await isGitAvailable();
+
+      if (!gitAvailable) {
+        const result: UpdateInfo = {
+          installPath,
+          currentVersion: null,
+          currentVersionShort: null,
+          currentBranch: null,
+          hasLocalChanges: false,
+          sourceUrl: autoUpdateSettings.upstreamUrl,
+          autoUpdateEnabled: autoUpdateSettings.enabled,
+          checkIntervalMinutes: autoUpdateSettings.checkIntervalMinutes,
+          updateType: 'git',
+          mechanismInfo: {
+            isGitRepo: false,
+            gitAvailable: false,
+          },
+        };
+
+        res.json({
+          success: true,
+          result,
+        });
+        return;
+      }
+
+      // Check if it's a git repo
+      const isRepo = await isGitRepo(installPath);
+
+      if (!isRepo) {
+        const result: UpdateInfo = {
+          installPath,
+          currentVersion: null,
+          currentVersionShort: null,
+          currentBranch: null,
+          hasLocalChanges: false,
+          sourceUrl: autoUpdateSettings.upstreamUrl,
+          autoUpdateEnabled: autoUpdateSettings.enabled,
+          checkIntervalMinutes: autoUpdateSettings.checkIntervalMinutes,
+          updateType: 'git',
+          mechanismInfo: {
+            isGitRepo: false,
+            gitAvailable: true,
+          },
+        };
+
+        res.json({
+          success: true,
+          result,
+        });
+        return;
+      }
+
+      // Get git info
+      const currentVersion = await getCurrentCommit(installPath);
+      const currentVersionShort = await getShortCommit(installPath);
+
+      // Get current branch
+      const { stdout: branchOutput } = await execAsync('git rev-parse --abbrev-ref HEAD', {
+        cwd: installPath,
+        env: execEnv,
+      });
+      const currentBranch = branchOutput.trim();
+
+      // Check for local changes
+      const localChanges = await hasLocalChanges(installPath);
+
+      const result: UpdateInfo = {
+        installPath,
+        currentVersion,
+        currentVersionShort,
+        currentBranch,
+        hasLocalChanges: localChanges,
+        sourceUrl: autoUpdateSettings.upstreamUrl,
+        autoUpdateEnabled: autoUpdateSettings.enabled,
+        checkIntervalMinutes: autoUpdateSettings.checkIntervalMinutes,
+        updateType: 'git',
+        mechanismInfo: {
+          isGitRepo: true,
+          gitAvailable: true,
+        },
+      };
+
+      res.json({
+        success: true,
+        result,
+      });
+    } catch (error) {
+      logError(error, 'Failed to get update info');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/updates/routes/pull.ts

@@ -0,0 +1,170 @@
+/**
+ * POST /pull endpoint - Pull updates from upstream
+ *
+ * Executes git pull from the configured upstream repository.
+ */
+
+import type { Request, Response } from 'express';
+import type { SettingsService } from '../../../services/settings-service.js';
+import type { UpdatePullResult } from '@automaker/types';
+import crypto from 'crypto';
+import {
+  execAsync,
+  execEnv,
+  getAutomakerRoot,
+  getCurrentCommit,
+  getShortCommit,
+  isGitRepo,
+  isGitAvailable,
+  isValidGitUrl,
+  hasLocalChanges,
+  getErrorMessage,
+  logError,
+} from '../common.js';
+
+/**
+ * Create an Express handler for POST /pull that updates the local Automaker installation by pulling from the configured upstream Git repository.
+ *
+ * The handler validates Git availability and that the install directory is a git repository, ensures there are no local uncommitted changes, validates the upstream URL from global settings, and performs a fast-forward-only pull using a temporary remote. It returns a JSON UpdatePullResult on success, or an error JSON with appropriate HTTP status codes for invalid input, merge conflicts, non-fast-forward divergence, or unexpected failures.
+ *
+ * @param settingsService - Service used to read global settings (used to obtain the upstream URL)
+ * @returns An Express request handler that performs the safe fast-forward pull and sends a JSON response describing the result or error
+ */
+export function createPullHandler(settingsService: SettingsService) {
+  return async (_req: Request, res: Response): Promise<void> => {
+    try {
+      const installPath = getAutomakerRoot();
+
+      // Check if git is available
+      if (!(await isGitAvailable())) {
+        res.status(500).json({
+          success: false,
+          error: 'Git is not installed or not available in PATH',
+        });
+        return;
+      }
+
+      // Check if automaker directory is a git repo
+      if (!(await isGitRepo(installPath))) {
+        res.status(500).json({
+          success: false,
+          error: 'Automaker installation is not a git repository',
+        });
+        return;
+      }
+
+      // Check for local changes
+      if (await hasLocalChanges(installPath)) {
+        res.status(400).json({
+          success: false,
+          error: 'You have local uncommitted changes. Please commit or stash them before updating.',
+        });
+        return;
+      }
+
+      // Get settings for upstream URL
+      const settings = await settingsService.getGlobalSettings();
+      const sourceUrl =
+        settings.autoUpdate?.upstreamUrl || 'https://github.com/AutoMaker-Org/automaker.git';
+
+      // Validate URL to prevent command injection
+      if (!isValidGitUrl(sourceUrl)) {
+        res.status(400).json({
+          success: false,
+          error: 'Invalid upstream URL format',
+        });
+        return;
+      }
+
+      // Get current version before pull
+      const previousVersion = await getCurrentCommit(installPath);
+      const previousVersionShort = await getShortCommit(installPath);
+
+      // Use a random remote name to avoid conflicts with concurrent pulls
+      const tempRemoteName = `automaker-update-pull-${crypto.randomBytes(8).toString('hex')}`;
+
+      try {
+        // Add temporary remote
+        await execAsync(`git remote add ${tempRemoteName} "${sourceUrl}"`, {
+          cwd: installPath,
+          env: execEnv,
+        });
+
+        // Fetch first
+        await execAsync(`git fetch ${tempRemoteName} main`, {
+          cwd: installPath,
+          env: execEnv,
+        });
+
+        // Merge the fetched changes
+        const { stdout: mergeOutput } = await execAsync(
+          `git merge ${tempRemoteName}/main --ff-only`,
+          { cwd: installPath, env: execEnv }
+        );
+
+        // Get new version after merge
+        const newVersion = await getCurrentCommit(installPath);
+        const newVersionShort = await getShortCommit(installPath);
+
+        const alreadyUpToDate =
+          mergeOutput.includes('Already up to date') || previousVersion === newVersion;
+
+        const result: UpdatePullResult = {
+          success: true,
+          previousVersion,
+          previousVersionShort,
+          newVersion,
+          newVersionShort,
+          alreadyUpToDate,
+          message: alreadyUpToDate
+            ? 'Already up to date'
+            : `Updated from ${previousVersionShort} to ${newVersionShort}`,
+        };
+
+        res.json({
+          success: true,
+          result,
+        });
+      } catch (pullError) {
+        const errorMsg = getErrorMessage(pullError);
+        logError(pullError, 'Failed to pull updates');
+
+        // Check for common errors
+        if (errorMsg.includes('not possible to fast-forward')) {
+          res.status(400).json({
+            success: false,
+            error:
+              'Cannot fast-forward merge. Your local branch has diverged from upstream. Please resolve manually.',
+          });
+          return;
+        }
+
+        if (errorMsg.includes('CONFLICT')) {
+          res.status(400).json({
+            success: false,
+            error: 'Merge conflict detected. Please resolve conflicts manually.',
+          });
+          return;
+        }
+
+        res.status(500).json({
+          success: false,
+          error: `Failed to pull updates: ${errorMsg}`,
+        });
+      } finally {
+        // Always clean up temp remote
+        try {
+          await execAsync(`git remote remove ${tempRemoteName}`, {
+            cwd: installPath,
+            env: execEnv,
+          });
+        } catch {
+          // Ignore cleanup errors
+        }
+      }
+    } catch (error) {
+      logError(error, 'Update pull failed');
+      res.status(500).json({ success: false, error: getErrorMessage(error) });
+    }
+  };
+}

apps/server/src/routes/worktree/common.ts

@@ -111,6 +111,19 @@ export async function isGitRepo(repoPath: string): Promise<boolean> {
   }
 }
 
+/**
+ * Check if a git repository has at least one commit (i.e., HEAD exists)
+ * Returns false for freshly initialized repos with no commits
+ */
+export async function hasCommits(repoPath: string): Promise<boolean> {
+  try {
+    await execAsync('git rev-parse --verify HEAD', { cwd: repoPath });
+    return true;
+  } catch {
+    return false;
+  }
+}
+
 /**
  * Check if an error is ENOENT (file/path not found or spawn failed)
  * These are expected in test environments with mock paths

apps/server/src/routes/worktree/index.ts

@@ -4,6 +4,7 @@
 
 import { Router } from 'express';
 import { validatePathParams } from '../../middleware/validate-paths.js';
+import { requireValidWorktree, requireValidProject, requireGitRepoOnly } from './middleware.js';
 import { createInfoHandler } from './routes/info.js';
 import { createStatusHandler } from './routes/status.js';
 import { createListHandler } from './routes/list.js';
@@ -38,17 +39,42 @@ export function createWorktreeRoutes(): Router {
   router.post('/list', createListHandler());
   router.post('/diffs', validatePathParams('projectPath'), createDiffsHandler());
   router.post('/file-diff', validatePathParams('projectPath', 'filePath'), createFileDiffHandler());
-  router.post('/merge', validatePathParams('projectPath'), createMergeHandler());
+  router.post(
+    '/merge',
+    validatePathParams('projectPath'),
+    requireValidProject,
+    createMergeHandler()
+  );
   router.post('/create', validatePathParams('projectPath'), createCreateHandler());
   router.post('/delete', validatePathParams('projectPath', 'worktreePath'), createDeleteHandler());
   router.post('/create-pr', createCreatePRHandler());
   router.post('/pr-info', createPRInfoHandler());
-  router.post('/commit', validatePathParams('worktreePath'), createCommitHandler());
-  router.post('/push', validatePathParams('worktreePath'), createPushHandler());
-  router.post('/pull', validatePathParams('worktreePath'), createPullHandler());
-  router.post('/checkout-branch', createCheckoutBranchHandler());
-  router.post('/list-branches', validatePathParams('worktreePath'), createListBranchesHandler());
-  router.post('/switch-branch', createSwitchBranchHandler());
+  router.post(
+    '/commit',
+    validatePathParams('worktreePath'),
+    requireGitRepoOnly,
+    createCommitHandler()
+  );
+  router.post(
+    '/push',
+    validatePathParams('worktreePath'),
+    requireValidWorktree,
+    createPushHandler()
+  );
+  router.post(
+    '/pull',
+    validatePathParams('worktreePath'),
+    requireValidWorktree,
+    createPullHandler()
+  );
+  router.post('/checkout-branch', requireValidWorktree, createCheckoutBranchHandler());
+  router.post(
+    '/list-branches',
+    validatePathParams('worktreePath'),
+    requireValidWorktree,
+    createListBranchesHandler()
+  );
+  router.post('/switch-branch', requireValidWorktree, createSwitchBranchHandler());
   router.post('/open-in-editor', validatePathParams('worktreePath'), createOpenInEditorHandler());
   router.get('/default-editor', createGetDefaultEditorHandler());
   router.post('/init-git', validatePathParams('projectPath'), createInitGitHandler());

apps/server/src/routes/worktree/middleware.ts

@@ -0,0 +1,74 @@
+/**
+ * Middleware for worktree route validation
+ */
+
+import type { Request, Response, NextFunction } from 'express';
+import { isGitRepo, hasCommits } from './common.js';
+
+interface ValidationOptions {
+  /** Check if the path is a git repository (default: true) */
+  requireGitRepo?: boolean;
+  /** Check if the repository has at least one commit (default: true) */
+  requireCommits?: boolean;
+  /** The name of the request body field containing the path (default: 'worktreePath') */
+  pathField?: 'worktreePath' | 'projectPath';
+}
+
+/**
+ * Middleware factory to validate that a path is a valid git repository with commits.
+ * This reduces code duplication across route handlers.
+ *
+ * @param options - Validation options
+ * @returns Express middleware function
+ */
+export function requireValidGitRepo(options: ValidationOptions = {}) {
+  const { requireGitRepo = true, requireCommits = true, pathField = 'worktreePath' } = options;
+
+  return async (req: Request, res: Response, next: NextFunction): Promise<void> => {
+    const repoPath = req.body[pathField] as string | undefined;
+
+    if (!repoPath) {
+      // Let the route handler deal with missing path validation
+      next();
+      return;
+    }
+
+    if (requireGitRepo && !(await isGitRepo(repoPath))) {
+      res.status(400).json({
+        success: false,
+        error: 'Not a git repository',
+        code: 'NOT_GIT_REPO',
+      });
+      return;
+    }
+
+    if (requireCommits && !(await hasCommits(repoPath))) {
+      res.status(400).json({
+        success: false,
+        error: 'Repository has no commits yet',
+        code: 'NO_COMMITS',
+      });
+      return;
+    }
+
+    next();
+  };
+}
+
+/**
+ * Middleware to validate git repo for worktreePath field
+ */
+export const requireValidWorktree = requireValidGitRepo({ pathField: 'worktreePath' });
+
+/**
+ * Middleware to validate git repo for projectPath field
+ */
+export const requireValidProject = requireValidGitRepo({ pathField: 'projectPath' });
+
+/**
+ * Middleware to validate git repo without requiring commits (for commit route)
+ */
+export const requireGitRepoOnly = requireValidGitRepo({
+  pathField: 'worktreePath',
+  requireCommits: false,
+});

apps/server/src/routes/worktree/routes/checkout-branch.ts

@@ -1,5 +1,8 @@
 /**
  * POST /checkout-branch endpoint - Create and checkout a new branch
+ *
+ * Note: Git repository validation (isGitRepo, hasCommits) is handled by
+ * the requireValidWorktree middleware in index.ts
  */
 
 import type { Request, Response } from 'express';

apps/server/src/routes/worktree/routes/commit.ts

@@ -1,5 +1,8 @@
 /**
  * POST /commit endpoint - Commit changes in a worktree
+ *
+ * Note: Git repository validation (isGitRepo) is handled by
+ * the requireGitRepoOnly middleware in index.ts
  */
 
 import type { Request, Response } from 'express';

apps/server/src/routes/worktree/routes/create-pr.ts

@@ -56,32 +56,56 @@ export function createCreatePRHandler() {
       }
 
       // Check for uncommitted changes
+      console.log(`[CreatePR] Checking for uncommitted changes in: ${worktreePath}`);
       const { stdout: status } = await execAsync('git status --porcelain', {
         cwd: worktreePath,
         env: execEnv,
       });
       const hasChanges = status.trim().length > 0;
+      console.log(`[CreatePR] Has uncommitted changes: ${hasChanges}`);
+      if (hasChanges) {
+        console.log(`[CreatePR] Changed files:\n${status}`);
+      }
 
       // If there are changes, commit them
       let commitHash: string | null = null;
+      let commitError: string | null = null;
       if (hasChanges) {
         const message = commitMessage || `Changes from ${branchName}`;
+        console.log(`[CreatePR] Committing changes with message: ${message}`);
 
-        // Stage all changes
-        await execAsync('git add -A', { cwd: worktreePath, env: execEnv });
+        try {
+          // Stage all changes
+          console.log(`[CreatePR] Running: git add -A`);
+          await execAsync('git add -A', { cwd: worktreePath, env: execEnv });
 
-        // Create commit
-        await execAsync(`git commit -m "${message.replace(/"/g, '\\"')}"`, {
-          cwd: worktreePath,
-          env: execEnv,
-        });
+          // Create commit
+          console.log(`[CreatePR] Running: git commit`);
+          await execAsync(`git commit -m "${message.replace(/"/g, '\\"')}"`, {
+            cwd: worktreePath,
+            env: execEnv,
+          });
 
-        // Get commit hash
-        const { stdout: hashOutput } = await execAsync('git rev-parse HEAD', {
-          cwd: worktreePath,
-          env: execEnv,
-        });
-        commitHash = hashOutput.trim().substring(0, 8);
+          // Get commit hash
+          const { stdout: hashOutput } = await execAsync('git rev-parse HEAD', {
+            cwd: worktreePath,
+            env: execEnv,
+          });
+          commitHash = hashOutput.trim().substring(0, 8);
+          console.log(`[CreatePR] Commit successful: ${commitHash}`);
+        } catch (commitErr: unknown) {
+          const err = commitErr as { stderr?: string; message?: string };
+          commitError = err.stderr || err.message || 'Commit failed';
+          console.error(`[CreatePR] Commit failed: ${commitError}`);
+
+          // Return error immediately - don't proceed with push/PR if commit fails
+          res.status(500).json({
+            success: false,
+            error: `Failed to commit changes: ${commitError}`,
+            commitError,
+          });
+          return;
+        }
       }
 
       // Push the branch to remote
@@ -360,8 +384,9 @@ export function createCreatePRHandler() {
         success: true,
         result: {
           branch: branchName,
-          committed: hasChanges,
+          committed: hasChanges && !commitError,
           commitHash,
+          commitError: commitError || undefined,
           pushed: true,
           prUrl,
           prNumber,

apps/server/src/routes/worktree/routes/list-branches.ts

@@ -1,5 +1,8 @@
 /**
  * POST /list-branches endpoint - List all local branches
+ *
+ * Note: Git repository validation (isGitRepo, hasCommits) is handled by
+ * the requireValidWorktree middleware in index.ts
  */
 
 import type { Request, Response } from 'express';

apps/server/src/routes/worktree/routes/merge.ts

@@ -1,5 +1,8 @@
 /**
  * POST /merge endpoint - Merge feature (merge worktree branch into main)
+ *
+ * Note: Git repository validation (isGitRepo, hasCommits) is handled by
+ * the requireValidProject middleware in index.ts
  */
 
 import type { Request, Response } from 'express';

apps/server/src/routes/worktree/routes/pull.ts

@@ -1,5 +1,8 @@
 /**
  * POST /pull endpoint - Pull latest changes for a worktree/branch
+ *
+ * Note: Git repository validation (isGitRepo, hasCommits) is handled by
+ * the requireValidWorktree middleware in index.ts
  */
 
 import type { Request, Response } from 'express';

apps/server/src/routes/worktree/routes/push.ts

@@ -1,5 +1,8 @@
 /**
  * POST /push endpoint - Push a worktree branch to remote
+ *
+ * Note: Git repository validation (isGitRepo, hasCommits) is handled by
+ * the requireValidWorktree middleware in index.ts
  */
 
 import type { Request, Response } from 'express';

apps/server/src/routes/worktree/routes/switch-branch.ts

@@ -4,6 +4,9 @@
  * Simple branch switching.
  * If there are uncommitted changes, the switch will fail and
  * the user should commit first.
+ *
+ * Note: Git repository validation (isGitRepo, hasCommits) is handled by
+ * the requireValidWorktree middleware in index.ts
  */
 
 import type { Request, Response } from 'express';

apps/server/src/services/agent-service.ts

@@ -16,6 +16,12 @@ import {
 import { ProviderFactory } from '../providers/provider-factory.js';
 import { createChatOptions, validateWorkingDirectory } from '../lib/sdk-options.js';
 import { PathNotAllowedError } from '@automaker/platform';
+import type { SettingsService } from './settings-service.js';
+import {
+  getAutoLoadClaudeMdSetting,
+  getEnableSandboxModeSetting,
+  filterClaudeMdFromContext,
+} from '../lib/settings-helpers.js';
 
 interface Message {
   id: string;
@@ -30,6 +36,14 @@ interface Message {
   isError?: boolean;
 }
 
+interface QueuedPrompt {
+  id: string;
+  message: string;
+  imagePaths?: string[];
+  model?: string;
+  addedAt: string;
+}
+
 interface Session {
   messages: Message[];
   isRunning: boolean;
@@ -37,6 +51,7 @@ interface Session {
   workingDirectory: string;
   model?: string;
   sdkSessionId?: string; // Claude SDK session ID for conversation continuity
+  promptQueue: QueuedPrompt[]; // Queue of prompts to auto-run after current task
 }
 
 interface SessionMetadata {
@@ -57,11 +72,13 @@ export class AgentService {
   private stateDir: string;
   private metadataFile: string;
   private events: EventEmitter;
+  private settingsService: SettingsService | null = null;
 
-  constructor(dataDir: string, events: EventEmitter) {
+  constructor(dataDir: string, events: EventEmitter, settingsService?: SettingsService) {
     this.stateDir = path.join(dataDir, 'agent-sessions');
     this.metadataFile = path.join(dataDir, 'sessions-metadata.json');
     this.events = events;
+    this.settingsService = settingsService ?? null;
   }
 
   async initialize(): Promise<void> {
@@ -90,12 +107,16 @@ export class AgentService {
       // Validate that the working directory is allowed using centralized validation
       validateWorkingDirectory(resolvedWorkingDirectory);
 
+      // Load persisted queue
+      const promptQueue = await this.loadQueueState(sessionId);
+
       this.sessions.set(sessionId, {
         messages,
         isRunning: false,
         abortController: null,
         workingDirectory: resolvedWorkingDirectory,
         sdkSessionId: sessionMetadata?.sdkSessionId, // Load persisted SDK session ID
+        promptQueue,
       });
     }
 
@@ -125,10 +146,12 @@ export class AgentService {
   }) {
     const session = this.sessions.get(sessionId);
     if (!session) {
+      console.error('[AgentService] ERROR: Session not found:', sessionId);
       throw new Error(`Session ${sessionId} not found`);
     }
 
     if (session.isRunning) {
+      console.error('[AgentService] ERROR: Agent already running for session:', sessionId);
       throw new Error('Agent is already processing a message');
     }
 
@@ -174,6 +197,11 @@ export class AgentService {
     session.isRunning = true;
     session.abortController = new AbortController();
 
+    // Emit started event so UI can show thinking indicator
+    this.emitAgentEvent(sessionId, {
+      type: 'started',
+    });
+
     // Emit user message event
     this.emitAgentEvent(sessionId, {
       type: 'message',
@@ -186,12 +214,29 @@ export class AgentService {
       // Determine the effective working directory for context loading
       const effectiveWorkDir = workingDirectory || session.workingDirectory;
 
+      // Load autoLoadClaudeMd setting (project setting takes precedence over global)
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        effectiveWorkDir,
+        this.settingsService,
+        '[AgentService]'
+      );
+
+      // Load enableSandboxMode setting (global setting only)
+      const enableSandboxMode = await getEnableSandboxModeSetting(
+        this.settingsService,
+        '[AgentService]'
+      );
+
       // Load project context files (CLAUDE.md, CODE_QUALITY.md, etc.)
-      const { formattedPrompt: contextFilesPrompt } = await loadContextFiles({
+      const contextResult = await loadContextFiles({
         projectPath: effectiveWorkDir,
         fsModule: secureFs as Parameters<typeof loadContextFiles>[0]['fsModule'],
       });
 
+      // When autoLoadClaudeMd is enabled, filter out CLAUDE.md to avoid duplication
+      // (SDK handles CLAUDE.md via settingSources), but keep other context files like CODE_QUALITY.md
+      const contextFilesPrompt = filterClaudeMdFromContext(contextResult, autoLoadClaudeMd);
+
       // Build combined system prompt with base prompt and context files
       const baseSystemPrompt = this.getSystemPrompt();
       const combinedSystemPrompt = contextFilesPrompt
@@ -205,6 +250,8 @@ export class AgentService {
         sessionModel: session.model,
         systemPrompt: combinedSystemPrompt,
         abortController: session.abortController!,
+        autoLoadClaudeMd,
+        enableSandboxMode,
       });
 
       // Extract model, maxTurns, and allowedTools from SDK options
@@ -215,20 +262,18 @@ export class AgentService {
       // Get provider for this model
       const provider = ProviderFactory.getProviderForModel(effectiveModel);
 
-      console.log(
-        `[AgentService] Using provider "${provider.getName()}" for model "${effectiveModel}"`
-      );
-
       // Build options for provider
       const options: ExecuteOptions = {
         prompt: '', // Will be set below based on images
         model: effectiveModel,
         cwd: effectiveWorkDir,
-        systemPrompt: combinedSystemPrompt,
+        systemPrompt: sdkOptions.systemPrompt,
         maxTurns: maxTurns,
         allowedTools: allowedTools,
         abortController: session.abortController!,
         conversationHistory: conversationHistory.length > 0 ? conversationHistory : undefined,
+        settingSources: sdkOptions.settingSources,
+        sandbox: sdkOptions.sandbox, // Pass sandbox configuration
         sdkSessionId: session.sdkSessionId, // Pass SDK session ID for resuming
       };
 
@@ -254,7 +299,6 @@ export class AgentService {
         // Capture SDK session ID from any message and persist it
         if (msg.session_id && !session.sdkSessionId) {
           session.sdkSessionId = msg.session_id;
-          console.log(`[AgentService] Captured SDK session ID: ${msg.session_id}`);
           // Persist the SDK session ID to ensure conversation continuity across server restarts
           await this.updateSession(sessionId, { sdkSessionId: msg.session_id });
         }
@@ -319,6 +363,9 @@ export class AgentService {
       session.isRunning = false;
       session.abortController = null;
 
+      // Process next item in queue after completion
+      setImmediate(() => this.processNextInQueue(sessionId));
+
       return {
         success: true,
         message: currentAssistantMessage,
@@ -557,6 +604,165 @@ export class AgentService {
     return true;
   }
 
+  // Queue management methods
+
+  /**
+   * Add a prompt to the queue for later execution
+   */
+  async addToQueue(
+    sessionId: string,
+    prompt: { message: string; imagePaths?: string[]; model?: string }
+  ): Promise<{ success: boolean; queuedPrompt?: QueuedPrompt; error?: string }> {
+    const session = this.sessions.get(sessionId);
+    if (!session) {
+      return { success: false, error: 'Session not found' };
+    }
+
+    const queuedPrompt: QueuedPrompt = {
+      id: this.generateId(),
+      message: prompt.message,
+      imagePaths: prompt.imagePaths,
+      model: prompt.model,
+      addedAt: new Date().toISOString(),
+    };
+
+    session.promptQueue.push(queuedPrompt);
+    await this.saveQueueState(sessionId, session.promptQueue);
+
+    // Emit queue update event
+    this.emitAgentEvent(sessionId, {
+      type: 'queue_updated',
+      queue: session.promptQueue,
+    });
+
+    return { success: true, queuedPrompt };
+  }
+
+  /**
+   * Get the current queue for a session
+   */
+  getQueue(sessionId: string): { success: boolean; queue?: QueuedPrompt[]; error?: string } {
+    const session = this.sessions.get(sessionId);
+    if (!session) {
+      return { success: false, error: 'Session not found' };
+    }
+    return { success: true, queue: session.promptQueue };
+  }
+
+  /**
+   * Remove a specific prompt from the queue
+   */
+  async removeFromQueue(
+    sessionId: string,
+    promptId: string
+  ): Promise<{ success: boolean; error?: string }> {
+    const session = this.sessions.get(sessionId);
+    if (!session) {
+      return { success: false, error: 'Session not found' };
+    }
+
+    const index = session.promptQueue.findIndex((p) => p.id === promptId);
+    if (index === -1) {
+      return { success: false, error: 'Prompt not found in queue' };
+    }
+
+    session.promptQueue.splice(index, 1);
+    await this.saveQueueState(sessionId, session.promptQueue);
+
+    this.emitAgentEvent(sessionId, {
+      type: 'queue_updated',
+      queue: session.promptQueue,
+    });
+
+    return { success: true };
+  }
+
+  /**
+   * Clear all prompts from the queue
+   */
+  async clearQueue(sessionId: string): Promise<{ success: boolean; error?: string }> {
+    const session = this.sessions.get(sessionId);
+    if (!session) {
+      return { success: false, error: 'Session not found' };
+    }
+
+    session.promptQueue = [];
+    await this.saveQueueState(sessionId, []);
+
+    this.emitAgentEvent(sessionId, {
+      type: 'queue_updated',
+      queue: [],
+    });
+
+    return { success: true };
+  }
+
+  /**
+   * Save queue state to disk for persistence
+   */
+  private async saveQueueState(sessionId: string, queue: QueuedPrompt[]): Promise<void> {
+    const queueFile = path.join(this.stateDir, `${sessionId}-queue.json`);
+    try {
+      await secureFs.writeFile(queueFile, JSON.stringify(queue, null, 2), 'utf-8');
+    } catch (error) {
+      console.error('[AgentService] Failed to save queue state:', error);
+    }
+  }
+
+  /**
+   * Load queue state from disk
+   */
+  private async loadQueueState(sessionId: string): Promise<QueuedPrompt[]> {
+    const queueFile = path.join(this.stateDir, `${sessionId}-queue.json`);
+    try {
+      const data = (await secureFs.readFile(queueFile, 'utf-8')) as string;
+      return JSON.parse(data);
+    } catch {
+      return [];
+    }
+  }
+
+  /**
+   * Process the next item in the queue (called after task completion)
+   */
+  private async processNextInQueue(sessionId: string): Promise<void> {
+    const session = this.sessions.get(sessionId);
+    if (!session || session.promptQueue.length === 0) {
+      return;
+    }
+
+    // Don't process if already running
+    if (session.isRunning) {
+      return;
+    }
+
+    const nextPrompt = session.promptQueue.shift();
+    if (!nextPrompt) return;
+
+    await this.saveQueueState(sessionId, session.promptQueue);
+
+    this.emitAgentEvent(sessionId, {
+      type: 'queue_updated',
+      queue: session.promptQueue,
+    });
+
+    try {
+      await this.sendMessage({
+        sessionId,
+        message: nextPrompt.message,
+        imagePaths: nextPrompt.imagePaths,
+        model: nextPrompt.model,
+      });
+    } catch (error) {
+      console.error('[AgentService] Failed to process queued prompt:', error);
+      this.emitAgentEvent(sessionId, {
+        type: 'queue_error',
+        error: (error as Error).message,
+        promptId: nextPrompt.id,
+      });
+    }
+  }
+
   private emitAgentEvent(sessionId: string, data: Record<string, unknown>): void {
     this.events.emit('agent:stream', { sessionId, ...data });
   }

apps/server/src/services/auto-mode-service.ts

@@ -25,8 +25,18 @@ import { promisify } from 'util';
 import path from 'path';
 import * as secureFs from '../lib/secure-fs.js';
 import type { EventEmitter } from '../lib/events.js';
-import { createAutoModeOptions, validateWorkingDirectory } from '../lib/sdk-options.js';
+import {
+  createAutoModeOptions,
+  createCustomOptions,
+  validateWorkingDirectory,
+} from '../lib/sdk-options.js';
 import { FeatureLoader } from './feature-loader.js';
+import type { SettingsService } from './settings-service.js';
+import {
+  getAutoLoadClaudeMdSetting,
+  getEnableSandboxModeSetting,
+  filterClaudeMdFromContext,
+} from '../lib/settings-helpers.js';
 
 const execAsync = promisify(exec);
 
@@ -341,9 +351,11 @@ export class AutoModeService {
   private autoLoopAbortController: AbortController | null = null;
   private config: AutoModeConfig | null = null;
   private pendingApprovals = new Map<string, PendingApproval>();
+  private settingsService: SettingsService | null = null;
 
-  constructor(events: EventEmitter) {
+  constructor(events: EventEmitter, settingsService?: SettingsService) {
     this.events = events;
+    this.settingsService = settingsService ?? null;
   }
 
   /**
@@ -551,14 +563,25 @@ export class AutoModeService {
       // Update feature status to in_progress
       await this.updateFeatureStatus(projectPath, featureId, 'in_progress');
 
+      // Load autoLoadClaudeMd setting to determine context loading strategy
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        projectPath,
+        this.settingsService,
+        '[AutoMode]'
+      );
+
       // Build the prompt - use continuation prompt if provided (for recovery after plan approval)
       let prompt: string;
       // Load project context files (CLAUDE.md, CODE_QUALITY.md, etc.) - passed as system prompt
-      const { formattedPrompt: contextFilesPrompt } = await loadContextFiles({
+      const contextResult = await loadContextFiles({
         projectPath,
         fsModule: secureFs as Parameters<typeof loadContextFiles>[0]['fsModule'],
       });
 
+      // When autoLoadClaudeMd is enabled, filter out CLAUDE.md to avoid duplication
+      // (SDK handles CLAUDE.md via settingSources), but keep other context files like CODE_QUALITY.md
+      const contextFilesPrompt = filterClaudeMdFromContext(contextResult, autoLoadClaudeMd);
+
       if (options?.continuationPrompt) {
         // Continuation prompt is used when recovering from a plan approval
         // The plan was already approved, so skip the planning phase
@@ -604,6 +627,7 @@ export class AutoModeService {
           planningMode: feature.planningMode,
           requirePlanApproval: feature.requirePlanApproval,
           systemPrompt: contextFilesPrompt || undefined,
+          autoLoadClaudeMd,
         }
       );
 
@@ -746,12 +770,23 @@ export class AutoModeService {
       // No previous context
     }
 
+    // Load autoLoadClaudeMd setting to determine context loading strategy
+    const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+      projectPath,
+      this.settingsService,
+      '[AutoMode]'
+    );
+
     // Load project context files (CLAUDE.md, CODE_QUALITY.md, etc.) - passed as system prompt
-    const { formattedPrompt: contextFilesPrompt } = await loadContextFiles({
+    const contextResult = await loadContextFiles({
       projectPath,
       fsModule: secureFs as Parameters<typeof loadContextFiles>[0]['fsModule'],
     });
 
+    // When autoLoadClaudeMd is enabled, filter out CLAUDE.md to avoid duplication
+    // (SDK handles CLAUDE.md via settingSources), but keep other context files like CODE_QUALITY.md
+    const contextFilesPrompt = filterClaudeMdFromContext(contextResult, autoLoadClaudeMd);
+
     // Build complete prompt with feature info, previous context, and follow-up instructions
     let fullPrompt = `## Follow-up on Feature Implementation
 
@@ -879,6 +914,7 @@ Address the follow-up instructions above. Review the previous work and make the
           planningMode: 'skip', // Follow-ups don't require approval
           previousContent: previousContext || undefined,
           systemPrompt: contextFilesPrompt || undefined,
+          autoLoadClaudeMd,
         }
       );
 
@@ -1065,11 +1101,6 @@ Address the follow-up instructions above. Review the previous work and make the
    * Analyze project to gather context
    */
   async analyzeProject(projectPath: string): Promise<void> {
-    // Validate project path before proceeding
-    // This is called here because analyzeProject builds ExecuteOptions directly
-    // without using a factory function from sdk-options.ts
-    validateWorkingDirectory(projectPath);
-
     const abortController = new AbortController();
 
     const analysisFeatureId = `analysis-${Date.now()}`;
@@ -1097,13 +1128,32 @@ Format your response as a structured markdown document.`;
       const analysisModel = resolveModelString(undefined, DEFAULT_MODELS.claude);
       const provider = ProviderFactory.getProviderForModel(analysisModel);
 
-      const options: ExecuteOptions = {
-        prompt,
+      // Load autoLoadClaudeMd setting
+      const autoLoadClaudeMd = await getAutoLoadClaudeMdSetting(
+        projectPath,
+        this.settingsService,
+        '[AutoMode]'
+      );
+
+      // Use createCustomOptions for centralized SDK configuration with CLAUDE.md support
+      const sdkOptions = createCustomOptions({
+        cwd: projectPath,
         model: analysisModel,
         maxTurns: 5,
-        cwd: projectPath,
         allowedTools: ['Read', 'Glob', 'Grep'],
         abortController,
+        autoLoadClaudeMd,
+      });
+
+      const options: ExecuteOptions = {
+        prompt,
+        model: sdkOptions.model ?? analysisModel,
+        cwd: sdkOptions.cwd ?? projectPath,
+        maxTurns: sdkOptions.maxTurns,
+        allowedTools: sdkOptions.allowedTools as string[],
+        abortController,
+        settingSources: sdkOptions.settingSources,
+        sandbox: sdkOptions.sandbox, // Pass sandbox configuration
       };
 
       const stream = provider.executeQuery(options);
@@ -1708,6 +1758,7 @@ This helps parse your summary correctly in the output logs.`;
       requirePlanApproval?: boolean;
       previousContent?: string;
       systemPrompt?: string;
+      autoLoadClaudeMd?: boolean;
     }
   ): Promise<void> {
     const finalProjectPath = options?.projectPath || projectPath;
@@ -1780,11 +1831,23 @@ This mock response was generated because AUTOMAKER_MOCK_AGENT=true was set.
       return;
     }
 
+    // Load autoLoadClaudeMd setting (project setting takes precedence over global)
+    // Use provided value if available, otherwise load from settings
+    const autoLoadClaudeMd =
+      options?.autoLoadClaudeMd !== undefined
+        ? options.autoLoadClaudeMd
+        : await getAutoLoadClaudeMdSetting(finalProjectPath, this.settingsService, '[AutoMode]');
+
+    // Load enableSandboxMode setting (global setting only)
+    const enableSandboxMode = await getEnableSandboxModeSetting(this.settingsService, '[AutoMode]');
+
     // Build SDK options using centralized configuration for feature implementation
     const sdkOptions = createAutoModeOptions({
       cwd: workDir,
       model: model,
       abortController,
+      autoLoadClaudeMd,
+      enableSandboxMode,
     });
 
     // Extract model, maxTurns, and allowedTools from SDK options
@@ -1823,7 +1886,9 @@ This mock response was generated because AUTOMAKER_MOCK_AGENT=true was set.
       cwd: workDir,
       allowedTools: allowedTools,
       abortController,
-      systemPrompt: options?.systemPrompt,
+      systemPrompt: sdkOptions.systemPrompt,
+      settingSources: sdkOptions.settingSources,
+      sandbox: sdkOptions.sandbox, // Pass sandbox configuration
     };
 
     // Execute via provider

apps/server/tests/unit/lib/sdk-options.test.ts

@@ -179,7 +179,7 @@ describe('sdk-options.ts', () => {
     it('should create options with chat settings', async () => {
       const { createChatOptions, TOOL_PRESETS, MAX_TURNS } = await import('@/lib/sdk-options.js');
 
-      const options = createChatOptions({ cwd: '/test/path' });
+      const options = createChatOptions({ cwd: '/test/path', enableSandboxMode: true });
 
       expect(options.cwd).toBe('/test/path');
       expect(options.maxTurns).toBe(MAX_TURNS.standard);
@@ -212,6 +212,27 @@ describe('sdk-options.ts', () => {
 
       expect(options.model).toBe('claude-sonnet-4-20250514');
     });
+
+    it('should not set sandbox when enableSandboxMode is false', async () => {
+      const { createChatOptions } = await import('@/lib/sdk-options.js');
+
+      const options = createChatOptions({
+        cwd: '/test/path',
+        enableSandboxMode: false,
+      });
+
+      expect(options.sandbox).toBeUndefined();
+    });
+
+    it('should not set sandbox when enableSandboxMode is not provided', async () => {
+      const { createChatOptions } = await import('@/lib/sdk-options.js');
+
+      const options = createChatOptions({
+        cwd: '/test/path',
+      });
+
+      expect(options.sandbox).toBeUndefined();
+    });
   });
 
   describe('createAutoModeOptions', () => {
@@ -219,7 +240,7 @@ describe('sdk-options.ts', () => {
       const { createAutoModeOptions, TOOL_PRESETS, MAX_TURNS } =
         await import('@/lib/sdk-options.js');
 
-      const options = createAutoModeOptions({ cwd: '/test/path' });
+      const options = createAutoModeOptions({ cwd: '/test/path', enableSandboxMode: true });
 
       expect(options.cwd).toBe('/test/path');
       expect(options.maxTurns).toBe(MAX_TURNS.maximum);
@@ -252,6 +273,27 @@ describe('sdk-options.ts', () => {
 
       expect(options.abortController).toBe(abortController);
     });
+
+    it('should not set sandbox when enableSandboxMode is false', async () => {
+      const { createAutoModeOptions } = await import('@/lib/sdk-options.js');
+
+      const options = createAutoModeOptions({
+        cwd: '/test/path',
+        enableSandboxMode: false,
+      });
+
+      expect(options.sandbox).toBeUndefined();
+    });
+
+    it('should not set sandbox when enableSandboxMode is not provided', async () => {
+      const { createAutoModeOptions } = await import('@/lib/sdk-options.js');
+
+      const options = createAutoModeOptions({
+        cwd: '/test/path',
+      });
+
+      expect(options.sandbox).toBeUndefined();
+    });
   });
 
   describe('createCustomOptions', () => {

apps/server/tests/unit/lib/validation-storage.test.ts

@@ -0,0 +1,307 @@
+import { describe, it, expect, beforeEach, afterEach, vi } from 'vitest';
+import {
+  writeValidation,
+  readValidation,
+  getAllValidations,
+  deleteValidation,
+  isValidationStale,
+  getValidationWithFreshness,
+  markValidationViewed,
+  getUnviewedValidationsCount,
+  type StoredValidation,
+} from '@/lib/validation-storage.js';
+import fs from 'fs/promises';
+import path from 'path';
+import os from 'os';
+
+describe('validation-storage.ts', () => {
+  let testProjectPath: string;
+
+  beforeEach(async () => {
+    testProjectPath = path.join(os.tmpdir(), `validation-storage-test-${Date.now()}`);
+    await fs.mkdir(testProjectPath, { recursive: true });
+  });
+
+  afterEach(async () => {
+    try {
+      await fs.rm(testProjectPath, { recursive: true, force: true });
+    } catch {
+      // Ignore cleanup errors
+    }
+  });
+
+  const createMockValidation = (overrides: Partial<StoredValidation> = {}): StoredValidation => ({
+    issueNumber: 123,
+    issueTitle: 'Test Issue',
+    validatedAt: new Date().toISOString(),
+    model: 'haiku',
+    result: {
+      verdict: 'valid',
+      confidence: 'high',
+      reasoning: 'Test reasoning',
+    },
+    ...overrides,
+  });
+
+  describe('writeValidation', () => {
+    it('should write validation to storage', async () => {
+      const validation = createMockValidation();
+
+      await writeValidation(testProjectPath, 123, validation);
+
+      // Verify file was created
+      const validationPath = path.join(
+        testProjectPath,
+        '.automaker',
+        'validations',
+        '123',
+        'validation.json'
+      );
+      const content = await fs.readFile(validationPath, 'utf-8');
+      expect(JSON.parse(content)).toEqual(validation);
+    });
+
+    it('should create nested directories if they do not exist', async () => {
+      const validation = createMockValidation({ issueNumber: 456 });
+
+      await writeValidation(testProjectPath, 456, validation);
+
+      const validationPath = path.join(
+        testProjectPath,
+        '.automaker',
+        'validations',
+        '456',
+        'validation.json'
+      );
+      const content = await fs.readFile(validationPath, 'utf-8');
+      expect(JSON.parse(content)).toEqual(validation);
+    });
+  });
+
+  describe('readValidation', () => {
+    it('should read validation from storage', async () => {
+      const validation = createMockValidation();
+      await writeValidation(testProjectPath, 123, validation);
+
+      const result = await readValidation(testProjectPath, 123);
+
+      expect(result).toEqual(validation);
+    });
+
+    it('should return null when validation does not exist', async () => {
+      const result = await readValidation(testProjectPath, 999);
+
+      expect(result).toBeNull();
+    });
+  });
+
+  describe('getAllValidations', () => {
+    it('should return all validations for a project', async () => {
+      const validation1 = createMockValidation({ issueNumber: 1, issueTitle: 'Issue 1' });
+      const validation2 = createMockValidation({ issueNumber: 2, issueTitle: 'Issue 2' });
+      const validation3 = createMockValidation({ issueNumber: 3, issueTitle: 'Issue 3' });
+
+      await writeValidation(testProjectPath, 1, validation1);
+      await writeValidation(testProjectPath, 2, validation2);
+      await writeValidation(testProjectPath, 3, validation3);
+
+      const result = await getAllValidations(testProjectPath);
+
+      expect(result).toHaveLength(3);
+      expect(result[0]).toEqual(validation1);
+      expect(result[1]).toEqual(validation2);
+      expect(result[2]).toEqual(validation3);
+    });
+
+    it('should return empty array when no validations exist', async () => {
+      const result = await getAllValidations(testProjectPath);
+
+      expect(result).toEqual([]);
+    });
+
+    it('should skip non-numeric directories', async () => {
+      const validation = createMockValidation({ issueNumber: 1 });
+      await writeValidation(testProjectPath, 1, validation);
+
+      // Create a non-numeric directory
+      const invalidDir = path.join(testProjectPath, '.automaker', 'validations', 'invalid');
+      await fs.mkdir(invalidDir, { recursive: true });
+
+      const result = await getAllValidations(testProjectPath);
+
+      expect(result).toHaveLength(1);
+      expect(result[0]).toEqual(validation);
+    });
+  });
+
+  describe('deleteValidation', () => {
+    it('should delete validation from storage', async () => {
+      const validation = createMockValidation();
+      await writeValidation(testProjectPath, 123, validation);
+
+      const result = await deleteValidation(testProjectPath, 123);
+
+      expect(result).toBe(true);
+
+      const readResult = await readValidation(testProjectPath, 123);
+      expect(readResult).toBeNull();
+    });
+
+    it('should return true even when validation does not exist', async () => {
+      const result = await deleteValidation(testProjectPath, 999);
+
+      expect(result).toBe(true);
+    });
+  });
+
+  describe('isValidationStale', () => {
+    it('should return false for recent validation', () => {
+      const validation = createMockValidation({
+        validatedAt: new Date().toISOString(),
+      });
+
+      const result = isValidationStale(validation);
+
+      expect(result).toBe(false);
+    });
+
+    it('should return true for validation older than 24 hours', () => {
+      const oldDate = new Date();
+      oldDate.setHours(oldDate.getHours() - 25); // 25 hours ago
+
+      const validation = createMockValidation({
+        validatedAt: oldDate.toISOString(),
+      });
+
+      const result = isValidationStale(validation);
+
+      expect(result).toBe(true);
+    });
+
+    it('should return false for validation exactly at 24 hours', () => {
+      const exactDate = new Date();
+      exactDate.setHours(exactDate.getHours() - 24);
+
+      const validation = createMockValidation({
+        validatedAt: exactDate.toISOString(),
+      });
+
+      const result = isValidationStale(validation);
+
+      expect(result).toBe(false);
+    });
+  });
+
+  describe('getValidationWithFreshness', () => {
+    it('should return validation with isStale false for recent validation', async () => {
+      const validation = createMockValidation({
+        validatedAt: new Date().toISOString(),
+      });
+      await writeValidation(testProjectPath, 123, validation);
+
+      const result = await getValidationWithFreshness(testProjectPath, 123);
+
+      expect(result).not.toBeNull();
+      expect(result!.validation).toEqual(validation);
+      expect(result!.isStale).toBe(false);
+    });
+
+    it('should return validation with isStale true for old validation', async () => {
+      const oldDate = new Date();
+      oldDate.setHours(oldDate.getHours() - 25);
+
+      const validation = createMockValidation({
+        validatedAt: oldDate.toISOString(),
+      });
+      await writeValidation(testProjectPath, 123, validation);
+
+      const result = await getValidationWithFreshness(testProjectPath, 123);
+
+      expect(result).not.toBeNull();
+      expect(result!.isStale).toBe(true);
+    });
+
+    it('should return null when validation does not exist', async () => {
+      const result = await getValidationWithFreshness(testProjectPath, 999);
+
+      expect(result).toBeNull();
+    });
+  });
+
+  describe('markValidationViewed', () => {
+    it('should mark validation as viewed', async () => {
+      const validation = createMockValidation();
+      await writeValidation(testProjectPath, 123, validation);
+
+      const result = await markValidationViewed(testProjectPath, 123);
+
+      expect(result).toBe(true);
+
+      const updated = await readValidation(testProjectPath, 123);
+      expect(updated).not.toBeNull();
+      expect(updated!.viewedAt).toBeDefined();
+    });
+
+    it('should return false when validation does not exist', async () => {
+      const result = await markValidationViewed(testProjectPath, 999);
+
+      expect(result).toBe(false);
+    });
+  });
+
+  describe('getUnviewedValidationsCount', () => {
+    it('should return count of unviewed non-stale validations', async () => {
+      const validation1 = createMockValidation({ issueNumber: 1 });
+      const validation2 = createMockValidation({ issueNumber: 2 });
+      const validation3 = createMockValidation({
+        issueNumber: 3,
+        viewedAt: new Date().toISOString(),
+      });
+
+      await writeValidation(testProjectPath, 1, validation1);
+      await writeValidation(testProjectPath, 2, validation2);
+      await writeValidation(testProjectPath, 3, validation3);
+
+      const result = await getUnviewedValidationsCount(testProjectPath);
+
+      expect(result).toBe(2);
+    });
+
+    it('should not count stale validations', async () => {
+      const oldDate = new Date();
+      oldDate.setHours(oldDate.getHours() - 25);
+
+      const validation1 = createMockValidation({ issueNumber: 1 });
+      const validation2 = createMockValidation({
+        issueNumber: 2,
+        validatedAt: oldDate.toISOString(),
+      });
+
+      await writeValidation(testProjectPath, 1, validation1);
+      await writeValidation(testProjectPath, 2, validation2);
+
+      const result = await getUnviewedValidationsCount(testProjectPath);
+
+      expect(result).toBe(1);
+    });
+
+    it('should return 0 when no validations exist', async () => {
+      const result = await getUnviewedValidationsCount(testProjectPath);
+
+      expect(result).toBe(0);
+    });
+
+    it('should return 0 when all validations are viewed', async () => {
+      const validation = createMockValidation({
+        issueNumber: 1,
+        viewedAt: new Date().toISOString(),
+      });
+
+      await writeValidation(testProjectPath, 1, validation);
+
+      const result = await getUnviewedValidationsCount(testProjectPath);
+
+      expect(result).toBe(0);
+    });
+  });
+});

apps/server/tests/unit/providers/claude-provider.test.ts

@@ -73,7 +73,7 @@ describe('claude-provider.ts', () => {
           maxTurns: 10,
           cwd: '/test/dir',
           allowedTools: ['Read', 'Write'],
-          permissionMode: 'acceptEdits',
+          permissionMode: 'default',
         }),
       });
     });
@@ -100,7 +100,7 @@ describe('claude-provider.ts', () => {
       });
     });
 
-    it('should enable sandbox by default', async () => {
+    it('should pass sandbox configuration when provided', async () => {
       vi.mocked(sdk.query).mockReturnValue(
         (async function* () {
           yield { type: 'text', text: 'test' };
@@ -110,6 +110,10 @@ describe('claude-provider.ts', () => {
       const generator = provider.executeQuery({
         prompt: 'Test',
         cwd: '/test',
+        sandbox: {
+          enabled: true,
+          autoAllowBashIfSandboxed: true,
+        },
       });
 
       await collectAsyncGenerator(generator);
@@ -242,11 +246,21 @@ describe('claude-provider.ts', () => {
       });
 
       await expect(collectAsyncGenerator(generator)).rejects.toThrow('SDK execution failed');
-      expect(consoleErrorSpy).toHaveBeenCalledWith(
-        '[ClaudeProvider] executeQuery() error during execution:',
+
+      // Should log error message
+      expect(consoleErrorSpy).toHaveBeenNthCalledWith(
+        1,
+        '[ClaudeProvider] ERROR: executeQuery() error during execution:',
         testError
       );
 
+      // Should log stack trace
+      expect(consoleErrorSpy).toHaveBeenNthCalledWith(
+        2,
+        '[ClaudeProvider] ERROR stack:',
+        testError.stack
+      );
+
       consoleErrorSpy.mockRestore();
     });
   });

apps/server/tests/unit/services/agent-service.test.ts

@@ -106,9 +106,9 @@ describe('agent-service.ts', () => {
       });
 
       expect(result.success).toBe(true);
-      // First call reads session file and metadata file (2 calls)
+      // First call reads session file, metadata file, and queue state file (3 calls)
       // Second call should reuse in-memory session (no additional calls)
-      expect(fs.readFile).toHaveBeenCalledTimes(2);
+      expect(fs.readFile).toHaveBeenCalledTimes(3);
     });
   });
 

apps/ui/package.json

@@ -44,6 +44,7 @@
     "@dnd-kit/utilities": "^3.2.2",
     "@lezer/highlight": "^1.2.3",
     "@radix-ui/react-checkbox": "^1.3.3",
+    "@radix-ui/react-collapsible": "^1.1.12",
     "@radix-ui/react-dialog": "^1.1.15",
     "@radix-ui/react-dropdown-menu": "^2.1.16",
     "@radix-ui/react-label": "^2.1.8",
@@ -74,10 +75,11 @@
     "react": "19.2.3",
     "react-dom": "19.2.3",
     "react-markdown": "^10.1.0",
-    "rehype-raw": "^7.0.0",
     "react-resizable-panels": "^3.0.6",
+    "rehype-raw": "^7.0.0",
     "sonner": "^2.0.7",
     "tailwind-merge": "^3.4.0",
+    "usehooks-ts": "^3.1.1",
     "zustand": "^5.0.9"
   },
   "optionalDependencies": {

apps/ui/src/components/dialogs/file-browser-dialog.tsx

@@ -1,15 +1,5 @@
-import { useState, useEffect, useRef, useCallback } from 'react';
-import {
-  FolderOpen,
-  Folder,
-  ChevronRight,
-  Home,
-  ArrowLeft,
-  HardDrive,
-  CornerDownLeft,
-  Clock,
-  X,
-} from 'lucide-react';
+import { useState, useEffect, useCallback } from 'react';
+import { FolderOpen, Folder, ChevronRight, HardDrive, Clock, X } from 'lucide-react';
 import {
   Dialog,
   DialogContent,
@@ -19,9 +9,11 @@ import {
   DialogTitle,
 } from '@/components/ui/dialog';
 import { Button } from '@/components/ui/button';
-import { Input } from '@/components/ui/input';
+import { PathInput } from '@/components/ui/path-input';
+import { Kbd, KbdGroup } from '@/components/ui/kbd';
 import { getJSON, setJSON } from '@/lib/storage';
 import { getDefaultWorkspaceDirectory, saveLastProjectDirectory } from '@/lib/workspace-config';
+import { useOSDetection } from '@/hooks';
 
 interface DirectoryEntry {
   name: string;
@@ -77,8 +69,8 @@ export function FileBrowserDialog({
   description = 'Navigate to your project folder or paste a path directly',
   initialPath,
 }: FileBrowserDialogProps) {
+  const { isMac } = useOSDetection();
   const [currentPath, setCurrentPath] = useState<string>('');
-  const [pathInput, setPathInput] = useState<string>('');
   const [parentPath, setParentPath] = useState<string | null>(null);
   const [directories, setDirectories] = useState<DirectoryEntry[]>([]);
   const [drives, setDrives] = useState<string[]>([]);
@@ -86,7 +78,6 @@ export function FileBrowserDialog({
   const [error, setError] = useState('');
   const [warning, setWarning] = useState('');
   const [recentFolders, setRecentFolders] = useState<string[]>([]);
-  const pathInputRef = useRef<HTMLInputElement>(null);
 
   // Load recent folders when dialog opens
   useEffect(() => {
@@ -120,7 +111,6 @@ export function FileBrowserDialog({
 
       if (result.success) {
         setCurrentPath(result.currentPath);
-        setPathInput(result.currentPath);
         setParentPath(result.parentPath);
         setDirectories(result.directories);
         setDrives(result.drives || []);
@@ -142,11 +132,10 @@ export function FileBrowserDialog({
     [browseDirectory]
   );
 
-  // Reset current path when dialog closes
+  // Reset state when dialog closes
   useEffect(() => {
     if (!open) {
       setCurrentPath('');
-      setPathInput('');
       setParentPath(null);
       setDirectories([]);
       setError('');
@@ -172,9 +161,6 @@ export function FileBrowserDialog({
           const pathToUse = initialPath || defaultDir;
 
           if (pathToUse) {
-            // Pre-fill the path input immediately
-            setPathInput(pathToUse);
-            // Then browse to that directory
             browseDirectory(pathToUse);
           } else {
             // No default directory, browse home directory
@@ -183,7 +169,6 @@ export function FileBrowserDialog({
         } catch {
           // If config fetch fails, try initialPath or fall back to home directory
           if (initialPath) {
-            setPathInput(initialPath);
             browseDirectory(initialPath);
           } else {
             browseDirectory();
@@ -199,34 +184,21 @@ export function FileBrowserDialog({
     browseDirectory(dir.path);
   };
 
-  const handleGoToParent = () => {
-    if (parentPath) {
-      browseDirectory(parentPath);
-    }
-  };
-
-  const handleGoHome = () => {
+  const handleGoHome = useCallback(() => {
     browseDirectory();
-  };
+  }, [browseDirectory]);
+
+  const handleNavigate = useCallback(
+    (path: string) => {
+      browseDirectory(path);
+    },
+    [browseDirectory]
+  );
 
   const handleSelectDrive = (drivePath: string) => {
     browseDirectory(drivePath);
   };
 
-  const handleGoToPath = () => {
-    const trimmedPath = pathInput.trim();
-    if (trimmedPath) {
-      browseDirectory(trimmedPath);
-    }
-  };
-
-  const handlePathInputKeyDown = (e: React.KeyboardEvent<HTMLInputElement>) => {
-    if (e.key === 'Enter') {
-      e.preventDefault();
-      handleGoToPath();
-    }
-  };
-
   const handleSelect = useCallback(() => {
     if (currentPath) {
       addRecentFolder(currentPath);
@@ -263,7 +235,7 @@ export function FileBrowserDialog({
 
   return (
     <Dialog open={open} onOpenChange={onOpenChange}>
-      <DialogContent className="bg-popover border-border max-w-3xl max-h-[85vh] overflow-hidden flex flex-col p-4">
+      <DialogContent className="bg-popover border-border max-w-3xl max-h-[85vh] overflow-hidden flex flex-col p-4 focus:outline-none focus-visible:outline-none">
         <DialogHeader className="pb-1">
           <DialogTitle className="flex items-center gap-2 text-base">
             <FolderOpen className="w-4 h-4 text-brand-500" />
@@ -275,31 +247,21 @@ export function FileBrowserDialog({
         </DialogHeader>
 
         <div className="flex flex-col gap-2 min-h-[350px] flex-1 overflow-hidden py-1">
-          {/* Direct path input */}
-          <div className="flex items-center gap-1.5">
-            <Input
-              ref={pathInputRef}
-              type="text"
-              placeholder="Paste or type a full path (e.g., /home/user/projects/myapp)"
-              value={pathInput}
-              onChange={(e) => setPathInput(e.target.value)}
-              onKeyDown={handlePathInputKeyDown}
-              className="flex-1 font-mono text-xs h-8"
-              data-testid="path-input"
-              disabled={loading}
-            />
-            <Button
-              variant="secondary"
-              size="sm"
-              onClick={handleGoToPath}
-              disabled={loading || !pathInput.trim()}
-              data-testid="go-to-path-button"
-              className="h-8 px-2"
-            >
-              <CornerDownLeft className="w-3.5 h-3.5 mr-1" />
-              Go
-            </Button>
-          </div>
+          {/* Path navigation */}
+          <PathInput
+            currentPath={currentPath}
+            parentPath={parentPath}
+            loading={loading}
+            error={!!error}
+            onNavigate={handleNavigate}
+            onHome={handleGoHome}
+            entries={directories.map((dir) => ({ ...dir, isDirectory: true }))}
+            onSelectEntry={(entry) => {
+              if (entry.isDirectory) {
+                handleSelectDirectory(entry);
+              }
+            }}
+          />
 
           {/* Recent folders */}
           {recentFolders.length > 0 && (
@@ -352,35 +314,8 @@ export function FileBrowserDialog({
             </div>
           )}
 
-          {/* Current path breadcrumb */}
-          <div className="flex items-center gap-1.5 p-2 rounded-md bg-sidebar-accent/10 border border-sidebar-border">
-            <Button
-              variant="ghost"
-              size="sm"
-              onClick={handleGoHome}
-              className="h-6 px-1.5"
-              disabled={loading}
-            >
-              <Home className="w-3.5 h-3.5" />
-            </Button>
-            {parentPath && (
-              <Button
-                variant="ghost"
-                size="sm"
-                onClick={handleGoToParent}
-                className="h-6 px-1.5"
-                disabled={loading}
-              >
-                <ArrowLeft className="w-3.5 h-3.5" />
-              </Button>
-            )}
-            <div className="flex-1 font-mono text-xs truncate text-muted-foreground">
-              {currentPath || 'Loading...'}
-            </div>
-          </div>
-
           {/* Directory list */}
-          <div className="flex-1 overflow-y-auto border border-sidebar-border rounded-md">
+          <div className="flex-1 overflow-y-auto border border-sidebar-border rounded-md scrollbar-styled">
             {loading && (
               <div className="flex items-center justify-center h-full p-4">
                 <div className="text-xs text-muted-foreground">Loading directories...</div>
@@ -423,8 +358,8 @@ export function FileBrowserDialog({
           </div>
 
           <div className="text-[10px] text-muted-foreground">
-            Paste a full path above, or click on folders to navigate. Press Enter or click Go to
-            jump to a path.
+            Paste a full path above, or click on folders to navigate. Press Enter or click → to jump
+            to a path.
           </div>
         </div>
 
@@ -440,12 +375,10 @@ export function FileBrowserDialog({
           >
             <FolderOpen className="w-3.5 h-3.5 mr-1.5" />
             Select Current Folder
-            <kbd className="ml-2 px-1.5 py-0.5 text-[10px] bg-background/50 rounded border border-border">
-              {typeof navigator !== 'undefined' && navigator.platform?.includes('Mac')
-                ? '⌘'
-                : 'Ctrl'}
-              +↵
-            </kbd>
+            <KbdGroup className="ml-1">
+              <Kbd>{isMac ? '⌘' : 'Ctrl'}</Kbd>
+              <Kbd>↵</Kbd>
+            </KbdGroup>
           </Button>
         </DialogFooter>
       </DialogContent>

apps/ui/src/components/dialogs/new-project-modal.tsx

@@ -245,18 +245,21 @@ export function NewProjectModal({
           {/* Workspace Directory Display */}
           <div
             className={cn(
-              'flex items-center gap-2 text-sm',
+              'flex items-start gap-2 text-sm',
               errors.workspaceDir ? 'text-red-500' : 'text-muted-foreground'
             )}
           >
-            <Folder className="w-4 h-4 shrink-0" />
-            <span className="flex-1 min-w-0">
+            <Folder className="w-4 h-4 shrink-0 mt-0.5" />
+            <span className="flex-1 min-w-0 flex flex-col gap-1">
               {isLoadingWorkspace ? (
                 'Loading workspace...'
               ) : workspaceDir ? (
                 <>
-                  Will be created at:{' '}
-                  <code className="text-xs bg-muted px-1.5 py-0.5 rounded truncate">
+                  <span>Will be created at:</span>
+                  <code
+                    className="text-xs bg-muted px-1.5 py-0.5 rounded truncate block max-w-full"
+                    title={projectPath || workspaceDir}
+                  >
                     {projectPath || workspaceDir}
                   </code>
                 </>

apps/ui/src/components/layout/sidebar.tsx

@@ -28,8 +28,9 @@ import {
   useNavigation,
   useProjectCreation,
   useSetupDialog,
-  useTrashDialog,
+  useTrashOperations,
   useProjectTheme,
+  useUnviewedValidations,
 } from './sidebar/hooks';
 
 export function Sidebar() {
@@ -67,6 +68,9 @@ export function Sidebar() {
   // State for delete project confirmation dialog
   const [showDeleteProjectDialog, setShowDeleteProjectDialog] = useState(false);
 
+  // State for trash dialog
+  const [showTrashDialog, setShowTrashDialog] = useState(false);
+
   // Project theme management (must come before useProjectCreation which uses globalTheme)
   const { globalTheme } = useProjectTheme();
 
@@ -127,20 +131,20 @@ export function Sidebar() {
   // Running agents count
   const { runningAgentsCount } = useRunningAgents();
 
-  // Trash dialog and operations
+  // Unviewed validations count
+  const { count: unviewedValidationsCount } = useUnviewedValidations(currentProject);
+
+  // Trash operations
   const {
-    showTrashDialog,
-    setShowTrashDialog,
     activeTrashId,
     isEmptyingTrash,
     handleRestoreProject,
     handleDeleteProjectFromDisk,
     handleEmptyTrash,
-  } = useTrashDialog({
+  } = useTrashOperations({
     restoreTrashedProject,
     deleteTrashedProject,
     emptyTrash,
-    trashedProjects,
   });
 
   // Spec regeneration events
@@ -235,6 +239,7 @@ export function Sidebar() {
     setIsProjectPickerOpen,
     cyclePrevProject,
     cycleNextProject,
+    unviewedValidationsCount,
   });
 
   // Register keyboard shortcuts

apps/ui/src/components/layout/sidebar/components/project-selector-with-options.tsx

@@ -47,7 +47,6 @@ export function ProjectSelectorWithOptions({
   setIsProjectPickerOpen,
   setShowDeleteProjectDialog,
 }: ProjectSelectorWithOptionsProps) {
-  // Get data from store
   const {
     projects,
     currentProject,
@@ -59,25 +58,24 @@ export function ProjectSelectorWithOptions({
     clearProjectHistory,
   } = useAppStore();
 
-  // Get keyboard shortcuts
   const shortcuts = useKeyboardShortcutsConfig();
   const {
     projectSearchQuery,
     setProjectSearchQuery,
     selectedProjectIndex,
     projectSearchInputRef,
+    scrollContainerRef,
     filteredProjects,
   } = useProjectPicker({
     projects,
+    currentProject,
     isProjectPickerOpen,
     setIsProjectPickerOpen,
     setCurrentProject,
   });
 
-  // Drag-and-drop handlers
   const { sensors, handleDragEnd } = useDragAndDrop({ projects, reorderProjects });
 
-  // Theme management
   const {
     globalTheme,
     setTheme,
@@ -106,7 +104,6 @@ export function ProjectSelectorWithOptions({
               'shadow-sm shadow-black/5',
               'text-foreground titlebar-no-drag min-w-0',
               'transition-all duration-200 ease-out',
-              'hover:scale-[1.01] active:scale-[0.99]',
               isProjectPickerOpen &&
                 'from-brand-500/10 to-brand-600/5 border-brand-500/30 ring-2 ring-brand-500/20 shadow-lg shadow-brand-500/5'
             )}
@@ -139,7 +136,7 @@ export function ProjectSelectorWithOptions({
           align="start"
           data-testid="project-picker-dropdown"
         >
-          {/* Search input for type-ahead filtering */}
+          {/* Search input */}
           <div className="px-1 pb-2">
             <div className="relative">
               <Search className="absolute left-2.5 top-1/2 -translate-y-1/2 h-3.5 w-3.5 text-muted-foreground" />
@@ -150,10 +147,10 @@ export function ProjectSelectorWithOptions({
                 value={projectSearchQuery}
                 onChange={(e) => setProjectSearchQuery(e.target.value)}
                 className={cn(
-                  'w-full h-9 pl-8 pr-3 text-sm rounded-lg',
+                  'w-full h-8 pl-8 pr-3 text-sm rounded-lg',
                   'border border-border bg-background/50',
                   'text-foreground placeholder:text-muted-foreground',
-                  'focus:outline-none focus:ring-2 focus:ring-brand-500/30 focus:border-brand-500/50',
+                  'focus:outline-none focus:ring-1 focus:ring-brand-500/30 focus:border-brand-500/50',
                   'transition-all duration-200'
                 )}
                 data-testid="project-search-input"
@@ -175,7 +172,10 @@ export function ProjectSelectorWithOptions({
                 items={filteredProjects.map((p) => p.id)}
                 strategy={verticalListSortingStrategy}
               >
-                <div className="space-y-0.5 max-h-64 overflow-y-auto">
+                <div
+                  ref={scrollContainerRef}
+                  className="space-y-0.5 max-h-64 overflow-y-auto overflow-x-hidden scroll-smooth scrollbar-styled"
+                >
                   {filteredProjects.map((project, index) => (
                     <SortableProjectItem
                       key={project.id}
@@ -196,9 +196,9 @@ export function ProjectSelectorWithOptions({
           {/* Keyboard hint */}
           <div className="px-2 pt-2 mt-1.5 border-t border-border/50">
             <p className="text-[10px] text-muted-foreground text-center tracking-wide">
-              <span className="text-foreground/60">arrow</span> navigate{' '}
+              <span className="text-foreground/60">↑↓</span> navigate{' '}
               <span className="mx-1 text-foreground/30">|</span>{' '}
-              <span className="text-foreground/60">enter</span> select{' '}
+              <span className="text-foreground/60">↵</span> select{' '}
               <span className="mx-1 text-foreground/30">|</span>{' '}
               <span className="text-foreground/60">esc</span> close
             </p>
@@ -206,7 +206,7 @@ export function ProjectSelectorWithOptions({
         </DropdownMenuContent>
       </DropdownMenu>
 
-      {/* Project Options Menu - theme and history */}
+      {/* Project Options Menu */}
       {currentProject && (
         <DropdownMenu
           onOpenChange={(open) => {
@@ -223,8 +223,7 @@ export function ProjectSelectorWithOptions({
                 'text-muted-foreground hover:text-foreground',
                 'bg-transparent hover:bg-accent/60',
                 'border border-border/50 hover:border-border',
-                'transition-all duration-200 ease-out titlebar-no-drag',
-                'hover:scale-[1.02] active:scale-[0.98]'
+                'transition-all duration-200 ease-out titlebar-no-drag'
               )}
               title="Project options"
               data-testid="project-options-menu"
@@ -252,7 +251,6 @@ export function ProjectSelectorWithOptions({
                   setPreviewTheme(null);
                 }}
               >
-                {/* Use Global Option */}
                 <DropdownMenuRadioGroup
                   value={currentProject.theme || ''}
                   onValueChange={(value) => {
@@ -328,7 +326,7 @@ export function ProjectSelectorWithOptions({
               </DropdownMenuSubContent>
             </DropdownMenuSub>
 
-            {/* Project History Section - only show when there's history */}
+            {/* Project History Section */}
             {projectHistory.length > 1 && (
               <>
                 <DropdownMenuSeparator />

apps/ui/src/components/layout/sidebar/components/sidebar-navigation.tsx

@@ -78,14 +78,29 @@ export function SidebarNavigation({
                     title={!sidebarOpen ? item.label : undefined}
                     data-testid={`nav-${item.id}`}
                   >
-                    <Icon
-                      className={cn(
-                        'w-[18px] h-[18px] shrink-0 transition-all duration-200',
-                        isActive
-                          ? 'text-brand-500 drop-shadow-sm'
-                          : 'group-hover:text-brand-400 group-hover:scale-110'
+                    <div className="relative">
+                      <Icon
+                        className={cn(
+                          'w-[18px] h-[18px] shrink-0 transition-all duration-200',
+                          isActive
+                            ? 'text-brand-500 drop-shadow-sm'
+                            : 'group-hover:text-brand-400 group-hover:scale-110'
+                        )}
+                      />
+                      {/* Count badge for collapsed state */}
+                      {!sidebarOpen && item.count !== undefined && item.count > 0 && (
+                        <span
+                          className={cn(
+                            'absolute -top-1.5 -right-1.5 flex items-center justify-center',
+                            'min-w-4 h-4 px-1 text-[9px] font-bold rounded-full',
+                            'bg-primary text-primary-foreground shadow-sm',
+                            'animate-in fade-in zoom-in duration-200'
+                          )}
+                        >
+                          {item.count > 99 ? '99' : item.count}
+                        </span>
                       )}
-                    />
+                    </div>
                     <span
                       className={cn(
                         'ml-3 font-medium text-sm flex-1 text-left',
@@ -94,7 +109,21 @@ export function SidebarNavigation({
                     >
                       {item.label}
                     </span>
-                    {item.shortcut && sidebarOpen && (
+                    {/* Count badge */}
+                    {item.count !== undefined && item.count > 0 && sidebarOpen && (
+                      <span
+                        className={cn(
+                          'hidden lg:flex items-center justify-center',
+                          'min-w-5 h-5 px-1.5 text-[10px] font-bold rounded-full',
+                          'bg-primary text-primary-foreground shadow-sm',
+                          'animate-in fade-in zoom-in duration-200'
+                        )}
+                        data-testid={`count-${item.id}`}
+                      >
+                        {item.count > 99 ? '99+' : item.count}
+                      </span>
+                    )}
+                    {item.shortcut && sidebarOpen && !item.count && (
                       <span
                         className={cn(
                           'hidden lg:flex items-center justify-center min-w-5 h-5 px-1.5 text-[10px] font-mono rounded-md transition-all duration-200',

apps/ui/src/components/layout/sidebar/components/sortable-project-item.tsx

@@ -31,6 +31,7 @@ export function SortableProjectItem({
         isHighlighted && 'bg-brand-500/10 text-foreground ring-1 ring-brand-500/20'
       )}
       data-testid={`project-option-${project.id}`}
+      onClick={() => onSelect(project)}
     >
       {/* Drag Handle */}
       <button
@@ -43,9 +44,14 @@ export function SortableProjectItem({
         <GripVertical className="h-3.5 w-3.5 text-muted-foreground/60" />
       </button>
 
-      {/* Project content - clickable area */}
-      <div className="flex items-center gap-2.5 flex-1 min-w-0" onClick={() => onSelect(project)}>
-        <Folder className="h-4 w-4 shrink-0 text-muted-foreground" />
+      {/* Project content */}
+      <div className="flex items-center gap-2.5 flex-1 min-w-0">
+        <Folder
+          className={cn(
+            'h-4 w-4 shrink-0',
+            currentProjectId === project.id ? 'text-brand-500' : 'text-muted-foreground'
+          )}
+        />
         <span className="flex-1 truncate text-sm font-medium">{project.name}</span>
         {currentProjectId === project.id && <Check className="h-4 w-4 text-brand-500 shrink-0" />}
       </div>

apps/ui/src/components/layout/sidebar/dialogs/onboarding-dialog.tsx

@@ -37,11 +37,11 @@ export function OnboardingDialog({
       <DialogContent className="max-w-2xl bg-popover/95 backdrop-blur-xl">
         <DialogHeader>
           <div className="flex items-center gap-3 mb-2">
-            <div className="flex items-center justify-center w-12 h-12 rounded-full bg-brand-500/10 border border-brand-500/20">
+            <div className="flex items-center justify-center w-12 h-12 rounded-full bg-brand-500/10 border border-brand-500/20 shrink-0">
               <Rocket className="w-6 h-6 text-brand-500" />
             </div>
-            <div>
-              <DialogTitle className="text-2xl">Welcome to {newProjectName}!</DialogTitle>
+            <div className="min-w-0 flex-1">
+              <DialogTitle className="text-2xl truncate">Welcome to {newProjectName}!</DialogTitle>
               <DialogDescription className="text-muted-foreground mt-1">
                 Your new project is ready. Let&apos;s get you started.
               </DialogDescription>

apps/ui/src/components/layout/sidebar/dialogs/trash-dialog.tsx

@@ -1,3 +1,4 @@
+import { useState } from 'react';
 import { X, Trash2, Undo2 } from 'lucide-react';
 import {
   Dialog,
@@ -8,6 +9,8 @@ import {
   DialogTitle,
 } from '@/components/ui/dialog';
 import { Button } from '@/components/ui/button';
+import { DeleteConfirmDialog } from '@/components/ui/delete-confirm-dialog';
+import { ConfirmDialog } from '@/components/ui/confirm-dialog';
 import type { TrashedProject } from '@/lib/electron';
 
 interface TrashDialogProps {
@@ -33,84 +36,146 @@ export function TrashDialog({
   handleEmptyTrash,
   isEmptyingTrash,
 }: TrashDialogProps) {
+  // Confirmation dialog state (managed internally to avoid prop drilling)
+  const [deleteFromDiskProject, setDeleteFromDiskProject] = useState<TrashedProject | null>(null);
+  const [showEmptyTrashConfirm, setShowEmptyTrashConfirm] = useState(false);
+
+  // Reset confirmation dialog state when main dialog closes
+  const handleOpenChange = (isOpen: boolean) => {
+    if (!isOpen) {
+      setDeleteFromDiskProject(null);
+      setShowEmptyTrashConfirm(false);
+    }
+    onOpenChange(isOpen);
+  };
+
+  const onDeleteFromDiskClick = (project: TrashedProject) => {
+    setDeleteFromDiskProject(project);
+  };
+
+  const onConfirmDeleteFromDisk = () => {
+    if (deleteFromDiskProject) {
+      handleDeleteProjectFromDisk(deleteFromDiskProject);
+      setDeleteFromDiskProject(null);
+    }
+  };
+
+  const onEmptyTrashClick = () => {
+    setShowEmptyTrashConfirm(true);
+  };
+
+  const onConfirmEmptyTrash = () => {
+    handleEmptyTrash();
+    setShowEmptyTrashConfirm(false);
+  };
+
   return (
-    <Dialog open={open} onOpenChange={onOpenChange}>
-      <DialogContent className="bg-popover/95 backdrop-blur-xl border-border max-w-2xl">
-        <DialogHeader>
-          <DialogTitle>Recycle Bin</DialogTitle>
-          <DialogDescription className="text-muted-foreground">
-            Restore projects to the sidebar or delete their folders using your system Trash.
-          </DialogDescription>
-        </DialogHeader>
+    <>
+      <Dialog open={open} onOpenChange={handleOpenChange}>
+        <DialogContent className="bg-popover/95 backdrop-blur-xl border-border max-w-2xl">
+          <DialogHeader>
+            <DialogTitle>Recycle Bin</DialogTitle>
+            <DialogDescription className="text-muted-foreground">
+              Restore projects to the sidebar or delete their folders using your system Trash.
+            </DialogDescription>
+          </DialogHeader>
 
-        {trashedProjects.length === 0 ? (
-          <p className="text-sm text-muted-foreground">Recycle bin is empty.</p>
-        ) : (
-          <div className="space-y-3 max-h-[360px] overflow-y-auto pr-1">
-            {trashedProjects.map((project) => (
-              <div
-                key={project.id}
-                className="flex items-start justify-between gap-3 rounded-lg border border-border bg-card/50 p-4"
-              >
-                <div className="space-y-1 min-w-0">
-                  <p className="text-sm font-medium text-foreground truncate">{project.name}</p>
-                  <p className="text-xs text-muted-foreground break-all">{project.path}</p>
-                  <p className="text-[11px] text-muted-foreground/80">
-                    Trashed {new Date(project.trashedAt).toLocaleString()}
-                  </p>
+          {trashedProjects.length === 0 ? (
+            <p className="text-sm text-muted-foreground">Recycle bin is empty.</p>
+          ) : (
+            <div className="space-y-3 max-h-[360px] overflow-y-auto pr-1">
+              {trashedProjects.map((project) => (
+                <div
+                  key={project.id}
+                  className="flex items-start justify-between gap-3 rounded-lg border border-border bg-card/50 p-4"
+                >
+                  <div className="space-y-1 min-w-0">
+                    <p className="text-sm font-medium text-foreground truncate">{project.name}</p>
+                    <p className="text-xs text-muted-foreground break-all">{project.path}</p>
+                    <p className="text-[11px] text-muted-foreground/80">
+                      Trashed {new Date(project.trashedAt).toLocaleString()}
+                    </p>
+                  </div>
+                  <div className="flex flex-col gap-2 shrink-0">
+                    <Button
+                      size="sm"
+                      variant="secondary"
+                      onClick={() => handleRestoreProject(project.id)}
+                      data-testid={`restore-project-${project.id}`}
+                    >
+                      <Undo2 className="h-3.5 w-3.5 mr-1.5" />
+                      Restore
+                    </Button>
+                    <Button
+                      size="sm"
+                      variant="destructive"
+                      onClick={() => onDeleteFromDiskClick(project)}
+                      disabled={activeTrashId === project.id}
+                      data-testid={`delete-project-disk-${project.id}`}
+                    >
+                      <Trash2 className="h-3.5 w-3.5 mr-1.5" />
+                      {activeTrashId === project.id ? 'Deleting...' : 'Delete from disk'}
+                    </Button>
+                    <Button
+                      size="sm"
+                      variant="ghost"
+                      className="text-muted-foreground hover:text-foreground"
+                      onClick={() => deleteTrashedProject(project.id)}
+                      data-testid={`remove-project-${project.id}`}
+                    >
+                      <X className="h-3.5 w-3.5 mr-1.5" />
+                      Remove from list
+                    </Button>
+                  </div>
                 </div>
-                <div className="flex flex-col gap-2 shrink-0">
-                  <Button
-                    size="sm"
-                    variant="secondary"
-                    onClick={() => handleRestoreProject(project.id)}
-                    data-testid={`restore-project-${project.id}`}
-                  >
-                    <Undo2 className="h-3.5 w-3.5 mr-1.5" />
-                    Restore
-                  </Button>
-                  <Button
-                    size="sm"
-                    variant="destructive"
-                    onClick={() => handleDeleteProjectFromDisk(project)}
-                    disabled={activeTrashId === project.id}
-                    data-testid={`delete-project-disk-${project.id}`}
-                  >
-                    <Trash2 className="h-3.5 w-3.5 mr-1.5" />
-                    {activeTrashId === project.id ? 'Deleting...' : 'Delete from disk'}
-                  </Button>
-                  <Button
-                    size="sm"
-                    variant="ghost"
-                    className="text-muted-foreground hover:text-foreground"
-                    onClick={() => deleteTrashedProject(project.id)}
-                    data-testid={`remove-project-${project.id}`}
-                  >
-                    <X className="h-3.5 w-3.5 mr-1.5" />
-                    Remove from list
-                  </Button>
-                </div>
-              </div>
-            ))}
-          </div>
-        )}
-
-        <DialogFooter className="flex justify-between">
-          <Button variant="ghost" onClick={() => onOpenChange(false)}>
-            Close
-          </Button>
-          {trashedProjects.length > 0 && (
-            <Button
-              variant="outline"
-              onClick={handleEmptyTrash}
-              disabled={isEmptyingTrash}
-              data-testid="empty-trash"
-            >
-              {isEmptyingTrash ? 'Clearing...' : 'Empty Recycle Bin'}
-            </Button>
+              ))}
+            </div>
           )}
-        </DialogFooter>
-      </DialogContent>
-    </Dialog>
+
+          <DialogFooter className="flex justify-between">
+            <Button variant="ghost" onClick={() => onOpenChange(false)}>
+              Close
+            </Button>
+            {trashedProjects.length > 0 && (
+              <Button
+                variant="outline"
+                onClick={onEmptyTrashClick}
+                disabled={isEmptyingTrash}
+                data-testid="empty-trash"
+              >
+                {isEmptyingTrash ? 'Clearing...' : 'Empty Recycle Bin'}
+              </Button>
+            )}
+          </DialogFooter>
+        </DialogContent>
+      </Dialog>
+
+      {/* Delete from disk confirmation dialog */}
+      {deleteFromDiskProject && (
+        <DeleteConfirmDialog
+          open
+          onOpenChange={(isOpen) => !isOpen && setDeleteFromDiskProject(null)}
+          onConfirm={onConfirmDeleteFromDisk}
+          title={`Delete "${deleteFromDiskProject.name}" from disk?`}
+          description="This sends the folder to your system Trash."
+          confirmText="Delete from disk"
+          testId="delete-from-disk-confirm-dialog"
+          confirmTestId="confirm-delete-from-disk-button"
+        />
+      )}
+
+      {/* Empty trash confirmation dialog */}
+      <ConfirmDialog
+        open={showEmptyTrashConfirm}
+        onOpenChange={setShowEmptyTrashConfirm}
+        onConfirm={onConfirmEmptyTrash}
+        title="Empty Recycle Bin"
+        description="Clear all projects from recycle bin? This does not delete folders from disk."
+        confirmText="Empty"
+        confirmVariant="destructive"
+        icon={Trash2}
+        iconClassName="text-destructive"
+      />
+    </>
   );
 }

apps/ui/src/components/layout/sidebar/hooks/index.ts

@@ -8,5 +8,5 @@ export { useSpecRegeneration } from './use-spec-regeneration';
 export { useNavigation } from './use-navigation';
 export { useProjectCreation } from './use-project-creation';
 export { useSetupDialog } from './use-setup-dialog';
-export { useTrashDialog } from './use-trash-dialog';
 export { useProjectTheme } from './use-project-theme';
+export { useUnviewedValidations } from './use-unviewed-validations';

apps/ui/src/components/layout/sidebar/hooks/use-navigation.ts

@@ -44,6 +44,8 @@ interface UseNavigationProps {
   setIsProjectPickerOpen: (value: boolean | ((prev: boolean) => boolean)) => void;
   cyclePrevProject: () => void;
   cycleNextProject: () => void;
+  /** Count of unviewed validations to show on GitHub Issues nav item */
+  unviewedValidationsCount?: number;
 }
 
 export function useNavigation({
@@ -61,6 +63,7 @@ export function useNavigation({
   setIsProjectPickerOpen,
   cyclePrevProject,
   cycleNextProject,
+  unviewedValidationsCount,
 }: UseNavigationProps) {
   // Track if current project has a GitHub remote
   const [hasGitHubRemote, setHasGitHubRemote] = useState(false);
@@ -169,6 +172,7 @@ export function useNavigation({
             id: 'github-issues',
             label: 'Issues',
             icon: CircleDot,
+            count: unviewedValidationsCount,
           },
           {
             id: 'github-prs',
@@ -180,7 +184,15 @@ export function useNavigation({
     }
 
     return sections;
-  }, [shortcuts, hideSpecEditor, hideContext, hideTerminal, hideAiProfiles, hasGitHubRemote]);
+  }, [
+    shortcuts,
+    hideSpecEditor,
+    hideContext,
+    hideTerminal,
+    hideAiProfiles,
+    hasGitHubRemote,
+    unviewedValidationsCount,
+  ]);
 
   // Build keyboard shortcuts for navigation
   const navigationShortcuts: KeyboardShortcut[] = useMemo(() => {

apps/ui/src/components/layout/sidebar/hooks/use-project-picker.ts

@@ -3,6 +3,7 @@ import type { Project } from '@/lib/electron';
 
 interface UseProjectPickerProps {
   projects: Project[];
+  currentProject: Project | null;
   isProjectPickerOpen: boolean;
   setIsProjectPickerOpen: (value: boolean | ((prev: boolean) => boolean)) => void;
   setCurrentProject: (project: Project) => void;
@@ -10,6 +11,7 @@ interface UseProjectPickerProps {
 
 export function useProjectPicker({
   projects,
+  currentProject,
   isProjectPickerOpen,
   setIsProjectPickerOpen,
   setCurrentProject,
@@ -17,6 +19,7 @@ export function useProjectPicker({
   const [projectSearchQuery, setProjectSearchQuery] = useState('');
   const [selectedProjectIndex, setSelectedProjectIndex] = useState(0);
   const projectSearchInputRef = useRef<HTMLInputElement>(null);
+  const scrollContainerRef = useRef<HTMLDivElement>(null);
 
   // Filtered projects based on search query
   const filteredProjects = useMemo(() => {
@@ -27,29 +30,67 @@ export function useProjectPicker({
     return projects.filter((project) => project.name.toLowerCase().includes(query));
   }, [projects, projectSearchQuery]);
 
-  // Reset selection when filtered results change
-  useEffect(() => {
-    setSelectedProjectIndex(0);
-  }, [filteredProjects.length, projectSearchQuery]);
+  // Helper function to scroll to a specific project
+  const scrollToProject = useCallback((projectId: string) => {
+    if (!scrollContainerRef.current) return;
 
-  // Reset search query when dropdown closes
-  useEffect(() => {
-    if (!isProjectPickerOpen) {
-      setProjectSearchQuery('');
-      setSelectedProjectIndex(0);
+    const element = scrollContainerRef.current.querySelector(
+      `[data-testid="project-option-${projectId}"]`
+    );
+
+    if (element) {
+      element.scrollIntoView({
+        behavior: 'smooth',
+        block: 'nearest',
+      });
     }
-  }, [isProjectPickerOpen]);
+  }, []);
 
-  // Focus the search input when dropdown opens
+  // On open/close, handle search query reset and focus
   useEffect(() => {
     if (isProjectPickerOpen) {
-      // Small delay to ensure the dropdown is rendered
-      setTimeout(() => {
+      // Focus search input after DOM renders
+      requestAnimationFrame(() => {
         projectSearchInputRef.current?.focus();
-      }, 0);
+      });
+    } else {
+      // Reset search when closing
+      setProjectSearchQuery('');
     }
   }, [isProjectPickerOpen]);
 
+  // Update selection when search query changes (while picker is open)
+  useEffect(() => {
+    if (!isProjectPickerOpen) {
+      setSelectedProjectIndex(0);
+      return;
+    }
+
+    if (projectSearchQuery.trim()) {
+      // When searching, reset to first result
+      setSelectedProjectIndex(0);
+    } else {
+      // When not searching (e.g., on open or search cleared), find and select the current project
+      const currentIndex = currentProject
+        ? filteredProjects.findIndex((p) => p.id === currentProject.id)
+        : -1;
+      setSelectedProjectIndex(currentIndex !== -1 ? currentIndex : 0);
+    }
+  }, [isProjectPickerOpen, projectSearchQuery, filteredProjects, currentProject]);
+
+  // Scroll to highlighted item when selection changes
+  useEffect(() => {
+    if (!isProjectPickerOpen) return;
+
+    const targetProject = filteredProjects[selectedProjectIndex];
+    if (targetProject) {
+      // Use requestAnimationFrame to ensure DOM is rendered before scrolling
+      requestAnimationFrame(() => {
+        scrollToProject(targetProject.id);
+      });
+    }
+  }, [selectedProjectIndex, isProjectPickerOpen, filteredProjects, scrollToProject]);
+
   // Handle selecting the currently highlighted project
   const selectHighlightedProject = useCallback(() => {
     if (filteredProjects.length > 0 && selectedProjectIndex < filteredProjects.length) {
@@ -99,6 +140,7 @@ export function useProjectPicker({
     selectedProjectIndex,
     setSelectedProjectIndex,
     projectSearchInputRef,
+    scrollContainerRef,
     filteredProjects,
     selectHighlightedProject,
   };

apps/ui/src/components/layout/sidebar/hooks/use-trash-dialog.ts

@@ -1,40 +0,0 @@
-import { useState } from 'react';
-import { useTrashOperations } from './use-trash-operations';
-import type { TrashedProject } from '@/lib/electron';
-
-interface UseTrashDialogProps {
-  restoreTrashedProject: (projectId: string) => void;
-  deleteTrashedProject: (projectId: string) => void;
-  emptyTrash: () => void;
-  trashedProjects: TrashedProject[];
-}
-
-/**
- * Hook that combines trash operations with dialog state management
- */
-export function useTrashDialog({
-  restoreTrashedProject,
-  deleteTrashedProject,
-  emptyTrash,
-  trashedProjects,
-}: UseTrashDialogProps) {
-  // Dialog state
-  const [showTrashDialog, setShowTrashDialog] = useState(false);
-
-  // Reuse existing trash operations logic
-  const trashOperations = useTrashOperations({
-    restoreTrashedProject,
-    deleteTrashedProject,
-    emptyTrash,
-    trashedProjects,
-  });
-
-  return {
-    // Dialog state
-    showTrashDialog,
-    setShowTrashDialog,
-
-    // Trash operations (spread from existing hook)
-    ...trashOperations,
-  };
-}

apps/ui/src/components/layout/sidebar/hooks/use-trash-operations.ts

@@ -6,35 +6,35 @@ interface UseTrashOperationsProps {
   restoreTrashedProject: (projectId: string) => void;
   deleteTrashedProject: (projectId: string) => void;
   emptyTrash: () => void;
-  trashedProjects: TrashedProject[];
 }
 
 export function useTrashOperations({
   restoreTrashedProject,
   deleteTrashedProject,
   emptyTrash,
-  trashedProjects,
 }: UseTrashOperationsProps) {
   const [activeTrashId, setActiveTrashId] = useState<string | null>(null);
   const [isEmptyingTrash, setIsEmptyingTrash] = useState(false);
 
   const handleRestoreProject = useCallback(
     (projectId: string) => {
-      restoreTrashedProject(projectId);
-      toast.success('Project restored', {
-        description: 'Added back to your project list.',
-      });
+      try {
+        restoreTrashedProject(projectId);
+        toast.success('Project restored', {
+          description: 'Added back to your project list.',
+        });
+      } catch (error) {
+        console.error('[Sidebar] Failed to restore project:', error);
+        toast.error('Failed to restore project', {
+          description: error instanceof Error ? error.message : 'Unknown error',
+        });
+      }
     },
     [restoreTrashedProject]
   );
 
   const handleDeleteProjectFromDisk = useCallback(
     async (trashedProject: TrashedProject) => {
-      const confirmed = window.confirm(
-        `Delete "${trashedProject.name}" from disk?\nThis sends the folder to your system Trash.`
-      );
-      if (!confirmed) return;
-
       setActiveTrashId(trashedProject.id);
       try {
         const api = getElectronAPI();
@@ -64,23 +64,19 @@ export function useTrashOperations({
   );
 
   const handleEmptyTrash = useCallback(() => {
-    if (trashedProjects.length === 0) {
-      return;
-    }
-
-    const confirmed = window.confirm(
-      'Clear all projects from recycle bin? This does not delete folders from disk.'
-    );
-    if (!confirmed) return;
-
     setIsEmptyingTrash(true);
     try {
       emptyTrash();
       toast.success('Recycle bin cleared');
+    } catch (error) {
+      console.error('[Sidebar] Failed to empty trash:', error);
+      toast.error('Failed to clear recycle bin', {
+        description: error instanceof Error ? error.message : 'Unknown error',
+      });
     } finally {
       setIsEmptyingTrash(false);
     }
-  }, [emptyTrash, trashedProjects.length]);
+  }, [emptyTrash]);
 
   return {
     activeTrashId,

apps/ui/src/components/layout/sidebar/hooks/use-unviewed-validations.ts

@@ -0,0 +1,82 @@
+import { useState, useEffect, useCallback, useRef } from 'react';
+import { getElectronAPI } from '@/lib/electron';
+import type { Project, StoredValidation } from '@/lib/electron';
+
+/**
+ * Hook to track the count of unviewed (fresh) issue validations for a project.
+ * Also provides a function to decrement the count when a validation is viewed.
+ */
+export function useUnviewedValidations(currentProject: Project | null) {
+  const [count, setCount] = useState(0);
+  const projectPathRef = useRef<string | null>(null);
+
+  // Keep project path in ref for use in async functions
+  useEffect(() => {
+    projectPathRef.current = currentProject?.path ?? null;
+  }, [currentProject?.path]);
+
+  // Fetch and update count from server
+  const fetchUnviewedCount = useCallback(async () => {
+    const projectPath = projectPathRef.current;
+    if (!projectPath) return;
+
+    try {
+      const api = getElectronAPI();
+      if (api.github?.getValidations) {
+        const result = await api.github.getValidations(projectPath);
+        if (result.success && result.validations) {
+          const unviewed = result.validations.filter((v: StoredValidation) => {
+            if (v.viewedAt) return false;
+            // Check if not stale (< 24 hours)
+            const hoursSince = (Date.now() - new Date(v.validatedAt).getTime()) / (1000 * 60 * 60);
+            return hoursSince <= 24;
+          });
+          // Only update count if we're still on the same project (guard against race condition)
+          if (projectPathRef.current === projectPath) {
+            setCount(unviewed.length);
+          }
+        }
+      }
+    } catch (err) {
+      console.error('[useUnviewedValidations] Failed to load count:', err);
+    }
+  }, []);
+
+  // Load initial count and subscribe to events
+  useEffect(() => {
+    if (!currentProject?.path) {
+      setCount(0);
+      return;
+    }
+
+    // Load initial count
+    fetchUnviewedCount();
+
+    // Subscribe to validation events to update count
+    const api = getElectronAPI();
+    if (api.github?.onValidationEvent) {
+      const unsubscribe = api.github.onValidationEvent((event) => {
+        if (event.projectPath === currentProject.path) {
+          if (event.type === 'issue_validation_complete') {
+            // New validation completed - refresh count from server for consistency
+            fetchUnviewedCount();
+          } else if (event.type === 'issue_validation_viewed') {
+            // Validation was viewed - refresh count from server for consistency
+            fetchUnviewedCount();
+          }
+        }
+      });
+      return () => unsubscribe();
+    }
+  }, [currentProject?.path, fetchUnviewedCount]);
+
+  // Function to decrement count when a validation is viewed
+  const decrementCount = useCallback(() => {
+    setCount((prev) => Math.max(0, prev - 1));
+  }, []);
+
+  // Expose refreshCount as an alias to fetchUnviewedCount for external use
+  const refreshCount = fetchUnviewedCount;
+
+  return { count, decrementCount, refreshCount };
+}

apps/ui/src/components/layout/sidebar/types.ts

@@ -11,6 +11,8 @@ export interface NavItem {
   label: string;
   icon: React.ComponentType<{ className?: string }>;
   shortcut?: string;
+  /** Optional count badge to display next to the nav item */
+  count?: number;
 }
 
 export interface SortableProjectItemProps {

apps/ui/src/components/ui/breadcrumb.tsx

@@ -0,0 +1,102 @@
+import * as React from 'react';
+import { Slot } from '@radix-ui/react-slot';
+import { ChevronRight, MoreHorizontal } from 'lucide-react';
+
+import { cn } from '@/lib/utils';
+
+function Breadcrumb({ ...props }: React.ComponentProps<'nav'>) {
+  return <nav aria-label="breadcrumb" data-slot="breadcrumb" {...props} />;
+}
+
+function BreadcrumbList({ className, ...props }: React.ComponentProps<'ol'>) {
+  return (
+    <ol
+      data-slot="breadcrumb-list"
+      className={cn(
+        'text-muted-foreground flex flex-wrap items-center gap-1.5 text-sm break-words sm:gap-2.5',
+        className
+      )}
+      {...props}
+    />
+  );
+}
+
+function BreadcrumbItem({ className, ...props }: React.ComponentProps<'li'>) {
+  return (
+    <li
+      data-slot="breadcrumb-item"
+      className={cn('inline-flex items-center gap-1.5', className)}
+      {...props}
+    />
+  );
+}
+
+function BreadcrumbLink({
+  asChild,
+  className,
+  ...props
+}: React.ComponentProps<'a'> & {
+  asChild?: boolean;
+}) {
+  const Comp = asChild ? Slot : 'a';
+
+  return (
+    <Comp
+      data-slot="breadcrumb-link"
+      className={cn('hover:text-foreground transition-colors', className)}
+      {...props}
+    />
+  );
+}
+
+function BreadcrumbPage({ className, ...props }: React.ComponentProps<'span'>) {
+  return (
+    <span
+      data-slot="breadcrumb-page"
+      role="link"
+      aria-disabled="true"
+      aria-current="page"
+      className={cn('text-foreground font-normal', className)}
+      {...props}
+    />
+  );
+}
+
+function BreadcrumbSeparator({ children, className, ...props }: React.ComponentProps<'li'>) {
+  return (
+    <li
+      data-slot="breadcrumb-separator"
+      role="presentation"
+      aria-hidden="true"
+      className={cn('[&>svg]:size-3.5', className)}
+      {...props}
+    >
+      {children ?? <ChevronRight />}
+    </li>
+  );
+}
+
+function BreadcrumbEllipsis({ className, ...props }: React.ComponentProps<'span'>) {
+  return (
+    <span
+      data-slot="breadcrumb-ellipsis"
+      role="presentation"
+      aria-hidden="true"
+      className={cn('flex size-9 items-center justify-center', className)}
+      {...props}
+    >
+      <MoreHorizontal className="size-4" />
+      <span className="sr-only">More</span>
+    </span>
+  );
+}
+
+export {
+  Breadcrumb,
+  BreadcrumbList,
+  BreadcrumbItem,
+  BreadcrumbLink,
+  BreadcrumbPage,
+  BreadcrumbSeparator,
+  BreadcrumbEllipsis,
+};

apps/ui/src/components/ui/collapsible.tsx

@@ -0,0 +1,10 @@
+import * as React from 'react';
+import * as CollapsiblePrimitive from '@radix-ui/react-collapsible';
+
+const Collapsible = CollapsiblePrimitive.Root;
+
+const CollapsibleTrigger = CollapsiblePrimitive.CollapsibleTrigger;
+
+const CollapsibleContent = CollapsiblePrimitive.CollapsibleContent;
+
+export { Collapsible, CollapsibleTrigger, CollapsibleContent };

apps/ui/src/components/ui/confirm-dialog.tsx

@@ -0,0 +1,83 @@
+import type { ReactNode } from 'react';
+import { LucideIcon } from 'lucide-react';
+import {
+  Dialog,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+} from '@/components/ui/dialog';
+import { Button } from '@/components/ui/button';
+import { HotkeyButton } from '@/components/ui/hotkey-button';
+
+interface ConfirmDialogProps {
+  open: boolean;
+  onOpenChange: (open: boolean) => void;
+  onConfirm: () => void;
+  title: string;
+  description: string;
+  /** Optional icon to show in the title */
+  icon?: LucideIcon;
+  /** Icon color class. Defaults to "text-primary" */
+  iconClassName?: string;
+  /** Optional content to show between description and buttons */
+  children?: ReactNode;
+  /** Text for the confirm button. Defaults to "Confirm" */
+  confirmText?: string;
+  /** Text for the cancel button. Defaults to "Cancel" */
+  cancelText?: string;
+  /** Variant for the confirm button. Defaults to "default" */
+  confirmVariant?: 'default' | 'destructive' | 'outline' | 'secondary' | 'ghost' | 'link';
+}
+
+export function ConfirmDialog({
+  open,
+  onOpenChange,
+  onConfirm,
+  title,
+  description,
+  icon: Icon,
+  iconClassName = 'text-primary',
+  children,
+  confirmText = 'Confirm',
+  cancelText = 'Cancel',
+  confirmVariant = 'default',
+}: ConfirmDialogProps) {
+  const handleConfirm = () => {
+    onConfirm();
+    onOpenChange(false);
+  };
+
+  return (
+    <Dialog open={open} onOpenChange={onOpenChange}>
+      <DialogContent className="bg-popover border-border max-w-md">
+        <DialogHeader>
+          <DialogTitle className="flex items-center gap-2">
+            {Icon && <Icon className={`w-5 h-5 ${iconClassName}`} />}
+            {title}
+          </DialogTitle>
+          <DialogDescription className="text-muted-foreground">{description}</DialogDescription>
+        </DialogHeader>
+
+        {children}
+
+        <DialogFooter className="gap-2 sm:gap-2 pt-4">
+          <Button variant="ghost" onClick={() => onOpenChange(false)} className="px-4">
+            {cancelText}
+          </Button>
+          <HotkeyButton
+            variant={confirmVariant}
+            onClick={handleConfirm}
+            hotkey={{ key: 'Enter', cmdCtrl: true }}
+            hotkeyActive={open}
+            className="px-4"
+          >
+            {Icon && <Icon className="w-4 h-4 mr-2" />}
+            {confirmText}
+          </HotkeyButton>
+        </DialogFooter>
+      </DialogContent>
+    </Dialog>
+  );
+}

apps/ui/src/components/ui/error-state.tsx

@@ -0,0 +1,36 @@
+import { CircleDot, RefreshCw } from 'lucide-react';
+import { Button } from './button';
+
+interface ErrorStateProps {
+  /** Error message to display */
+  error: string;
+  /** Title for the error state (default: "Failed to Load") */
+  title?: string;
+  /** Callback when retry button is clicked */
+  onRetry?: () => void;
+  /** Text for the retry button (default: "Try Again") */
+  retryText?: string;
+}
+
+export function ErrorState({
+  error,
+  title = 'Failed to Load',
+  onRetry,
+  retryText = 'Try Again',
+}: ErrorStateProps) {
+  return (
+    <div className="flex-1 flex flex-col items-center justify-center text-center p-6">
+      <div className="p-4 rounded-full bg-destructive/10 mb-4">
+        <CircleDot className="h-12 w-12 text-destructive" />
+      </div>
+      <h2 className="text-lg font-medium mb-2">{title}</h2>
+      <p className="text-muted-foreground max-w-md mb-4">{error}</p>
+      {onRetry && (
+        <Button variant="outline" onClick={onRetry}>
+          <RefreshCw className="h-4 w-4 mr-2" />
+          {retryText}
+        </Button>
+      )}
+    </div>
+  );
+}

apps/ui/src/components/ui/kbd.tsx

@@ -0,0 +1,28 @@
+import { cn } from '@/lib/utils';
+
+function Kbd({ className, ...props }: React.ComponentProps<'kbd'>) {
+  return (
+    <kbd
+      data-slot="kbd"
+      className={cn(
+        'bg-muted text-muted-foreground pointer-events-none inline-flex h-5 w-fit min-w-5 items-center justify-center gap-1 rounded-sm px-1 font-sans text-xs font-medium select-none',
+        "[&_svg:not([class*='size-'])]:size-3",
+        'in-data-[slot=tooltip-content]:bg-background/20 in-data-[slot=tooltip-content]:text-background dark:in-data-[slot=tooltip-content]:bg-background/10',
+        className
+      )}
+      {...props}
+    />
+  );
+}
+
+function KbdGroup({ className, ...props }: React.ComponentProps<'span'>) {
+  return (
+    <span
+      data-slot="kbd-group"
+      className={cn('inline-flex items-center gap-1', className)}
+      {...props}
+    />
+  );
+}
+
+export { Kbd, KbdGroup };

apps/ui/src/components/ui/loading-state.tsx

@@ -0,0 +1,17 @@
+import { Loader2 } from 'lucide-react';
+
+interface LoadingStateProps {
+  /** Optional custom message to display below the spinner */
+  message?: string;
+  /** Optional custom size class for the spinner (default: h-8 w-8) */
+  size?: string;
+}
+
+export function LoadingState({ message, size = 'h-8 w-8' }: LoadingStateProps) {
+  return (
+    <div className="flex-1 flex flex-col items-center justify-center">
+      <Loader2 className={`${size} animate-spin text-muted-foreground`} />
+      {message && <p className="mt-4 text-sm text-muted-foreground">{message}</p>}
+    </div>
+  );
+}

apps/ui/src/components/ui/path-input.tsx

@@ -0,0 +1,442 @@
+import { useEffect, Fragment, FocusEvent, KeyboardEvent, MouseEvent } from 'react';
+import { useState, useRef, useCallback, useMemo } from 'react';
+import { Home, ArrowLeft, Pencil, ArrowRight, Search, Folder, File, X } from 'lucide-react';
+import { Button } from '@/components/ui/button';
+import { Input } from '@/components/ui/input';
+import { Kbd } from '@/components/ui/kbd';
+import {
+  Breadcrumb,
+  BreadcrumbList,
+  BreadcrumbItem,
+  BreadcrumbLink,
+  BreadcrumbPage,
+  BreadcrumbSeparator,
+} from '@/components/ui/breadcrumb';
+import {
+  Command,
+  CommandInput,
+  CommandList,
+  CommandEmpty,
+  CommandGroup,
+  CommandItem,
+} from '@/components/ui/command';
+import { cn } from '@/lib/utils';
+
+interface BreadcrumbSegment {
+  name: string;
+  path: string;
+  isLast: boolean;
+}
+
+function parseBreadcrumbs(path: string): BreadcrumbSegment[] {
+  if (!path) return [];
+
+  // Handle root path on Unix-like systems
+  if (path === '/') {
+    return [{ name: '/', path: '/', isLast: true }];
+  }
+
+  const segments = path.split(/[/\\]/).filter(Boolean);
+  const isWindows = segments[0]?.includes(':');
+
+  return segments.map((segment, index) => {
+    let fullPath: string;
+
+    if (isWindows) {
+      const pathParts = segments.slice(0, index + 1);
+      if (index === 0) {
+        fullPath = `${pathParts[0]}\\`;
+      } else {
+        fullPath = pathParts.join('\\');
+      }
+    } else {
+      fullPath = '/' + segments.slice(0, index + 1).join('/');
+    }
+
+    return {
+      name: segment,
+      path: fullPath,
+      isLast: index === segments.length - 1,
+    };
+  });
+}
+
+interface FileSystemEntry {
+  name: string;
+  path: string;
+  isDirectory: boolean;
+}
+
+interface PathInputProps {
+  /** Current resolved path */
+  currentPath: string;
+  /** Parent path for back navigation (null if at root) */
+  parentPath: string | null;
+  /** Whether the component is in a loading state */
+  loading?: boolean;
+  /** Whether there's an error (shows input mode and red border when true) */
+  error?: boolean;
+  /** Placeholder text for the input field */
+  placeholder?: string;
+  /** Placeholder text for the search input field */
+  searchPlaceholder?: string;
+  /** Called when user navigates to a path (via breadcrumb click, enter key, or navigation buttons) */
+  onNavigate: (path: string) => void;
+  /** Called when user clicks home button (navigates to home directory) */
+  onHome: () => void;
+  /** Additional className for the container */
+  className?: string;
+  /** List of files and directories in current path for search functionality */
+  entries?: FileSystemEntry[];
+  /** Called when user selects an entry from search results */
+  onSelectEntry?: (entry: FileSystemEntry) => void;
+}
+
+function PathInput({
+  currentPath,
+  parentPath,
+  loading = false,
+  error,
+  placeholder = 'Paste or type a full path (e.g., /home/user/projects/myapp)',
+  searchPlaceholder = 'Search...',
+  onNavigate,
+  onHome,
+  className,
+  entries = [],
+  onSelectEntry,
+}: PathInputProps) {
+  const [isEditing, setIsEditing] = useState(false);
+  const [isSearchOpen, setIsSearchOpen] = useState(false);
+  const [pathInput, setPathInput] = useState(currentPath);
+  const inputRef = useRef<HTMLInputElement>(null);
+  const containerRef = useRef<HTMLDivElement>(null);
+
+  // Sync pathInput with currentPath when it changes externally
+  useEffect(() => {
+    if (!isEditing) {
+      setPathInput(currentPath);
+    }
+  }, [currentPath, isEditing]);
+
+  // Focus input when error occurs or entering edit mode
+  useEffect(() => {
+    if ((error || isEditing) && inputRef.current) {
+      inputRef.current.focus();
+      if (error) {
+        inputRef.current.select();
+      }
+    }
+  }, [error, isEditing]);
+
+  const handleGoToParent = useCallback(() => {
+    if (parentPath) {
+      onNavigate(parentPath);
+    }
+  }, [parentPath, onNavigate]);
+
+  const handleBreadcrumbClick = useCallback(
+    (path: string) => {
+      onNavigate(path);
+    },
+    [onNavigate]
+  );
+
+  const handleStartEditing = useCallback(() => {
+    setIsEditing(true);
+  }, []);
+
+  const handleInputBlur = useCallback(
+    (e: FocusEvent) => {
+      // Check if focus is moving to another element within this component
+      if (containerRef.current?.contains(e.relatedTarget)) {
+        return;
+      }
+      if (pathInput !== currentPath) {
+        setPathInput(currentPath);
+      }
+      setIsEditing(false);
+    },
+    [pathInput, currentPath]
+  );
+
+  const handleGoToPath = useCallback(() => {
+    const trimmedPath = pathInput.trim();
+    if (trimmedPath) {
+      onNavigate(trimmedPath);
+      setIsEditing(false);
+    }
+  }, [pathInput, onNavigate]);
+
+  const handleKeyDown = useCallback(
+    (e: KeyboardEvent<HTMLInputElement>) => {
+      if (e.key === 'Enter') {
+        e.preventDefault();
+        handleGoToPath();
+      } else if (e.key === 'Escape') {
+        e.preventDefault();
+        setPathInput(currentPath);
+        setIsEditing(false);
+        inputRef.current?.blur();
+      }
+    },
+    [handleGoToPath, currentPath]
+  );
+
+  // Handle click on the path container to start editing
+  const handleContainerClick = useCallback(
+    (e: MouseEvent) => {
+      // Don't trigger if clicking on a button or already editing
+      if (
+        isEditing ||
+        isSearchOpen ||
+        (e.target as HTMLElement).closest('button') ||
+        (e.target as HTMLElement).closest('a')
+      ) {
+        return;
+      }
+      setIsEditing(true);
+    },
+    [isEditing, isSearchOpen]
+  );
+
+  const handleSelectEntry = useCallback(
+    (entry: FileSystemEntry) => {
+      if (onSelectEntry) {
+        onSelectEntry(entry);
+      }
+      setIsSearchOpen(false);
+    },
+    [onSelectEntry]
+  );
+
+  // Global keyboard shortcut to activate search (/)
+  useEffect(() => {
+    const handleGlobalKeyDown = (e: globalThis.KeyboardEvent) => {
+      // Activate search with '/' key (unless in an input field or contenteditable)
+      if (
+        e.key === '/' &&
+        !isEditing &&
+        !isSearchOpen &&
+        entries.length > 0 &&
+        !(e.target as HTMLElement).matches('input, textarea, [contenteditable="true"]')
+      ) {
+        e.preventDefault();
+        setIsSearchOpen(true);
+      }
+      // Close search with Escape key
+      if (e.key === 'Escape' && isSearchOpen) {
+        e.preventDefault();
+        e.stopPropagation(); // Stop propagation so parent modal doesn't close
+        setIsSearchOpen(false);
+      }
+    };
+
+    // Use capture phase to intercept ESC before parent modal handlers
+    // This allows us to close search first, then let ESC bubble to close modal on second press
+    window.addEventListener('keydown', handleGlobalKeyDown, true);
+    return () => window.removeEventListener('keydown', handleGlobalKeyDown, true);
+  }, [isEditing, isSearchOpen, entries.length]);
+
+  // Close search when clicking outside
+  useEffect(() => {
+    if (!isSearchOpen) return;
+
+    const handleClickOutside = (e: globalThis.MouseEvent) => {
+      const target = e.target as HTMLElement;
+      if (containerRef.current && !containerRef.current.contains(target)) {
+        setIsSearchOpen(false);
+      }
+    };
+
+    document.addEventListener('mousedown', handleClickOutside);
+    return () => document.removeEventListener('mousedown', handleClickOutside);
+  }, [isSearchOpen]);
+
+  const breadcrumbs = useMemo(() => parseBreadcrumbs(currentPath), [currentPath]);
+
+  const entryItems = useMemo(
+    () =>
+      entries.map((entry) => (
+        <CommandItem key={entry.path} value={entry.name} onSelect={() => handleSelectEntry(entry)}>
+          {entry.isDirectory ? (
+            <Folder className="w-3.5 h-3.5 text-brand-500 mr-2" />
+          ) : (
+            <File className="w-3.5 h-3.5 text-muted-foreground mr-2" />
+          )}
+          <span className="flex-1 truncate font-mono text-xs">{entry.name}</span>
+        </CommandItem>
+      )),
+    [entries, handleSelectEntry]
+  );
+
+  const showBreadcrumbs = currentPath && !isEditing && !loading && !error;
+
+  return (
+    <div
+      ref={containerRef}
+      className={cn('flex items-center gap-2', className)}
+      role="navigation"
+      aria-label="Path navigation"
+    >
+      {/* Navigation buttons */}
+      <div className="flex items-center gap-1 shrink-0">
+        <Button
+          variant="ghost"
+          size="icon"
+          onClick={onHome}
+          className="h-7 w-7"
+          disabled={loading}
+          aria-label="Go to home directory"
+        >
+          <Home className="w-4 h-4" />
+        </Button>
+
+        <Button
+          variant="ghost"
+          size="icon"
+          onClick={handleGoToParent}
+          className="h-7 w-7"
+          disabled={loading || !parentPath}
+          aria-label="Go to parent directory"
+        >
+          <ArrowLeft className="w-4 h-4" />
+        </Button>
+      </div>
+
+      {/* Path display / input */}
+      <div className="flex-1 relative min-w-0">
+        {/* Search Popover - positioned to overlap the input */}
+        {isSearchOpen && (
+          <div className="absolute inset-0 z-50">
+            <div className="relative w-full h-full">
+              <div className="absolute inset-0 bg-popover border border-border rounded-md shadow-lg">
+                <Command className="h-auto max-h-[300px]">
+                  <div className="flex items-center gap-2 px-3 **:data-[slot=command-input-wrapper]:border-0 **:data-[slot=command-input-wrapper]:px-0">
+                    <CommandInput
+                      autoFocus
+                      placeholder={searchPlaceholder}
+                      className="h-8 flex-1"
+                    />
+                    <div className="flex items-center gap-1 shrink-0 ml-auto">
+                      <Button
+                        variant="ghost"
+                        size="icon"
+                        onClick={() => setIsSearchOpen(false)}
+                        className="h-6 w-6 text-muted-foreground hover:text-foreground"
+                        aria-label="Close search"
+                      >
+                        <X className="w-3.5 h-3.5" />
+                      </Button>
+                      <Kbd className="hidden py-0.5 sm:inline-block">ESC</Kbd>
+                    </div>
+                  </div>
+                  <CommandList className="scrollbar-styled">
+                    <CommandEmpty>No files or directories found</CommandEmpty>
+                    <CommandGroup>{entryItems}</CommandGroup>
+                  </CommandList>
+                </Command>
+              </div>
+            </div>
+          </div>
+        )}
+
+        <div
+          onClick={handleContainerClick}
+          className={cn(
+            'flex items-center gap-2 min-w-0 h-8 px-3 rounded-md border bg-background/50 transition-colors',
+            error
+              ? 'border-destructive focus-within:border-destructive'
+              : 'border-input focus-within:border-ring focus-within:ring-1 focus-within:ring-ring',
+            !isEditing && !error && 'cursor-text hover:border-ring/50'
+          )}
+        >
+          {showBreadcrumbs ? (
+            <>
+              <Breadcrumb className="flex-1 min-w-0 overflow-hidden">
+                <BreadcrumbList className="flex-nowrap overflow-x-auto scrollbar-none">
+                  {breadcrumbs.map((crumb) => (
+                    <Fragment key={crumb.path}>
+                      <BreadcrumbItem className="shrink-0">
+                        {crumb.isLast ? (
+                          <BreadcrumbPage className="font-mono text-xs font-medium truncate max-w-[200px]">
+                            {crumb.name}
+                          </BreadcrumbPage>
+                        ) : (
+                          <BreadcrumbLink
+                            href="#"
+                            onClick={(e) => {
+                              e.preventDefault();
+                              handleBreadcrumbClick(crumb.path);
+                            }}
+                            className="font-mono text-xs text-muted-foreground hover:text-foreground transition-colors truncate max-w-[150px]"
+                          >
+                            {crumb.name}
+                          </BreadcrumbLink>
+                        )}
+                      </BreadcrumbItem>
+                      {!crumb.isLast && (
+                        <BreadcrumbSeparator className="[&>svg]:size-3.5 shrink-0" />
+                      )}
+                    </Fragment>
+                  ))}
+                </BreadcrumbList>
+              </Breadcrumb>
+              <div className="flex items-center gap-0.5 shrink-0">
+                <Button
+                  variant="ghost"
+                  size="icon"
+                  onClick={() => setIsSearchOpen(true)}
+                  className="h-6 w-6 text-muted-foreground hover:text-foreground"
+                  aria-label="Search files and directories"
+                  title="Search files and directories"
+                  disabled={loading || entries.length === 0}
+                >
+                  <Search className="w-3.5 h-3.5" />
+                </Button>
+                <Button
+                  variant="ghost"
+                  size="icon"
+                  onClick={handleStartEditing}
+                  className="h-6 w-6 text-muted-foreground hover:text-foreground"
+                  aria-label="Edit path"
+                >
+                  <Pencil className="w-3.5 h-3.5" />
+                </Button>
+              </div>
+            </>
+          ) : (
+            <>
+              <Input
+                ref={inputRef}
+                type="text"
+                placeholder={placeholder}
+                value={pathInput}
+                onChange={(e) => setPathInput(e.target.value)}
+                onKeyDown={handleKeyDown}
+                onBlur={handleInputBlur}
+                className="flex-1 font-mono text-xs h-7 px-0 border-0 shadow-none focus-visible:ring-0 bg-transparent"
+                data-testid="path-input"
+                disabled={loading}
+                aria-label="Path input"
+                aria-invalid={error}
+              />
+              <Button
+                variant="ghost"
+                size="icon"
+                onClick={handleGoToPath}
+                disabled={!pathInput.trim() || loading}
+                className="h-6 w-6 shrink-0"
+                aria-label="Go to path"
+              >
+                <ArrowRight className="w-3.5 h-3.5" />
+              </Button>
+            </>
+          )}
+        </div>
+      </div>
+    </div>
+  );
+}
+
+export { PathInput, parseBreadcrumbs };
+export type { PathInputProps, BreadcrumbSegment, FileSystemEntry };

apps/ui/src/components/updates/update-notifier.tsx

@@ -0,0 +1,173 @@
+/**
+ * Update Notifier Component
+ *
+ * Responsible for displaying toast notifications related to updates.
+ * Subscribes to the updates store and reacts to state changes.
+ *
+ * This component handles the UI notifications, keeping them separate
+ * from the business logic in the store.
+ */
+
+import { useEffect, useRef, useCallback } from 'react';
+import { toast } from 'sonner';
+import { useUpdatesStore } from '@/store/updates-store';
+import { useUpdatePolling } from '@/hooks/use-update-polling';
+import { useAppStore } from '@/store/app-store';
+import { getRepoDisplayName } from '@/lib/utils';
+
+// ============================================================================
+// Types
+// ============================================================================
+
+export interface UpdateNotifierProps {
+  /** Custom handler for update available (for testing/DI) */
+  onUpdateAvailable?: (remoteVersion: string) => void;
+
+  /** Custom handler for update installed (for testing/DI) */
+  onUpdateInstalled?: (newVersion: string, alreadyUpToDate: boolean) => void;
+}
+
+// ============================================================================
+// Component
+// ============================================================================
+
+/**
+ * Displays persistent toasts for available and installed application updates.
+ *
+ * Shows a persistent "Update Available" toast when a new remote version is detected and,
+ * after initiating an update, shows success toasts for either "Already up to date!" or
+ * "Update installed!" with actions to restart now or later.
+ *
+ * @param onUpdateAvailable - Optional callback invoked with `remoteVersion` when an update is detected; providing this prevents the default availability toast.
+ * @param onUpdateInstalled - Optional callback invoked with `(newVersion, alreadyUpToDate)` after attempting to install updates; providing this prevents the default installation toasts.
+ * @returns Null (this component renders no visible UI; it manages global toast notifications).
+ */
+export function UpdateNotifier({ onUpdateAvailable, onUpdateInstalled }: UpdateNotifierProps = {}) {
+  // Store state
+  const { updateAvailable, remoteVersionShort, pullUpdates, isPulling } = useUpdatesStore();
+
+  const { autoUpdate } = useAppStore();
+
+  // Start polling
+  useUpdatePolling();
+
+  // Track shown toasts to avoid duplicates
+  const shownToastForCommitRef = useRef<string | null>(null);
+  const toastIdRef = useRef<string | number | null>(null);
+
+  // Handle "Update Now" click
+  const handleUpdateNow = useCallback(async () => {
+    const result = await pullUpdates();
+
+    if (result) {
+      // Dismiss the "update available" toast
+      if (toastIdRef.current) {
+        toast.dismiss(toastIdRef.current);
+        toastIdRef.current = null;
+      }
+
+      // Call custom handler if provided
+      if (onUpdateInstalled) {
+        onUpdateInstalled(result.newVersionShort, result.alreadyUpToDate);
+        return;
+      }
+
+      // Show appropriate toast based on result
+      if (result.alreadyUpToDate) {
+        toast.success('Already up to date!');
+      } else {
+        toast.success('Update installed!', {
+          description: result.message,
+          duration: Infinity,
+          action: {
+            label: 'Restart Now',
+            onClick: () => {
+              window.location.reload();
+            },
+          },
+          cancel: {
+            label: 'Later',
+            onClick: () => {
+              // Just dismiss - user will restart manually later
+            },
+          },
+        });
+      }
+    }
+  }, [pullUpdates, onUpdateInstalled]);
+
+  // Show toast when update becomes available
+  useEffect(() => {
+    if (!updateAvailable || !remoteVersionShort) {
+      return;
+    }
+
+    // Don't show toast if we've already shown it for this version
+    if (shownToastForCommitRef.current === remoteVersionShort) {
+      return;
+    }
+
+    shownToastForCommitRef.current = remoteVersionShort;
+
+    // Call custom handler if provided
+    if (onUpdateAvailable) {
+      onUpdateAvailable(remoteVersionShort);
+      return;
+    }
+
+    // Dismiss any existing toast
+    if (toastIdRef.current) {
+      toast.dismiss(toastIdRef.current);
+    }
+
+    // Extract repo name for display
+    const repoName = getRepoDisplayName(autoUpdate.upstreamUrl);
+
+    // Show persistent toast with update button
+    toastIdRef.current = toast.info('Update Available', {
+      description: `New version (${remoteVersionShort}) available from ${repoName}`,
+      duration: Infinity,
+      action: {
+        label: isPulling ? 'Updating...' : 'Update Now',
+        onClick: handleUpdateNow,
+      },
+      cancel: {
+        label: 'Later',
+        onClick: () => {
+          // Dismiss toast - won't show again for this version until a new version appears
+          shownToastForCommitRef.current = remoteVersionShort;
+        },
+      },
+    });
+  }, [
+    updateAvailable,
+    remoteVersionShort,
+    autoUpdate.upstreamUrl,
+    isPulling,
+    handleUpdateNow,
+    onUpdateAvailable,
+  ]);
+
+  // Clean up toast on unmount
+  useEffect(() => {
+    return () => {
+      if (toastIdRef.current) {
+        toast.dismiss(toastIdRef.current);
+      }
+    };
+  }, []);
+
+  // Reset shown toast when update is no longer available
+  useEffect(() => {
+    if (!updateAvailable) {
+      shownToastForCommitRef.current = null;
+      if (toastIdRef.current) {
+        toast.dismiss(toastIdRef.current);
+        toastIdRef.current = null;
+      }
+    }
+  }, [updateAvailable]);
+
+  // This component doesn't render anything visible
+  return null;
+}

apps/ui/src/components/views/agent-view.tsx

@@ -17,6 +17,8 @@ import {
   ImageIcon,
   ChevronDown,
   FileText,
+  Square,
+  ListOrdered,
 } from 'lucide-react';
 import { cn } from '@/lib/utils';
 import { useElectronAgent } from '@/hooks/use-electron-agent';
@@ -83,7 +85,12 @@ export function AgentView() {
     isConnected,
     sendMessage,
     clearHistory,
+    stopExecution,
     error: agentError,
+    serverQueue,
+    addToServerQueue,
+    removeFromServerQueue,
+    clearServerQueue,
   } = useElectronAgent({
     sessionId: currentSessionId || '',
     workingDirectory: currentProject?.path,
@@ -132,11 +139,7 @@ export function AgentView() {
   }, [currentProject?.path]);
 
   const handleSend = useCallback(async () => {
-    if (
-      (!input.trim() && selectedImages.length === 0 && selectedTextFiles.length === 0) ||
-      isProcessing
-    )
-      return;
+    if (!input.trim() && selectedImages.length === 0 && selectedTextFiles.length === 0) return;
 
     const messageContent = input;
     const messageImages = selectedImages;
@@ -147,8 +150,13 @@ export function AgentView() {
     setSelectedTextFiles([]);
     setShowImageDropZone(false);
 
-    await sendMessage(messageContent, messageImages, messageTextFiles);
-  }, [input, selectedImages, selectedTextFiles, isProcessing, sendMessage]);
+    // If already processing, add to server queue instead
+    if (isProcessing) {
+      await addToServerQueue(messageContent, messageImages, messageTextFiles);
+    } else {
+      await sendMessage(messageContent, messageImages, messageTextFiles);
+    }
+  }, [input, selectedImages, selectedTextFiles, isProcessing, sendMessage, addToServerQueue]);
 
   const handleImagesSelected = useCallback((images: ImageAttachment[]) => {
     setSelectedImages(images);
@@ -534,41 +542,6 @@ export function AgentView() {
 
           {/* Status indicators & actions */}
           <div className="flex items-center gap-3">
-            {/* Model Selector */}
-            <DropdownMenu>
-              <DropdownMenuTrigger asChild>
-                <Button
-                  variant="outline"
-                  size="sm"
-                  className="h-8 gap-1.5 text-xs font-medium"
-                  disabled={isProcessing}
-                  data-testid="model-selector"
-                >
-                  <Bot className="w-3.5 h-3.5" />
-                  {CLAUDE_MODELS.find((m) => m.id === selectedModel)?.label.replace(
-                    'Claude ',
-                    ''
-                  ) || 'Sonnet'}
-                  <ChevronDown className="w-3 h-3 opacity-50" />
-                </Button>
-              </DropdownMenuTrigger>
-              <DropdownMenuContent align="end" className="w-48">
-                {CLAUDE_MODELS.map((model) => (
-                  <DropdownMenuItem
-                    key={model.id}
-                    onClick={() => setSelectedModel(model.id)}
-                    className={cn('cursor-pointer', selectedModel === model.id && 'bg-accent')}
-                    data-testid={`model-option-${model.id}`}
-                  >
-                    <div className="flex flex-col">
-                      <span className="font-medium">{model.label}</span>
-                      <span className="text-xs text-muted-foreground">{model.description}</span>
-                    </div>
-                  </DropdownMenuItem>
-                ))}
-              </DropdownMenuContent>
-            </DropdownMenu>
-
             {currentTool && (
               <div className="flex items-center gap-2 text-xs text-muted-foreground bg-muted/50 px-3 py-1.5 rounded-full border border-border">
                 <Wrench className="w-3 h-3 text-primary" />
@@ -758,10 +731,52 @@ export function AgentView() {
                 images={selectedImages}
                 maxFiles={5}
                 className="mb-4"
-                disabled={isProcessing || !isConnected}
+                disabled={!isConnected}
               />
             )}
 
+            {/* Queued Prompts List */}
+            {serverQueue.length > 0 && (
+              <div className="mb-4 space-y-2">
+                <div className="flex items-center justify-between">
+                  <p className="text-xs font-medium text-muted-foreground">
+                    {serverQueue.length} prompt{serverQueue.length > 1 ? 's' : ''} queued
+                  </p>
+                  <button
+                    onClick={clearServerQueue}
+                    className="text-xs text-muted-foreground hover:text-foreground transition-colors"
+                  >
+                    Clear all
+                  </button>
+                </div>
+                <div className="space-y-1.5">
+                  {serverQueue.map((item, index) => (
+                    <div
+                      key={item.id}
+                      className="group flex items-center gap-2 text-sm bg-muted/50 rounded-lg px-3 py-2 border border-border"
+                    >
+                      <span className="text-xs text-muted-foreground font-medium min-w-[1.5rem]">
+                        {index + 1}.
+                      </span>
+                      <span className="flex-1 truncate text-foreground">{item.message}</span>
+                      {item.imagePaths && item.imagePaths.length > 0 && (
+                        <span className="text-xs text-muted-foreground">
+                          +{item.imagePaths.length} file{item.imagePaths.length > 1 ? 's' : ''}
+                        </span>
+                      )}
+                      <button
+                        onClick={() => removeFromServerQueue(item.id)}
+                        className="opacity-0 group-hover:opacity-100 p-1 hover:bg-destructive/10 hover:text-destructive rounded transition-all"
+                        title="Remove from queue"
+                      >
+                        <X className="w-3 h-3" />
+                      </button>
+                    </div>
+                  ))}
+                </div>
+              </div>
+            )}
+
             {/* Selected Files Preview - only show when ImageDropZone is hidden to avoid duplicate display */}
             {(selectedImages.length > 0 || selectedTextFiles.length > 0) && !showImageDropZone && (
               <div className="mb-4 space-y-2">
@@ -776,7 +791,6 @@ export function AgentView() {
                       setSelectedTextFiles([]);
                     }}
                     className="text-xs text-muted-foreground hover:text-foreground transition-colors"
-                    disabled={isProcessing}
                   >
                     Clear all
                   </button>
@@ -867,13 +881,17 @@ export function AgentView() {
                 <Input
                   ref={inputRef}
                   placeholder={
-                    isDragOver ? 'Drop your files here...' : 'Describe what you want to build...'
+                    isDragOver
+                      ? 'Drop your files here...'
+                      : isProcessing
+                        ? 'Type to queue another prompt...'
+                        : 'Describe what you want to build...'
                   }
                   value={input}
                   onChange={(e) => setInput(e.target.value)}
                   onKeyPress={handleKeyPress}
                   onPaste={handlePaste}
-                  disabled={isProcessing || !isConnected}
+                  disabled={!isConnected}
                   data-testid="agent-input"
                   className={cn(
                     'h-11 bg-background border-border rounded-xl pl-4 pr-20 text-sm transition-all',
@@ -897,12 +915,44 @@ export function AgentView() {
                 )}
               </div>
 
+              {/* Model Selector */}
+              <DropdownMenu>
+                <DropdownMenuTrigger asChild>
+                  <Button
+                    variant="outline"
+                    className="h-11 gap-1 text-xs font-medium rounded-xl border-border px-2.5"
+                    data-testid="model-selector"
+                  >
+                    {CLAUDE_MODELS.find((m) => m.id === selectedModel)?.label.replace(
+                      'Claude ',
+                      ''
+                    ) || 'Sonnet'}
+                    <ChevronDown className="w-3 h-3 opacity-50" />
+                  </Button>
+                </DropdownMenuTrigger>
+                <DropdownMenuContent align="end" className="w-48">
+                  {CLAUDE_MODELS.map((model) => (
+                    <DropdownMenuItem
+                      key={model.id}
+                      onClick={() => setSelectedModel(model.id)}
+                      className={cn('cursor-pointer', selectedModel === model.id && 'bg-accent')}
+                      data-testid={`model-option-${model.id}`}
+                    >
+                      <div className="flex flex-col">
+                        <span className="font-medium">{model.label}</span>
+                        <span className="text-xs text-muted-foreground">{model.description}</span>
+                      </div>
+                    </DropdownMenuItem>
+                  ))}
+                </DropdownMenuContent>
+              </DropdownMenu>
+
               {/* File Attachment Button */}
               <Button
                 variant="outline"
                 size="icon"
                 onClick={toggleImageDropZone}
-                disabled={isProcessing || !isConnected}
+                disabled={!isConnected}
                 className={cn(
                   'h-11 w-11 rounded-xl border-border',
                   showImageDropZone && 'bg-primary/10 text-primary border-primary/30',
@@ -914,20 +964,35 @@ export function AgentView() {
                 <Paperclip className="w-4 h-4" />
               </Button>
 
-              {/* Send Button */}
+              {/* Stop Button (only when processing) */}
+              {isProcessing && (
+                <Button
+                  onClick={stopExecution}
+                  disabled={!isConnected}
+                  className="h-11 px-4 rounded-xl"
+                  variant="destructive"
+                  data-testid="stop-agent"
+                  title="Stop generation"
+                >
+                  <Square className="w-4 h-4 fill-current" />
+                </Button>
+              )}
+
+              {/* Send / Queue Button */}
               <Button
                 onClick={handleSend}
                 disabled={
                   (!input.trim() &&
                     selectedImages.length === 0 &&
                     selectedTextFiles.length === 0) ||
-                  isProcessing ||
                   !isConnected
                 }
                 className="h-11 px-4 rounded-xl"
+                variant={isProcessing ? 'outline' : 'default'}
                 data-testid="send-message"
+                title={isProcessing ? 'Add to queue' : 'Send message'}
               >
-                <Send className="w-4 h-4" />
+                {isProcessing ? <ListOrdered className="w-4 h-4" /> : <Send className="w-4 h-4" />}
               </Button>
             </div>
 

apps/ui/src/components/views/board-view.tsx

@@ -9,7 +9,9 @@ import {
 import { useAppStore, Feature } from '@/store/app-store';
 import { getElectronAPI } from '@/lib/electron';
 import type { AutoModeEvent } from '@/types/electron';
+import type { BacklogPlanResult } from '@automaker/types';
 import { pathsEqual } from '@/lib/utils';
+import { toast } from 'sonner';
 import { getBlockingDependencies } from '@automaker/dependency-resolver';
 import { BoardBackgroundModal } from '@/components/dialogs/board-background-modal';
 import { RefreshCw } from 'lucide-react';
@@ -25,6 +27,7 @@ import { GraphView } from './graph-view';
 import {
   AddFeatureDialog,
   AgentOutputModal,
+  BacklogPlanDialog,
   CompletedFeaturesModal,
   ArchiveAllVerifiedDialog,
   DeleteCompletedFeatureDialog,
@@ -57,9 +60,6 @@ import {
 // Stable empty array to avoid infinite loop in selector
 const EMPTY_WORKTREES: ReturnType<ReturnType<typeof useAppStore.getState>['getWorktrees']> = [];
 
-/** Delay before starting a newly created feature to allow state to settle */
-const FEATURE_CREATION_SETTLE_DELAY_MS = 500;
-
 export function BoardView() {
   const {
     currentProject,
@@ -107,6 +107,9 @@ export function BoardView() {
   // State for viewing plan in read-only mode
   const [viewPlanFeature, setViewPlanFeature] = useState<Feature | null>(null);
 
+  // State for spawn task mode
+  const [spawnParentFeature, setSpawnParentFeature] = useState<Feature | null>(null);
+
   // Worktree dialog states
   const [showCreateWorktreeDialog, setShowCreateWorktreeDialog] = useState(false);
   const [showDeleteWorktreeDialog, setShowDeleteWorktreeDialog] = useState(false);
@@ -122,6 +125,11 @@ export function BoardView() {
   } | null>(null);
   const [worktreeRefreshKey, setWorktreeRefreshKey] = useState(0);
 
+  // Backlog plan dialog state
+  const [showPlanDialog, setShowPlanDialog] = useState(false);
+  const [pendingBacklogPlan, setPendingBacklogPlan] = useState<BacklogPlanResult | null>(null);
+  const [isGeneratingPlan, setIsGeneratingPlan] = useState(false);
+
   // Follow-up state hook
   const {
     showFollowUpDialog,
@@ -450,23 +458,22 @@ export function BoardView() {
         requirePlanApproval: false,
       };
 
+      // Capture existing feature IDs before adding
+      const featuresBeforeIds = new Set(useAppStore.getState().features.map((f) => f.id));
       await handleAddFeature(featureData);
 
-      // Find the newly created feature and start it
-      // We need to wait a moment for the feature to be created
-      setTimeout(async () => {
-        const latestFeatures = useAppStore.getState().features;
-        const newFeature = latestFeatures.find(
-          (f) =>
-            f.branchName === worktree.branch &&
-            f.status === 'backlog' &&
-            f.description.includes(`PR #${prNumber}`)
-        );
+      // Find the newly created feature by looking for an ID that wasn't in the original set
+      const latestFeatures = useAppStore.getState().features;
+      const newFeature = latestFeatures.find((f) => !featuresBeforeIds.has(f.id));
 
-        if (newFeature) {
-          await handleStartImplementation(newFeature);
-        }
-      }, FEATURE_CREATION_SETTLE_DELAY_MS);
+      if (newFeature) {
+        await handleStartImplementation(newFeature);
+      } else {
+        console.error('Could not find newly created feature to start it automatically.');
+        toast.error('Failed to auto-start feature', {
+          description: 'The feature was created but could not be started automatically.',
+        });
+      }
     },
     [handleAddFeature, handleStartImplementation, defaultSkipTests]
   );
@@ -492,26 +499,49 @@ export function BoardView() {
         requirePlanApproval: false,
       };
 
+      // Capture existing feature IDs before adding
+      const featuresBeforeIds = new Set(useAppStore.getState().features.map((f) => f.id));
       await handleAddFeature(featureData);
 
-      // Find the newly created feature and start it
-      setTimeout(async () => {
-        const latestFeatures = useAppStore.getState().features;
-        const newFeature = latestFeatures.find(
-          (f) =>
-            f.branchName === worktree.branch &&
-            f.status === 'backlog' &&
-            f.description.includes('Pull latest from origin/main')
-        );
+      // Find the newly created feature by looking for an ID that wasn't in the original set
+      const latestFeatures = useAppStore.getState().features;
+      const newFeature = latestFeatures.find((f) => !featuresBeforeIds.has(f.id));
 
-        if (newFeature) {
-          await handleStartImplementation(newFeature);
-        }
-      }, FEATURE_CREATION_SETTLE_DELAY_MS);
+      if (newFeature) {
+        await handleStartImplementation(newFeature);
+      } else {
+        console.error('Could not find newly created feature to start it automatically.');
+        toast.error('Failed to auto-start feature', {
+          description: 'The feature was created but could not be started automatically.',
+        });
+      }
     },
     [handleAddFeature, handleStartImplementation, defaultSkipTests]
   );
 
+  // Handler for "Make" button - creates a feature and immediately starts it
+  const handleAddAndStartFeature = useCallback(
+    async (featureData: Parameters<typeof handleAddFeature>[0]) => {
+      // Capture existing feature IDs before adding
+      const featuresBeforeIds = new Set(useAppStore.getState().features.map((f) => f.id));
+      await handleAddFeature(featureData);
+
+      // Find the newly created feature by looking for an ID that wasn't in the original set
+      const latestFeatures = useAppStore.getState().features;
+      const newFeature = latestFeatures.find((f) => !featuresBeforeIds.has(f.id));
+
+      if (newFeature) {
+        await handleStartImplementation(newFeature);
+      } else {
+        console.error('Could not find newly created feature to start it automatically.');
+        toast.error('Failed to auto-start feature', {
+          description: 'The feature was created but could not be started automatically.',
+        });
+      }
+    },
+    [handleAddFeature, handleStartImplementation]
+  );
+
   // Client-side auto mode: periodically check for backlog items and move them to in-progress
   // Use a ref to track the latest auto mode state so async operations always check the current value
   const autoModeRunningRef = useRef(autoMode.isRunning);
@@ -575,6 +605,37 @@ export function BoardView() {
     return unsubscribe;
   }, [currentProject]);
 
+  // Listen for backlog plan events (for background generation)
+  useEffect(() => {
+    const api = getElectronAPI();
+    if (!api?.backlogPlan) return;
+
+    const unsubscribe = api.backlogPlan.onEvent(
+      (event: { type: string; result?: BacklogPlanResult; error?: string }) => {
+        if (event.type === 'backlog_plan_complete') {
+          setIsGeneratingPlan(false);
+          if (event.result && event.result.changes?.length > 0) {
+            setPendingBacklogPlan(event.result);
+            toast.success('Plan ready! Click to review.', {
+              duration: 10000,
+              action: {
+                label: 'Review',
+                onClick: () => setShowPlanDialog(true),
+              },
+            });
+          } else {
+            toast.info('No changes generated. Try again with a different prompt.');
+          }
+        } else if (event.type === 'backlog_plan_error') {
+          setIsGeneratingPlan(false);
+          toast.error(`Plan generation failed: ${event.error}`);
+        }
+      }
+    );
+
+    return unsubscribe;
+  }, []);
+
   useEffect(() => {
     if (!autoMode.isRunning || !currentProject) {
       return;
@@ -932,6 +993,7 @@ export function BoardView() {
           }
         }}
         onAddFeature={() => setShowAddDialog(true)}
+        onOpenPlanDialog={() => setShowPlanDialog(true)}
         addFeatureShortcut={{
           key: shortcuts.addFeature,
           action: () => setShowAddDialog(true),
@@ -1021,6 +1083,10 @@ export function BoardView() {
             onImplement={handleStartImplementation}
             onViewPlan={(feature) => setViewPlanFeature(feature)}
             onApprovePlan={handleOpenApprovalDialog}
+            onSpawnTask={(feature) => {
+              setSpawnParentFeature(feature);
+              setShowAddDialog(true);
+            }}
             featuresWithContext={featuresWithContext}
             runningAutoTasks={runningAutoTasks}
             shortcuts={shortcuts}
@@ -1036,8 +1102,19 @@ export function BoardView() {
             currentWorktreePath={currentWorktreePath}
             currentWorktreeBranch={currentWorktreeBranch}
             projectPath={currentProject?.path || null}
+            searchQuery={searchQuery}
+            onSearchQueryChange={setSearchQuery}
             onEditFeature={(feature) => setEditingFeature(feature)}
             onViewOutput={handleViewOutput}
+            onStartTask={handleStartImplementation}
+            onStopTask={handleForceStopFeature}
+            onResumeTask={handleResumeFeature}
+            onUpdateFeature={updateFeature}
+            onSpawnTask={(feature) => {
+              setSpawnParentFeature(feature);
+              setShowAddDialog(true);
+            }}
+            onDeleteTask={(feature) => handleDeleteFeature(feature.id)}
           />
         )}
       </div>
@@ -1072,8 +1149,14 @@ export function BoardView() {
       {/* Add Feature Dialog */}
       <AddFeatureDialog
         open={showAddDialog}
-        onOpenChange={setShowAddDialog}
+        onOpenChange={(open) => {
+          setShowAddDialog(open);
+          if (!open) {
+            setSpawnParentFeature(null);
+          }
+        }}
         onAdd={handleAddFeature}
+        onAddAndStart={handleAddAndStartFeature}
         categorySuggestions={categorySuggestions}
         branchSuggestions={branchSuggestions}
         branchCardCounts={branchCardCounts}
@@ -1083,6 +1166,8 @@ export function BoardView() {
         isMaximized={isMaximized}
         showProfilesOnly={showProfilesOnly}
         aiProfiles={aiProfiles}
+        parentFeature={spawnParentFeature}
+        allFeatures={hookFeatures}
       />
 
       {/* Edit Feature Dialog */}
@@ -1147,6 +1232,18 @@ export function BoardView() {
         setIsGenerating={setIsGeneratingSuggestions}
       />
 
+      {/* Backlog Plan Dialog */}
+      <BacklogPlanDialog
+        open={showPlanDialog}
+        onClose={() => setShowPlanDialog(false)}
+        projectPath={currentProject.path}
+        onPlanApplied={loadFeatures}
+        pendingPlanResult={pendingBacklogPlan}
+        setPendingPlanResult={setPendingBacklogPlan}
+        isGeneratingPlan={isGeneratingPlan}
+        setIsGeneratingPlan={setIsGeneratingPlan}
+      />
+
       {/* Plan Approval Dialog */}
       <PlanApprovalDialog
         open={pendingPlanApproval !== null}

apps/ui/src/components/views/board-view/board-header.tsx

@@ -1,8 +1,9 @@
 import { HotkeyButton } from '@/components/ui/hotkey-button';
+import { Button } from '@/components/ui/button';
 import { Slider } from '@/components/ui/slider';
 import { Switch } from '@/components/ui/switch';
 import { Label } from '@/components/ui/label';
-import { Plus, Bot } from 'lucide-react';
+import { Plus, Bot, Wand2 } from 'lucide-react';
 import { KeyboardShortcut } from '@/hooks/use-keyboard-shortcuts';
 import { ClaudeUsagePopover } from '@/components/claude-usage-popover';
 import { useAppStore } from '@/store/app-store';
@@ -15,6 +16,7 @@ interface BoardHeaderProps {
   isAutoModeRunning: boolean;
   onAutoModeToggle: (enabled: boolean) => void;
   onAddFeature: () => void;
+  onOpenPlanDialog: () => void;
   addFeatureShortcut: KeyboardShortcut;
   isMounted: boolean;
 }
@@ -27,6 +29,7 @@ export function BoardHeader({
   isAutoModeRunning,
   onAutoModeToggle,
   onAddFeature,
+  onOpenPlanDialog,
   addFeatureShortcut,
   isMounted,
 }: BoardHeaderProps) {
@@ -89,6 +92,16 @@ export function BoardHeader({
           </div>
         )}
 
+        <Button
+          size="sm"
+          variant="outline"
+          onClick={onOpenPlanDialog}
+          data-testid="plan-backlog-button"
+        >
+          <Wand2 className="w-4 h-4 mr-2" />
+          Plan
+        </Button>
+
         <HotkeyButton
           size="sm"
           onClick={onAddFeature}

apps/ui/src/components/views/board-view/components/kanban-card/card-header.tsx

@@ -19,6 +19,7 @@ import {
   ChevronDown,
   ChevronUp,
   Cpu,
+  GitFork,
 } from 'lucide-react';
 import { CountUpTimer } from '@/components/ui/count-up-timer';
 import { formatModelName, DEFAULT_MODEL } from '@/lib/agent-context-parser';
@@ -31,6 +32,7 @@ interface CardHeaderProps {
   onEdit: () => void;
   onDelete: () => void;
   onViewOutput?: () => void;
+  onSpawnTask?: () => void;
 }
 
 export function CardHeaderSection({
@@ -40,6 +42,7 @@ export function CardHeaderSection({
   onEdit,
   onDelete,
   onViewOutput,
+  onSpawnTask,
 }: CardHeaderProps) {
   const [isDescriptionExpanded, setIsDescriptionExpanded] = useState(false);
   const [isDeleteDialogOpen, setIsDeleteDialogOpen] = useState(false);
@@ -92,6 +95,17 @@ export function CardHeaderSection({
                 <Edit className="w-3 h-3 mr-2" />
                 Edit
               </DropdownMenuItem>
+              <DropdownMenuItem
+                onClick={(e) => {
+                  e.stopPropagation();
+                  onSpawnTask?.();
+                }}
+                data-testid={`spawn-running-${feature.id}`}
+                className="text-xs"
+              >
+                <GitFork className="w-3 h-3 mr-2" />
+                Spawn Sub-Task
+              </DropdownMenuItem>
               {/* Model info in dropdown */}
               <div className="px-2 py-1.5 text-[10px] text-muted-foreground border-t mt-1 pt-1.5">
                 <div className="flex items-center gap-1">
@@ -106,7 +120,21 @@ export function CardHeaderSection({
 
       {/* Backlog header */}
       {!isCurrentAutoTask && feature.status === 'backlog' && (
-        <div className="absolute top-2 right-2">
+        <div className="absolute top-2 right-2 flex items-center gap-1">
+          <Button
+            variant="ghost"
+            size="sm"
+            className="h-6 w-6 p-0 hover:bg-white/10 text-muted-foreground hover:text-foreground"
+            onClick={(e) => {
+              e.stopPropagation();
+              onSpawnTask?.();
+            }}
+            onPointerDown={(e) => e.stopPropagation()}
+            data-testid={`spawn-backlog-${feature.id}`}
+            title="Spawn Sub-Task"
+          >
+            <GitFork className="w-4 h-4" />
+          </Button>
           <Button
             variant="ghost"
             size="sm"
@@ -141,6 +169,22 @@ export function CardHeaderSection({
               >
                 <Edit className="w-4 h-4" />
               </Button>
+              <Button
+                variant="ghost"
+                size="sm"
+                className="h-6 w-6 p-0 hover:bg-white/10 text-muted-foreground hover:text-foreground"
+                onClick={(e) => {
+                  e.stopPropagation();
+                  onSpawnTask?.();
+                }}
+                onPointerDown={(e) => e.stopPropagation()}
+                data-testid={`spawn-${
+                  feature.status === 'waiting_approval' ? 'waiting' : 'verified'
+                }-${feature.id}`}
+                title="Spawn Sub-Task"
+              >
+                <GitFork className="w-4 h-4" />
+              </Button>
               {onViewOutput && (
                 <Button
                   variant="ghost"
@@ -229,6 +273,17 @@ export function CardHeaderSection({
                     View Logs
                   </DropdownMenuItem>
                 )}
+                <DropdownMenuItem
+                  onClick={(e) => {
+                    e.stopPropagation();
+                    onSpawnTask?.();
+                  }}
+                  data-testid={`spawn-feature-${feature.id}`}
+                  className="text-xs"
+                >
+                  <GitFork className="w-3 h-3 mr-2" />
+                  Spawn Sub-Task
+                </DropdownMenuItem>
                 {/* Model info in dropdown */}
                 <div className="px-2 py-1.5 text-[10px] text-muted-foreground border-t mt-1 pt-1.5">
                   <div className="flex items-center gap-1">

apps/ui/src/components/views/board-view/components/kanban-card/kanban-card.tsx

@@ -25,6 +25,7 @@ interface KanbanCardProps {
   onComplete?: () => void;
   onViewPlan?: () => void;
   onApprovePlan?: () => void;
+  onSpawnTask?: () => void;
   hasContext?: boolean;
   isCurrentAutoTask?: boolean;
   shortcutKey?: string;
@@ -51,6 +52,7 @@ export const KanbanCard = memo(function KanbanCard({
   onComplete,
   onViewPlan,
   onApprovePlan,
+  onSpawnTask,
   hasContext,
   isCurrentAutoTask,
   shortcutKey,
@@ -146,6 +148,7 @@ export const KanbanCard = memo(function KanbanCard({
         onEdit={onEdit}
         onDelete={onDelete}
         onViewOutput={onViewOutput}
+        onSpawnTask={onSpawnTask}
       />
 
       <CardContent className="px-3 pt-0 pb-0">

apps/ui/src/components/views/board-view/dialogs/add-feature-dialog.tsx

@@ -23,9 +23,9 @@ import {
   MessageSquare,
   Settings2,
   SlidersHorizontal,
-  FlaskConical,
   Sparkles,
   ChevronDown,
+  Play,
 } from 'lucide-react';
 import { toast } from 'sonner';
 import { getElectronAPI } from '@/lib/electron';
@@ -37,6 +37,7 @@ import {
   FeatureImage,
   AIProfile,
   PlanningMode,
+  Feature,
 } from '@/store/app-store';
 import {
   ModelSelector,
@@ -46,6 +47,7 @@ import {
   PrioritySelector,
   BranchSelector,
   PlanningModeSelector,
+  AncestorContextSection,
 } from '../shared';
 import {
   DropdownMenu,
@@ -54,25 +56,34 @@ import {
   DropdownMenuTrigger,
 } from '@/components/ui/dropdown-menu';
 import { useNavigate } from '@tanstack/react-router';
+import {
+  getAncestors,
+  formatAncestorContextForPrompt,
+  type AncestorContext,
+} from '@automaker/dependency-resolver';
+
+type FeatureData = {
+  title: string;
+  category: string;
+  description: string;
+  images: FeatureImage[];
+  imagePaths: DescriptionImagePath[];
+  textFilePaths: DescriptionTextFilePath[];
+  skipTests: boolean;
+  model: AgentModel;
+  thinkingLevel: ThinkingLevel;
+  branchName: string; // Can be empty string to use current branch
+  priority: number;
+  planningMode: PlanningMode;
+  requirePlanApproval: boolean;
+  dependencies?: string[];
+};
 
 interface AddFeatureDialogProps {
   open: boolean;
   onOpenChange: (open: boolean) => void;
-  onAdd: (feature: {
-    title: string;
-    category: string;
-    description: string;
-    images: FeatureImage[];
-    imagePaths: DescriptionImagePath[];
-    textFilePaths: DescriptionTextFilePath[];
-    skipTests: boolean;
-    model: AgentModel;
-    thinkingLevel: ThinkingLevel;
-    branchName: string; // Can be empty string to use current branch
-    priority: number;
-    planningMode: PlanningMode;
-    requirePlanApproval: boolean;
-  }) => void;
+  onAdd: (feature: FeatureData) => void;
+  onAddAndStart?: (feature: FeatureData) => void;
   categorySuggestions: string[];
   branchSuggestions: string[];
   branchCardCounts?: Record<string, number>; // Map of branch name to unarchived card count
@@ -82,12 +93,16 @@ interface AddFeatureDialogProps {
   isMaximized: boolean;
   showProfilesOnly: boolean;
   aiProfiles: AIProfile[];
+  // Spawn task mode props
+  parentFeature?: Feature | null;
+  allFeatures?: Feature[];
 }
 
 export function AddFeatureDialog({
   open,
   onOpenChange,
   onAdd,
+  onAddAndStart,
   categorySuggestions,
   branchSuggestions,
   branchCardCounts,
@@ -97,7 +112,10 @@ export function AddFeatureDialog({
   isMaximized,
   showProfilesOnly,
   aiProfiles,
+  parentFeature = null,
+  allFeatures = [],
 }: AddFeatureDialogProps) {
+  const isSpawnMode = !!parentFeature;
   const navigate = useNavigate();
   const [useCurrentBranch, setUseCurrentBranch] = useState(true);
   const [newFeature, setNewFeature] = useState({
@@ -125,6 +143,10 @@ export function AddFeatureDialog({
   const [planningMode, setPlanningMode] = useState<PlanningMode>('skip');
   const [requirePlanApproval, setRequirePlanApproval] = useState(false);
 
+  // Spawn mode state
+  const [ancestors, setAncestors] = useState<AncestorContext[]>([]);
+  const [selectedAncestorIds, setSelectedAncestorIds] = useState<Set<string>>(new Set());
+
   // Get enhancement model, planning mode defaults, and worktrees setting from store
   const {
     enhancementModel,
@@ -153,6 +175,17 @@ export function AddFeatureDialog({
       setUseCurrentBranch(true);
       setPlanningMode(defaultPlanningMode);
       setRequirePlanApproval(defaultRequirePlanApproval);
+
+      // Initialize ancestors for spawn mode
+      if (parentFeature) {
+        const ancestorList = getAncestors(parentFeature, allFeatures);
+        setAncestors(ancestorList);
+        // Only select parent by default - ancestors are optional context
+        setSelectedAncestorIds(new Set([parentFeature.id]));
+      } else {
+        setAncestors([]);
+        setSelectedAncestorIds(new Set());
+      }
     }
   }, [
     open,
@@ -162,18 +195,20 @@ export function AddFeatureDialog({
     defaultRequirePlanApproval,
     defaultAIProfileId,
     aiProfiles,
+    parentFeature,
+    allFeatures,
   ]);
 
-  const handleAdd = () => {
+  const buildFeatureData = (): FeatureData | null => {
     if (!newFeature.description.trim()) {
       setDescriptionError(true);
-      return;
+      return null;
     }
 
     // Validate branch selection when "other branch" is selected
     if (useWorktrees && !useCurrentBranch && !newFeature.branchName.trim()) {
       toast.error('Please select a branch name');
-      return;
+      return null;
     }
 
     const category = newFeature.category || 'Uncategorized';
@@ -187,10 +222,34 @@ export function AddFeatureDialog({
     // Otherwise (primary worktree), use empty string which means "unassigned" (show only on primary)
     const finalBranchName = useCurrentBranch ? currentBranch || '' : newFeature.branchName || '';
 
-    onAdd({
+    // Build final description - prepend ancestor context in spawn mode
+    let finalDescription = newFeature.description;
+    if (isSpawnMode && parentFeature && selectedAncestorIds.size > 0) {
+      // Create parent context as an AncestorContext
+      const parentContext: AncestorContext = {
+        id: parentFeature.id,
+        title: parentFeature.title,
+        description: parentFeature.description,
+        spec: parentFeature.spec,
+        summary: parentFeature.summary,
+        depth: -1,
+      };
+
+      const allAncestorsWithParent = [parentContext, ...ancestors];
+      const contextText = formatAncestorContextForPrompt(
+        allAncestorsWithParent,
+        selectedAncestorIds
+      );
+
+      if (contextText) {
+        finalDescription = `${contextText}\n\n---\n\n## Task Description\n\n${newFeature.description}`;
+      }
+    }
+
+    return {
       title: newFeature.title,
       category,
-      description: newFeature.description,
+      description: finalDescription,
       images: newFeature.images,
       imagePaths: newFeature.imagePaths,
       textFilePaths: newFeature.textFilePaths,
@@ -201,9 +260,12 @@ export function AddFeatureDialog({
       priority: newFeature.priority,
       planningMode,
       requirePlanApproval,
-    });
+      // In spawn mode, automatically add parent as dependency
+      dependencies: isSpawnMode && parentFeature ? [parentFeature.id] : undefined,
+    };
+  };
 
-    // Reset form
+  const resetForm = () => {
     setNewFeature({
       title: '',
       category: '',
@@ -226,6 +288,20 @@ export function AddFeatureDialog({
     onOpenChange(false);
   };
 
+  const handleAction = (actionFn?: (data: FeatureData) => void) => {
+    if (!actionFn) return;
+
+    const featureData = buildFeatureData();
+    if (!featureData) return;
+
+    actionFn(featureData);
+    resetForm();
+  };
+
+  const handleAdd = () => handleAction(onAdd);
+
+  const handleAddAndStart = () => handleAction(onAddAndStart);
+
   const handleDialogClose = (open: boolean) => {
     onOpenChange(open);
     if (!open) {
@@ -299,8 +375,12 @@ export function AddFeatureDialog({
         }}
       >
         <DialogHeader>
-          <DialogTitle>Add New Feature</DialogTitle>
-          <DialogDescription>Create a new feature card for the Kanban board.</DialogDescription>
+          <DialogTitle>{isSpawnMode ? 'Spawn Sub-Task' : 'Add New Feature'}</DialogTitle>
+          <DialogDescription>
+            {isSpawnMode
+              ? `Create a sub-task that depends on "${parentFeature?.title || parentFeature?.description.slice(0, 50)}..."`
+              : 'Create a new feature card for the Kanban board.'}
+          </DialogDescription>
         </DialogHeader>
         <Tabs defaultValue="prompt" className="py-4 flex-1 min-h-0 flex flex-col">
           <TabsList className="w-full grid grid-cols-3 mb-4">
@@ -320,6 +400,22 @@ export function AddFeatureDialog({
 
           {/* Prompt Tab */}
           <TabsContent value="prompt" className="space-y-4 overflow-y-auto cursor-default">
+            {/* Ancestor Context Section - only in spawn mode */}
+            {isSpawnMode && parentFeature && (
+              <AncestorContextSection
+                parentFeature={{
+                  id: parentFeature.id,
+                  title: parentFeature.title,
+                  description: parentFeature.description,
+                  spec: parentFeature.spec,
+                  summary: parentFeature.summary,
+                }}
+                ancestors={ancestors}
+                selectedAncestorIds={selectedAncestorIds}
+                onSelectionChange={setSelectedAncestorIds}
+              />
+            )}
+
             <div className="space-y-2">
               <Label htmlFor="description">Description</Label>
               <DescriptionImageDropZone
@@ -505,6 +601,17 @@ export function AddFeatureDialog({
           <Button variant="ghost" onClick={() => onOpenChange(false)}>
             Cancel
           </Button>
+          {onAddAndStart && (
+            <Button
+              onClick={handleAddAndStart}
+              variant="secondary"
+              data-testid="confirm-add-and-start-feature"
+              disabled={useWorktrees && !useCurrentBranch && !newFeature.branchName.trim()}
+            >
+              <Play className="w-4 h-4 mr-2" />
+              Make
+            </Button>
+          )}
           <HotkeyButton
             onClick={handleAdd}
             hotkey={{ key: 'Enter', cmdCtrl: true }}
@@ -512,7 +619,7 @@ export function AddFeatureDialog({
             data-testid="confirm-add-feature"
             disabled={useWorktrees && !useCurrentBranch && !newFeature.branchName.trim()}
           >
-            Add Feature
+            {isSpawnMode ? 'Spawn Task' : 'Add Feature'}
           </HotkeyButton>
         </DialogFooter>
       </DialogContent>

apps/ui/src/components/views/board-view/dialogs/archive-all-verified-dialog.tsx

@@ -45,7 +45,7 @@ export function ArchiveAllVerifiedDialog({
           </Button>
           <Button variant="default" onClick={onConfirm} data-testid="confirm-archive-all-verified">
             <Archive className="w-4 h-4 mr-2" />
-            Archive All
+            Complete All
           </Button>
         </DialogFooter>
       </DialogContent>

apps/ui/src/components/views/board-view/dialogs/backlog-plan-dialog.tsx

@@ -0,0 +1,418 @@
+import { useEffect, useState, useCallback } from 'react';
+import {
+  Dialog,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+} from '@/components/ui/dialog';
+import { Button } from '@/components/ui/button';
+import { Textarea } from '@/components/ui/textarea';
+import { Checkbox } from '@/components/ui/checkbox';
+import {
+  Loader2,
+  Wand2,
+  Check,
+  Plus,
+  Pencil,
+  Trash2,
+  ChevronDown,
+  ChevronRight,
+} from 'lucide-react';
+import { getElectronAPI } from '@/lib/electron';
+import { toast } from 'sonner';
+import { cn } from '@/lib/utils';
+import type { BacklogPlanResult, BacklogChange } from '@automaker/types';
+
+interface BacklogPlanDialogProps {
+  open: boolean;
+  onClose: () => void;
+  projectPath: string;
+  onPlanApplied?: () => void;
+  // Props for background generation
+  pendingPlanResult: BacklogPlanResult | null;
+  setPendingPlanResult: (result: BacklogPlanResult | null) => void;
+  isGeneratingPlan: boolean;
+  setIsGeneratingPlan: (generating: boolean) => void;
+}
+
+type DialogMode = 'input' | 'review' | 'applying';
+
+export function BacklogPlanDialog({
+  open,
+  onClose,
+  projectPath,
+  onPlanApplied,
+  pendingPlanResult,
+  setPendingPlanResult,
+  isGeneratingPlan,
+  setIsGeneratingPlan,
+}: BacklogPlanDialogProps) {
+  const [mode, setMode] = useState<DialogMode>('input');
+  const [prompt, setPrompt] = useState('');
+  const [expandedChanges, setExpandedChanges] = useState<Set<number>>(new Set());
+  const [selectedChanges, setSelectedChanges] = useState<Set<number>>(new Set());
+
+  // Set mode based on whether we have a pending result
+  useEffect(() => {
+    if (open) {
+      if (pendingPlanResult) {
+        setMode('review');
+        // Select all changes by default
+        setSelectedChanges(new Set(pendingPlanResult.changes.map((_, i) => i)));
+        setExpandedChanges(new Set());
+      } else {
+        setMode('input');
+      }
+    }
+  }, [open, pendingPlanResult]);
+
+  const handleGenerate = useCallback(async () => {
+    if (!prompt.trim()) {
+      toast.error('Please enter a prompt describing the changes you want');
+      return;
+    }
+
+    const api = getElectronAPI();
+    if (!api?.backlogPlan) {
+      toast.error('API not available');
+      return;
+    }
+
+    // Start generation in background
+    setIsGeneratingPlan(true);
+
+    const result = await api.backlogPlan.generate(projectPath, prompt);
+    if (!result.success) {
+      setIsGeneratingPlan(false);
+      toast.error(result.error || 'Failed to start plan generation');
+      return;
+    }
+
+    // Show toast and close dialog - generation runs in background
+    toast.info('Generating plan... This will be ready soon!', {
+      duration: 3000,
+    });
+    setPrompt('');
+    onClose();
+  }, [projectPath, prompt, setIsGeneratingPlan, onClose]);
+
+  const handleApply = useCallback(async () => {
+    if (!pendingPlanResult) return;
+
+    // Filter to only selected changes
+    const selectedChangesList = pendingPlanResult.changes.filter((_, index) =>
+      selectedChanges.has(index)
+    );
+
+    if (selectedChangesList.length === 0) {
+      toast.error('Please select at least one change to apply');
+      return;
+    }
+
+    const api = getElectronAPI();
+    if (!api?.backlogPlan) {
+      toast.error('API not available');
+      return;
+    }
+
+    setMode('applying');
+
+    // Create a filtered plan result with only selected changes
+    const filteredPlanResult: BacklogPlanResult = {
+      ...pendingPlanResult,
+      changes: selectedChangesList,
+      // Filter dependency updates to only include those for selected features
+      dependencyUpdates:
+        pendingPlanResult.dependencyUpdates?.filter((update) => {
+          const isDeleting = selectedChangesList.some(
+            (c) => c.type === 'delete' && c.featureId === update.featureId
+          );
+          return !isDeleting;
+        }) || [],
+    };
+
+    const result = await api.backlogPlan.apply(projectPath, filteredPlanResult);
+    if (result.success) {
+      toast.success(`Applied ${result.appliedChanges?.length || 0} changes`);
+      setPendingPlanResult(null);
+      onPlanApplied?.();
+      onClose();
+    } else {
+      toast.error(result.error || 'Failed to apply plan');
+      setMode('review');
+    }
+  }, [
+    projectPath,
+    pendingPlanResult,
+    selectedChanges,
+    setPendingPlanResult,
+    onPlanApplied,
+    onClose,
+  ]);
+
+  const handleDiscard = useCallback(() => {
+    setPendingPlanResult(null);
+    setMode('input');
+  }, [setPendingPlanResult]);
+
+  const toggleChangeExpanded = (index: number) => {
+    setExpandedChanges((prev) => {
+      const next = new Set(prev);
+      if (next.has(index)) {
+        next.delete(index);
+      } else {
+        next.add(index);
+      }
+      return next;
+    });
+  };
+
+  const toggleChangeSelected = (index: number) => {
+    setSelectedChanges((prev) => {
+      const next = new Set(prev);
+      if (next.has(index)) {
+        next.delete(index);
+      } else {
+        next.add(index);
+      }
+      return next;
+    });
+  };
+
+  const toggleAllChanges = () => {
+    if (!pendingPlanResult) return;
+    if (selectedChanges.size === pendingPlanResult.changes.length) {
+      setSelectedChanges(new Set());
+    } else {
+      setSelectedChanges(new Set(pendingPlanResult.changes.map((_, i) => i)));
+    }
+  };
+
+  const getChangeIcon = (type: BacklogChange['type']) => {
+    switch (type) {
+      case 'add':
+        return <Plus className="w-4 h-4 text-green-500" />;
+      case 'update':
+        return <Pencil className="w-4 h-4 text-yellow-500" />;
+      case 'delete':
+        return <Trash2 className="w-4 h-4 text-red-500" />;
+    }
+  };
+
+  const getChangeLabel = (change: BacklogChange) => {
+    switch (change.type) {
+      case 'add':
+        return change.feature?.title || 'New Feature';
+      case 'update':
+        return `Update: ${change.featureId}`;
+      case 'delete':
+        return `Delete: ${change.featureId}`;
+    }
+  };
+
+  const renderContent = () => {
+    switch (mode) {
+      case 'input':
+        return (
+          <div className="space-y-4">
+            <div className="text-sm text-muted-foreground">
+              Describe the changes you want to make to your backlog. The AI will analyze your
+              current features and propose additions, updates, or deletions.
+            </div>
+            <Textarea
+              placeholder="e.g., Add authentication features with login, signup, and password reset. Also add a dashboard feature that depends on authentication."
+              value={prompt}
+              onChange={(e) => setPrompt(e.target.value)}
+              className="min-h-[150px] resize-none"
+              autoFocus
+            />
+            <div className="text-xs text-muted-foreground">
+              The AI will automatically handle dependency graph updates when adding or removing
+              features.
+            </div>
+            {isGeneratingPlan && (
+              <div className="flex items-center gap-2 text-sm text-muted-foreground bg-muted/50 rounded-lg p-3">
+                <Loader2 className="w-4 h-4 animate-spin" />A plan is currently being generated in
+                the background...
+              </div>
+            )}
+          </div>
+        );
+
+      case 'review':
+        if (!pendingPlanResult) return null;
+
+        const additions = pendingPlanResult.changes.filter((c) => c.type === 'add');
+        const updates = pendingPlanResult.changes.filter((c) => c.type === 'update');
+        const deletions = pendingPlanResult.changes.filter((c) => c.type === 'delete');
+        const allSelected = selectedChanges.size === pendingPlanResult.changes.length;
+        const someSelected = selectedChanges.size > 0 && !allSelected;
+
+        return (
+          <div className="space-y-4">
+            {/* Summary */}
+            <div className="rounded-lg border bg-muted/30 p-4">
+              <h4 className="font-medium mb-2">Summary</h4>
+              <p className="text-sm text-muted-foreground">{pendingPlanResult.summary}</p>
+            </div>
+
+            {/* Stats */}
+            <div className="flex gap-4 text-sm">
+              {additions.length > 0 && (
+                <span className="flex items-center gap-1 text-green-600">
+                  <Plus className="w-4 h-4" /> {additions.length} additions
+                </span>
+              )}
+              {updates.length > 0 && (
+                <span className="flex items-center gap-1 text-yellow-600">
+                  <Pencil className="w-4 h-4" /> {updates.length} updates
+                </span>
+              )}
+              {deletions.length > 0 && (
+                <span className="flex items-center gap-1 text-red-600">
+                  <Trash2 className="w-4 h-4" /> {deletions.length} deletions
+                </span>
+              )}
+            </div>
+
+            {/* Select all */}
+            <div className="flex items-center gap-2 pb-2 border-b">
+              <Checkbox
+                id="select-all"
+                checked={allSelected}
+                // @ts-expect-error - indeterminate is valid but not in types
+                indeterminate={someSelected}
+                onCheckedChange={toggleAllChanges}
+              />
+              <label htmlFor="select-all" className="text-sm font-medium cursor-pointer">
+                {allSelected ? 'Deselect all' : 'Select all'} ({selectedChanges.size}/
+                {pendingPlanResult.changes.length})
+              </label>
+            </div>
+
+            {/* Changes list */}
+            <div className="max-h-[300px] overflow-y-auto space-y-2">
+              {pendingPlanResult.changes.map((change, index) => (
+                <div
+                  key={index}
+                  className={cn(
+                    'rounded-lg border p-3',
+                    change.type === 'add' && 'border-green-500/30 bg-green-500/5',
+                    change.type === 'update' && 'border-yellow-500/30 bg-yellow-500/5',
+                    change.type === 'delete' && 'border-red-500/30 bg-red-500/5',
+                    !selectedChanges.has(index) && 'opacity-50'
+                  )}
+                >
+                  <div className="flex items-center gap-2">
+                    <Checkbox
+                      checked={selectedChanges.has(index)}
+                      onCheckedChange={() => toggleChangeSelected(index)}
+                    />
+                    <button
+                      className="flex-1 flex items-center gap-2 text-left"
+                      onClick={() => toggleChangeExpanded(index)}
+                    >
+                      {expandedChanges.has(index) ? (
+                        <ChevronDown className="w-4 h-4 text-muted-foreground" />
+                      ) : (
+                        <ChevronRight className="w-4 h-4 text-muted-foreground" />
+                      )}
+                      {getChangeIcon(change.type)}
+                      <span className="font-medium text-sm">{getChangeLabel(change)}</span>
+                    </button>
+                  </div>
+
+                  {expandedChanges.has(index) && (
+                    <div className="mt-3 pl-10 space-y-2 text-sm">
+                      <p className="text-muted-foreground">{change.reason}</p>
+                      {change.feature && (
+                        <div className="rounded bg-background/50 p-2 text-xs font-mono">
+                          {change.feature.description && (
+                            <p className="text-foreground">{change.feature.description}</p>
+                          )}
+                          {change.feature.dependencies &&
+                            change.feature.dependencies.length > 0 && (
+                              <p className="text-muted-foreground mt-1">
+                                Dependencies: {change.feature.dependencies.join(', ')}
+                              </p>
+                            )}
+                        </div>
+                      )}
+                    </div>
+                  )}
+                </div>
+              ))}
+            </div>
+          </div>
+        );
+
+      case 'applying':
+        return (
+          <div className="flex flex-col items-center justify-center py-12">
+            <Loader2 className="w-8 h-8 animate-spin text-primary mb-4" />
+            <p className="text-muted-foreground">Applying changes...</p>
+          </div>
+        );
+    }
+  };
+
+  return (
+    <Dialog open={open} onOpenChange={(isOpen) => !isOpen && onClose()}>
+      <DialogContent className="max-w-2xl">
+        <DialogHeader>
+          <DialogTitle className="flex items-center gap-2">
+            <Wand2 className="w-5 h-5 text-primary" />
+            {mode === 'review' ? 'Review Plan' : 'Plan Backlog Changes'}
+          </DialogTitle>
+          <DialogDescription>
+            {mode === 'review'
+              ? 'Select which changes to apply to your backlog'
+              : 'Use AI to add, update, or remove features from your backlog'}
+          </DialogDescription>
+        </DialogHeader>
+
+        <div className="py-4">{renderContent()}</div>
+
+        <DialogFooter>
+          {mode === 'input' && (
+            <>
+              <Button variant="outline" onClick={onClose}>
+                Cancel
+              </Button>
+              <Button onClick={handleGenerate} disabled={!prompt.trim() || isGeneratingPlan}>
+                {isGeneratingPlan ? (
+                  <>
+                    <Loader2 className="w-4 h-4 mr-2 animate-spin" />
+                    Generating...
+                  </>
+                ) : (
+                  <>
+                    <Wand2 className="w-4 h-4 mr-2" />
+                    Generate Plan
+                  </>
+                )}
+              </Button>
+            </>
+          )}
+
+          {mode === 'review' && (
+            <>
+              <Button variant="outline" onClick={handleDiscard}>
+                Discard
+              </Button>
+              <Button variant="outline" onClick={onClose}>
+                Review Later
+              </Button>
+              <Button onClick={handleApply} disabled={selectedChanges.size === 0}>
+                <Check className="w-4 h-4 mr-2" />
+                Apply {selectedChanges.size} Change{selectedChanges.size !== 1 ? 's' : ''}
+              </Button>
+            </>
+          )}
+        </DialogFooter>
+      </DialogContent>
+    </Dialog>
+  );
+}

apps/ui/src/components/views/board-view/dialogs/feature-suggestions-dialog.tsx

@@ -21,6 +21,8 @@ import {
   RefreshCw,
   Shield,
   Zap,
+  List,
+  FileText,
 } from 'lucide-react';
 import {
   getElectronAPI,
@@ -30,6 +32,7 @@ import {
 } from '@/lib/electron';
 import { useAppStore, Feature } from '@/store/app-store';
 import { toast } from 'sonner';
+import { LogViewer } from '@/components/ui/log-viewer';
 
 interface FeatureSuggestionsDialogProps {
   open: boolean;
@@ -92,6 +95,7 @@ export function FeatureSuggestionsDialog({
   const [expandedIds, setExpandedIds] = useState<Set<string>>(new Set());
   const [isImporting, setIsImporting] = useState(false);
   const [currentSuggestionType, setCurrentSuggestionType] = useState<SuggestionType | null>(null);
+  const [viewMode, setViewMode] = useState<'parsed' | 'raw'>('parsed');
   const scrollRef = useRef<HTMLDivElement>(null);
   const autoScrollRef = useRef(true);
 
@@ -123,7 +127,9 @@ export function FeatureSuggestionsDialog({
         setProgress((prev) => [...prev, event.content || '']);
       } else if (event.type === 'suggestions_tool') {
         const toolName = event.tool || 'Unknown Tool';
-        setProgress((prev) => [...prev, `Using tool: ${toolName}\n`]);
+        const toolInput = event.input ? JSON.stringify(event.input, null, 2) : '';
+        const formattedTool = `\n🔧 Tool: ${toolName}\n${toolInput ? `Input: ${toolInput}\n` : ''}`;
+        setProgress((prev) => [...prev, formattedTool]);
       } else if (event.type === 'suggestions_complete') {
         setIsGenerating(false);
         if (event.suggestions && event.suggestions.length > 0) {
@@ -245,6 +251,7 @@ export function FeatureSuggestionsDialog({
         id: `feature-${Date.now()}-${Math.random().toString(36).substr(2, 9)}`,
         category: s.category,
         description: s.description,
+        steps: [], // Required empty steps array for new features
         status: 'backlog' as const,
         skipTests: true, // As specified, testing mode true
         priority: s.priority, // Preserve priority from suggestion
@@ -297,7 +304,7 @@ export function FeatureSuggestionsDialog({
     setCurrentSuggestionType(null);
   }, [setSuggestions]);
 
-  const hasStarted = progress.length > 0 || suggestions.length > 0;
+  const hasStarted = isGenerating || progress.length > 0 || suggestions.length > 0;
   const hasSuggestions = suggestions.length > 0;
   const currentConfig = currentSuggestionType ? suggestionTypeConfig[currentSuggestionType] : null;
 
@@ -371,19 +378,56 @@ export function FeatureSuggestionsDialog({
                 <Loader2 className="w-4 h-4 animate-spin" />
                 Analyzing project...
               </div>
-              <Button variant="destructive" size="sm" onClick={handleStop}>
-                <StopCircle className="w-4 h-4 mr-2" />
-                Stop
-              </Button>
+              <div className="flex items-center gap-2">
+                <div className="flex items-center gap-1 bg-muted rounded-lg p-1">
+                  <button
+                    onClick={() => setViewMode('parsed')}
+                    className={`flex items-center gap-1.5 px-2 py-1 rounded-md text-xs font-medium transition-all ${
+                      viewMode === 'parsed'
+                        ? 'bg-primary/20 text-primary shadow-sm'
+                        : 'text-muted-foreground hover:text-foreground hover:bg-accent'
+                    }`}
+                    data-testid="view-mode-parsed"
+                  >
+                    <List className="w-3 h-3" />
+                    Logs
+                  </button>
+                  <button
+                    onClick={() => setViewMode('raw')}
+                    className={`flex items-center gap-1.5 px-2 py-1 rounded-md text-xs font-medium transition-all ${
+                      viewMode === 'raw'
+                        ? 'bg-primary/20 text-primary shadow-sm'
+                        : 'text-muted-foreground hover:text-foreground hover:bg-accent'
+                    }`}
+                    data-testid="view-mode-raw"
+                  >
+                    <FileText className="w-3 h-3" />
+                    Raw
+                  </button>
+                </div>
+                <Button variant="destructive" size="sm" onClick={handleStop}>
+                  <StopCircle className="w-4 h-4 mr-2" />
+                  Stop
+                </Button>
+              </div>
             </div>
             <div
               ref={scrollRef}
               onScroll={handleScroll}
               className="flex-1 overflow-y-auto bg-zinc-950 rounded-lg p-4 font-mono text-xs min-h-[200px] max-h-[400px]"
             >
-              <div className="whitespace-pre-wrap break-words text-zinc-300">
-                {progress.join('')}
-              </div>
+              {progress.length === 0 ? (
+                <div className="flex items-center justify-center min-h-[168px] text-muted-foreground">
+                  <Loader2 className="w-6 h-6 animate-spin mr-2" />
+                  Waiting for AI response...
+                </div>
+              ) : viewMode === 'parsed' ? (
+                <LogViewer output={progress.join('')} />
+              ) : (
+                <div className="whitespace-pre-wrap break-words text-zinc-300">
+                  {progress.join('')}
+                </div>
+              )}
             </div>
           </div>
         ) : hasSuggestions ? (

apps/ui/src/components/views/board-view/dialogs/index.ts

@@ -1,5 +1,6 @@
 export { AddFeatureDialog } from './add-feature-dialog';
 export { AgentOutputModal } from './agent-output-modal';
+export { BacklogPlanDialog } from './backlog-plan-dialog';
 export { CompletedFeaturesModal } from './completed-features-modal';
 export { ArchiveAllVerifiedDialog } from './archive-all-verified-dialog';
 export { DeleteCompletedFeatureDialog } from './delete-completed-feature-dialog';

apps/ui/src/components/views/board-view/hooks/use-board-actions.ts

@@ -98,6 +98,7 @@ export function useBoardActions({
       priority: number;
       planningMode: PlanningMode;
       requirePlanApproval: boolean;
+      dependencies?: string[];
     }) => {
       // Empty string means "unassigned" (show only on primary worktree) - convert to undefined
       // Non-empty string is the actual branch name (for non-primary worktrees)
@@ -150,6 +151,7 @@ export function useBoardActions({
         titleGenerating: needsTitleGeneration,
         status: 'backlog' as const,
         branchName: finalBranchName,
+        dependencies: featureData.dependencies || [],
       };
       const createdFeature = addFeature(newFeatureData);
       // Must await to ensure feature exists on server before user can drag it

apps/ui/src/components/views/board-view/kanban-board.tsx

@@ -41,6 +41,7 @@ interface KanbanBoardProps {
   onImplement: (feature: Feature) => void;
   onViewPlan: (feature: Feature) => void;
   onApprovePlan: (feature: Feature) => void;
+  onSpawnTask?: (feature: Feature) => void;
   featuresWithContext: Set<string>;
   runningAutoTasks: string[];
   shortcuts: ReturnType<typeof useKeyboardShortcutsConfig>;
@@ -73,6 +74,7 @@ export function KanbanBoard({
   onImplement,
   onViewPlan,
   onApprovePlan,
+  onSpawnTask,
   featuresWithContext,
   runningAutoTasks,
   shortcuts,
@@ -117,7 +119,7 @@ export function KanbanBoard({
                       data-testid="archive-all-verified-button"
                     >
                       <Archive className="w-3 h-3 mr-1" />
-                      Archive All
+                      Complete All
                     </Button>
                   ) : column.id === 'backlog' ? (
                     <div className="flex items-center gap-1">
@@ -184,6 +186,7 @@ export function KanbanBoard({
                         onImplement={() => onImplement(feature)}
                         onViewPlan={() => onViewPlan(feature)}
                         onApprovePlan={() => onApprovePlan(feature)}
+                        onSpawnTask={() => onSpawnTask?.(feature)}
                         hasContext={featuresWithContext.has(feature.id)}
                         isCurrentAutoTask={runningAutoTasks.includes(feature.id)}
                         shortcutKey={shortcutKey}

apps/ui/src/components/views/board-view/shared/ancestor-context-section.tsx

@@ -0,0 +1,211 @@
+import { useState } from 'react';
+import { Checkbox } from '@/components/ui/checkbox';
+import { Label } from '@/components/ui/label';
+import { Button } from '@/components/ui/button';
+import { ChevronDown, ChevronRight, Users, CheckCircle2 } from 'lucide-react';
+import { cn } from '@/lib/utils';
+import type { AncestorContext } from '@automaker/dependency-resolver';
+import { Collapsible, CollapsibleContent, CollapsibleTrigger } from '@/components/ui/collapsible';
+
+interface ParentFeatureContext {
+  id: string;
+  title?: string;
+  description: string;
+  spec?: string;
+  summary?: string;
+}
+
+interface AncestorContextSectionProps {
+  parentFeature: ParentFeatureContext;
+  ancestors: AncestorContext[];
+  selectedAncestorIds: Set<string>;
+  onSelectionChange: (ids: Set<string>) => void;
+}
+
+export function AncestorContextSection({
+  parentFeature,
+  ancestors,
+  selectedAncestorIds,
+  onSelectionChange,
+}: AncestorContextSectionProps) {
+  const [expandedIds, setExpandedIds] = useState<Set<string>>(new Set());
+
+  const toggleExpanded = (id: string) => {
+    const newExpanded = new Set(expandedIds);
+    if (newExpanded.has(id)) {
+      newExpanded.delete(id);
+    } else {
+      newExpanded.add(id);
+    }
+    setExpandedIds(newExpanded);
+  };
+
+  const toggleSelected = (id: string) => {
+    const newSelected = new Set(selectedAncestorIds);
+    if (newSelected.has(id)) {
+      newSelected.delete(id);
+    } else {
+      newSelected.add(id);
+    }
+    onSelectionChange(newSelected);
+  };
+
+  const selectAll = () => {
+    const allIds = new Set([parentFeature.id, ...ancestors.map((a) => a.id)]);
+    onSelectionChange(allIds);
+  };
+
+  const selectNone = () => {
+    onSelectionChange(new Set());
+  };
+
+  // Combine parent and ancestors into a single list
+  const allAncestorItems: Array<
+    (AncestorContext | ParentFeatureContext) & { isParent: boolean; depth: number }
+  > = [
+    { ...parentFeature, depth: -1, isParent: true },
+    ...ancestors.map((a) => ({ ...a, isParent: false })),
+  ];
+
+  const totalCount = allAncestorItems.length;
+
+  return (
+    <div className="space-y-3">
+      <div className="flex items-center justify-between">
+        <div className="flex items-center gap-2">
+          <Users className="w-4 h-4 text-muted-foreground" />
+          <Label className="text-sm font-medium">Ancestor Context</Label>
+          <span className="text-xs text-muted-foreground">
+            ({selectedAncestorIds.size}/{totalCount} selected)
+          </span>
+        </div>
+        <div className="flex items-center gap-1">
+          <Button
+            type="button"
+            variant="ghost"
+            size="sm"
+            onClick={selectAll}
+            className="h-6 px-2 text-xs"
+          >
+            All
+          </Button>
+          <Button
+            type="button"
+            variant="ghost"
+            size="sm"
+            onClick={selectNone}
+            className="h-6 px-2 text-xs"
+          >
+            None
+          </Button>
+        </div>
+      </div>
+
+      <p className="text-xs text-muted-foreground">
+        The parent task context will be included to help the AI understand the background.
+        Additional ancestors can optionally be included for more context.
+      </p>
+
+      <div className="space-y-1 max-h-[200px] overflow-y-auto border rounded-lg p-2 bg-muted/20">
+        {allAncestorItems.map((item) => {
+          const isSelected = selectedAncestorIds.has(item.id);
+          const isExpanded = expandedIds.has(item.id);
+          const hasContent =
+            item.description ||
+            ('spec' in item && item.spec) ||
+            ('summary' in item && item.summary);
+          const displayTitle =
+            item.title ||
+            item.description.slice(0, 50) + (item.description.length > 50 ? '...' : '');
+
+          return (
+            <Collapsible key={item.id} open={isExpanded}>
+              <div
+                className={cn(
+                  'flex items-start gap-2 p-2 rounded-md transition-colors',
+                  item.isParent
+                    ? isSelected
+                      ? 'bg-[var(--status-success-bg)] border border-[var(--status-success)]/30'
+                      : 'bg-muted/30 border border-border hover:bg-muted/50'
+                    : isSelected
+                      ? 'bg-primary/10'
+                      : 'hover:bg-muted/50'
+                )}
+                style={{ marginLeft: item.isParent ? 0 : `${item.depth * 12}px` }}
+              >
+                <Checkbox
+                  id={`ancestor-${item.id}`}
+                  checked={isSelected}
+                  onCheckedChange={() => toggleSelected(item.id)}
+                  className="mt-0.5"
+                />
+                <div className="flex-1 min-w-0">
+                  <div className="flex items-center gap-1">
+                    {hasContent && (
+                      <CollapsibleTrigger asChild>
+                        <Button
+                          type="button"
+                          variant="ghost"
+                          size="sm"
+                          className="h-5 w-5 p-0"
+                          onClick={() => toggleExpanded(item.id)}
+                        >
+                          {isExpanded ? (
+                            <ChevronDown className="w-3 h-3" />
+                          ) : (
+                            <ChevronRight className="w-3 h-3" />
+                          )}
+                        </Button>
+                      </CollapsibleTrigger>
+                    )}
+                    <label
+                      htmlFor={`ancestor-${item.id}`}
+                      className="text-sm font-medium cursor-pointer truncate flex-1"
+                    >
+                      {displayTitle}
+                    </label>
+                    {item.isParent && (
+                      <span className="ml-2 inline-flex items-center gap-1 text-xs text-[var(--status-success)] font-medium">
+                        <CheckCircle2 className="w-3 h-3" />
+                        Completed Parent
+                      </span>
+                    )}
+                  </div>
+
+                  <CollapsibleContent>
+                    <div className="mt-2 space-y-2 text-xs text-muted-foreground pl-5">
+                      {item.description && (
+                        <div>
+                          <span className="font-medium text-foreground">Description:</span>
+                          <p className="mt-0.5 line-clamp-3">{item.description}</p>
+                        </div>
+                      )}
+                      {'spec' in item && item.spec && (
+                        <div>
+                          <span className="font-medium text-foreground">Specification:</span>
+                          <p className="mt-0.5 line-clamp-3">{item.spec}</p>
+                        </div>
+                      )}
+                      {'summary' in item && item.summary && (
+                        <div>
+                          <span className="font-medium text-foreground">Summary:</span>
+                          <p className="mt-0.5 line-clamp-3">{item.summary}</p>
+                        </div>
+                      )}
+                    </div>
+                  </CollapsibleContent>
+                </div>
+              </div>
+            </Collapsible>
+          );
+        })}
+
+        {ancestors.length === 0 && (
+          <p className="text-xs text-muted-foreground text-center py-2">
+            Parent task has no additional ancestors
+          </p>
+        )}
+      </div>
+    </div>
+  );
+}