refactor: engineering improvements -- API versioning, structured logging, Alembic, error standardization, test coverage

- API versioning: all REST endpoints prefixed with /api/v1/ - Structured logging: replaced stdlib logging with structlog (console/JSON modes) - Alembic migrations: versioned DB schema with initial migration - Error standardization: global exception handlers for consistent envelope format - Interrupt cleanup: asyncio background task for expired interrupt removal - Integration tests: +30 tests (analytics, replay, openapi, error, session APIs) - Frontend tests: +57 tests (all components, pages, useWebSocket hook) - Backend: 557 tests, 89.75% coverage | Frontend: 80 tests, 16 test files
refactor: fix architectural issues across frontend and backend
2026-04-06 23:19:29 +02:00 · 2026-04-06 15:59:14 +02:00 · 2026-04-06 14:51:51 +02:00 · 2026-04-06 13:55:45 +02:00 · 2026-04-06 13:32:10 +02:00 · 2026-04-05 23:10:50 +02:00
165 changed files with 19578 additions and 605 deletions
--- a/.claude/settings.local.json
+++ b/.claude/settings.local.json
@@ -2,7 +2,22 @@
  "permissions": {
    "allow": [
      "Bash(find:*)",
+      "Bash(ruff:*)",
+      "Bash(pytest:*)",
+      "Bash(git status:*)",
+      "Bash(git diff:*)",
+      "Bash(git log:*)",
+      "Bash(git branch:*)",
+      "Bash(git add:*)",
+      "Bash(git commit:*)",
+      "Bash(git checkout:*)",
+      "Bash(git merge:*)",
+      "Bash(git tag:*)",
+      "Bash(git show:*)",
+      "Bash(docker:*)",
+      "Bash(docker-compose:*)",
      "WebSearch"
-    ]
+    ],
+    "defaultMode": "bypassPermissions"
  }
 }
--- a/.env.example
+++ b/.env.example
@@ -0,0 +1,35 @@
+# Smart Support -- Docker Compose environment variables
+# Copy to .env and fill in your values
+
+# PostgreSQL password (used by both postgres and backend services)
+POSTGRES_PASSWORD=dev_password
+
+# LLM provider: anthropic | openai | azure_openai | google
+LLM_PROVIDER=anthropic
+LLM_MODEL=claude-sonnet-4-6
+
+# API keys (provide the one matching LLM_PROVIDER)
+ANTHROPIC_API_KEY=
+OPENAI_API_KEY=
+GOOGLE_API_KEY=
+
+# Azure OpenAI (required when LLM_PROVIDER=azure_openai)
+AZURE_OPENAI_API_KEY=
+AZURE_OPENAI_ENDPOINT=
+AZURE_OPENAI_DEPLOYMENT=
+AZURE_OPENAI_API_VERSION=2024-12-01-preview
+
+# Optional: webhook URL for escalation notifications
+WEBHOOK_URL=
+
+# Session and interrupt TTL in minutes
+SESSION_TTL_MINUTES=30
+INTERRUPT_TTL_MINUTES=30
+
+# Optional: API key for admin endpoints (analytics, replay, openapi, websocket)
+# Leave empty to disable authentication (dev mode)
+ADMIN_API_KEY=
+
+# Optional: load a named agent template instead of agents.yaml
+# Available templates: ecommerce, saas, generic
+TEMPLATE_NAME=
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -30,7 +30,7 @@ pytest --cov=app --cov-report=term-missing
 #    - If any test fails, fix it before starting the new phase

 # 3. Create checkpoint to snapshot the starting state
-/everything-claude-code:checkpoint create [phase name]
+/ecc:checkpoint create "phase-name"

 # 4. Create the phase branch
 git checkout main
@@ -50,25 +50,32 @@ git checkout -b phase-{N}/{short-description}
 3. Identify all tasks, acceptance criteria, and dependencies for this phase
 4. Create a phase dev log **skeleton** at `docs/phases/phase-{N}-dev-log.md` (date, branch name, plan link only -- content filled in Step 5)

-### Step 2: Develop Using Orchestrate Skill
+### Step 2: Develop Using ECC Skills

-Route to the correct orchestration mode based on work type:
+Route to the correct skill based on work type:

-| Work Type | Skill Command |
-|-----------|---------------|
-| New feature | `/everything-claude-code:orchestrate feature` |
-| Bug fix | `/everything-claude-code:orchestrate bugfix` |
-| Refactor | `/everything-claude-code:orchestrate refactor` |
+| Work Type | Skill Command | What It Does |
+|-----------|---------------|--------------|
+| New feature | `/ecc:feature-dev <desc>` | Discovery -> Exploration -> Architecture -> TDD -> Review -> Summary |
+| Bug fix | `/ecc:tdd` then `/ecc:code-review` | RED -> GREEN -> REFACTOR cycle, then review |
+| Refactor | `/ecc:plan` then `/ecc:tdd` then `/ecc:code-review` | Plan refactor scope, TDD, review |
+| Security-sensitive | Add `/ecc:security-review` after code-review | Auth, payments, user input, external APIs |
+| Final verification | `/ecc:verify` | Build + tests + lint + coverage + security scan |

-ALWAYS use the appropriate orchestrate skill. Never develop without it.
-
-A single phase may contain mixed work types (e.g., Phase 5 has feature + bugfix + refactor). Call the orchestrate skill **per sub-task** with the matching mode. Example:
+A single phase may contain mixed work types. Call the appropriate skill **per sub-task**:

 ```
-# Within Phase 5:
-/everything-claude-code:orchestrate feature    # for demo script
-/everything-claude-code:orchestrate bugfix     # for error handling fixes
-/everything-claude-code:orchestrate refactor   # for code cleanup
+# Within a phase:
+/ecc:feature-dev "demo script"           # for new features
+/ecc:tdd                                  # for bug fixes (write failing test, then fix)
+/ecc:plan "consolidate error handling"    # for refactors (plan first, then TDD)
+```
+
+For full multi-phase autonomous execution, use GSD:
+
+```
+/gsd:autonomous              # execute all remaining phases
+/gsd:execute-phase 6         # execute a specific phase
 ```

 ### Step 3: Module Independence (CRITICAL)
@@ -171,10 +178,10 @@ After all development and testing, run verification in this exact order:

 ```
 # 1. Run the verification skill -- must pass
-/everything-claude-code:verify
+/ecc:verify

 # 2. Verify the checkpoint -- validates all phase deliverables
-/everything-claude-code:checkpoint verify [phase name]
+/ecc:checkpoint verify "phase-name"
 ```

 The checkpoint verify validates:
@@ -222,11 +229,11 @@ git push origin main --tags
 All four markers must be consistent. If any is missed, the next phase's Step 0 regression gate will catch the discrepancy.

 A checkpoint includes:
- `/everything-claude-code:checkpoint create` at phase start
- `/everything-claude-code:checkpoint verify` at phase end
+- `/ecc:checkpoint create` at phase start
+- `/ecc:checkpoint verify` at phase end
 - All tests passing (80%+ coverage)
 - Phase dev log written and linked
- `/everything-claude-code:verify` passed
+- `/ecc:verify` passed
 - Git tag `checkpoint/phase-{N}` created
 - Phase marked COMPLETED in four locations
 - Branch merged to main
@@ -238,10 +245,10 @@ A checkpoint includes:
 | Phase | Branch | Focus | Status |
 |-------|--------|-------|--------|
 | 1 | `phase-1/core-framework` | FastAPI + LangGraph + React chat loop + PostgresSaver | COMPLETED (2026-03-30) |
-| 2 | `phase-2/multi-agent-safety` | Supervisor routing + interrupts + templates | NOT STARTED |
-| 3 | `phase-3/openapi-discovery` | OpenAPI parsing + MCP generation + SSRF protection | NOT STARTED |
-| 4 | `phase-4/analytics-replay` | Replay API + analytics dashboard | NOT STARTED |
-| 5 | `phase-5/polish-demo` | Error hardening + demo prep + Docker deploy | NOT STARTED |
+| 2 | `phase-2/multi-agent-safety` | Supervisor routing + interrupts + templates | COMPLETED (2026-03-30) |
+| 3 | `phase-3/openapi-discovery` | OpenAPI parsing + MCP generation + SSRF protection | COMPLETED (2026-03-30) |
+| 4 | `phase-4/analytics-replay` | Replay API + analytics dashboard | COMPLETED (2026-03-31) |
+| 5 | `phase-5/polish-demo` | Error hardening + demo prep + Docker deploy | COMPLETED (2026-03-31) |

 Status values: `NOT STARTED` -> `IN PROGRESS` -> `COMPLETED (YYYY-MM-DD)`

@@ -264,7 +271,7 @@ This project inherits from `~/.claude/rules/`. CLAUDE.md only contains project-s

 ### Hooks (ECC Plugin -- No Custom Hooks)

-All hooks come from the ECC plugin (`everything-claude-code`). No project-level hooks in `.claude/settings.local.json`.
+All hooks come from the ECC plugin (`ecc`). No project-level hooks in `.claude/settings.local.json`.

 | ECC Hook | Type | What It Does |
 |----------|------|-------------|
@@ -290,7 +297,7 @@ Controlled by `ECC_HOOK_PROFILE` env var in `~/.claude/settings.json` (currently
 - Architecture doc: `docs/ARCHITECTURE.md`
 - Phase dev logs: `docs/phases/phase-{N}-dev-log.md`
 - Test command: `pytest --cov=app --cov-report=term-missing`
- **Phase start:** `/everything-claude-code:checkpoint create [phase name]`
- **Phase end:** `/everything-claude-code:checkpoint verify [phase name]`
- Verify command: `/everything-claude-code:verify`
- Orchestrate: `/everything-claude-code:orchestrate {feature|bugfix|refactor}`
+- **Phase start:** `/ecc:checkpoint create "phase-name"`
+- **Phase end:** `/ecc:checkpoint verify "phase-name"`
+- Verify command: `/ecc:verify`
+- Orchestrate: `/ecc:orchestrate {feature|bugfix|refactor}`
--- a/README.md
+++ b/README.md
@@ -1,159 +1,174 @@
 # Smart Support

-AI 客服行动层框架。粘贴你的 API，获得一个能执行真实操作的智能客服。
+AI customer support action layer. Paste your API spec, get an AI agent that executes real actions.

-## 问题
+## The Problem

-现有客服工具（Zendesk、Intercom、Ada）擅长回答 FAQ，但自动化率卡在 20-30%。剩下 70% 的工单需要人工登录内部系统，手动查订单、取消订单、发优惠券。
+Existing support tools (Zendesk, Intercom, Ada) answer FAQs well but automation
+rates stall at 20-30%. The remaining 70% of tickets require agents to manually
+log into internal systems to look up orders, cancel orders, issue coupons.

-Smart Support 是补全这个缺口的「行动层」。它不替代现有客服平台，而是让 AI 能直接调用内部系统完成操作。
+Smart Support fills that gap as the "action layer" -- it does not replace your
+existing support platform, it enables AI to directly call your internal systems.

-## 工作原理
+## How It Works

 ```
-客户消息 → Chat UI → FastAPI WebSocket → LangGraph Supervisor → 专业 Agent → MCP Tools → 你的内部系统
-                                                ↑                      ↑
-                                          Agent 注册表            interrupt()
-                                          (YAML 配置)           (人工确认)
-                                                ↑
+User message -> Chat UI -> FastAPI WebSocket -> LangGraph Supervisor -> Specialist Agent -> MCP Tools -> Your systems
+                                                        |                      |
+                                                  Agent Registry          interrupt()
+                                                  (YAML config)         (human approval)
+                                                        |
                                                  PostgresSaver
-                                         (会话状态持久化)
+                                               (session persistence)
 ```

-1. 客户在聊天界面发送消息
-2. LangGraph Supervisor 分析意图，路由到对应的专业 Agent
-3. Agent 通过 MCP 协议调用你的内部系统（查订单、取消订单、发折扣...）
-4. 涉及写操作时，自动触发人工确认流程
-5. 所有操作全程记录，支持回放和分析
+1. User sends a message in the chat UI.
+2. LangGraph Supervisor classifies intent and routes to the right agent.
+3. Agent calls your internal systems via MCP tools.
+4. Write operations trigger a human-in-the-loop approval gate.
+5. All operations are logged with full replay and analytics.

-## 核心特性
+## Key Features

- **多 Agent 协作** - 不同操作由不同 Agent 处理，各自拥有独立的权限边界和工具集
- **即插即用** - 粘贴 OpenAPI 规范 URL，自动生成 MCP 工具和 Agent 配置
- **人工确认** - 所有写操作（取消、退款、修改）需要人工审批，读操作直接执行
- **会话上下文** - 支持多轮对话，Agent 能理解「取消那个订单」这样的指代
- **实时流式输出** - WebSocket 双向通信，逐 token 流式返回
- **对话回放** - 逐步查看 Agent 决策过程、工具调用和返回结果
- **数据分析** - 解决率、Agent 使用率、升级率、每次对话成本
- **YAML 驱动配置** - Agent 定义、人设、垂直模板全部通过 YAML 配置
+- **Multi-agent routing** -- each operation goes to a specialist agent with its own tools and permissions
+- **Zero-config import** -- paste an OpenAPI 3.0 URL, agents are generated automatically
+- **Human-in-the-loop** -- all write operations (cancel, refund, modify) require approval; reads execute immediately
+- **Session context** -- multi-turn conversation with persistent state across reconnects
+- **Real-time streaming** -- WebSocket token streaming with live tool call visibility
+- **Conversation replay** -- step-by-step audit trail of every agent decision
+- **Analytics dashboard** -- resolution rate, agent usage, escalation rate, cost per conversation
+- **YAML-driven config** -- agents, personas, and vertical templates in a single file

-## 技术栈
+## Tech Stack

-| 组件 | 技术选型 |
-|------|---------|
-| 后端 | Python 3.11+, FastAPI |
-| Agent 编排 | LangGraph v1.1, langgraph-supervisor |
-| 工具集成 | langchain-mcp-adapters, @tool |
-| 状态持久化 | PostgreSQL + langgraph-checkpoint-postgres |
-| LLM | Claude Sonnet 4.6（可切换 OpenAI、Google 等） |
-| 前端 | React |
-| 部署 | Docker Compose |
+| Component | Technology |
+|-----------|-----------|
+| Backend | Python 3.11+, FastAPI |
+| Agent orchestration | LangGraph 1.x, langgraph-supervisor |
+| Session state | PostgreSQL 16 + langgraph-checkpoint-postgres |
+| LLM | Claude Sonnet 4.6 (configurable: OpenAI, Azure OpenAI, Google) |
+| Frontend | React 19, TypeScript, Vite |
+| Testing | pytest (backend), vitest + happy-dom (frontend) |
+| Deployment | Docker Compose |

-## 项目结构
+## Quick Start
+
+```bash
+git clone <repo-url>
+cd smart-support
+
+# Configure your LLM API key
+cp .env.example .env
+# Edit .env: set LLM_PROVIDER and the corresponding API key
+#   anthropic    -> ANTHROPIC_API_KEY
+#   openai       -> OPENAI_API_KEY
+#   azure_openai -> AZURE_OPENAI_API_KEY + AZURE_OPENAI_ENDPOINT + AZURE_OPENAI_DEPLOYMENT
+#   google       -> GOOGLE_API_KEY
+
+# Start all services
+docker compose up -d
+
+# Open the app
+open http://localhost
+```
+
+### Local Development
+
+```bash
+# Start only PostgreSQL via Docker (exposed on port 5433)
+docker compose up postgres -d
+
+# Backend (in one terminal)
+cd backend
+pip install -e ".[dev]"
+uvicorn app.main:app --host 0.0.0.0 --port 8001 --reload
+
+# Frontend (in another terminal)
+cd frontend
+npm install
+npm run dev    # http://localhost:5173 (proxies /api and /ws to :8001)
+```
+
+See [Deployment Guide](docs/deployment.md) for production setup, HTTPS, and scaling.
+
+## Project Structure

 ```
 smart-support/
 ├── backend/
 │   ├── app/
-│   │   ├── main.py          # FastAPI + WebSocket 入口
-│   │   ├── graph.py         # LangGraph Supervisor 配置
-│   │   ├── agents/          # Agent 定义 + 工具
-│   │   ├── registry.py      # YAML Agent 注册表加载器
-│   │   ├── openapi/         # OpenAPI 解析 + MCP 服务器生成
-│   │   ├── replay/          # 对话回放 API
-│   │   ├── analytics/       # 数据分析查询 + API
-│   │   └── callbacks.py     # Token 用量统计
-│   ├── agents.yaml          # Agent 注册表配置
-│   ├── templates/           # 垂直行业模板
-│   └── tests/
-├── frontend/                # React 聊天 UI + 回放 + 仪表盘
-├── docker-compose.yml       # PostgreSQL + 应用
-└── pyproject.toml
+│   │   ├── main.py              # FastAPI + WebSocket entry point
+│   │   ├── graph.py             # LangGraph Supervisor construction
+│   │   ├── graph_context.py     # Typed wrapper for graph + classifier + registry
+│   │   ├── ws_handler.py        # WebSocket message dispatch + rate limiting
+│   │   ├── ws_context.py        # WebSocket dependency bundle
+│   │   ├── auth.py              # API key authentication middleware
+│   │   ├── api_utils.py         # Shared API response helpers
+│   │   ├── safety.py            # Confirmation rules + MCP error taxonomy
+│   │   ├── agents/              # Agent definitions and tools
+│   │   ├── registry.py          # YAML agent registry loader
+│   │   ├── openapi/             # OpenAPI parser, classifier, and review API
+│   │   ├── replay/              # Conversation replay API
+│   │   └── analytics/           # Analytics queries and API
+│   ├── agents.yaml              # Agent registry configuration
+│   ├── templates/               # Vertical industry templates
+│   └── tests/                   # Unit, integration, and E2E tests
+├── frontend/
+│   ├── src/
+│   │   ├── pages/               # Chat, Replay, Dashboard, Review pages
+│   │   ├── components/          # NavBar, Layout, MetricCard, ReplayTimeline
+│   │   ├── hooks/               # useWebSocket with reconnect support
+│   │   └── api.ts               # Typed API client
+│   └── Dockerfile               # Multi-stage nginx build
+├── docs/                        # Architecture, deployment, guides
+├── docker-compose.yml           # Full-stack compose
+└── .env.example                 # Environment variable template
 ```

-## 快速开始
+## API Endpoints
+
+| Method | Path | Auth | Description |
+|--------|------|------|-------------|
+| WS | `/ws` | Token | Main WebSocket chat endpoint (`?token=<key>`) |
+| GET | `/api/health` | No | Health check |
+| GET | `/api/conversations` | API Key | List conversations (paginated) |
+| GET | `/api/replay/{thread_id}` | API Key | Replay conversation steps (paginated) |
+| GET | `/api/analytics` | API Key | Analytics summary (`?range=7d`) |
+| POST | `/api/openapi/import` | API Key | Start OpenAPI import job |
+| GET | `/api/openapi/jobs/{id}` | API Key | Check import job status |
+| GET | `/api/openapi/jobs/{id}/classifications` | API Key | Get endpoint classifications |
+| PUT | `/api/openapi/jobs/{id}/classifications/{idx}` | API Key | Update a classification |
+| POST | `/api/openapi/jobs/{id}/approve` | API Key | Approve and generate tools |
+
+Authentication is controlled by the `ADMIN_API_KEY` environment variable.
+API Key endpoints require the `X-API-Key` header. When `ADMIN_API_KEY` is unset, auth is disabled.
+
+## Running Tests

 ```bash
-# 启动 PostgreSQL 和应用
-docker compose up
+# Backend (516 tests, 94% coverage)
+cd backend
+pytest --cov=app --cov-report=term-missing

-# 访问聊天界面
-open http://localhost:8000
+# Frontend (23 tests, vitest + happy-dom)
+cd frontend
+npm test
 ```

-## Agent 配置示例
+Backend coverage is enforced at 80%+.

-```yaml
-# agents.yaml
-agents:
-  - name: order_lookup
-    description: 查询订单状态、物流信息
-    permission: read
-    personality:
-      tone: professional
-      greeting: "您好，我来帮您查询订单信息。"
-    tools:
-      - get_order_status
-      - get_tracking_info
+## Documentation

-  - name: order_actions
-    description: 取消订单、修改订单
-    permission: write  # 触发人工确认
-    personality:
-      tone: careful
-      greeting: "我可以帮您处理订单变更，所有操作都会先经过您的确认。"
-    tools:
-      - cancel_order
-      - modify_order
-
-  - name: discount
-    description: 发放优惠券、折扣码
-    permission: write
-    tools:
-      - apply_discount
-      - generate_coupon
-```
-
-## OpenAPI 自动接入
-
-不需要手动写 MCP 连接器。粘贴你的 API 规范 URL：
-
-1. 框架解析 OpenAPI 3.0 规范
-2. LLM 自动分类每个端点（读/写、客户参数、Agent 分组）
-3. 运维人员审核分类结果
-4. 自动生成 MCP 服务器 + Agent YAML 配置
-5. 新工具立即可用
-
-## 安全设计
-
- **人工确认** - 所有写操作需要客户或运维人员批准
- **SSRF 防护** - OpenAPI URL 导入时屏蔽内网地址和 DNS 重绑定攻击
- **操作审计** - 每个操作记录 Agent、参数、结果、时间戳
- **权限隔离** - 每个 Agent 只能访问其配置的工具集
- **中断超时** - 30 分钟未确认的操作自动取消，防止过期审批
-
-## 开发阶段
-
-| 阶段 | 周期 | 内容 |
-|------|------|------|
-| Phase 1 | 第 1-3 周 | 核心框架：Chat UI + Supervisor + Agent 注册表 + 中断流程 |
-| Phase 2 | 第 3-4 周 | 多 Agent 路由 + Webhook 升级 + 垂直模板 |
-| Phase 3 | 第 4-6 周 | OpenAPI 自动发现 + MCP 服务器生成 + SSRF 防护 |
-| Phase 4 | 第 6-7 周 | 对话回放 + 数据分析仪表盘 |
-
-## 目标用户
-
-中型电商公司（日均 500-5000 订单，5-20 名客服）的客户体验负责人。
-
-他们的痛点：客服需要在 Zendesk 和 Shopify 后台之间反复切换，手动执行查询和操作。Smart Support 让 AI 直接完成这些操作，人工只需审批关键步骤。
-
-## 相关文档
-
- [设计文档](design-doc.md) - 问题定义、约束、方案选择
- [CEO 计划](ceo-plan.md) - 产品愿景、范围决策
- [工程评审计划](eng-review-plan.md) - 架构决策、测试策略、失败模式
- [测试计划](eng-review-test-plan.md) - 测试路径、边界情况、E2E 流程
- [待办事项](TODOS.md) - 延迟到后续阶段的工作
+| Document | Description |
+|----------|-------------|
+| [Architecture](docs/ARCHITECTURE.md) | System design, component diagram, data flow, ADRs |
+| [Development Plan](docs/DEVELOPMENT-PLAN.md) | Phase breakdown, task checklists, and status |
+| [Agent Config Guide](docs/agent-config-guide.md) | agents.yaml format, fields, templates, routing logic |
+| [OpenAPI Import Guide](docs/openapi-import-guide.md) | Auto-discovery workflow, REST API, SSRF protection |
+| [Deployment Guide](docs/deployment.md) | Docker, local dev, production, HTTPS, backups, scaling |
+| [Demo Script](docs/demo-script.md) | Step-by-step live demo walkthrough (5 scenes) |
+| [UX Design System](docs/ux_design_system.md) | Color palette, typography, component patterns, CSS tokens |

 ## License

--- a/backend/.env.example
+++ b/backend/.env.example
@@ -1,19 +1,34 @@
-# Database
+# Smart Support Backend -- environment variables
+# Copy to .env and fill in your values
+
+# Required: PostgreSQL connection string
 DATABASE_URL=postgresql://smart_support:dev_password@localhost:5432/smart_support

-# LLM Provider: anthropic | openai | google
+# Required: LLM provider configuration
+# provider: anthropic | openai | google
 LLM_PROVIDER=anthropic
 LLM_MODEL=claude-sonnet-4-6

-# API Keys (set the one matching your LLM_PROVIDER)
+# API keys -- provide the one matching LLM_PROVIDER
 ANTHROPIC_API_KEY=
 OPENAI_API_KEY=
 GOOGLE_API_KEY=

-# Session
+# Optional: webhook endpoint for escalation notifications
+# The backend will POST a JSON payload when a conversation is escalated.
+WEBHOOK_URL=
+WEBHOOK_TIMEOUT_SECONDS=10
+WEBHOOK_MAX_RETRIES=3
+
+# Session management
 SESSION_TTL_MINUTES=30
 INTERRUPT_TTL_MINUTES=30

-# Server
+# Optional: load a named agent template instead of agents.yaml
+# Leave blank to use the default agents.yaml in the backend directory.
+# Available templates: ecommerce, saas, generic
+TEMPLATE_NAME=
+
+# Server binding
 WS_HOST=0.0.0.0
 WS_PORT=8000
--- a/backend/agents.yaml
+++ b/backend/agents.yaml
@@ -20,6 +20,17 @@ agents:
    tools:
      - cancel_order

+  - name: discount
+    description: "Applies discounts and generates coupon codes. Use when the customer asks for discounts, promotions, or coupon codes."
+    permission: write
+    personality:
+      tone: "generous and accommodating"
+      greeting: "I can help you with discounts and coupons!"
+      escalation_message: "Let me connect you with our promotions team."
+    tools:
+      - apply_discount
+      - generate_coupon
+
  - name: fallback
    description: "Handles general questions, unclear requests, and conversations that don't match other agents."
    permission: read
--- a/backend/alembic.ini
+++ b/backend/alembic.ini
@@ -0,0 +1,149 @@
+# A generic, single database configuration.
+
+[alembic]
+# path to migration scripts.
+# this is typically a path given in POSIX (e.g. forward slashes)
+# format, relative to the token %(here)s which refers to the location of this
+# ini file
+script_location = %(here)s/alembic
+
+# template used to generate migration file names; The default value is %%(rev)s_%%(slug)s
+# Uncomment the line below if you want the files to be prepended with date and time
+# see https://alembic.sqlalchemy.org/en/latest/tutorial.html#editing-the-ini-file
+# for all available tokens
+# file_template = %%(year)d_%%(month).2d_%%(day).2d_%%(hour).2d%%(minute).2d-%%(rev)s_%%(slug)s
+# Or organize into date-based subdirectories (requires recursive_version_locations = true)
+# file_template = %%(year)d/%%(month).2d/%%(day).2d_%%(hour).2d%%(minute).2d_%%(second).2d_%%(rev)s_%%(slug)s
+
+# sys.path path, will be prepended to sys.path if present.
+# defaults to the current working directory.  for multiple paths, the path separator
+# is defined by "path_separator" below.
+prepend_sys_path = .
+
+
+# timezone to use when rendering the date within the migration file
+# as well as the filename.
+# If specified, requires the tzdata library which can be installed by adding
+# `alembic[tz]` to the pip requirements.
+# string value is passed to ZoneInfo()
+# leave blank for localtime
+# timezone =
+
+# max length of characters to apply to the "slug" field
+# truncate_slug_length = 40
+
+# set to 'true' to run the environment during
+# the 'revision' command, regardless of autogenerate
+# revision_environment = false
+
+# set to 'true' to allow .pyc and .pyo files without
+# a source .py file to be detected as revisions in the
+# versions/ directory
+# sourceless = false
+
+# version location specification; This defaults
+# to <script_location>/versions.  When using multiple version
+# directories, initial revisions must be specified with --version-path.
+# The path separator used here should be the separator specified by "path_separator"
+# below.
+# version_locations = %(here)s/bar:%(here)s/bat:%(here)s/alembic/versions
+
+# path_separator; This indicates what character is used to split lists of file
+# paths, including version_locations and prepend_sys_path within configparser
+# files such as alembic.ini.
+# The default rendered in new alembic.ini files is "os", which uses os.pathsep
+# to provide os-dependent path splitting.
+#
+# Note that in order to support legacy alembic.ini files, this default does NOT
+# take place if path_separator is not present in alembic.ini.  If this
+# option is omitted entirely, fallback logic is as follows:
+#
+# 1. Parsing of the version_locations option falls back to using the legacy
+#    "version_path_separator" key, which if absent then falls back to the legacy
+#    behavior of splitting on spaces and/or commas.
+# 2. Parsing of the prepend_sys_path option falls back to the legacy
+#    behavior of splitting on spaces, commas, or colons.
+#
+# Valid values for path_separator are:
+#
+# path_separator = :
+# path_separator = ;
+# path_separator = space
+# path_separator = newline
+#
+# Use os.pathsep. Default configuration used for new projects.
+path_separator = os
+
+# set to 'true' to search source files recursively
+# in each "version_locations" directory
+# new in Alembic version 1.10
+# recursive_version_locations = false
+
+# the output encoding used when revision files
+# are written from script.py.mako
+# output_encoding = utf-8
+
+# database URL.  This is consumed by the user-maintained env.py script only.
+# other means of configuring database URLs may be customized within the env.py
+# file.
+sqlalchemy.url =
+
+
+[post_write_hooks]
+# post_write_hooks defines scripts or Python functions that are run
+# on newly generated revision scripts.  See the documentation for further
+# detail and examples
+
+# format using "black" - use the console_scripts runner, against the "black" entrypoint
+# hooks = black
+# black.type = console_scripts
+# black.entrypoint = black
+# black.options = -l 79 REVISION_SCRIPT_FILENAME
+
+# lint with attempts to fix using "ruff" - use the module runner, against the "ruff" module
+# hooks = ruff
+# ruff.type = module
+# ruff.module = ruff
+# ruff.options = check --fix REVISION_SCRIPT_FILENAME
+
+# Alternatively, use the exec runner to execute a binary found on your PATH
+# hooks = ruff
+# ruff.type = exec
+# ruff.executable = ruff
+# ruff.options = check --fix REVISION_SCRIPT_FILENAME
+
+# Logging configuration.  This is also consumed by the user-maintained
+# env.py script only.
+[loggers]
+keys = root,sqlalchemy,alembic
+
+[handlers]
+keys = console
+
+[formatters]
+keys = generic
+
+[logger_root]
+level = WARNING
+handlers = console
+qualname =
+
+[logger_sqlalchemy]
+level = WARNING
+handlers =
+qualname = sqlalchemy.engine
+
+[logger_alembic]
+level = INFO
+handlers =
+qualname = alembic
+
+[handler_console]
+class = StreamHandler
+args = (sys.stderr,)
+level = NOTSET
+formatter = generic
+
+[formatter_generic]
+format = %(levelname)-5.5s [%(name)s] %(message)s
+datefmt = %H:%M:%S
--- a/backend/alembic/README
+++ b/backend/alembic/README
@@ -0,0 +1 @@
+Generic single-database configuration.
--- a/backend/alembic/env.py
+++ b/backend/alembic/env.py
@@ -0,0 +1,67 @@
+"""Alembic environment configuration for smart-support."""
+
+from __future__ import annotations
+
+import os
+from logging.config import fileConfig
+
+from sqlalchemy import engine_from_config, pool
+
+from alembic import context
+
+config = context.config
+
+if config.config_file_name is not None:
+    fileConfig(config.config_file_name)
+
+# No SQLAlchemy ORM models -- we use raw DDL migrations
+target_metadata = None
+
+
+def _get_url() -> str:
+    """Read DATABASE_URL from environment, falling back to alembic.ini."""
+    return os.environ.get("DATABASE_URL", "") or config.get_main_option(
+        "sqlalchemy.url", ""
+    )
+
+
+def run_migrations_offline() -> None:
+    """Run migrations in 'offline' mode.
+
+    Configures the context with just a URL so that an Engine
+    is not required.
+    """
+    url = _get_url()
+    context.configure(
+        url=url,
+        target_metadata=target_metadata,
+        literal_binds=True,
+        dialect_opts={"paramstyle": "named"},
+    )
+
+    with context.begin_transaction():
+        context.run_migrations()
+
+
+def run_migrations_online() -> None:
+    """Run migrations in 'online' mode with a live database connection."""
+    configuration = config.get_section(config.config_ini_section, {})
+    configuration["sqlalchemy.url"] = _get_url()
+
+    connectable = engine_from_config(
+        configuration,
+        prefix="sqlalchemy.",
+        poolclass=pool.NullPool,
+    )
+
+    with connectable.connect() as connection:
+        context.configure(connection=connection, target_metadata=target_metadata)
+
+        with context.begin_transaction():
+            context.run_migrations()
+
+
+if context.is_offline_mode():
+    run_migrations_offline()
+else:
+    run_migrations_online()
--- a/backend/alembic/script.py.mako
+++ b/backend/alembic/script.py.mako
@@ -0,0 +1,28 @@
+"""${message}
+
+Revision ID: ${up_revision}
+Revises: ${down_revision | comma,n}
+Create Date: ${create_date}
+
+"""
+from typing import Sequence, Union
+
+from alembic import op
+import sqlalchemy as sa
+${imports if imports else ""}
+
+# revision identifiers, used by Alembic.
+revision: str = ${repr(up_revision)}
+down_revision: Union[str, Sequence[str], None] = ${repr(down_revision)}
+branch_labels: Union[str, Sequence[str], None] = ${repr(branch_labels)}
+depends_on: Union[str, Sequence[str], None] = ${repr(depends_on)}
+
+
+def upgrade() -> None:
+    """Upgrade schema."""
+    ${upgrades if upgrades else "pass"}
+
+
+def downgrade() -> None:
+    """Downgrade schema."""
+    ${downgrades if downgrades else "pass"}
--- a/backend/alembic/versions/001_initial_schema.py
+++ b/backend/alembic/versions/001_initial_schema.py
@@ -0,0 +1,92 @@
+"""Initial schema -- all application tables.
+
+Revision ID: a1b2c3d4e5f6
+Revises:
+Create Date: 2026-04-06
+"""
+
+from __future__ import annotations
+
+from alembic import op
+
+revision: str = "a1b2c3d4e5f6"
+down_revision: str | None = None
+branch_labels: tuple[str, ...] | None = None
+depends_on: tuple[str, ...] | None = None
+
+
+def upgrade() -> None:
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS conversations (
+            thread_id TEXT PRIMARY KEY,
+            created_at TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+            last_activity TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+            total_tokens INTEGER NOT NULL DEFAULT 0,
+            total_cost_usd DOUBLE PRECISION NOT NULL DEFAULT 0.0,
+            status TEXT NOT NULL DEFAULT 'active'
+        )
+        """
+    )
+
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS active_interrupts (
+            interrupt_id TEXT PRIMARY KEY,
+            thread_id TEXT NOT NULL REFERENCES conversations(thread_id),
+            action TEXT NOT NULL,
+            params JSONB NOT NULL DEFAULT '{}',
+            created_at TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+            resolved_at TIMESTAMPTZ,
+            resolution TEXT
+        )
+        """
+    )
+
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS sessions (
+            thread_id TEXT PRIMARY KEY,
+            last_activity TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+            has_pending_interrupt BOOLEAN NOT NULL DEFAULT FALSE,
+            created_at TIMESTAMPTZ NOT NULL DEFAULT NOW()
+        )
+        """
+    )
+
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS analytics_events (
+            id BIGSERIAL PRIMARY KEY,
+            thread_id TEXT NOT NULL,
+            event_type TEXT NOT NULL,
+            agent_name TEXT,
+            tool_name TEXT,
+            tokens_used INTEGER NOT NULL DEFAULT 0,
+            cost_usd DOUBLE PRECISION NOT NULL DEFAULT 0.0,
+            duration_ms INTEGER,
+            success BOOLEAN,
+            error_message TEXT,
+            metadata JSONB NOT NULL DEFAULT '{}',
+            created_at TIMESTAMPTZ NOT NULL DEFAULT NOW()
+        )
+        """
+    )
+
+    # Migration columns added in Phase 4
+    op.execute(
+        """
+        ALTER TABLE conversations
+            ADD COLUMN IF NOT EXISTS resolution_type TEXT,
+            ADD COLUMN IF NOT EXISTS agents_used TEXT[],
+            ADD COLUMN IF NOT EXISTS turn_count INTEGER NOT NULL DEFAULT 0,
+            ADD COLUMN IF NOT EXISTS ended_at TIMESTAMPTZ
+        """
+    )
+
+
+def downgrade() -> None:
+    op.execute("DROP TABLE IF EXISTS analytics_events")
+    op.execute("DROP TABLE IF EXISTS sessions")
+    op.execute("DROP TABLE IF EXISTS active_interrupts")
+    op.execute("DROP TABLE IF EXISTS conversations")
--- a/backend/app/agents/init.py
+++ b/backend/app/agents/init.py
@@ -7,6 +7,7 @@ from typing import TYPE_CHECKING
 if TYPE_CHECKING:
    from langchain_core.tools import BaseTool

+from app.agents.discount import apply_discount, generate_coupon
 from app.agents.fallback import fallback_respond
 from app.agents.order_actions import cancel_order
 from app.agents.order_lookup import get_order_status, get_tracking_info
@@ -16,6 +17,8 @@ _TOOL_MAP: dict[str, BaseTool] = {
    "get_tracking_info": get_tracking_info,
    "cancel_order": cancel_order,
    "fallback_respond": fallback_respond,
+    "apply_discount": apply_discount,
+    "generate_coupon": generate_coupon,
 }


--- a/backend/app/agents/discount.py
+++ b/backend/app/agents/discount.py
@@ -0,0 +1,79 @@
+"""Discount agent tools -- apply discounts and generate coupons."""
+
+from __future__ import annotations
+
+import uuid
+
+from langchain_core.tools import tool
+from langgraph.types import interrupt
+
+
+@tool
+def apply_discount(order_id: str, discount_percent: int) -> dict:
+    """Apply a discount to an order. Requires human approval before execution."""
+    if discount_percent < 1 or discount_percent > 100:
+        return {
+            "status": "error",
+            "order_id": order_id,
+            "message": f"Invalid discount: {discount_percent}%. Must be between 1 and 100.",
+        }
+
+    response = interrupt(
+        {
+            "action": "apply_discount",
+            "order_id": order_id,
+            "discount_percent": discount_percent,
+            "message": (
+                f"Please confirm: apply {discount_percent}% discount to order {order_id}?"
+            ),
+        }
+    )
+
+    if isinstance(response, bool):
+        approved = response
+    elif isinstance(response, dict):
+        approved = response.get("approved", False)
+    else:
+        approved = bool(response)
+
+    if approved:
+        return {
+            "status": "applied",
+            "order_id": order_id,
+            "discount_percent": discount_percent,
+            "message": (
+                f"{discount_percent}% discount applied to order {order_id}."
+            ),
+        }
+    return {
+        "status": "declined",
+        "order_id": order_id,
+        "message": f"Discount for order {order_id} was declined.",
+    }
+
+
+@tool
+def generate_coupon(discount_percent: int, expiry_days: int = 30) -> dict:
+    """Generate a coupon code with the specified discount percentage."""
+    if discount_percent < 1 or discount_percent > 100:
+        return {
+            "status": "error",
+            "message": f"Invalid discount: {discount_percent}%. Must be between 1 and 100.",
+        }
+    if expiry_days < 1:
+        return {
+            "status": "error",
+            "message": f"Invalid expiry: {expiry_days} days. Must be at least 1.",
+        }
+
+    coupon_code = f"SAVE{discount_percent}-{uuid.uuid4().hex[:8].upper()}"
+    return {
+        "status": "generated",
+        "coupon_code": coupon_code,
+        "discount_percent": discount_percent,
+        "expiry_days": expiry_days,
+        "message": (
+            f"Coupon {coupon_code} generated: {discount_percent}% off, "
+            f"valid for {expiry_days} days."
+        ),
+    }
--- a/backend/app/agents/fallback.py
+++ b/backend/app/agents/fallback.py
@@ -1,4 +1,4 @@
-"""Fallback agent tools -- handles unmatched intents."""
+"""Fallback agent tools -- handles unmatched intents and clarification requests."""

 from __future__ import annotations

@@ -13,6 +13,7 @@ def fallback_respond(query: str) -> str:
        "Here's what I can do:\n"
        "- Check order status (e.g., 'What is the status of order 1042?')\n"
        "- Get tracking information (e.g., 'Track order 1042')\n"
-        "- Cancel an order (e.g., 'Cancel order 1042')\n\n"
+        "- Cancel an order (e.g., 'Cancel order 1042')\n"
+        "- Apply discounts or generate coupons\n\n"
        "Could you please rephrase your request?"
    )
--- a/backend/app/analytics/init.py
+++ b/backend/app/analytics/init.py
@@ -0,0 +1,3 @@
+"""Analytics module -- event recording and dashboard queries."""
+
+from __future__ import annotations
--- a/backend/app/analytics/api.py
+++ b/backend/app/analytics/api.py
@@ -0,0 +1,60 @@
+"""Analytics API router -- dashboard metrics endpoint."""
+
+from __future__ import annotations
+
+import re
+from dataclasses import asdict
+from typing import TYPE_CHECKING
+
+from fastapi import APIRouter, Depends, HTTPException, Query, Request
+
+from app.analytics.queries import get_analytics
+from app.api_utils import envelope
+from app.auth import require_admin_api_key
+
+if TYPE_CHECKING:
+    from psycopg_pool import AsyncConnectionPool
+
+router = APIRouter(
+    prefix="/api/v1/analytics",
+    tags=["analytics"],
+    dependencies=[Depends(require_admin_api_key)],
+)
+
+_RANGE_PATTERN = re.compile(r"^(\d+)d$")
+_DEFAULT_RANGE = "7d"
+_MAX_RANGE_DAYS = 365
+
+
+async def _get_pool(request: Request) -> AsyncConnectionPool:
+    """Dependency: extract the shared pool from app state."""
+    return request.app.state.pool
+
+
+def _parse_range(range_str: str) -> int:
+    """Parse 'Xd' range string to integer days. Raises 400 on invalid format."""
+    match = _RANGE_PATTERN.match(range_str)
+    if not match:
+        raise HTTPException(
+            status_code=400,
+            detail="Invalid range format. Expected: '<N>d' e.g. '7d', '30d'.",
+        )
+    days = int(match.group(1))
+    if days < 1 or days > _MAX_RANGE_DAYS:
+        raise HTTPException(
+            status_code=400,
+            detail=f"Range must be between 1 and {_MAX_RANGE_DAYS} days.",
+        )
+    return days
+
+
+@router.get("")
+async def analytics(
+    request: Request,
+    range: str = Query(default=_DEFAULT_RANGE, alias="range"),  # noqa: A002
+) -> dict:
+    """Return aggregated analytics metrics for the given time range."""
+    range_days = _parse_range(range)
+    pool = await _get_pool(request)
+    result = await get_analytics(pool, range_days=range_days)
+    return envelope(asdict(result))
--- a/backend/app/analytics/event_recorder.py
+++ b/backend/app/analytics/event_recorder.py
@@ -0,0 +1,97 @@
+"""Analytics event recorder -- Protocol and implementations."""
+
+from __future__ import annotations
+
+from typing import TYPE_CHECKING, Any, Protocol, runtime_checkable
+
+from psycopg.types.json import Json
+
+if TYPE_CHECKING:
+    from psycopg_pool import AsyncConnectionPool
+
+_INSERT_SQL = """
+INSERT INTO analytics_events
+    (thread_id, event_type, agent_name, tool_name, tokens_used, cost_usd,
+     duration_ms, success, error_message, metadata)
+VALUES
+    (%(thread_id)s, %(event_type)s, %(agent_name)s, %(tool_name)s,
+     %(tokens_used)s, %(cost_usd)s, %(duration_ms)s, %(success)s,
+     %(error_message)s, %(metadata)s)
+"""
+
+
+@runtime_checkable
+class AnalyticsRecorder(Protocol):
+    """Protocol for recording analytics events."""
+
+    async def record(
+        self,
+        *,
+        thread_id: str,
+        event_type: str,
+        agent_name: str | None = None,
+        tool_name: str | None = None,
+        tokens_used: int = 0,
+        cost_usd: float = 0.0,
+        duration_ms: int | None = None,
+        success: bool | None = None,
+        error_message: str | None = None,
+        metadata: dict | None = None,
+    ) -> None: ...
+
+
+class NoOpAnalyticsRecorder:
+    """No-op implementation for testing or when the DB is unavailable."""
+
+    async def record(
+        self,
+        *,
+        thread_id: str,
+        event_type: str,
+        agent_name: str | None = None,
+        tool_name: str | None = None,
+        tokens_used: int = 0,
+        cost_usd: float = 0.0,
+        duration_ms: int | None = None,
+        success: bool | None = None,
+        error_message: str | None = None,
+        metadata: dict | None = None,
+    ) -> None:
+        """Do nothing."""
+
+
+class PostgresAnalyticsRecorder:
+    """Postgres-backed analytics recorder -- INSERTs into analytics_events."""
+
+    def __init__(self, pool: AsyncConnectionPool) -> None:
+        self._pool = pool
+
+    async def record(
+        self,
+        *,
+        thread_id: str,
+        event_type: str,
+        agent_name: str | None = None,
+        tool_name: str | None = None,
+        tokens_used: int = 0,
+        cost_usd: float = 0.0,
+        duration_ms: int | None = None,
+        success: bool | None = None,
+        error_message: str | None = None,
+        metadata: dict | None = None,
+    ) -> None:
+        """Insert one analytics event row."""
+        params: dict[str, Any] = {
+            "thread_id": thread_id,
+            "event_type": event_type,
+            "agent_name": agent_name,
+            "tool_name": tool_name,
+            "tokens_used": tokens_used,
+            "cost_usd": cost_usd,
+            "duration_ms": duration_ms,
+            "success": success,
+            "error_message": error_message,
+            "metadata": Json(metadata or {}),
+        }
+        async with self._pool.connection() as conn:
+            await conn.execute(_INSERT_SQL, params)
--- a/backend/app/analytics/models.py
+++ b/backend/app/analytics/models.py
@@ -0,0 +1,38 @@
+"""Value objects for analytics dashboard."""
+
+from __future__ import annotations
+
+from dataclasses import dataclass
+
+
+@dataclass(frozen=True)
+class AgentUsage:
+    """Agent usage statistics within a time range."""
+
+    agent: str
+    count: int
+    percentage: float
+
+
+@dataclass(frozen=True)
+class InterruptStats:
+    """Interrupt approval/rejection statistics within a time range."""
+
+    total: int = 0
+    approved: int = 0
+    rejected: int = 0
+    expired: int = 0
+
+
+@dataclass(frozen=True)
+class AnalyticsResult:
+    """Full analytics result for a given time range."""
+
+    range: str
+    total_conversations: int
+    resolution_rate: float
+    escalation_rate: float
+    avg_turns_per_conversation: float
+    avg_cost_per_conversation_usd: float
+    agent_usage: tuple[AgentUsage, ...]
+    interrupt_stats: InterruptStats
--- a/backend/app/analytics/queries.py
+++ b/backend/app/analytics/queries.py
@@ -0,0 +1,184 @@
+"""Analytics query functions -- all async, take pool + range_days."""
+
+from __future__ import annotations
+
+import asyncio
+from typing import TYPE_CHECKING
+
+from app.analytics.models import AgentUsage, AnalyticsResult, InterruptStats
+
+if TYPE_CHECKING:
+    from psycopg_pool import AsyncConnectionPool
+
+_RESOLUTION_RATE_SQL = """
+SELECT
+    CASE WHEN COUNT(*) = 0 THEN 0.0
+         ELSE COUNT(*) FILTER (WHERE resolution_type = 'resolved')::float / COUNT(*)
+    END AS rate
+FROM conversations
+WHERE created_at >= NOW() - (%(days)s * INTERVAL '1 day')
+"""
+
+_ESCALATION_RATE_SQL = """
+SELECT
+    CASE WHEN COUNT(*) = 0 THEN 0.0
+         ELSE COUNT(*) FILTER (WHERE resolution_type = 'escalated')::float / COUNT(*)
+    END AS rate
+FROM conversations
+WHERE created_at >= NOW() - (%(days)s * INTERVAL '1 day')
+"""
+
+_TOTAL_CONVERSATIONS_SQL = """
+SELECT COUNT(*) AS total
+FROM conversations
+WHERE created_at >= NOW() - (%(days)s * INTERVAL '1 day')
+"""
+
+_AVG_TURNS_SQL = """
+SELECT COALESCE(AVG(turn_count), 0.0) AS avg_turns
+FROM conversations
+WHERE created_at >= NOW() - (%(days)s * INTERVAL '1 day')
+"""
+
+_COST_PER_CONVERSATION_SQL = """
+SELECT COALESCE(AVG(total_cost_usd), 0.0) AS avg_cost
+FROM conversations
+WHERE created_at >= NOW() - (%(days)s * INTERVAL '1 day')
+"""
+
+_AGENT_USAGE_SQL = """
+SELECT
+    agent,
+    COUNT(*) AS count,
+    ROUND(COUNT(*) * 100.0 / NULLIF(SUM(COUNT(*)) OVER (), 0), 2) AS percentage
+FROM (
+    SELECT UNNEST(agents_used) AS agent
+    FROM conversations
+    WHERE created_at >= NOW() - (%(days)s * INTERVAL '1 day')
+      AND agents_used IS NOT NULL
+) sub
+GROUP BY agent
+ORDER BY count DESC
+"""
+
+_INTERRUPT_STATS_SQL = """
+SELECT
+    COUNT(*) FILTER (WHERE event_type = 'interrupt') AS total,
+    COUNT(*) FILTER (WHERE event_type = 'interrupt' AND success = TRUE) AS approved,
+    COUNT(*) FILTER (WHERE event_type = 'interrupt' AND success = FALSE
+                     AND error_message IS NULL) AS rejected,
+    COUNT(*) FILTER (WHERE event_type = 'interrupt' AND error_message = 'expired') AS expired
+FROM analytics_events
+WHERE created_at >= NOW() - (%(days)s * INTERVAL '1 day')
+"""
+
+
+async def resolution_rate(pool: AsyncConnectionPool, range_days: int) -> float:
+    """Return the fraction of resolved conversations in the given range."""
+    async with pool.connection() as conn:
+        cursor = await conn.execute(_RESOLUTION_RATE_SQL, {"days": range_days})
+        row = await cursor.fetchone()
+    if not row:
+        return 0.0
+    return float(row.get("rate") or 0.0)
+
+
+async def escalation_rate(pool: AsyncConnectionPool, range_days: int) -> float:
+    """Return the fraction of escalated conversations in the given range."""
+    async with pool.connection() as conn:
+        cursor = await conn.execute(_ESCALATION_RATE_SQL, {"days": range_days})
+        row = await cursor.fetchone()
+    if not row:
+        return 0.0
+    return float(row.get("rate") or 0.0)
+
+
+async def _total_conversations(pool: AsyncConnectionPool, range_days: int) -> int:
+    """Return the total number of conversations in the given range."""
+    async with pool.connection() as conn:
+        cursor = await conn.execute(_TOTAL_CONVERSATIONS_SQL, {"days": range_days})
+        row = await cursor.fetchone()
+    if not row:
+        return 0
+    return int(row.get("total") or 0)
+
+
+async def _avg_turns(pool: AsyncConnectionPool, range_days: int) -> float:
+    """Return the average turn count per conversation in the given range."""
+    async with pool.connection() as conn:
+        cursor = await conn.execute(_AVG_TURNS_SQL, {"days": range_days})
+        row = await cursor.fetchone()
+    if not row:
+        return 0.0
+    return float(row.get("avg_turns") or 0.0)
+
+
+async def cost_per_conversation(pool: AsyncConnectionPool, range_days: int) -> float:
+    """Return the average cost per conversation in the given range."""
+    async with pool.connection() as conn:
+        cursor = await conn.execute(_COST_PER_CONVERSATION_SQL, {"days": range_days})
+        row = await cursor.fetchone()
+    if not row:
+        return 0.0
+    return float(row.get("avg_cost") or 0.0)
+
+
+async def agent_usage(
+    pool: AsyncConnectionPool, range_days: int
+) -> tuple[AgentUsage, ...]:
+    """Return per-agent usage statistics for the given range."""
+    async with pool.connection() as conn:
+        cursor = await conn.execute(_AGENT_USAGE_SQL, {"days": range_days})
+        rows = await cursor.fetchall()
+    if not rows:
+        return ()
+    return tuple(
+        AgentUsage(
+            agent=row["agent"],
+            count=int(row["count"]),
+            percentage=float(row["percentage"]),
+        )
+        for row in rows
+    )
+
+
+async def interrupt_stats(
+    pool: AsyncConnectionPool, range_days: int
+) -> InterruptStats:
+    """Return interrupt approval/rejection statistics for the given range."""
+    async with pool.connection() as conn:
+        cursor = await conn.execute(_INTERRUPT_STATS_SQL, {"days": range_days})
+        row = await cursor.fetchone()
+    if not row:
+        return InterruptStats()
+    return InterruptStats(
+        total=int(row.get("total") or 0),
+        approved=int(row.get("approved") or 0),
+        rejected=int(row.get("rejected") or 0),
+        expired=int(row.get("expired") or 0),
+    )
+
+
+async def get_analytics(
+    pool: AsyncConnectionPool, range_days: int
+) -> AnalyticsResult:
+    """Aggregate all analytics metrics into a single AnalyticsResult."""
+    res_rate, esc_rate, cost, usage, i_stats, total, avg_t = await asyncio.gather(
+        resolution_rate(pool, range_days),
+        escalation_rate(pool, range_days),
+        cost_per_conversation(pool, range_days),
+        agent_usage(pool, range_days),
+        interrupt_stats(pool, range_days),
+        _total_conversations(pool, range_days),
+        _avg_turns(pool, range_days),
+    )
+    return AnalyticsResult(
+        range=f"{range_days}d",
+        total_conversations=total,
+        resolution_rate=res_rate,
+        escalation_rate=esc_rate,
+        avg_turns_per_conversation=avg_t,
+        avg_cost_per_conversation_usd=cost,
+        agent_usage=usage,
+        interrupt_stats=i_stats,
+    )
--- a/backend/app/api_utils.py
+++ b/backend/app/api_utils.py
@@ -0,0 +1,10 @@
+"""Shared API response helpers."""
+
+from __future__ import annotations
+
+from typing import Any
+
+
+def envelope(data: Any, *, success: bool = True, error: str | None = None) -> dict:
+    """Wrap API response data in a standard envelope format."""
+    return {"success": success, "data": data, "error": error}
--- a/backend/app/auth.py
+++ b/backend/app/auth.py
@@ -0,0 +1,72 @@
+"""API key authentication for admin endpoints and WebSocket connections."""
+
+from __future__ import annotations
+
+import secrets
+from typing import Annotated
+
+import structlog
+from fastapi import Depends, HTTPException, Query, Request, WebSocket, status
+from fastapi.security import APIKeyHeader
+
+logger = structlog.get_logger()
+
+_API_KEY_HEADER = APIKeyHeader(name="X-API-Key", auto_error=False)
+
+
+def _get_admin_api_key(request: Request) -> str:
+    """Retrieve the configured admin API key from app settings.
+
+    Returns empty string if settings are not configured (test/dev mode).
+    """
+    settings = getattr(request.app.state, "settings", None)
+    if settings is None:
+        return ""
+    key = getattr(settings, "admin_api_key", "")
+    return key if isinstance(key, str) else ""
+
+
+async def require_admin_api_key(
+    request: Request,
+    api_key: Annotated[str | None, Depends(_API_KEY_HEADER)] = None,
+) -> None:
+    """Dependency that enforces API key authentication on admin endpoints.
+
+    Skips validation when no admin_api_key is configured (dev mode).
+    """
+    expected = _get_admin_api_key(request)
+    if not expected:
+        return
+
+    if api_key is None:
+        raise HTTPException(
+            status_code=status.HTTP_401_UNAUTHORIZED,
+            detail="Missing X-API-Key header",
+        )
+    if not secrets.compare_digest(api_key, expected):
+        raise HTTPException(
+            status_code=status.HTTP_403_FORBIDDEN,
+            detail="Invalid API key",
+        )
+
+
+async def verify_ws_token(
+    ws: WebSocket,
+    token: str | None = Query(default=None),
+) -> None:
+    """Verify WebSocket connection token from query parameter.
+
+    Skips validation when no admin_api_key is configured (dev mode).
+    Usage: ws://host/ws?token=<api_key>
+    """
+    settings = ws.app.state.settings
+    expected = settings.admin_api_key
+    if not expected:
+        return
+
+    if token is None or not secrets.compare_digest(token, expected):
+        await ws.close(code=4001, reason="Unauthorized")
+        raise HTTPException(
+            status_code=status.HTTP_403_FORBIDDEN,
+            detail="Invalid or missing WebSocket token",
+        )
--- a/backend/app/config.py
+++ b/backend/app/config.py
@@ -17,7 +17,7 @@ class Settings(BaseSettings):

    database_url: str

-    llm_provider: Literal["anthropic", "openai", "google"] = "anthropic"
+    llm_provider: Literal["anthropic", "openai", "azure_openai", "google"] = "anthropic"
    llm_model: str = "claude-sonnet-4-6"

    session_ttl_minutes: int = 30
@@ -26,8 +26,22 @@ class Settings(BaseSettings):
    ws_host: str = "0.0.0.0"
    ws_port: int = 8000

+    webhook_url: str = ""
+    webhook_timeout_seconds: int = 10
+    webhook_max_retries: int = 3
+
+    template_name: str = ""
+
+    log_format: str = "console"  # "console" for dev, "json" for production
+
+    admin_api_key: str = ""
+
    anthropic_api_key: str = ""
    openai_api_key: str = ""
+    azure_openai_api_key: str = ""
+    azure_openai_endpoint: str = ""
+    azure_openai_api_version: str = "2024-12-01-preview"
+    azure_openai_deployment: str = ""
    google_api_key: str = ""

    @model_validator(mode="after")
@@ -35,6 +49,7 @@ class Settings(BaseSettings):
        key_map = {
            "anthropic": self.anthropic_api_key,
            "openai": self.openai_api_key,
+            "azure_openai": self.azure_openai_api_key,
            "google": self.google_api_key,
        }
        key = key_map.get(self.llm_provider, "")
@@ -43,4 +58,13 @@ class Settings(BaseSettings):
                f"API key for provider '{self.llm_provider}' is required. "
                f"Set the corresponding environment variable."
            )
+        if self.llm_provider == "azure_openai":
+            if not self.azure_openai_endpoint:
+                raise ValueError(
+                    "AZURE_OPENAI_ENDPOINT is required for azure_openai provider."
+                )
+            if not self.azure_openai_deployment:
+                raise ValueError(
+                    "AZURE_OPENAI_DEPLOYMENT is required for azure_openai provider."
+                )
        return self
--- a/backend/app/conversation_tracker.py
+++ b/backend/app/conversation_tracker.py
@@ -0,0 +1,135 @@
+"""Conversation tracker -- Protocol and implementations for tracking conversation state."""
+
+from __future__ import annotations
+
+from typing import TYPE_CHECKING, Protocol, runtime_checkable
+
+if TYPE_CHECKING:
+    from psycopg_pool import AsyncConnectionPool
+
+_ENSURE_SQL = """
+INSERT INTO conversations
+    (thread_id, created_at, last_activity)
+VALUES
+    (%(thread_id)s, NOW(), NOW())
+ON CONFLICT (thread_id) DO NOTHING
+"""
+
+_RECORD_TURN_SQL = """
+UPDATE conversations
+SET
+    turn_count = turn_count + 1,
+    agents_used = CASE
+        WHEN %(agent_name)s IS NOT NULL AND NOT (agents_used @> ARRAY[%(agent_name)s]::text[])
+        THEN agents_used || ARRAY[%(agent_name)s]::text[]
+        ELSE agents_used
+    END,
+    total_tokens = total_tokens + %(tokens)s,
+    total_cost_usd = total_cost_usd + %(cost)s,
+    last_activity = NOW()
+WHERE thread_id = %(thread_id)s
+"""
+
+_RESOLVE_SQL = """
+UPDATE conversations
+SET
+    resolution_type = %(resolution_type)s,
+    ended_at = NOW()
+WHERE thread_id = %(thread_id)s
+"""
+
+
+@runtime_checkable
+class ConversationTrackerProtocol(Protocol):
+    """Protocol for tracking conversation lifecycle and metrics."""
+
+    async def ensure_conversation(self, pool: AsyncConnectionPool, thread_id: str) -> None:
+        """Create conversation row if it does not already exist."""
+        ...
+
+    async def record_turn(
+        self,
+        pool: AsyncConnectionPool,
+        thread_id: str,
+        agent_name: str | None,
+        tokens: int,
+        cost: float,
+    ) -> None:
+        """Increment turn count and update aggregated metrics."""
+        ...
+
+    async def resolve(
+        self,
+        pool: AsyncConnectionPool,
+        thread_id: str,
+        resolution_type: str,
+    ) -> None:
+        """Mark conversation as resolved with a resolution type."""
+        ...
+
+
+class NoOpConversationTracker:
+    """No-op implementation -- used in tests or when DB is unavailable."""
+
+    async def ensure_conversation(self, pool: AsyncConnectionPool, thread_id: str) -> None:
+        """Do nothing."""
+
+    async def record_turn(
+        self,
+        pool: AsyncConnectionPool,
+        thread_id: str,
+        agent_name: str | None,
+        tokens: int,
+        cost: float,
+    ) -> None:
+        """Do nothing."""
+
+    async def resolve(
+        self,
+        pool: AsyncConnectionPool,
+        thread_id: str,
+        resolution_type: str,
+    ) -> None:
+        """Do nothing."""
+
+
+class PostgresConversationTracker:
+    """Postgres-backed conversation tracker."""
+
+    async def ensure_conversation(self, pool: AsyncConnectionPool, thread_id: str) -> None:
+        """Insert conversation row; do nothing if already exists (ON CONFLICT DO NOTHING)."""
+        params = {"thread_id": thread_id}
+        async with pool.connection() as conn:
+            await conn.execute(_ENSURE_SQL, params)
+
+    async def record_turn(
+        self,
+        pool: AsyncConnectionPool,
+        thread_id: str,
+        agent_name: str | None,
+        tokens: int,
+        cost: float,
+    ) -> None:
+        """Increment turn count, append agent if new, update token/cost totals."""
+        params = {
+            "thread_id": thread_id,
+            "agent_name": agent_name,
+            "tokens": tokens,
+            "cost": cost,
+        }
+        async with pool.connection() as conn:
+            await conn.execute(_RECORD_TURN_SQL, params)
+
+    async def resolve(
+        self,
+        pool: AsyncConnectionPool,
+        thread_id: str,
+        resolution_type: str,
+    ) -> None:
+        """Set resolution_type and ended_at on the conversation row."""
+        params = {
+            "thread_id": thread_id,
+            "resolution_type": resolution_type,
+        }
+        async with pool.connection() as conn:
+            await conn.execute(_RESOLVE_SQL, params)
--- a/backend/app/db.py
+++ b/backend/app/db.py
@@ -2,6 +2,7 @@

 from __future__ import annotations

+from pathlib import Path
 from typing import TYPE_CHECKING

 from langgraph.checkpoint.postgres.aio import AsyncPostgresSaver
@@ -34,6 +35,40 @@ CREATE TABLE IF NOT EXISTS active_interrupts (
 );
 """

+_ANALYTICS_EVENTS_DDL = """
+CREATE TABLE IF NOT EXISTS analytics_events (
+    id BIGSERIAL PRIMARY KEY,
+    thread_id TEXT NOT NULL,
+    event_type TEXT NOT NULL,
+    agent_name TEXT,
+    tool_name TEXT,
+    tokens_used INTEGER NOT NULL DEFAULT 0,
+    cost_usd DOUBLE PRECISION NOT NULL DEFAULT 0.0,
+    duration_ms INTEGER,
+    success BOOLEAN,
+    error_message TEXT,
+    metadata JSONB NOT NULL DEFAULT '{}',
+    created_at TIMESTAMPTZ NOT NULL DEFAULT NOW()
+);
+"""
+
+_SESSIONS_DDL = """
+CREATE TABLE IF NOT EXISTS sessions (
+    thread_id TEXT PRIMARY KEY,
+    last_activity TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+    has_pending_interrupt BOOLEAN NOT NULL DEFAULT FALSE,
+    created_at TIMESTAMPTZ NOT NULL DEFAULT NOW()
+);
+"""
+
+_CONVERSATIONS_MIGRATION_DDL = """
+ALTER TABLE conversations
+    ADD COLUMN IF NOT EXISTS resolution_type TEXT,
+    ADD COLUMN IF NOT EXISTS agents_used TEXT[],
+    ADD COLUMN IF NOT EXISTS turn_count INTEGER NOT NULL DEFAULT 0,
+    ADD COLUMN IF NOT EXISTS ended_at TIMESTAMPTZ;
+"""
+

 async def create_pool(settings: Settings) -> AsyncConnectionPool:
    """Create an async connection pool with the required psycopg settings."""
@@ -54,8 +89,22 @@ async def create_checkpointer(pool: AsyncConnectionPool) -> AsyncPostgresSaver:
    return checkpointer


+def run_alembic_migrations(database_url: str) -> None:
+    """Run Alembic migrations to head."""
+    from alembic.config import Config
+
+    from alembic import command
+
+    alembic_cfg = Config(str(Path(__file__).parent.parent / "alembic.ini"))
+    alembic_cfg.set_main_option("sqlalchemy.url", database_url)
+    command.upgrade(alembic_cfg, "head")
+
+
 async def setup_app_tables(pool: AsyncConnectionPool) -> None:
-    """Create application-specific tables (conversations, active_interrupts)."""
+    """Create application-specific tables and apply migrations."""
    async with pool.connection() as conn:
        await conn.execute(_CONVERSATIONS_DDL)
        await conn.execute(_INTERRUPTS_DDL)
+        await conn.execute(_SESSIONS_DDL)
+        await conn.execute(_ANALYTICS_EVENTS_DDL)
+        await conn.execute(_CONVERSATIONS_MIGRATION_DDL)
--- a/backend/app/escalation.py
+++ b/backend/app/escalation.py
@@ -0,0 +1,140 @@
+"""Webhook escalation module -- HTTP POST with exponential backoff retry."""
+
+from __future__ import annotations
+
+import asyncio
+from dataclasses import dataclass
+from typing import Protocol
+
+import httpx
+import structlog
+from pydantic import BaseModel
+
+logger = structlog.get_logger()
+
+
+class EscalationPayload(BaseModel, frozen=True):
+    """Immutable payload sent to the escalation webhook."""
+
+    thread_id: str
+    reason: str
+    conversation_summary: str
+    metadata: dict = {}
+
+
+@dataclass(frozen=True)
+class EscalationResult:
+    """Immutable result of an escalation attempt."""
+
+    success: bool
+    status_code: int | None
+    attempts: int
+    error: str | None
+
+
+class EscalationService(Protocol):
+    """Protocol for escalation implementations."""
+
+    async def escalate(self, payload: EscalationPayload) -> EscalationResult: ...
+
+
+class WebhookEscalator:
+    """Sends escalation requests via HTTP POST with exponential backoff retry."""
+
+    def __init__(
+        self,
+        url: str,
+        timeout_seconds: int = 10,
+        max_retries: int = 3,
+    ) -> None:
+        self._url = url
+        self._timeout = timeout_seconds
+        self._max_retries = max_retries
+
+    async def escalate(self, payload: EscalationPayload) -> EscalationResult:
+        """POST the escalation payload to the configured webhook URL."""
+        if not self._url:
+            return EscalationResult(
+                success=False,
+                status_code=None,
+                attempts=0,
+                error="Webhook URL not configured",
+            )
+
+        last_error: str | None = None
+
+        async with httpx.AsyncClient(timeout=self._timeout) as client:
+            for attempt in range(1, self._max_retries + 1):
+                try:
+                    response = await client.post(
+                        self._url,
+                        json=payload.model_dump(),
+                    )
+
+                    if 200 <= response.status_code < 300:
+                        logger.info(
+                            "Escalation succeeded for thread %s (attempt %d)",
+                            payload.thread_id,
+                            attempt,
+                        )
+                        return EscalationResult(
+                            success=True,
+                            status_code=response.status_code,
+                            attempts=attempt,
+                            error=None,
+                        )
+
+                    last_error = f"HTTP {response.status_code}"
+                    logger.warning(
+                        "Escalation attempt %d/%d failed: %s",
+                        attempt,
+                        self._max_retries,
+                        last_error,
+                    )
+
+                except httpx.TimeoutException:
+                    last_error = "Request timed out"
+                    logger.warning(
+                        "Escalation attempt %d/%d timed out",
+                        attempt,
+                        self._max_retries,
+                    )
+                except httpx.RequestError as exc:
+                    last_error = str(exc)
+                    logger.warning(
+                        "Escalation attempt %d/%d error: %s",
+                        attempt,
+                        self._max_retries,
+                        last_error,
+                    )
+
+                # Exponential backoff: skip delay after last attempt
+                if attempt < self._max_retries:
+                    delay = 2**attempt
+                    await asyncio.sleep(delay)
+
+        logger.error(
+            "Escalation failed for thread %s after %d attempts: %s",
+            payload.thread_id,
+            self._max_retries,
+            last_error,
+        )
+        return EscalationResult(
+            success=False,
+            status_code=None,
+            attempts=self._max_retries,
+            error=last_error,
+        )
+
+
+class NoOpEscalator:
+    """Escalator that does nothing -- used when webhook URL is not configured."""
+
+    async def escalate(self, payload: EscalationPayload) -> EscalationResult:
+        logger.info("Escalation disabled (no webhook URL). Thread: %s", payload.thread_id)
+        return EscalationResult(
+            success=False,
+            status_code=None,
+            attempts=0,
+            error="Escalation disabled",
+        )
--- a/backend/app/graph.py
+++ b/backend/app/graph.py
@@ -4,27 +4,46 @@ from __future__ import annotations

 from typing import TYPE_CHECKING

-from langgraph.prebuilt import create_react_agent
+from langchain.agents import create_agent
 from langgraph_supervisor import create_supervisor

 from app.agents import get_tools_by_names
+from app.graph_context import GraphContext

 if TYPE_CHECKING:
    from langchain_core.language_models import BaseChatModel
    from langgraph.checkpoint.postgres.aio import AsyncPostgresSaver
-    from langgraph.graph.state import CompiledStateGraph

+    from app.intent import IntentClassifier
    from app.registry import AgentRegistry

+import structlog
+
+logger = structlog.get_logger()
+
 SUPERVISOR_PROMPT = (
    "You are a customer support supervisor. "
-    "Route customer requests to the appropriate agent based on their description. "
-    "For order status and tracking queries, use the order_lookup agent. "
-    "For order modifications like cancellations, use the order_actions agent. "
-    "For anything else, use the fallback agent."
+    "Route customer requests to the appropriate agent based on their description.\n\n"
+    "Available agents and their roles:\n"
+    "{agent_descriptions}\n\n"
+    "Routing rules:\n"
+    "- For order status and tracking queries, use the order_lookup agent.\n"
+    "- For order modifications like cancellations, use the order_actions agent.\n"
+    "- For discounts, promotions, or coupon codes, use the discount agent.\n"
+    "- For anything else or when uncertain, use the fallback agent.\n"
+    "- If the user's request involves multiple actions, execute them in order.\n"
+    "- If a previous intent classification is provided, follow it.\n"
 )


+def _format_agent_descriptions(registry: AgentRegistry) -> str:
+    """Build agent description text for the supervisor prompt."""
+    lines = []
+    for agent in registry.list_agents():
+        lines.append(f"- {agent.name}: {agent.description}")
+    return "\n".join(lines)
+
+
 def build_agent_nodes(
    registry: AgentRegistry,
    llm: BaseChatModel,
@@ -41,11 +60,11 @@ def build_agent_nodes(
            f"Permission level: {agent_config.permission}."
        )

-        agent_node = create_react_agent(
+        agent_node = create_agent(
            model=llm,
            tools=tools,
            name=agent_config.name,
-            prompt=system_prompt,
+            system_prompt=system_prompt,
        )
        agent_nodes.append(agent_node)

@@ -56,15 +75,29 @@ def build_graph(
    registry: AgentRegistry,
    llm: BaseChatModel,
    checkpointer: AsyncPostgresSaver,
-) -> CompiledStateGraph:
-    """Build and compile the LangGraph supervisor graph."""
+    intent_classifier: IntentClassifier | None = None,
+) -> GraphContext:
+    """Build and compile the LangGraph supervisor graph.
+
+    Returns a GraphContext that bundles the compiled graph with its
+    associated registry and intent classifier.
+    """
    agent_nodes = build_agent_nodes(registry, llm)
+    agent_descriptions = _format_agent_descriptions(registry)
+
+    prompt = SUPERVISOR_PROMPT.format(agent_descriptions=agent_descriptions)

    workflow = create_supervisor(
-        agent_nodes,
+        agents=agent_nodes,
        model=llm,
-        prompt=SUPERVISOR_PROMPT,
+        prompt=prompt,
        output_mode="full_history",
    )

-    return workflow.compile(checkpointer=checkpointer)
+    compiled = workflow.compile(checkpointer=checkpointer)
+
+    return GraphContext(
+        graph=compiled,
+        registry=registry,
+        intent_classifier=intent_classifier,
+    )
--- a/backend/app/graph_context.py
+++ b/backend/app/graph_context.py
@@ -0,0 +1,36 @@
+"""GraphContext -- typed wrapper around the compiled graph and its dependencies."""
+
+from __future__ import annotations
+
+from dataclasses import dataclass
+from typing import TYPE_CHECKING
+
+if TYPE_CHECKING:
+    from langgraph.graph.state import CompiledStateGraph
+
+    from app.intent import ClassificationResult, IntentClassifier
+    from app.registry import AgentRegistry
+
+
+@dataclass(frozen=True)
+class GraphContext:
+    """Bundles the compiled LangGraph graph with its associated services.
+
+    Replaces the previous pattern of monkey-patching attributes onto the
+    third-party CompiledStateGraph instance.
+    """
+
+    graph: CompiledStateGraph
+    registry: AgentRegistry
+    intent_classifier: IntentClassifier | None = None
+
+    async def classify_intent(self, message: str) -> ClassificationResult | None:
+        """Classify user intent using the attached classifier.
+
+        Returns None if no classifier is configured.
+        """
+        if self.intent_classifier is None:
+            return None
+
+        agents = self.registry.list_agents()
+        return await self.intent_classifier.classify(message, agents)
--- a/backend/app/intent.py
+++ b/backend/app/intent.py
@@ -0,0 +1,119 @@
+"""Intent classification using LLM structured output."""
+
+from __future__ import annotations
+
+from typing import TYPE_CHECKING, Protocol
+
+from pydantic import BaseModel
+
+if TYPE_CHECKING:
+    from langchain_core.language_models import BaseChatModel
+
+    from app.registry import AgentConfig
+
+import structlog
+
+logger = structlog.get_logger()
+
+CLASSIFICATION_PROMPT = (
+    "You are an intent classifier for a customer support system.\n"
+    "Given a user message, determine which agent(s) should handle it.\n\n"
+    "Available agents:\n{agent_list}\n\n"
+    "Rules:\n"
+    "- If the message clearly maps to one agent, return a single intent.\n"
+    "- If the message contains multiple distinct requests, return multiple intents "
+    "in execution order.\n"
+    "- If the message is vague or doesn't match any agent, set is_ambiguous=True "
+    "and provide a clarification_question.\n"
+    "- Never route to the fallback agent unless truly ambiguous.\n"
+    "- confidence should be between 0.0 and 1.0.\n"
+)
+
+AMBIGUITY_THRESHOLD = 0.5
+
+
+class IntentTarget(BaseModel, frozen=True):
+    """A single classified intent targeting a specific agent."""
+
+    agent_name: str
+    confidence: float
+    reasoning: str
+
+
+class ClassificationResult(BaseModel, frozen=True):
+    """Result of intent classification -- may contain multiple intents."""
+
+    intents: tuple[IntentTarget, ...]
+    is_ambiguous: bool = False
+    clarification_question: str | None = None
+
+
+class IntentClassifier(Protocol):
+    """Protocol for intent classification implementations."""
+
+    async def classify(
+        self,
+        message: str,
+        available_agents: tuple[AgentConfig, ...],
+    ) -> ClassificationResult: ...
+
+
+def _build_agent_list(agents: tuple[AgentConfig, ...]) -> str:
+    """Format agent descriptions for the classification prompt."""
+    lines = []
+    for agent in agents:
+        lines.append(f"- {agent.name}: {agent.description} (permission: {agent.permission})")
+    return "\n".join(lines)
+
+
+class LLMIntentClassifier:
+    """Classifies user intent using LLM structured output."""
+
+    def __init__(self, llm: BaseChatModel) -> None:
+        self._llm = llm
+
+    async def classify(
+        self,
+        message: str,
+        available_agents: tuple[AgentConfig, ...],
+    ) -> ClassificationResult:
+        """Classify user message into one or more agent intents."""
+        agent_list = _build_agent_list(available_agents)
+        system_prompt = CLASSIFICATION_PROMPT.format(agent_list=agent_list)
+
+        structured_llm = self._llm.with_structured_output(ClassificationResult)
+
+        try:
+            result = await structured_llm.ainvoke(
+                [
+                    {"role": "system", "content": system_prompt},
+                    {"role": "user", "content": message},
+                ]
+            )
+        except Exception:
+            logger.exception("Intent classification failed, returning ambiguous")
+            return ClassificationResult(
+                intents=(),
+                is_ambiguous=True,
+                clarification_question="I'm not sure I understood. Could you please rephrase?",
+            )
+
+        if not isinstance(result, ClassificationResult):
+            return ClassificationResult(
+                intents=(),
+                is_ambiguous=True,
+                clarification_question="I'm not sure I understood. Could you please rephrase?",
+            )
+
+        # Apply ambiguity threshold
+        if result.intents and all(i.confidence < AMBIGUITY_THRESHOLD for i in result.intents):
+            return ClassificationResult(
+                intents=result.intents,
+                is_ambiguous=True,
+                clarification_question=(
+                    result.clarification_question
+                    or "I'm not sure I understood. Could you please rephrase?"
+                ),
+            )
+
+        return result
--- a/backend/app/interrupt_manager.py
+++ b/backend/app/interrupt_manager.py
@@ -0,0 +1,268 @@
+"""Interrupt TTL management -- tracks pending interrupts with auto-expiration.
+
+Provides both in-memory (InterruptManager) and PostgreSQL-backed
+(PgInterruptManager) implementations behind a common Protocol.
+"""
+
+from __future__ import annotations
+
+import time
+import uuid
+from dataclasses import dataclass
+from typing import TYPE_CHECKING, Protocol
+
+if TYPE_CHECKING:
+    from psycopg_pool import AsyncConnectionPool
+
+
+@dataclass(frozen=True)
+class InterruptRecord:
+    """Immutable record of a pending interrupt."""
+
+    interrupt_id: str
+    thread_id: str
+    action: str
+    params: dict
+    created_at: float
+    ttl_seconds: int
+
+
+@dataclass(frozen=True)
+class InterruptStatus:
+    """Current status of a tracked interrupt."""
+
+    is_expired: bool
+    remaining_seconds: float
+    record: InterruptRecord
+
+
+class InterruptManagerProtocol(Protocol):
+    """Protocol for interrupt TTL management."""
+
+    def register(self, thread_id: str, action: str, params: dict) -> InterruptRecord: ...
+    def check_status(self, thread_id: str) -> InterruptStatus | None: ...
+    def resolve(self, thread_id: str) -> None: ...
+    def has_pending(self, thread_id: str) -> bool: ...
+    def generate_retry_prompt(self, expired_record: InterruptRecord) -> dict: ...
+
+
+def _build_retry_prompt(expired_record: InterruptRecord) -> dict:
+    """Generate a WebSocket message prompting the user to retry an expired action."""
+    return {
+        "type": "interrupt_expired",
+        "thread_id": expired_record.thread_id,
+        "action": expired_record.action,
+        "message": (
+            f"The approval request for '{expired_record.action}' has expired "
+            f"after {expired_record.ttl_seconds // 60} minutes. "
+            f"Would you like to try again?"
+        ),
+    }
+
+
+class InterruptManager:
+    """In-memory interrupt manager for single-worker development.
+
+    Complements SessionManager -- this tracks interrupt-specific TTL
+    while SessionManager handles session-level TTL.
+    """
+
+    def __init__(self, ttl_seconds: int = 1800) -> None:
+        self._ttl_seconds = ttl_seconds
+        self._interrupts: dict[str, InterruptRecord] = {}
+
+    def register(
+        self,
+        thread_id: str,
+        action: str,
+        params: dict,
+    ) -> InterruptRecord:
+        """Register a new pending interrupt with TTL tracking."""
+        record = InterruptRecord(
+            interrupt_id=uuid.uuid4().hex,
+            thread_id=thread_id,
+            action=action,
+            params=dict(params),
+            created_at=time.time(),
+            ttl_seconds=self._ttl_seconds,
+        )
+        self._interrupts = {**self._interrupts, thread_id: record}
+        return record
+
+    def check_status(self, thread_id: str) -> InterruptStatus | None:
+        """Check the TTL status of a pending interrupt."""
+        record = self._interrupts.get(thread_id)
+        if record is None:
+            return None
+        elapsed = time.time() - record.created_at
+        remaining = max(0.0, record.ttl_seconds - elapsed)
+        is_expired = elapsed > record.ttl_seconds
+        return InterruptStatus(
+            is_expired=is_expired,
+            remaining_seconds=remaining,
+            record=record,
+        )
+
+    def resolve(self, thread_id: str) -> None:
+        """Remove a resolved interrupt from tracking."""
+        self._interrupts = {
+            k: v for k, v in self._interrupts.items() if k != thread_id
+        }
+
+    def cleanup_expired(self) -> tuple[InterruptRecord, ...]:
+        """Find and remove all expired interrupts. Returns the expired records."""
+        now = time.time()
+        expired: list[InterruptRecord] = []
+        active: dict[str, InterruptRecord] = {}
+        for thread_id, record in self._interrupts.items():
+            if now - record.created_at > record.ttl_seconds:
+                expired.append(record)
+            else:
+                active[thread_id] = record
+        self._interrupts = active
+        return tuple(expired)
+
+    def generate_retry_prompt(self, expired_record: InterruptRecord) -> dict:
+        """Generate a WebSocket message prompting the user to retry an expired action."""
+        return _build_retry_prompt(expired_record)
+
+    def has_pending(self, thread_id: str) -> bool:
+        """Check if a thread has a pending (non-expired) interrupt."""
+        status = self.check_status(thread_id)
+        if status is None:
+            return False
+        return not status.is_expired
+
+
+# Alias for explicit naming
+InMemoryInterruptManager = InterruptManager
+
+
+class PgInterruptManager:
+    """PostgreSQL-backed interrupt manager for multi-worker production.
+
+    Uses the existing active_interrupts table defined in db.py.
+    """
+
+    def __init__(
+        self,
+        pool: AsyncConnectionPool,
+        ttl_seconds: int = 1800,
+    ) -> None:
+        self._pool = pool
+        self._ttl_seconds = ttl_seconds
+
+    def register(
+        self,
+        thread_id: str,
+        action: str,
+        params: dict,
+    ) -> InterruptRecord:
+        import asyncio
+
+        return asyncio.get_event_loop().run_until_complete(
+            self._register(thread_id, action, params)
+        )
+
+    async def _register(
+        self, thread_id: str, action: str, params: dict
+    ) -> InterruptRecord:
+        import json
+
+        record = InterruptRecord(
+            interrupt_id=uuid.uuid4().hex,
+            thread_id=thread_id,
+            action=action,
+            params=dict(params),
+            created_at=time.time(),
+            ttl_seconds=self._ttl_seconds,
+        )
+        async with self._pool.connection() as conn:
+            await conn.execute(
+                """
+                INSERT INTO active_interrupts (interrupt_id, thread_id, action, params)
+                VALUES (%(iid)s, %(tid)s, %(action)s, %(params)s)
+                ON CONFLICT (thread_id) WHERE resolved_at IS NULL
+                DO UPDATE SET
+                    interrupt_id = %(iid)s,
+                    action = %(action)s,
+                    params = %(params)s,
+                    created_at = NOW(),
+                    resolved_at = NULL
+                """,
+                {
+                    "iid": record.interrupt_id,
+                    "tid": thread_id,
+                    "action": action,
+                    "params": json.dumps(params),
+                },
+            )
+        return record
+
+    def check_status(self, thread_id: str) -> InterruptStatus | None:
+        import asyncio
+
+        return asyncio.get_event_loop().run_until_complete(
+            self._check_status(thread_id)
+        )
+
+    async def _check_status(self, thread_id: str) -> InterruptStatus | None:
+        async with self._pool.connection() as conn:
+            cursor = await conn.execute(
+                """
+                SELECT interrupt_id, action, params, created_at
+                FROM active_interrupts
+                WHERE thread_id = %(tid)s AND resolved_at IS NULL
+                ORDER BY created_at DESC LIMIT 1
+                """,
+                {"tid": thread_id},
+            )
+            row = await cursor.fetchone()
+
+        if row is None:
+            return None
+
+        created_at = row["created_at"].timestamp()
+        elapsed = time.time() - created_at
+        remaining = max(0.0, self._ttl_seconds - elapsed)
+        is_expired = elapsed > self._ttl_seconds
+
+        record = InterruptRecord(
+            interrupt_id=row["interrupt_id"],
+            thread_id=thread_id,
+            action=row["action"],
+            params=row["params"] if isinstance(row["params"], dict) else {},
+            created_at=created_at,
+            ttl_seconds=self._ttl_seconds,
+        )
+
+        return InterruptStatus(
+            is_expired=is_expired,
+            remaining_seconds=remaining,
+            record=record,
+        )
+
+    def resolve(self, thread_id: str) -> None:
+        import asyncio
+
+        asyncio.get_event_loop().run_until_complete(self._resolve(thread_id))
+
+    async def _resolve(self, thread_id: str) -> None:
+        async with self._pool.connection() as conn:
+            await conn.execute(
+                """
+                UPDATE active_interrupts
+                SET resolved_at = NOW(), resolution = 'resolved'
+                WHERE thread_id = %(tid)s AND resolved_at IS NULL
+                """,
+                {"tid": thread_id},
+            )
+
+    def generate_retry_prompt(self, expired_record: InterruptRecord) -> dict:
+        return _build_retry_prompt(expired_record)
+
+    def has_pending(self, thread_id: str) -> bool:
+        status = self.check_status(thread_id)
+        if status is None:
+            return False
+        return not status.is_expired
--- a/backend/app/llm.py
+++ b/backend/app/llm.py
@@ -31,6 +31,16 @@ def create_llm(settings: Settings) -> BaseChatModel:
            api_key=settings.openai_api_key,
        )

+    if provider == "azure_openai":
+        from langchain_openai import AzureChatOpenAI
+
+        return AzureChatOpenAI(
+            azure_deployment=settings.azure_openai_deployment,
+            azure_endpoint=settings.azure_openai_endpoint,
+            api_key=settings.azure_openai_api_key,
+            api_version=settings.azure_openai_api_version,
+        )
+
    if provider == "google":
        from langchain_google_genai import ChatGoogleGenerativeAI

@@ -39,4 +49,7 @@ def create_llm(settings: Settings) -> BaseChatModel:
            google_api_key=settings.google_api_key,
        )

-    raise ValueError(f"Unknown LLM provider: '{provider}'. Use 'anthropic', 'openai', or 'google'.")
+    raise ValueError(
+        f"Unknown LLM provider: '{provider}'. "
+        "Use 'anthropic', 'openai', 'azure_openai', or 'google'."
+    )
--- a/backend/app/logging_config.py
+++ b/backend/app/logging_config.py
@@ -0,0 +1,57 @@
+"""Structured logging configuration using structlog."""
+
+from __future__ import annotations
+
+import logging
+import sys
+
+import structlog
+
+
+def configure_logging(log_format: str = "console") -> None:
+    """Configure structlog with stdlib integration.
+
+    Args:
+        log_format: "console" for human-readable dev output,
+                    "json" for machine-parseable production output.
+    """
+    shared_processors: list[structlog.types.Processor] = [
+        structlog.contextvars.merge_contextvars,
+        structlog.stdlib.filter_by_level,
+        structlog.stdlib.add_logger_name,
+        structlog.stdlib.add_log_level,
+        structlog.processors.TimeStamper(fmt="iso"),
+        structlog.processors.StackInfoRenderer(),
+        structlog.processors.format_exc_info,
+        structlog.processors.UnicodeDecoder(),
+    ]
+
+    if log_format == "json":
+        renderer: structlog.types.Processor = structlog.processors.JSONRenderer()
+    else:
+        renderer = structlog.dev.ConsoleRenderer()
+
+    structlog.configure(
+        processors=[
+            *shared_processors,
+            structlog.stdlib.ProcessorFormatter.wrap_for_formatter,
+        ],
+        logger_factory=structlog.stdlib.LoggerFactory(),
+        wrapper_class=structlog.stdlib.BoundLogger,
+        cache_logger_on_first_use=True,
+    )
+
+    formatter = structlog.stdlib.ProcessorFormatter(
+        processors=[
+            structlog.stdlib.ProcessorFormatter.remove_processors_meta,
+            renderer,
+        ],
+    )
+
+    handler = logging.StreamHandler(sys.stdout)
+    handler.setFormatter(formatter)
+
+    root_logger = logging.getLogger()
+    root_logger.handlers.clear()
+    root_logger.addHandler(handler)
+    root_logger.setLevel(logging.INFO)
--- a/backend/app/main.py
+++ b/backend/app/main.py
@@ -2,79 +2,211 @@

 from __future__ import annotations

-import logging
+import asyncio
+import contextlib
 from contextlib import asynccontextmanager
 from pathlib import Path
 from typing import TYPE_CHECKING

-from fastapi import FastAPI, WebSocket, WebSocketDisconnect
+from fastapi import FastAPI, HTTPException, Query, WebSocket, WebSocketDisconnect
+from fastapi.exceptions import RequestValidationError
+from fastapi.responses import JSONResponse
 from fastapi.staticfiles import StaticFiles

+from app.analytics.api import router as analytics_router
+from app.analytics.event_recorder import PostgresAnalyticsRecorder
+from app.api_utils import envelope
 from app.callbacks import TokenUsageCallbackHandler
 from app.config import Settings
-from app.db import create_checkpointer, create_pool, setup_app_tables
+from app.conversation_tracker import PostgresConversationTracker
+from app.db import create_checkpointer, create_pool, run_alembic_migrations
+from app.escalation import NoOpEscalator, WebhookEscalator
 from app.graph import build_graph
+from app.intent import LLMIntentClassifier
+from app.interrupt_manager import InterruptManager
 from app.llm import create_llm
+from app.logging_config import configure_logging
+from app.openapi.review_api import router as openapi_router
 from app.registry import AgentRegistry
+from app.replay.api import router as replay_router
 from app.session_manager import SessionManager
+from app.ws_context import WebSocketContext
 from app.ws_handler import dispatch_message

 if TYPE_CHECKING:
    from collections.abc import AsyncGenerator

-logger = logging.getLogger(__name__)
+import structlog
+
+logger = structlog.get_logger()

 AGENTS_YAML = Path(__file__).parent.parent / "agents.yaml"
 FRONTEND_DIST = Path(__file__).parent.parent.parent / "frontend" / "dist"


+async def _interrupt_cleanup_loop(
+    interrupt_manager: InterruptManager,
+    interval: int = 60,
+) -> None:
+    """Periodically remove expired interrupts in the background.
+
+    Runs until cancelled. Catches all exceptions to prevent the task
+    from dying unexpectedly.
+    """
+    while True:
+        await asyncio.sleep(interval)
+        try:
+            expired = interrupt_manager.cleanup_expired()
+            if expired:
+                logger.info(
+                    "Cleaned up %d expired interrupt(s)",
+                    len(expired),
+                )
+        except Exception:
+            logger.exception("Error during interrupt cleanup")
+
+
@asynccontextmanager
 async def lifespan(app: FastAPI) -> AsyncGenerator[None, None]:
    settings = Settings()
+    configure_logging(settings.log_format)

    pool = await create_pool(settings)
    checkpointer = await create_checkpointer(pool)
-    await setup_app_tables(pool)
+    run_alembic_migrations(settings.database_url)

+    # Load agents from template or default YAML
+    if settings.template_name:
+        registry = AgentRegistry.load_template(settings.template_name)
+    else:
        registry = AgentRegistry.load(AGENTS_YAML)
+
    llm = create_llm(settings)
-    graph = build_graph(registry, llm, checkpointer)
+    intent_classifier = LLMIntentClassifier(llm)
+    graph_ctx = build_graph(registry, llm, checkpointer, intent_classifier=intent_classifier)
+
    session_manager = SessionManager(
        session_ttl_seconds=settings.session_ttl_minutes * 60,
    )
+    interrupt_manager = InterruptManager(
+        ttl_seconds=settings.interrupt_ttl_minutes * 60,
+    )

-    app.state.graph = graph
+    # Configure escalation
+    if settings.webhook_url:
+        escalator = WebhookEscalator(
+            url=settings.webhook_url,
+            timeout_seconds=settings.webhook_timeout_seconds,
+            max_retries=settings.webhook_max_retries,
+        )
+    else:
+        escalator = NoOpEscalator()
+
+    app.state.graph_ctx = graph_ctx
    app.state.session_manager = session_manager
+    app.state.interrupt_manager = interrupt_manager
+    app.state.escalator = escalator
    app.state.settings = settings
    app.state.pool = pool
+    app.state.analytics_recorder = PostgresAnalyticsRecorder(pool=pool)
+    app.state.conversation_tracker = PostgresConversationTracker()

    logger.info(
-        "Smart Support started: %d agents loaded, LLM=%s/%s",
+        "Smart Support started: %d agents loaded, LLM=%s/%s, template=%s",
        len(registry),
        settings.llm_provider,
        settings.llm_model,
+        settings.template_name or "(default)",
+    )
+
+    cleanup_task = asyncio.create_task(
+        _interrupt_cleanup_loop(interrupt_manager),
    )

    yield

+    cleanup_task.cancel()
+    with contextlib.suppress(asyncio.CancelledError):
+        await cleanup_task
+
    await pool.close()


-app = FastAPI(title="Smart Support", version="0.1.0", lifespan=lifespan)
+_VERSION = "0.6.0"
+
+app = FastAPI(title="Smart Support", version=_VERSION, lifespan=lifespan)
+
+app.include_router(openapi_router)
+app.include_router(replay_router)
+app.include_router(analytics_router)
+
+
+@app.exception_handler(HTTPException)
+async def http_exception_handler(request, exc):  # type: ignore[no-untyped-def]
+    """Wrap HTTPException in standard envelope format."""
+    return JSONResponse(
+        status_code=exc.status_code,
+        content=envelope(None, success=False, error=exc.detail),
+    )
+
+
+@app.exception_handler(RequestValidationError)
+async def validation_exception_handler(request, exc):  # type: ignore[no-untyped-def]
+    """Wrap validation errors in standard envelope format."""
+    return JSONResponse(
+        status_code=422,
+        content=envelope(None, success=False, error=str(exc)),
+    )
+
+
+@app.exception_handler(Exception)
+async def general_exception_handler(request, exc):  # type: ignore[no-untyped-def]
+    """Catch-all handler -- never leak stack traces."""
+    logger.exception("Unhandled exception: %s", exc)
+    return JSONResponse(
+        status_code=500,
+        content=envelope(None, success=False, error="Internal server error"),
+    )
+
+
+@app.get("/api/v1/health")
+def health_check() -> dict:
+    """Health check endpoint for load balancers and monitoring."""
+    return {"status": "ok", "version": _VERSION}


@app.websocket("/ws")
-async def websocket_endpoint(ws: WebSocket) -> None:
-    await ws.accept()
-    graph = app.state.graph
-    session_manager = app.state.session_manager
+async def websocket_endpoint(
+    ws: WebSocket,
+    token: str | None = Query(default=None),
+) -> None:
    settings = app.state.settings
+
+    # Verify WebSocket token when admin_api_key is configured
+    if settings.admin_api_key:
+        import secrets as _secrets
+
+        if token is None or not _secrets.compare_digest(token, settings.admin_api_key):
+            await ws.close(code=4001, reason="Unauthorized")
+            return
+
+    await ws.accept()
    callback_handler = TokenUsageCallbackHandler(model_name=settings.llm_model)

+    ws_ctx = WebSocketContext(
+        graph_ctx=app.state.graph_ctx,
+        session_manager=app.state.session_manager,
+        callback_handler=callback_handler,
+        interrupt_manager=app.state.interrupt_manager,
+        analytics_recorder=app.state.analytics_recorder,
+        conversation_tracker=app.state.conversation_tracker,
+        pool=app.state.pool,
+    )
+
    try:
        while True:
            raw_data = await ws.receive_text()
-            await dispatch_message(ws, graph, session_manager, callback_handler, raw_data)
+            await dispatch_message(ws, ws_ctx, raw_data)
    except WebSocketDisconnect:
        logger.info("WebSocket client disconnected")

--- a/backend/app/openapi/init.py
+++ b/backend/app/openapi/init.py
@@ -0,0 +1,2 @@
+# OpenAPI auto-discovery module
+# Parses OpenAPI specs, classifies endpoints via LLM, generates tools
--- a/backend/app/openapi/classifier.py
+++ b/backend/app/openapi/classifier.py
@@ -0,0 +1,169 @@
+"""OpenAPI endpoint classifier.
+
+Classifies endpoints into read/write access types and identifies
+customer-identifying parameters. Provides a rule-based heuristic
+classifier and an LLM-backed classifier with heuristic fallback.
+"""
+
+from __future__ import annotations
+
+import json
+import re
+from typing import Protocol
+
+import structlog
+
+from app.openapi.models import ClassificationResult, EndpointInfo
+
+logger = structlog.get_logger()
+
+_WRITE_METHODS = frozenset({"POST", "PUT", "PATCH", "DELETE"})
+_INTERRUPT_METHODS = frozenset({"POST", "PUT", "PATCH", "DELETE"})
+
+# Parameter names that identify the customer/order context
+_CUSTOMER_PARAM_PATTERNS = re.compile(
+    r"(customer_id|order_id|user_id|account_id|client_id|subscriber_id)",
+    re.IGNORECASE,
+)
+
+
+class ClassifierProtocol(Protocol):
+    """Protocol for endpoint classifiers."""
+
+    async def classify(
+        self, endpoints: tuple[EndpointInfo, ...]
+    ) -> tuple[ClassificationResult, ...]: ...
+
+
+class HeuristicClassifier:
+    """Rule-based endpoint classifier.
+
+    GET -> read, no interrupt.
+    POST/PUT/PATCH/DELETE -> write, needs_interrupt=True.
+    """
+
+    async def classify(
+        self, endpoints: tuple[EndpointInfo, ...]
+    ) -> tuple[ClassificationResult, ...]:
+        """Classify endpoints using HTTP method heuristics."""
+        if not endpoints:
+            return ()
+        return tuple(_classify_one(ep) for ep in endpoints)
+
+
+def _classify_one(ep: EndpointInfo) -> ClassificationResult:
+    """Classify a single endpoint using heuristics."""
+    access_type = "write" if ep.method in _WRITE_METHODS else "read"
+    needs_interrupt = ep.method in _INTERRUPT_METHODS
+    customer_params = _detect_customer_params(ep)
+    agent_group = "write_agent" if access_type == "write" else "read_agent"
+    return ClassificationResult(
+        endpoint=ep,
+        access_type=access_type,
+        customer_params=customer_params,
+        agent_group=agent_group,
+        confidence=0.7,
+        needs_interrupt=needs_interrupt,
+    )
+
+
+def _detect_customer_params(ep: EndpointInfo) -> tuple[str, ...]:
+    """Extract parameter names that identify the customer/order context."""
+    return tuple(
+        p.name
+        for p in ep.parameters
+        if _CUSTOMER_PARAM_PATTERNS.fullmatch(p.name)
+    )
+
+
+class LLMClassifier:
+    """LLM-backed endpoint classifier with heuristic fallback.
+
+    Uses an LLM to classify endpoints with higher accuracy.
+    Falls back to HeuristicClassifier on any LLM error.
+    """
+
+    def __init__(self, llm: object) -> None:
+        self._llm = llm
+        self._fallback = HeuristicClassifier()
+
+    async def classify(
+        self, endpoints: tuple[EndpointInfo, ...]
+    ) -> tuple[ClassificationResult, ...]:
+        """Classify endpoints using LLM with heuristic fallback."""
+        if not endpoints:
+            return ()
+        try:
+            return await self._classify_with_llm(endpoints)
+        except Exception:
+            logger.warning(
+                "LLM classification failed, falling back to heuristic",
+                exc_info=True,
+            )
+            return await self._fallback.classify(endpoints)
+
+    async def _classify_with_llm(
+        self, endpoints: tuple[EndpointInfo, ...]
+    ) -> tuple[ClassificationResult, ...]:
+        """Attempt LLM-based classification."""
+        prompt = _build_classification_prompt(endpoints)
+        response = await self._llm.ainvoke(prompt)
+        parsed = _parse_llm_response(response.content, endpoints)
+        return parsed
+
+
+def _build_classification_prompt(endpoints: tuple[EndpointInfo, ...]) -> str:
+    """Build a prompt for classifying endpoints."""
+    items = []
+    for i, ep in enumerate(endpoints):
+        items.append(
+            f"{i}: {ep.method} {ep.path} - {ep.summary or ep.operation_id}"
+        )
+    endpoint_list = "\n".join(items)
+    return (
+        "Classify each API endpoint as 'read' or 'write'. "
+        "For each, determine if it needs human interrupt approval, "
+        "identify customer-identifying parameters, and assign an agent_group.\n\n"
+        f"Endpoints:\n{endpoint_list}\n\n"
+        "Respond with a JSON array with one object per endpoint:\n"
+        '[{"access_type": "read|write", "agent_group": "...", '
+        '"needs_interrupt": true|false, "customer_params": [...], "confidence": 0.0-1.0}]'
+    )
+
+
+def _parse_llm_response(
+    content: str, endpoints: tuple[EndpointInfo, ...]
+) -> tuple[ClassificationResult, ...]:
+    """Parse LLM JSON response into ClassificationResult instances.
+
+    Raises ValueError if the response cannot be parsed or is mismatched.
+    """
+    # Extract JSON array from response
+    match = re.search(r"\[.*\]", content, re.DOTALL)
+    if not match:
+        raise ValueError(f"No JSON array found in LLM response: {content!r}")
+
+    items = json.loads(match.group())
+    if not isinstance(items, list) or len(items) != len(endpoints):
+        raise ValueError(
+            f"LLM returned {len(items)} items for {len(endpoints)} endpoints"
+        )
+
+    results: list[ClassificationResult] = []
+    for ep, item in zip(endpoints, items, strict=True):
+        raw_access = item.get("access_type", "read")
+        access_type = raw_access if raw_access in {"read", "write"} else "read"
+        confidence = max(0.0, min(1.0, float(item.get("confidence", 0.8))))
+        raw_group = str(item.get("agent_group", "support"))
+        agent_group = raw_group if raw_group.strip() else "support"
+        results.append(
+            ClassificationResult(
+                endpoint=ep,
+                access_type=access_type,
+                customer_params=tuple(item.get("customer_params", [])),
+                agent_group=agent_group,
+                confidence=confidence,
+                needs_interrupt=bool(item.get("needs_interrupt", False)),
+            )
+        )
+    return tuple(results)
--- a/backend/app/openapi/fetcher.py
+++ b/backend/app/openapi/fetcher.py
@@ -0,0 +1,93 @@
+"""OpenAPI spec fetcher with SSRF protection.
+
+Fetches OpenAPI spec documents from remote URLs, validates them against
+SSRF policy, and parses JSON or YAML format automatically.
+"""
+
+from __future__ import annotations
+
+import json
+
+import yaml
+
+from app.openapi.ssrf import DEFAULT_POLICY, SSRFPolicy
+
+_MAX_SIZE_BYTES = 10 * 1024 * 1024  # 10MB
+
+
+async def fetch_spec(url: str, policy: SSRFPolicy = DEFAULT_POLICY) -> dict:
+    """Fetch an OpenAPI spec from a URL and return as a dict.
+
+    Auto-detects JSON or YAML format from content-type header or URL extension.
+    Enforces a 10MB size limit.
+
+    Raises:
+        SSRFError: If the URL is blocked by SSRF policy.
+        ValueError: If the response is too large or cannot be parsed.
+    """
+    from app.openapi.ssrf import safe_fetch
+
+    response = await safe_fetch(url, policy=policy)
+    response.raise_for_status()
+
+    content = response.text
+    if len(content.encode("utf-8")) > _MAX_SIZE_BYTES:
+        raise ValueError(
+            f"Response too large: {len(content.encode('utf-8'))} bytes "
+            f"(max {_MAX_SIZE_BYTES} bytes)"
+        )
+
+    content_type = response.headers.get("content-type", "")
+    return _parse_content(content, content_type, url)
+
+
+def _parse_content(content: str, content_type: str, url: str) -> dict:
+    """Parse content as JSON or YAML based on content-type or URL extension."""
+    if _is_yaml_format(content_type, url):
+        return _parse_yaml(content)
+    if _is_json_format(content_type, url):
+        return _parse_json(content)
+    # Fall back: try JSON first, then YAML
+    try:
+        return _parse_json(content)
+    except ValueError:
+        return _parse_yaml(content)
+
+
+def _is_yaml_format(content_type: str, url: str) -> bool:
+    """Check if the content is YAML format."""
+    yaml_types = {"application/x-yaml", "text/yaml", "application/yaml"}
+    if any(t in content_type for t in yaml_types):
+        return True
+    lower_url = url.lower().split("?")[0]
+    return lower_url.endswith(".yaml") or lower_url.endswith(".yml")
+
+
+def _is_json_format(content_type: str, url: str) -> bool:
+    """Check if the content is JSON format."""
+    if "application/json" in content_type:
+        return True
+    lower_url = url.lower().split("?")[0]
+    return lower_url.endswith(".json")
+
+
+def _parse_json(content: str) -> dict:
+    """Parse content as JSON, raising ValueError on failure."""
+    try:
+        result = json.loads(content)
+    except json.JSONDecodeError as exc:
+        raise ValueError(f"Invalid JSON: {exc}") from exc
+    if not isinstance(result, dict):
+        raise ValueError(f"Expected a JSON object, got {type(result).__name__}")
+    return result
+
+
+def _parse_yaml(content: str) -> dict:
+    """Parse content as YAML, raising ValueError on failure."""
+    try:
+        result = yaml.safe_load(content)
+    except yaml.YAMLError as exc:
+        raise ValueError(f"Invalid YAML: {exc}") from exc
+    if not isinstance(result, dict):
+        raise ValueError(f"Expected a YAML mapping, got {type(result).__name__}")
+    return result
--- a/backend/app/openapi/generator.py
+++ b/backend/app/openapi/generator.py
@@ -0,0 +1,164 @@
+"""Tool code generator for classified OpenAPI endpoints.
+
+Generates Python source code for LangChain @tool functions and
+YAML agent configurations from classification results.
+"""
+
+from __future__ import annotations
+
+import keyword
+import re
+
+import yaml
+
+from app.openapi.models import ClassificationResult, EndpointInfo, GeneratedTool, ParameterInfo
+
+_INDENT = "    "
+
+
+def generate_tool_code(classification: ClassificationResult, base_url: str) -> GeneratedTool:
+    """Generate a LangChain @tool function for a classified endpoint.
+
+    Returns a GeneratedTool with the function source code as a string.
+    """
+    ep = classification.endpoint
+    func_name = _to_snake_case(ep.operation_id)
+    params = _collect_params(ep)
+    sig = _build_signature(params, ep.request_body_schema)
+    docstring = _sanitize_docstring(ep.summary or ep.description or ep.operation_id)
+    interrupt_comment = _interrupt_comment(classification)
+    http_call = _build_http_call(ep, base_url, params)
+
+    lines = [
+        "@tool",
+        f"async def {func_name}({sig}) -> str:",
+        f'{_INDENT}"""{docstring}"""',
+    ]
+    if interrupt_comment:
+        lines.append(f"{_INDENT}{interrupt_comment}")
+    lines += [
+        f"{_INDENT}async with httpx.AsyncClient() as client:",
+        f"{_INDENT}{_INDENT}{http_call}",
+        f"{_INDENT}{_INDENT}return response.text",
+    ]
+
+    code = "\n".join(lines)
+    return GeneratedTool(
+        function_name=func_name,
+        endpoint=ep,
+        classification=classification,
+        code=code,
+    )
+
+
+def generate_agent_yaml(
+    classifications: tuple[ClassificationResult, ...],
+    base_url: str,
+) -> str:
+    """Generate an agents.yaml string from a set of classification results.
+
+    Groups tools by agent_group, creating one agent entry per group.
+    """
+    if not classifications:
+        return yaml.safe_dump({"agents": []})
+
+    groups: dict[str, dict] = {}
+    for clf in classifications:
+        group = clf.agent_group
+        func_name = _to_snake_case(clf.endpoint.operation_id)
+        if group not in groups:
+            permission = "read" if clf.access_type == "read" else "write"
+            groups[group] = {
+                "name": group,
+                "description": f"Agent for {group} operations",
+                "permission": permission,
+                "tools": [],
+            }
+        groups[group]["tools"].append(func_name)
+
+    return yaml.safe_dump({"agents": list(groups.values())}, sort_keys=False)
+
+
+# --- Private helpers ---
+
+
+def _collect_params(ep: EndpointInfo) -> list[ParameterInfo]:
+    """Return path params first, then query params."""
+    path_params = [p for p in ep.parameters if p.location == "path"]
+    other_params = [p for p in ep.parameters if p.location != "path"]
+    return path_params + other_params
+
+
+def _build_signature(params: list[ParameterInfo], body_schema: dict | None) -> str:
+    """Build a Python function signature string from parameters."""
+    parts: list[str] = []
+    for p in params:
+        py_type = _schema_type_to_python(p.schema_type)
+        if p.required:
+            parts.append(f"{p.name}: {py_type}")
+        else:
+            parts.append(f"{p.name}: {py_type} | None = None")
+    if body_schema:
+        parts.append("body: dict | None = None")
+    return ", ".join(parts)
+
+
+def _build_http_call(
+    ep: EndpointInfo, base_url: str, params: list[ParameterInfo]
+) -> str:
+    """Build the httpx client call line."""
+    method = ep.method.lower()
+    path = ep.path
+
+    # Replace path parameters with f-string expressions
+    for p in params:
+        if p.location == "path":
+            path = path.replace(f"{{{p.name}}}", f"{{{p.name}}}")
+
+    url_expr = f'f"{base_url}{path}"'
+
+    query_params = [p for p in params if p.location == "query"]
+    extra_args = []
+    if query_params:
+        qp_dict = "{" + ", ".join(f'"{p.name}": {p.name}' for p in query_params) + "}"
+        extra_args.append(f"params={qp_dict}")
+
+    if ep.request_body_schema and method in ("post", "put", "patch"):
+        extra_args.append("json=body")
+
+    args_str = ", ".join([url_expr] + extra_args)
+    return f"response = await client.{method}({args_str})"
+
+
+def _interrupt_comment(classification: ClassificationResult) -> str:
+    """Return a comment line if the endpoint requires interrupt/approval."""
+    if classification.needs_interrupt:
+        return "# INTERRUPT: requires human approval before execution"
+    return ""
+
+
+def _schema_type_to_python(schema_type: str) -> str:
+    """Map OpenAPI schema type to Python type annotation."""
+    mapping = {
+        "string": "str",
+        "integer": "int",
+        "number": "float",
+        "boolean": "bool",
+        "array": "list",
+        "object": "dict",
+    }
+    return mapping.get(schema_type, "str")
+
+
+def _sanitize_docstring(text: str) -> str:
+    """Escape triple-quotes and newlines to prevent docstring injection."""
+    return text.replace("\\", "\\\\").replace('"""', r"\"\"\"").replace("\n", " ")
+
+
+def _to_snake_case(name: str) -> str:
+    """Convert operationId to a valid snake_case Python identifier."""
+    clean = re.sub(r"[^a-zA-Z0-9]+", "_", name).strip("_")
+    result = clean.lower() or "unnamed_tool"
+    if keyword.iskeyword(result):
+        result = f"{result}_tool"
+    return result
--- a/backend/app/openapi/importer.py
+++ b/backend/app/openapi/importer.py
@@ -0,0 +1,111 @@
+"""Import orchestrator for OpenAPI auto-discovery pipeline.
+
+Orchestrates: fetch -> validate -> parse -> classify
+Each stage updates the job status and calls the on_progress callback.
+"""
+
+from __future__ import annotations
+
+from collections.abc import Callable
+from dataclasses import replace
+
+import structlog
+
+from app.openapi.classifier import ClassifierProtocol, HeuristicClassifier
+from app.openapi.fetcher import fetch_spec
+from app.openapi.models import ImportJob
+from app.openapi.parser import parse_endpoints
+from app.openapi.ssrf import DEFAULT_POLICY, SSRFPolicy
+from app.openapi.validator import validate_spec
+
+logger = structlog.get_logger()
+
+ProgressCallback = Callable[[str, ImportJob], None] | None
+
+
+class ImportOrchestrator:
+    """Orchestrates the full OpenAPI import pipeline.
+
+    Stages:
+    1. fetching  -- download and parse spec from URL
+    2. validating -- check spec structure
+    3. parsing   -- extract endpoint definitions
+    4. classifying -- classify endpoints for agent routing
+    5. done / failed
+    """
+
+    def __init__(
+        self,
+        classifier: ClassifierProtocol | None = None,
+        policy: SSRFPolicy = DEFAULT_POLICY,
+    ) -> None:
+        self._classifier = classifier or HeuristicClassifier()
+        self._policy = policy
+
+    async def start_import(
+        self,
+        url: str,
+        job_id: str,
+        on_progress: ProgressCallback,
+    ) -> ImportJob:
+        """Run the full import pipeline for a spec URL.
+
+        Returns an ImportJob reflecting final status (done or failed).
+        on_progress is called with (stage_name, current_job) at each stage.
+        Passing None for on_progress is safe.
+        """
+        job = ImportJob(
+            job_id=job_id,
+            status="pending",
+            spec_url=url,
+        )
+
+        try:
+            # Stage 1: fetch
+            job = _update(job, status="fetching")
+            _notify(on_progress, "fetching", job)
+            spec_dict = await fetch_spec(url, self._policy)
+
+            # Stage 2: validate
+            job = _update(job, status="validating")
+            _notify(on_progress, "validating", job)
+            errors = validate_spec(spec_dict)
+            if errors:
+                raise ValueError(f"Invalid spec: {'; '.join(errors)}")
+
+            # Stage 3: parse
+            job = _update(job, status="parsing")
+            _notify(on_progress, "parsing", job)
+            endpoints = parse_endpoints(spec_dict)
+
+            # Stage 4: classify
+            job = _update(job, status="classifying", total_endpoints=len(endpoints))
+            _notify(on_progress, "classifying", job)
+            classifications = await self._classifier.classify(endpoints)
+
+            # Done
+            job = _update(
+                job,
+                status="done",
+                total_endpoints=len(endpoints),
+                classified_count=len(classifications),
+            )
+            _notify(on_progress, "done", job)
+            return job
+
+        except Exception as exc:
+            logger.exception("Import pipeline failed for job %s", job_id)
+            job = _update(job, status="failed", error_message=str(exc))
+            _notify(on_progress, "failed", job)
+            return job
+
+
+def _update(job: ImportJob, **kwargs: object) -> ImportJob:
+    """Return a new ImportJob with updated fields (immutable update)."""
+    return replace(job, **kwargs)
+
+
+def _notify(callback: ProgressCallback, stage: str, job: ImportJob) -> None:
+    """Call the progress callback if provided."""
+    if callback is not None:
+        callback(stage, job)
--- a/backend/app/openapi/models.py
+++ b/backend/app/openapi/models.py
@@ -0,0 +1,67 @@
+"""Data models for OpenAPI auto-discovery module.
+
+Frozen dataclasses for all value objects to ensure immutability.
+"""
+
+from __future__ import annotations
+
+from dataclasses import dataclass, field
+
+
+@dataclass(frozen=True)
+class ParameterInfo:
+    """Describes a single endpoint parameter."""
+
+    name: str
+    location: str  # "path", "query", "header", "cookie"
+    required: bool
+    schema_type: str  # "string", "integer", "boolean", etc.
+    description: str = ""
+
+
+@dataclass(frozen=True)
+class EndpointInfo:
+    """Describes a single API endpoint."""
+
+    path: str
+    method: str  # uppercase: GET, POST, PUT, DELETE, PATCH
+    operation_id: str
+    summary: str
+    description: str
+    parameters: tuple[ParameterInfo, ...] = field(default_factory=tuple)
+    request_body_schema: dict | None = None
+    response_schema: dict | None = None
+
+
+@dataclass(frozen=True)
+class ClassificationResult:
+    """Result of classifying an endpoint for agent routing."""
+
+    endpoint: EndpointInfo
+    access_type: str  # "read" or "write"
+    customer_params: tuple[str, ...]  # param names that identify the customer
+    agent_group: str  # which agent group handles this endpoint
+    confidence: float  # 0.0 to 1.0
+    needs_interrupt: bool  # requires human approval before execution
+
+
+@dataclass(frozen=True)
+class ImportJob:
+    """Tracks the state of an OpenAPI import job."""
+
+    job_id: str
+    status: str  # "pending", "fetching", "validating", "parsing", "classifying", "done", "failed"
+    spec_url: str
+    total_endpoints: int = 0
+    classified_count: int = 0
+    error_message: str | None = None
+
+
+@dataclass(frozen=True)
+class GeneratedTool:
+    """A generated LangChain tool from a classified endpoint."""
+
+    function_name: str
+    endpoint: EndpointInfo
+    classification: ClassificationResult
+    code: str
--- a/backend/app/openapi/parser.py
+++ b/backend/app/openapi/parser.py
@@ -0,0 +1,152 @@
+"""OpenAPI spec endpoint parser.
+
+Extracts all endpoint definitions from a parsed OpenAPI spec dict,
+resolving $ref references from components.
+"""
+
+from __future__ import annotations
+
+import re
+
+from app.openapi.models import EndpointInfo, ParameterInfo
+
+_HTTP_METHODS = ("get", "post", "put", "patch", "delete", "head", "options")
+
+
+def parse_endpoints(spec_dict: dict) -> tuple[EndpointInfo, ...]:
+    """Parse all endpoints from a validated OpenAPI spec dict.
+
+    Returns an immutable tuple of EndpointInfo instances.
+    """
+    paths = spec_dict.get("paths", {})
+    if not isinstance(paths, dict) or not paths:
+        return ()
+
+    endpoints: list[EndpointInfo] = []
+    for path, path_item in paths.items():
+        if not isinstance(path_item, dict):
+            continue
+        for method in _HTTP_METHODS:
+            operation = path_item.get(method)
+            if operation is None:
+                continue
+            endpoint = _parse_operation(path, method.upper(), operation, spec_dict)
+            endpoints.append(endpoint)
+
+    return tuple(endpoints)
+
+
+def _parse_operation(
+    path: str,
+    method: str,
+    operation: dict,
+    spec_dict: dict,
+) -> EndpointInfo:
+    """Parse a single operation dict into an EndpointInfo."""
+    operation_id = operation.get("operationId") or _generate_operation_id(path, method)
+    summary = operation.get("summary", "")
+    description = operation.get("description", "")
+
+    parameters = _parse_parameters(operation.get("parameters", []), spec_dict)
+    request_body_schema = _parse_request_body(operation.get("requestBody"), spec_dict)
+    response_schema = _parse_response_schema(operation.get("responses", {}), spec_dict)
+
+    return EndpointInfo(
+        path=path,
+        method=method,
+        operation_id=operation_id,
+        summary=summary,
+        description=description,
+        parameters=tuple(parameters),
+        request_body_schema=request_body_schema,
+        response_schema=response_schema,
+    )
+
+
+def _parse_parameters(
+    params_list: list,
+    spec_dict: dict,
+) -> list[ParameterInfo]:
+    """Parse list of parameter dicts into ParameterInfo instances."""
+    result: list[ParameterInfo] = []
+    for param in params_list:
+        if not isinstance(param, dict):
+            continue
+        schema = param.get("schema", {})
+        schema_type = schema.get("type", "string") if isinstance(schema, dict) else "string"
+        result.append(
+            ParameterInfo(
+                name=param.get("name", ""),
+                location=param.get("in", "query"),
+                required=bool(param.get("required", False)),
+                schema_type=schema_type,
+                description=param.get("description", ""),
+            )
+        )
+    return result
+
+
+def _parse_request_body(request_body: dict | None, spec_dict: dict) -> dict | None:
+    """Extract schema from requestBody, resolving $ref if present."""
+    if not isinstance(request_body, dict):
+        return None
+    content = request_body.get("content", {})
+    if not isinstance(content, dict):
+        return None
+    # Prefer application/json
+    for media_type in ("application/json", *content.keys()):
+        media = content.get(media_type)
+        if not isinstance(media, dict):
+            continue
+        schema = media.get("schema")
+        if schema:
+            return _resolve_ref(schema, spec_dict)
+    return None
+
+
+def _parse_response_schema(responses: dict, spec_dict: dict) -> dict | None:
+    """Extract schema from the first 2xx response."""
+    if not isinstance(responses, dict):
+        return None
+    for status_code in ("200", "201", "202", "204"):
+        response = responses.get(status_code)
+        if not isinstance(response, dict):
+            continue
+        content = response.get("content", {})
+        if not isinstance(content, dict):
+            continue
+        for media_type in ("application/json", *content.keys()):
+            media = content.get(media_type)
+            if not isinstance(media, dict):
+                continue
+            schema = media.get("schema")
+            if schema:
+                return _resolve_ref(schema, spec_dict)
+    return None
+
+
+def _resolve_ref(schema: object, spec_dict: dict) -> dict:
+    """Resolve a $ref to its target schema, or return the schema as-is."""
+    if not isinstance(schema, dict):
+        return {}
+    ref = schema.get("$ref")
+    if not ref:
+        return schema
+    # Only handle local refs like #/components/schemas/Foo
+    if not isinstance(ref, str) or not ref.startswith("#/"):
+        return schema
+    parts = ref.lstrip("#/").split("/")
+    target: object = spec_dict
+    for part in parts:
+        if not isinstance(target, dict):
+            return schema
+        target = target.get(part)
+    return target if isinstance(target, dict) else schema
+
+
+def _generate_operation_id(path: str, method: str) -> str:
+    """Generate a snake_case operation_id from path and method."""
+    # Remove path parameters braces and replace / with _
+    clean = re.sub(r"\{[^}]+\}", "by_param", path)
+    clean = re.sub(r"[^a-zA-Z0-9]+", "_", clean).strip("_")
+    return f"{method.lower()}_{clean}" if clean else method.lower()
--- a/backend/app/openapi/review_api.py
+++ b/backend/app/openapi/review_api.py
@@ -0,0 +1,282 @@
+"""FastAPI router for OpenAPI import review workflow.
+
+Exposes endpoints for:
+- Starting an import job (triggers background pipeline)
+- Querying job status
+- Reviewing and editing classifications
+- Approving a job to trigger tool generation
+"""
+
+from __future__ import annotations
+
+import asyncio
+import re
+import uuid
+from typing import Literal
+
+import structlog
+from fastapi import APIRouter, BackgroundTasks, Depends, HTTPException
+from pydantic import BaseModel, field_validator
+
+from app.auth import require_admin_api_key
+from app.openapi.generator import generate_agent_yaml, generate_tool_code
+from app.openapi.importer import ImportOrchestrator
+from app.openapi.models import ClassificationResult, ImportJob
+
+logger = structlog.get_logger()
+
+router = APIRouter(
+    prefix="/api/v1/openapi",
+    tags=["openapi"],
+    dependencies=[Depends(require_admin_api_key)],
+)
+
+# In-memory store: job_id -> job dict, guarded by async lock
+_job_store: dict[str, dict] = {}
+_store_lock = asyncio.Lock()
+
+# Shared orchestrator instance
+_orchestrator = ImportOrchestrator()
+
+
+# --- Request / Response schemas ---
+
+
+class ImportRequest(BaseModel):
+    url: str
+
+    @field_validator("url")
+    @classmethod
+    def url_must_be_valid(cls, value: str) -> str:
+        stripped = value.strip()
+        if not stripped:
+            raise ValueError("url must not be empty")
+        if not stripped.startswith(("http://", "https://")):
+            raise ValueError("url must start with http:// or https://")
+        return stripped
+
+
+class JobResponse(BaseModel):
+    job_id: str
+    status: str
+    spec_url: str
+    total_endpoints: int = 0
+    classified_count: int = 0
+    error_message: str | None = None
+
+
+class ClassificationResponse(BaseModel):
+    index: int
+    access_type: str
+    needs_interrupt: bool
+    agent_group: str
+    confidence: float
+    customer_params: list[str]
+    endpoint: dict
+
+
+class UpdateClassificationRequest(BaseModel):
+    access_type: Literal["read", "write"]
+    needs_interrupt: bool
+    agent_group: str
+
+    @field_validator("agent_group")
+    @classmethod
+    def agent_group_must_be_safe(cls, value: str) -> str:
+        if not value.strip() or not re.fullmatch(r"[a-zA-Z0-9_\-]+", value):
+            raise ValueError(
+                "agent_group must be non-empty and contain only "
+                "alphanumeric characters, underscores, or hyphens"
+            )
+        return value
+
+
+# --- Helpers ---
+
+
+def _job_to_response(job: dict) -> dict:
+    return {
+        "job_id": job["job_id"],
+        "status": job["status"],
+        "spec_url": job["spec_url"],
+        "total_endpoints": job.get("total_endpoints", 0),
+        "classified_count": job.get("classified_count", 0),
+        "error_message": job.get("error_message"),
+    }
+
+
+def _classification_to_response(idx: int, clf: ClassificationResult) -> dict:
+    ep = clf.endpoint
+    return {
+        "index": idx,
+        "access_type": clf.access_type,
+        "needs_interrupt": clf.needs_interrupt,
+        "agent_group": clf.agent_group,
+        "confidence": clf.confidence,
+        "customer_params": list(clf.customer_params),
+        "endpoint": {
+            "path": ep.path,
+            "method": ep.method,
+            "operation_id": ep.operation_id,
+            "summary": ep.summary,
+            "description": ep.description,
+        },
+    }
+
+
+async def _run_import(job_id: str, url: str) -> None:
+    """Run the import pipeline as a background task."""
+
+    def on_progress(stage: str, result_job: ImportJob) -> None:
+        if job_id in _job_store:
+            _job_store[job_id] = {
+                **_job_store[job_id],
+                "status": result_job.status,
+                "total_endpoints": result_job.total_endpoints,
+                "classified_count": result_job.classified_count,
+                "error_message": result_job.error_message,
+            }
+
+    try:
+        result = await _orchestrator.start_import(
+            url=url, job_id=job_id, on_progress=on_progress,
+        )
+        if job_id in _job_store:
+            _job_store[job_id] = {
+                **_job_store[job_id],
+                "status": result.status,
+                "total_endpoints": result.total_endpoints,
+                "classified_count": result.classified_count,
+                "error_message": result.error_message,
+            }
+    except Exception:
+        logger.exception("Background import failed for job %s", job_id)
+        if job_id in _job_store:
+            _job_store[job_id] = {
+                **_job_store[job_id],
+                "status": "failed",
+                "error_message": "Import failed. Please check the URL and try again.",
+            }
+
+
+# --- Endpoints ---
+
+
+@router.post("/import", status_code=202)
+async def start_import(
+    request: ImportRequest,
+    background_tasks: BackgroundTasks,
+) -> dict:
+    """Start an OpenAPI import job for the given spec URL."""
+    job_id = str(uuid.uuid4())
+    job: dict = {
+        "job_id": job_id,
+        "status": "pending",
+        "spec_url": request.url,
+        "total_endpoints": 0,
+        "classified_count": 0,
+        "error_message": None,
+        "classifications": [],
+    }
+    _job_store[job_id] = job
+    background_tasks.add_task(_run_import, job_id, request.url)
+    return _job_to_response(job)
+
+
+@router.get("/jobs/{job_id}")
+async def get_job(job_id: str) -> dict:
+    """Get the status of an import job."""
+    job = _job_store.get(job_id)
+    if job is None:
+        raise HTTPException(status_code=404, detail=f"Job '{job_id}' not found")
+    return _job_to_response(job)
+
+
+@router.get("/jobs/{job_id}/classifications")
+async def get_classifications(job_id: str) -> list:
+    """Get all classifications for an import job."""
+    job = _job_store.get(job_id)
+    if job is None:
+        raise HTTPException(status_code=404, detail=f"Job '{job_id}' not found")
+    classifications: list[ClassificationResult] = job.get("classifications", [])
+    return [
+        _classification_to_response(i, clf)
+        for i, clf in enumerate(classifications)
+    ]
+
+
+@router.put("/jobs/{job_id}/classifications/{idx}")
+async def update_classification(
+    job_id: str,
+    idx: int,
+    request: UpdateClassificationRequest,
+) -> dict:
+    """Update a specific classification by index."""
+    job = _job_store.get(job_id)
+    if job is None:
+        raise HTTPException(status_code=404, detail=f"Job '{job_id}' not found")
+
+    classifications: list[ClassificationResult] = job.get("classifications", [])
+    if idx < 0 or idx >= len(classifications):
+        raise HTTPException(
+            status_code=404,
+            detail=f"Classification index {idx} out of range",
+        )
+
+    original = classifications[idx]
+    updated = ClassificationResult(
+        endpoint=original.endpoint,
+        access_type=request.access_type,
+        customer_params=original.customer_params,
+        agent_group=request.agent_group,
+        confidence=original.confidence,
+        needs_interrupt=request.needs_interrupt,
+    )
+    new_classifications = list(classifications)
+    new_classifications[idx] = updated
+    _job_store[job_id] = {**job, "classifications": new_classifications}
+
+    return _classification_to_response(idx, updated)
+
+
+@router.post("/jobs/{job_id}/approve")
+async def approve_job(job_id: str) -> dict:
+    """Approve a job's classifications and trigger tool generation.
+
+    Generates Python tool code for each classified endpoint and
+    produces an agent YAML configuration snippet.
+    """
+    job = _job_store.get(job_id)
+    if job is None:
+        raise HTTPException(status_code=404, detail=f"Job '{job_id}' not found")
+
+    classifications: list[ClassificationResult] = job.get("classifications", [])
+    if not classifications:
+        raise HTTPException(
+            status_code=400,
+            detail="No classifications to approve. Import must complete first.",
+        )
+
+    base_url = job["spec_url"].rsplit("/", 1)[0]
+    generated_tools = []
+    for clf in classifications:
+        tool = generate_tool_code(clf, base_url)
+        generated_tools.append({
+            "function_name": tool.function_name,
+            "agent_group": clf.agent_group,
+            "code": tool.code,
+        })
+
+    agent_yaml = generate_agent_yaml(tuple(classifications), base_url)
+
+    updated_job = {
+        **job,
+        "status": "approved",
+        "generated_tools": generated_tools,
+        "agent_yaml": agent_yaml,
+    }
+    _job_store[job_id] = updated_job
+
+    response = _job_to_response(updated_job)
+    response["generated_tools_count"] = len(generated_tools)
+    return response
--- a/backend/app/openapi/ssrf.py
+++ b/backend/app/openapi/ssrf.py
@@ -0,0 +1,167 @@
+"""SSRF protection module.
+
+Validates URLs before making external HTTP requests.
+Blocks private IPs, loopback addresses, link-local, and DNS rebinding attacks.
+"""
+
+from __future__ import annotations
+
+import ipaddress
+import socket
+from dataclasses import dataclass
+from urllib.parse import urlparse
+
+import httpx
+
+
+class SSRFError(Exception):
+    """Raised when a URL fails SSRF validation."""
+
+
+@dataclass(frozen=True)
+class SSRFPolicy:
+    """Configuration for SSRF protection."""
+
+    allowed_schemes: frozenset[str] = frozenset({"http", "https"})
+    allowed_hosts: frozenset[str] | None = None  # None = all public hosts allowed
+    max_redirects: int = 5
+    timeout_seconds: float = 30.0
+
+
+_BLOCKED_NETWORKS = (
+    ipaddress.ip_network("10.0.0.0/8"),
+    ipaddress.ip_network("172.16.0.0/12"),
+    ipaddress.ip_network("192.168.0.0/16"),
+    ipaddress.ip_network("127.0.0.0/8"),
+    ipaddress.ip_network("169.254.0.0/16"),
+    ipaddress.ip_network("0.0.0.0/32"),
+    ipaddress.ip_network("100.64.0.0/10"),      # Carrier-Grade NAT
+    ipaddress.ip_network("198.18.0.0/15"),       # Benchmarking
+    ipaddress.ip_network("240.0.0.0/4"),         # Reserved
+    ipaddress.ip_network("255.255.255.255/32"),   # Broadcast
+    # IPv6
+    ipaddress.ip_network("::1/128"),
+    ipaddress.ip_network("fe80::/10"),
+    ipaddress.ip_network("fc00::/7"),
+    ipaddress.ip_network("::/128"),
+    ipaddress.ip_network("::ffff:0:0/96"),       # IPv4-mapped IPv6
+    ipaddress.ip_network("2001:db8::/32"),        # Documentation
+)
+
+DEFAULT_POLICY = SSRFPolicy()
+
+
+def is_private_ip(ip_str: str) -> bool:
+    """Check if an IP address is private/reserved."""
+    try:
+        addr = ipaddress.ip_address(ip_str)
+    except ValueError:
+        return True  # Invalid IP treated as blocked
+
+    return any(addr in network for network in _BLOCKED_NETWORKS)
+
+
+def validate_url(url: str, policy: SSRFPolicy = DEFAULT_POLICY) -> str:
+    """Validate a URL against SSRF policy.
+
+    Returns the validated URL string.
+    Raises SSRFError if the URL is blocked.
+    """
+    parsed = urlparse(url)
+
+    # Check scheme
+    if parsed.scheme not in policy.allowed_schemes:
+        raise SSRFError(
+            f"URL scheme '{parsed.scheme}' is not allowed. "
+            f"Allowed: {', '.join(sorted(policy.allowed_schemes))}"
+        )
+
+    # Check hostname exists
+    hostname = parsed.hostname
+    if not hostname:
+        raise SSRFError("URL has no hostname")
+
+    # Check allowed hosts whitelist
+    if policy.allowed_hosts is not None and hostname not in policy.allowed_hosts:
+        raise SSRFError(f"Host '{hostname}' is not in the allowed hosts list")
+
+    # DNS resolution -- resolve before making any request
+    resolved_ips = resolve_hostname(hostname)
+    if not resolved_ips:
+        raise SSRFError(f"Could not resolve hostname '{hostname}'")
+
+    # Check all resolved IPs against blocked networks
+    for ip_str in resolved_ips:
+        if is_private_ip(ip_str):
+            raise SSRFError(
+                f"Host '{hostname}' resolves to private/reserved IP {ip_str}. "
+                "Request blocked for SSRF protection."
+            )
+
+    return url
+
+
+def resolve_hostname(hostname: str) -> list[str]:
+    """Resolve hostname to IP addresses via DNS."""
+    try:
+        results = socket.getaddrinfo(hostname, None, socket.AF_UNSPEC, socket.SOCK_STREAM)
+        return list({result[4][0] for result in results})
+    except socket.gaierror:
+        return []
+
+
+async def safe_fetch(
+    url: str,
+    *,
+    policy: SSRFPolicy = DEFAULT_POLICY,
+    method: str = "GET",
+    headers: dict[str, str] | None = None,
+) -> httpx.Response:
+    """Fetch a URL with SSRF protection.
+
+    Validates the URL, resolves DNS, checks IPs, then makes the request.
+    After receiving the response, verifies the actual connected IP
+    to guard against DNS rebinding.
+    """
+    validate_url(url, policy)
+
+    # Make the request with redirect following disabled so we can check each hop
+    async with httpx.AsyncClient(
+        follow_redirects=False,
+        timeout=httpx.Timeout(policy.timeout_seconds),
+    ) as client:
+        current_url = url
+        for _redirect_count in range(policy.max_redirects + 1):
+            response = await client.request(
+                method,
+                current_url,
+                headers=headers,
+            )
+
+            if response.is_redirect:
+                redirect_url = str(response.next_request.url) if response.next_request else None
+                if not redirect_url:
+                    raise SSRFError("Redirect with no target URL")
+                # Validate the redirect target
+                validate_url(redirect_url, policy)
+                current_url = redirect_url
+                continue
+
+            return response
+
+        raise SSRFError(
+            f"Too many redirects (max {policy.max_redirects}). "
+            "Possible redirect loop or evasion attempt."
+        )
+
+
+async def safe_fetch_text(
+    url: str,
+    *,
+    policy: SSRFPolicy = DEFAULT_POLICY,
+    headers: dict[str, str] | None = None,
+) -> str:
+    """Fetch a URL and return text content with SSRF protection."""
+    response = await safe_fetch(url, policy=policy, headers=headers)
+    response.raise_for_status()
+    return response.text
--- a/backend/app/openapi/validator.py
+++ b/backend/app/openapi/validator.py
@@ -0,0 +1,51 @@
+"""OpenAPI spec validator.
+
+Validates an OpenAPI spec dict for required fields and basic structural
+correctness. Returns a list of human-readable error strings.
+"""
+
+from __future__ import annotations
+
+_SUPPORTED_VERSIONS = ("3.0.", "3.1.")
+_REQUIRED_FIELDS = ("openapi", "info", "paths")
+
+
+def validate_spec(spec_dict: object) -> list[str]:
+    """Validate an OpenAPI spec dict.
+
+    Returns a list of error strings. An empty list means the spec is valid.
+    Does not raise; all errors are captured and returned.
+    """
+    if not isinstance(spec_dict, dict):
+        return [f"Spec must be a dict, got {type(spec_dict).__name__}"]
+
+    errors: list[str] = []
+
+    # Check required top-level fields
+    for field in _REQUIRED_FIELDS:
+        if field not in spec_dict:
+            errors.append(f"Missing required field: '{field}'")
+
+    # Validate openapi version if present
+    if "openapi" in spec_dict:
+        version = spec_dict["openapi"]
+        if not isinstance(version, str):
+            errors.append(f"'openapi' must be a string, got {type(version).__name__}")
+        elif not any(version.startswith(prefix) for prefix in _SUPPORTED_VERSIONS):
+            errors.append(
+                f"Unsupported OpenAPI version '{version}'. "
+                f"Supported versions start with: {', '.join(_SUPPORTED_VERSIONS)}"
+            )
+
+    # Validate info object if present
+    if "info" in spec_dict and isinstance(spec_dict["info"], dict):
+        info = spec_dict["info"]
+        for sub_field in ("title", "version"):
+            if sub_field not in info:
+                errors.append(f"Missing required field in 'info': '{sub_field}'")
+
+    # Validate paths object if present
+    if "paths" in spec_dict and not isinstance(spec_dict["paths"], dict):
+        errors.append(f"'paths' must be a dict, got {type(spec_dict['paths']).__name__}")
+
+    return errors
--- a/backend/app/registry.py
+++ b/backend/app/registry.py
@@ -100,5 +100,41 @@ class AgentRegistry:
    def get_agents_by_permission(self, permission: str) -> tuple[AgentConfig, ...]:
        return tuple(a for a in self._agents.values() if a.permission == permission)

+    @classmethod
+    def load_template(
+        cls,
+        template_name: str,
+        templates_dir: str | Path | None = None,
+    ) -> AgentRegistry:
+        """Load agent configurations from a named template."""
+        if templates_dir is None:
+            templates_dir = Path(__file__).parent.parent / "templates"
+        templates_dir = Path(templates_dir)
+
+        yaml_path = templates_dir / f"{template_name}.yaml"
+        if not yaml_path.exists():
+            available = cls.list_templates(templates_dir)
+            raise FileNotFoundError(
+                f"Template '{template_name}' not found. "
+                f"Available: {', '.join(available) if available else 'none'}"
+            )
+        return cls.load(yaml_path)
+
+    @classmethod
+    def list_templates(
+        cls,
+        templates_dir: str | Path | None = None,
+    ) -> tuple[str, ...]:
+        """List available template names from the templates directory."""
+        if templates_dir is None:
+            templates_dir = Path(__file__).parent.parent / "templates"
+        templates_dir = Path(templates_dir)
+
+        if not templates_dir.is_dir():
+            return ()
+        return tuple(
+            sorted(p.stem for p in templates_dir.glob("*.yaml"))
+        )
+
    def __len__(self) -> int:
        return len(self._agents)
--- a/backend/app/replay/init.py
+++ b/backend/app/replay/init.py
@@ -0,0 +1,3 @@
+"""Replay module -- conversation replay API and transformer."""
+
+from __future__ import annotations
--- a/backend/app/replay/api.py
+++ b/backend/app/replay/api.py
@@ -0,0 +1,125 @@
+"""Replay API router -- conversation listing and step-by-step replay."""
+
+from __future__ import annotations
+
+import re
+from typing import TYPE_CHECKING, Annotated
+
+from fastapi import APIRouter, Depends, HTTPException, Query, Request
+
+from app.api_utils import envelope
+from app.auth import require_admin_api_key
+
+_THREAD_ID_PATTERN = re.compile(r"^[a-zA-Z0-9\-_]{1,128}$")
+
+if TYPE_CHECKING:
+    from psycopg_pool import AsyncConnectionPool
+
+router = APIRouter(
+    prefix="/api/v1",
+    tags=["replay"],
+    dependencies=[Depends(require_admin_api_key)],
+)
+
+_COUNT_CONVERSATIONS_SQL = """
+SELECT COUNT(*) FROM conversations
+"""
+
+_LIST_CONVERSATIONS_SQL = """
+SELECT thread_id, created_at, last_activity, status, total_tokens, total_cost_usd
+FROM conversations
+ORDER BY last_activity DESC
+LIMIT %(limit)s OFFSET %(offset)s
+"""
+
+_GET_CHECKPOINTS_SQL = """
+SELECT thread_id, checkpoint_id, checkpoint, metadata
+FROM checkpoints
+WHERE thread_id = %(thread_id)s
+ORDER BY checkpoint_id ASC
+"""
+
+
+async def get_pool(request: Request) -> AsyncConnectionPool:
+    """Dependency: extract the shared pool from app state."""
+    return request.app.state.pool
+
+
+@router.get("/conversations")
+async def list_conversations(
+    request: Request,
+    page: Annotated[int, Query(ge=1)] = 1,
+    per_page: Annotated[int, Query(ge=1, le=100)] = 20,
+) -> dict:
+    """List conversations with pagination."""
+    pool = await get_pool(request)
+    offset = (page - 1) * per_page
+    async with pool.connection() as conn:
+        count_cursor = await conn.execute(_COUNT_CONVERSATIONS_SQL)
+        count_row = await count_cursor.fetchone()
+        total = count_row[0] if count_row else 0
+
+        cursor = await conn.execute(
+            _LIST_CONVERSATIONS_SQL,
+            {"limit": per_page, "offset": offset},
+        )
+        rows = await cursor.fetchall()
+
+    return envelope({
+        "conversations": [dict(row) for row in rows],
+        "total": total,
+        "page": page,
+        "per_page": per_page,
+    })
+
+
+@router.get("/replay/{thread_id}")
+async def get_replay(
+    thread_id: str,
+    request: Request,
+    page: Annotated[int, Query(ge=1)] = 1,
+    per_page: Annotated[int, Query(ge=1, le=100)] = 20,
+) -> dict:
+    """Return paginated replay steps for a conversation thread."""
+    from app.replay.transformer import transform_checkpoints
+
+    if not _THREAD_ID_PATTERN.match(thread_id):
+        raise HTTPException(status_code=400, detail="Invalid thread_id format")
+
+    pool = await get_pool(request)
+    async with pool.connection() as conn:
+        cursor = await conn.execute(_GET_CHECKPOINTS_SQL, {"thread_id": thread_id})
+        rows = await cursor.fetchall()
+
+    if not rows:
+        raise HTTPException(status_code=404, detail="Thread not found")
+
+    all_steps = transform_checkpoints([dict(row) for row in rows])
+    total_steps = len(all_steps)
+    start = (page - 1) * per_page
+    end = start + per_page
+    page_steps = all_steps[start:end]
+
+    data = {
+        "thread_id": thread_id,
+        "total_steps": total_steps,
+        "page": page,
+        "per_page": per_page,
+        "steps": [
+            {
+                "step": s.step,
+                "type": s.type.value,
+                "timestamp": s.timestamp,
+                "content": s.content,
+                "agent": s.agent,
+                "tool": s.tool,
+                "params": s.params,
+                "result": s.result,
+                "reasoning": s.reasoning,
+                "tokens": s.tokens,
+                "duration_ms": s.duration_ms,
+            }
+            for s in page_steps
+        ],
+    }
+    return envelope(data)
--- a/backend/app/replay/models.py
+++ b/backend/app/replay/models.py
@@ -0,0 +1,52 @@
+"""Value objects for conversation replay."""
+
+from __future__ import annotations
+
+from dataclasses import dataclass
+from enum import Enum
+
+
+class StepType(str, Enum):
+    """Types of steps in a conversation replay."""
+
+    user_message = "user_message"
+    supervisor_routing = "supervisor_routing"
+    tool_call = "tool_call"
+    tool_result = "tool_result"
+    agent_response = "agent_response"
+    interrupt = "interrupt"
+
+
+@dataclass(frozen=True)
+class ReplayStep:
+    """A single step in a conversation replay."""
+
+    step: int
+    type: StepType
+    timestamp: str
+    content: str = ""
+    agent: str | None = None
+    tool: str | None = None
+    params: dict | None = None
+    result: dict | None = None
+    reasoning: str | None = None
+    tokens: int | None = None
+    duration_ms: int | None = None
+
+    def __post_init__(self) -> None:
+        # Store params as a frozen copy to prevent mutation from the outside
+        if self.params is not None:
+            object.__setattr__(self, "params", dict(self.params))
+        if self.result is not None:
+            object.__setattr__(self, "result", dict(self.result))
+
+
+@dataclass(frozen=True)
+class ReplayPage:
+    """A paginated page of replay steps for a conversation thread."""
+
+    thread_id: str
+    total_steps: int
+    page: int
+    per_page: int
+    steps: tuple[ReplayStep, ...]
--- a/backend/app/replay/transformer.py
+++ b/backend/app/replay/transformer.py
@@ -0,0 +1,116 @@
+"""Transforms PostgresSaver checkpoint rows into ReplayStep list."""
+
+from __future__ import annotations
+
+import structlog
+
+from app.replay.models import ReplayStep, StepType
+
+logger = structlog.get_logger()
+
+_EMPTY_TIMESTAMP = "1970-01-01T00:00:00Z"
+
+
+def _extract_messages(row: dict) -> list[dict]:
+    """Safely extract messages list from a checkpoint row."""
+    checkpoint = row.get("checkpoint")
+    if not checkpoint or not isinstance(checkpoint, dict):
+        return []
+    channel_values = checkpoint.get("channel_values")
+    if not channel_values or not isinstance(channel_values, dict):
+        return []
+    messages = channel_values.get("messages")
+    if not messages or not isinstance(messages, list):
+        return []
+    return messages
+
+
+def _step_from_message(msg: dict, step_number: int) -> ReplayStep | None:
+    """Convert a single message dict to a ReplayStep. Returns None for unknown types."""
+    msg_type = msg.get("type", "")
+    timestamp = msg.get("created_at") or _EMPTY_TIMESTAMP
+    content = msg.get("content") or ""
+    if isinstance(content, list):
+        # LangChain may encode content as a list of parts
+        content = " ".join(
+            part.get("text", "") if isinstance(part, dict) else str(part)
+            for part in content
+        )
+
+    if msg_type == "human":
+        return ReplayStep(
+            step=step_number,
+            type=StepType.user_message,
+            timestamp=timestamp,
+            content=content,
+        )
+
+    if msg_type == "ai":
+        tool_calls = msg.get("tool_calls") or []
+        if tool_calls:
+            first = tool_calls[0]
+            return ReplayStep(
+                step=step_number,
+                type=StepType.tool_call,
+                timestamp=timestamp,
+                content=content,
+                tool=first.get("name"),
+                params=dict(first.get("args") or {}),
+            )
+        return ReplayStep(
+            step=step_number,
+            type=StepType.agent_response,
+            timestamp=timestamp,
+            content=content,
+            agent=msg.get("name"),
+        )
+
+    if msg_type == "tool":
+        raw = content
+        result: dict | None = None
+        try:
+            import json
+
+            result = json.loads(raw)
+        except (ValueError, TypeError):
+            result = {"raw": raw}
+        return ReplayStep(
+            step=step_number,
+            type=StepType.tool_result,
+            timestamp=timestamp,
+            tool=msg.get("name"),
+            result=result,
+        )
+
+    logger.debug("Skipping unknown message type: %s", msg_type)
+    return None
+
+
+def transform_checkpoints(rows: list[dict]) -> list[ReplayStep]:
+    """Transform a list of checkpoint rows into an ordered list of ReplaySteps.
+
+    Steps are numbered sequentially starting from 1 across all rows.
+    Unknown or malformed messages are silently skipped.
+    """
+    steps: list[ReplayStep] = []
+    step_number = 1
+
+    for row in rows:
+        try:
+            messages = _extract_messages(row)
+        except Exception:  # noqa: BLE001
+            logger.exception("Error extracting messages from checkpoint row")
+            continue
+
+        for msg in messages:
+            try:
+                step = _step_from_message(msg, step_number)
+            except Exception:  # noqa: BLE001
+                logger.exception("Error converting message to ReplayStep")
+                step = None
+
+            if step is not None:
+                steps.append(step)
+                step_number += 1
+
+    return steps
--- a/backend/app/safety.py
+++ b/backend/app/safety.py
@@ -0,0 +1,131 @@
+"""Safety policy for destructive-action confirmation rules.
+
+This module makes the confirmation rules explicit and auditable. Every tool
+call passes through ``requires_confirmation`` before execution to decide
+whether human-in-the-loop approval is needed.
+
+Policy summary
+--------------
+- ``read`` actions: execute immediately, no confirmation required.
+- ``write`` actions: require human approval via interrupt gate.
+- OpenAPI-imported endpoints: use ``needs_interrupt`` from classification.
+- If both the agent permission AND the endpoint classification agree
+  the action is read-only, it executes without confirmation.
+
+Multi-intent semantics
+----------------------
+When a user message contains multiple intents (e.g. "cancel my order and
+apply a refund"), the supervisor routes them sequentially. Each action is
+evaluated independently:
+- If a write action is blocked by an interrupt, subsequent actions in the
+  same message are paused until the interrupt is resolved.
+- Read actions that follow a blocked write are also paused (sequential,
+  not best-effort) to preserve causal ordering.
+- If an interrupt is rejected, the remaining actions are skipped and the
+  agent informs the user.
+
+MCP error taxonomy
+------------------
+Tool execution errors are classified into categories for retry decisions:
+
+- ``transient``: network timeouts, rate limits, 5xx -- retryable up to 3 times.
+- ``validation``: bad parameters, 4xx -- not retryable, report to user.
+- ``auth``: 401/403 -- not retryable, escalate.
+- ``unknown``: unclassified -- not retryable, log and escalate.
+"""
+
+from __future__ import annotations
+
+from dataclasses import dataclass
+from typing import Literal
+
+
+@dataclass(frozen=True)
+class ConfirmationPolicy:
+    """Result of evaluating whether an action needs confirmation."""
+
+    requires_confirmation: bool
+    reason: str
+
+
+def requires_confirmation(
+    *,
+    agent_permission: Literal["read", "write"],
+    needs_interrupt: bool | None = None,
+) -> ConfirmationPolicy:
+    """Determine whether an action requires human confirmation.
+
+    Parameters
+    ----------
+    agent_permission:
+        The permission level of the agent executing the action.
+    needs_interrupt:
+        Override from OpenAPI classification. When ``None``, the decision
+        is based solely on ``agent_permission``.
+    """
+    if needs_interrupt is not None:
+        if needs_interrupt:
+            return ConfirmationPolicy(
+                requires_confirmation=True,
+                reason="Endpoint classified as requiring human approval",
+            )
+        return ConfirmationPolicy(
+            requires_confirmation=False,
+            reason="Endpoint classified as safe (no interrupt needed)",
+        )
+
+    if agent_permission == "write":
+        return ConfirmationPolicy(
+            requires_confirmation=True,
+            reason="Write-permission agent actions require confirmation",
+        )
+
+    return ConfirmationPolicy(
+        requires_confirmation=False,
+        reason="Read-only agent actions execute immediately",
+    )
+
+
+# --- MCP Error Taxonomy ---
+
+
+MCP_ERROR_CATEGORY = Literal["transient", "validation", "auth", "unknown"]
+
+_TRANSIENT_STATUS_CODES = frozenset({408, 429, 500, 502, 503, 504})
+_AUTH_STATUS_CODES = frozenset({401, 403})
+_MAX_RETRIES = 3
+
+
+def classify_mcp_error(
+    *,
+    status_code: int | None = None,
+    error_message: str = "",
+) -> MCP_ERROR_CATEGORY:
+    """Classify an MCP tool error for retry decisions."""
+    if status_code is not None:
+        if status_code in _TRANSIENT_STATUS_CODES:
+            return "transient"
+        if status_code in _AUTH_STATUS_CODES:
+            return "auth"
+        if 400 <= status_code < 500:
+            return "validation"
+
+    lower_msg = error_message.lower()
+    if any(kw in lower_msg for kw in ("timeout", "timed out", "rate limit")):
+        return "transient"
+    if any(kw in lower_msg for kw in ("unauthorized", "forbidden")):
+        return "auth"
+    if any(kw in lower_msg for kw in ("invalid", "missing", "bad request")):
+        return "validation"
+
+    return "unknown"
+
+
+def is_retryable(category: MCP_ERROR_CATEGORY) -> bool:
+    """Return whether a given error category is retryable."""
+    return category == "transient"
+
+
+def max_retries() -> int:
+    """Maximum retry attempts for transient errors."""
+    return _MAX_RETRIES
--- a/backend/app/session_manager.py
+++ b/backend/app/session_manager.py
@@ -1,9 +1,18 @@
-"""Session TTL management with sliding window and interrupt extension."""
+"""Session TTL management with sliding window and interrupt extension.
+
+Provides both in-memory (SessionManager) and PostgreSQL-backed
+(PgSessionManager) implementations behind a common Protocol.
+"""

 from __future__ import annotations

 import time
 from dataclasses import dataclass
+from datetime import datetime, timezone
+from typing import TYPE_CHECKING, Protocol
+
+if TYPE_CHECKING:
+    from psycopg_pool import AsyncConnectionPool


@dataclass(frozen=True)
@@ -13,8 +22,19 @@ class SessionState:
    has_pending_interrupt: bool


+class SessionManagerProtocol(Protocol):
+    """Protocol for session TTL management."""
+
+    def touch(self, thread_id: str) -> SessionState: ...
+    def is_expired(self, thread_id: str) -> bool: ...
+    def extend_for_interrupt(self, thread_id: str) -> SessionState: ...
+    def resolve_interrupt(self, thread_id: str) -> SessionState: ...
+    def get_state(self, thread_id: str) -> SessionState | None: ...
+    def remove(self, thread_id: str) -> None: ...
+
+
 class SessionManager:
-    """Manages session TTL with sliding window and interrupt extensions.
+    """In-memory session manager for single-worker development.

    - Each message resets the TTL (sliding window).
    - A pending interrupt suspends expiration until resolved.
@@ -40,10 +60,8 @@ class SessionManager:
        state = self._sessions.get(thread_id)
        if state is None:
            return True
-
        if state.has_pending_interrupt:
            return False
-
        elapsed = time.time() - state.last_activity
        return elapsed > self._session_ttl

@@ -52,7 +70,6 @@ class SessionManager:
        existing = self._sessions.get(thread_id)
        if existing is None:
            return self.touch(thread_id)
-
        new_state = SessionState(
            thread_id=thread_id,
            last_activity=existing.last_activity,
@@ -76,3 +93,120 @@ class SessionManager:

    def remove(self, thread_id: str) -> None:
        self._sessions = {k: v for k, v in self._sessions.items() if k != thread_id}
+
+
+# Alias for explicit naming
+InMemorySessionManager = SessionManager
+
+
+class PgSessionManager:
+    """PostgreSQL-backed session manager for multi-worker production."""
+
+    def __init__(
+        self,
+        pool: AsyncConnectionPool,
+        session_ttl_seconds: int = 1800,
+    ) -> None:
+        self._pool = pool
+        self._session_ttl = session_ttl_seconds
+
+    def touch(self, thread_id: str) -> SessionState:
+        import asyncio
+
+        return asyncio.get_event_loop().run_until_complete(self._touch(thread_id))
+
+    async def _touch(self, thread_id: str) -> SessionState:
+        now = datetime.now(timezone.utc)
+        async with self._pool.connection() as conn:
+            await conn.execute(
+                """
+                INSERT INTO sessions (thread_id, last_activity, has_pending_interrupt)
+                VALUES (%(tid)s, %(now)s, FALSE)
+                ON CONFLICT (thread_id) DO UPDATE
+                    SET last_activity = %(now)s
+                """,
+                {"tid": thread_id, "now": now},
+            )
+        return SessionState(
+            thread_id=thread_id,
+            last_activity=now.timestamp(),
+            has_pending_interrupt=False,
+        )
+
+    def is_expired(self, thread_id: str) -> bool:
+        state = self.get_state(thread_id)
+        if state is None:
+            return True
+        if state.has_pending_interrupt:
+            return False
+        elapsed = time.time() - state.last_activity
+        return elapsed > self._session_ttl
+
+    def extend_for_interrupt(self, thread_id: str) -> SessionState:
+        import asyncio
+
+        return asyncio.get_event_loop().run_until_complete(
+            self._set_interrupt(thread_id, True)
+        )
+
+    def resolve_interrupt(self, thread_id: str) -> SessionState:
+        import asyncio
+
+        return asyncio.get_event_loop().run_until_complete(
+            self._set_interrupt(thread_id, False)
+        )
+
+    async def _set_interrupt(
+        self, thread_id: str, has_interrupt: bool
+    ) -> SessionState:
+        now = datetime.now(timezone.utc)
+        async with self._pool.connection() as conn:
+            await conn.execute(
+                """
+                INSERT INTO sessions (thread_id, last_activity, has_pending_interrupt)
+                VALUES (%(tid)s, %(now)s, %(interrupt)s)
+                ON CONFLICT (thread_id) DO UPDATE
+                    SET last_activity = %(now)s,
+                        has_pending_interrupt = %(interrupt)s
+                """,
+                {"tid": thread_id, "now": now, "interrupt": has_interrupt},
+            )
+        return SessionState(
+            thread_id=thread_id,
+            last_activity=now.timestamp(),
+            has_pending_interrupt=has_interrupt,
+        )
+
+    def get_state(self, thread_id: str) -> SessionState | None:
+        import asyncio
+
+        return asyncio.get_event_loop().run_until_complete(
+            self._get_state(thread_id)
+        )
+
+    async def _get_state(self, thread_id: str) -> SessionState | None:
+        async with self._pool.connection() as conn:
+            cursor = await conn.execute(
+                "SELECT last_activity, has_pending_interrupt FROM sessions WHERE thread_id = %(tid)s",
+                {"tid": thread_id},
+            )
+            row = await cursor.fetchone()
+        if row is None:
+            return None
+        return SessionState(
+            thread_id=thread_id,
+            last_activity=row["last_activity"].timestamp(),
+            has_pending_interrupt=row["has_pending_interrupt"],
+        )
+
+    def remove(self, thread_id: str) -> None:
+        import asyncio
+
+        asyncio.get_event_loop().run_until_complete(self._remove(thread_id))
+
+    async def _remove(self, thread_id: str) -> None:
+        async with self._pool.connection() as conn:
+            await conn.execute(
+                "DELETE FROM sessions WHERE thread_id = %(tid)s",
+                {"tid": thread_id},
+            )
--- a/backend/app/tools/init.py
+++ b/backend/app/tools/init.py
@@ -0,0 +1,3 @@
+"""Tools package for smart-support backend."""
+
+from __future__ import annotations
--- a/backend/app/tools/error_handler.py
+++ b/backend/app/tools/error_handler.py
@@ -0,0 +1,72 @@
+"""Error classification and retry logic for tool calls."""
+
+from __future__ import annotations
+
+import asyncio
+from enum import Enum
+from typing import TYPE_CHECKING, Any
+
+if TYPE_CHECKING:
+    from collections.abc import Callable
+
+import httpx
+
+
+class ErrorCategory(Enum):
+    """Categories for error classification to guide retry decisions."""
+
+    RETRYABLE = "retryable"
+    NON_RETRYABLE = "non_retryable"
+    AUTH_FAILURE = "auth_failure"
+    TIMEOUT = "timeout"
+    NETWORK = "network"
+
+
+def classify_error(exc: Exception) -> ErrorCategory:
+    """Classify an exception into an ErrorCategory.
+
+    Rules:
+    - httpx.TimeoutException -> TIMEOUT
+    - httpx.ConnectError -> NETWORK
+    - httpx.HTTPStatusError 401/403 -> AUTH_FAILURE
+    - httpx.HTTPStatusError 429/500/502/503 -> RETRYABLE
+    - anything else -> NON_RETRYABLE
+    """
+    if isinstance(exc, httpx.TimeoutException):
+        return ErrorCategory.TIMEOUT
+    if isinstance(exc, httpx.ConnectError):
+        return ErrorCategory.NETWORK
+    if isinstance(exc, httpx.HTTPStatusError):
+        code = exc.response.status_code
+        if code in (401, 403):
+            return ErrorCategory.AUTH_FAILURE
+        if code in (429, 500, 502, 503):
+            return ErrorCategory.RETRYABLE
+        return ErrorCategory.NON_RETRYABLE
+    return ErrorCategory.NON_RETRYABLE
+
+
+async def with_retry(
+    fn: Callable[..., Any],
+    max_retries: int = 3,
+    base_delay: float = 1.0,
+) -> Any:
+    """Execute an async callable with exponential backoff for RETRYABLE errors.
+
+    Only ErrorCategory.RETRYABLE errors trigger retries. All other error
+    categories raise immediately after the first attempt.
+    """
+    last_exc: Exception | None = None
+    for attempt in range(1, max_retries + 1):
+        try:
+            return await fn()
+        except Exception as exc:
+            category = classify_error(exc)
+            if category != ErrorCategory.RETRYABLE:
+                raise
+            last_exc = exc
+            if attempt < max_retries:
+                delay = base_delay * (2 ** (attempt - 1))
+                await asyncio.sleep(delay)
+
+    raise last_exc  # type: ignore[misc]
--- a/backend/app/ws_context.py
+++ b/backend/app/ws_context.py
@@ -0,0 +1,30 @@
+"""WebSocketContext -- bundles all dependencies needed by dispatch_message."""
+
+from __future__ import annotations
+
+from dataclasses import dataclass
+from typing import TYPE_CHECKING, Any
+
+if TYPE_CHECKING:
+    from app.analytics.event_recorder import AnalyticsRecorder
+    from app.callbacks import TokenUsageCallbackHandler
+    from app.conversation_tracker import ConversationTrackerProtocol
+    from app.graph_context import GraphContext
+    from app.interrupt_manager import InterruptManager
+    from app.session_manager import SessionManager
+
+
+@dataclass(frozen=True)
+class WebSocketContext:
+    """All dependencies required for WebSocket message processing.
+
+    Replaces the previous 9-parameter function signature in dispatch_message.
+    """
+
+    graph_ctx: GraphContext
+    session_manager: SessionManager
+    callback_handler: TokenUsageCallbackHandler
+    interrupt_manager: InterruptManager | None = None
+    analytics_recorder: AnalyticsRecorder | None = None
+    conversation_tracker: ConversationTrackerProtocol | None = None
+    pool: Any = None
--- a/backend/app/ws_handler.py
+++ b/backend/app/ws_handler.py
@@ -3,47 +3,98 @@
 from __future__ import annotations

 import json
-import logging
 import re
-from typing import TYPE_CHECKING, Any
+import time
+from collections import defaultdict
+from typing import TYPE_CHECKING

 from langchain_core.messages import HumanMessage
 from langgraph.types import Command

 if TYPE_CHECKING:
    from fastapi import WebSocket
-    from langgraph.graph.state import CompiledStateGraph

    from app.callbacks import TokenUsageCallbackHandler
+    from app.graph_context import GraphContext
+    from app.interrupt_manager import InterruptManager
    from app.session_manager import SessionManager
+    from app.ws_context import WebSocketContext

-logger = logging.getLogger(__name__)
+import structlog
+
+logger = structlog.get_logger()

 MAX_MESSAGE_SIZE = 32_768  # 32 KB
-MAX_CONTENT_LENGTH = 8_000  # characters
+MAX_CONTENT_LENGTH = 10_000  # characters
 THREAD_ID_PATTERN = re.compile(r"^[a-zA-Z0-9\-_]{1,128}$")

+# Rate limiting: max 10 messages per 10-second window, per thread
+_RATE_LIMIT_MAX = 10
+_RATE_LIMIT_WINDOW = 10.0
+_MAX_TRACKED_THREADS = 10_000
+_thread_timestamps: dict[str, list[float]] = defaultdict(list)
+
+
+def _evict_stale_threads(cutoff: float) -> None:
+    """Remove thread entries with no recent timestamps to prevent memory leak."""
+    stale = [tid for tid, ts in _thread_timestamps.items() if not ts or ts[-1] < cutoff]
+    for tid in stale:
+        del _thread_timestamps[tid]
+

 async def handle_user_message(
    ws: WebSocket,
-    graph: CompiledStateGraph,
+    ctx: GraphContext,
    session_manager: SessionManager,
    callback_handler: TokenUsageCallbackHandler,
    thread_id: str,
    content: str,
+    interrupt_manager: InterruptManager | None = None,
 ) -> None:
    """Process a user message through the graph and stream results back."""
-    if session_manager.is_expired(thread_id):
+    existing = session_manager.get_state(thread_id)
+    if existing is not None and session_manager.is_expired(thread_id):
        msg = "Session expired. Please start a new conversation."
        await _send_json(ws, {"type": "error", "message": msg})
        return

    session_manager.touch(thread_id)
+
+    classification = await ctx.classify_intent(content)
+    if classification is not None:
+        logger.info(
+            "Intent classification for thread %s: ambiguous=%s, intents=%s",
+            thread_id,
+            classification.is_ambiguous,
+            [i.agent_name for i in classification.intents],
+        )
+
+        if classification.is_ambiguous and classification.clarification_question:
+            await _send_json(
+                ws,
+                {
+                    "type": "clarification",
+                    "thread_id": thread_id,
+                    "message": classification.clarification_question,
+                },
+            )
+            await _send_json(ws, {"type": "message_complete", "thread_id": thread_id})
+            return
+
    config = {"configurable": {"thread_id": thread_id}, "callbacks": [callback_handler]}
+
+    if classification and len(classification.intents) > 1:
+        agent_names = [i.agent_name for i in classification.intents]
+        hint = (
+            f"\n[System: This request involves multiple actions. "
+            f"Execute in order: {', '.join(agent_names)}]"
+        )
+        input_msg = {"messages": [HumanMessage(content=content + hint)]}
+    else:
        input_msg = {"messages": [HumanMessage(content=content)]}

    try:
-        async for chunk in graph.astream(input_msg, config=config, stream_mode="messages"):
+        async for chunk in ctx.graph.astream(input_msg, config=config, stream_mode="messages"):
            msg_chunk, metadata = chunk
            node = metadata.get("langgraph_node", "")

@@ -68,10 +119,18 @@ async def handle_user_message(
                    },
                )

-        state = await graph.aget_state(config)
+        state = await ctx.graph.aget_state(config)
        if _has_interrupt(state):
            interrupt_data = _extract_interrupt(state)
            session_manager.extend_for_interrupt(thread_id)
+
+            if interrupt_manager is not None:
+                interrupt_manager.register(
+                    thread_id=thread_id,
+                    action=interrupt_data.get("action", "unknown"),
+                    params=interrupt_data.get("params", {}),
+                )
+
            await _send_json(
                ws,
                {
@@ -91,20 +150,32 @@ async def handle_user_message(

 async def handle_interrupt_response(
    ws: WebSocket,
-    graph: CompiledStateGraph,
+    ctx: GraphContext,
    session_manager: SessionManager,
    callback_handler: TokenUsageCallbackHandler,
    thread_id: str,
    approved: bool,
+    interrupt_manager: InterruptManager | None = None,
 ) -> None:
    """Resume graph execution after interrupt approval/rejection."""
+    if interrupt_manager is not None:
+        status = interrupt_manager.check_status(thread_id)
+        if status is not None and status.is_expired:
+            retry_prompt = interrupt_manager.generate_retry_prompt(status.record)
+            interrupt_manager.resolve(thread_id)
+            session_manager.resolve_interrupt(thread_id)
+            await _send_json(ws, retry_prompt)
+            return
+
+        interrupt_manager.resolve(thread_id)
+
    session_manager.resolve_interrupt(thread_id)
    session_manager.touch(thread_id)

    config = {"configurable": {"thread_id": thread_id}, "callbacks": [callback_handler]}

    try:
-        async for chunk in graph.astream(
+        async for chunk in ctx.graph.astream(
            Command(resume=approved),
            config=config,
            stream_mode="messages",
@@ -132,9 +203,7 @@ async def handle_interrupt_response(

 async def dispatch_message(
    ws: WebSocket,
-    graph: CompiledStateGraph,
-    session_manager: SessionManager,
-    callback_handler: TokenUsageCallbackHandler,
+    ctx: WebSocketContext,
    raw_data: str,
 ) -> None:
    """Parse and route an incoming WebSocket message."""
@@ -144,10 +213,14 @@ async def dispatch_message(

    try:
        data = json.loads(raw_data)
-    except json.JSONDecodeError:
+    except (json.JSONDecodeError, ValueError):
        await _send_json(ws, {"type": "error", "message": "Invalid JSON"})
        return

+    if not isinstance(data, dict):
+        await _send_json(ws, {"type": "error", "message": "Invalid JSON: expected object"})
+        return
+
    msg_type = data.get("type")
    thread_id = data.get("thread_id", "")

@@ -161,24 +234,81 @@ async def dispatch_message(

    if msg_type == "message":
        content = data.get("content", "")
-        if not content:
+        if not content or not content.strip():
            await _send_json(ws, {"type": "error", "message": "Missing message content"})
            return
        if len(content) > MAX_CONTENT_LENGTH:
            await _send_json(ws, {"type": "error", "message": "Message content too long"})
            return
-        await handle_user_message(ws, graph, session_manager, callback_handler, thread_id, content)
+
+        # Rate limiting check (per-thread, with bounded memory)
+        now = time.time()
+        cutoff = now - _RATE_LIMIT_WINDOW
+        if len(_thread_timestamps) > _MAX_TRACKED_THREADS:
+            _evict_stale_threads(cutoff)
+        recent = [t for t in _thread_timestamps[thread_id] if t >= cutoff]
+        if len(recent) >= _RATE_LIMIT_MAX:
+            await _send_json(ws, {"type": "error", "message": "Rate limit exceeded"})
+            return
+        _thread_timestamps[thread_id] = [*recent, now]
+
+        await handle_user_message(
+            ws, ctx.graph_ctx, ctx.session_manager, ctx.callback_handler,
+            thread_id, content,
+            interrupt_manager=ctx.interrupt_manager,
+        )
+        await _fire_and_forget_tracking(
+            thread_id=thread_id,
+            pool=ctx.pool,
+            analytics_recorder=ctx.analytics_recorder,
+            conversation_tracker=ctx.conversation_tracker,
+            agent_name=None,
+            tokens=0,
+            cost=0.0,
+        )

    elif msg_type == "interrupt_response":
        approved = data.get("approved", False)
        await handle_interrupt_response(
-            ws, graph, session_manager, callback_handler, thread_id, approved
+            ws, ctx.graph_ctx, ctx.session_manager, ctx.callback_handler,
+            thread_id, approved,
+            interrupt_manager=ctx.interrupt_manager,
        )

    else:
        await _send_json(ws, {"type": "error", "message": "Unknown message type"})


+async def _fire_and_forget_tracking(
+    thread_id: str,
+    pool: object,
+    analytics_recorder: object | None,
+    conversation_tracker: object | None,
+    agent_name: str | None,
+    tokens: int,
+    cost: float,
+) -> None:
+    """Fire-and-forget analytics/tracking; failures must NOT break chat."""
+    try:
+        if conversation_tracker is not None and pool is not None:
+            await conversation_tracker.ensure_conversation(pool, thread_id)
+            await conversation_tracker.record_turn(pool, thread_id, agent_name, tokens, cost)
+    except Exception:
+        logger.exception("Conversation tracker error for thread %s (suppressed)", thread_id)
+
+    try:
+        if analytics_recorder is not None:
+            await analytics_recorder.record(
+                thread_id=thread_id,
+                event_type="message",
+                agent_name=agent_name,
+                tokens_used=tokens,
+                cost_usd=cost,
+            )
+    except Exception:
+        logger.exception("Analytics recorder error for thread %s (suppressed)", thread_id)
+
+
 def _has_interrupt(state: Any) -> bool:
    """Check if the graph state has a pending interrupt."""
    tasks = getattr(state, "tasks", ())
--- a/backend/fixtures/demo_data.py
+++ b/backend/fixtures/demo_data.py
@@ -0,0 +1,153 @@
+"""Seed script -- inserts sample conversations and analytics events for demo purposes.
+
+Usage:
+    cd backend
+    python fixtures/demo_data.py
+"""
+
+from __future__ import annotations
+
+import asyncio
+import os
+import sys
+from datetime import datetime, timedelta, timezone
+from pathlib import Path
+
+sys.path.insert(0, str(Path(__file__).parent.parent))
+
+import psycopg
+
+DATABASE_URL = os.environ.get(
+    "DATABASE_URL",
+    "postgresql://smart_support:dev_password@localhost:5432/smart_support",
+)
+
+SAMPLE_CONVERSATIONS = [
+    {
+        "thread_id": "demo-thread-001",
+        "agents_used": ["order_agent"],
+        "turn_count": 3,
+        "total_tokens": 1250,
+        "total_cost_usd": 0.00375,
+        "resolution_type": "resolved",
+        "minutes_ago": 5,
+    },
+    {
+        "thread_id": "demo-thread-002",
+        "agents_used": ["order_agent", "refund_agent"],
+        "turn_count": 6,
+        "total_tokens": 3200,
+        "total_cost_usd": 0.0096,
+        "resolution_type": "resolved",
+        "minutes_ago": 30,
+    },
+    {
+        "thread_id": "demo-thread-003",
+        "agents_used": ["general_agent"],
+        "turn_count": 2,
+        "total_tokens": 800,
+        "total_cost_usd": 0.0024,
+        "resolution_type": None,
+        "minutes_ago": 60,
+    },
+    {
+        "thread_id": "demo-thread-004",
+        "agents_used": ["order_agent", "general_agent"],
+        "turn_count": 8,
+        "total_tokens": 4500,
+        "total_cost_usd": 0.0135,
+        "resolution_type": "escalated",
+        "minutes_ago": 120,
+    },
+    {
+        "thread_id": "demo-thread-005",
+        "agents_used": ["refund_agent"],
+        "turn_count": 4,
+        "total_tokens": 2100,
+        "total_cost_usd": 0.0063,
+        "resolution_type": "resolved",
+        "minutes_ago": 240,
+    },
+]
+
+SAMPLE_EVENTS = [
+    {"thread_id": "demo-thread-001", "event_type": "message", "agent_name": "order_agent", "tokens_used": 400, "cost_usd": 0.0012, "success": True},
+    {"thread_id": "demo-thread-001", "event_type": "tool_call", "agent_name": "order_agent", "tool_name": "get_order_status", "tokens_used": 0, "cost_usd": 0.0, "success": True},
+    {"thread_id": "demo-thread-002", "event_type": "message", "agent_name": "order_agent", "tokens_used": 1600, "cost_usd": 0.0048, "success": True},
+    {"thread_id": "demo-thread-002", "event_type": "message", "agent_name": "refund_agent", "tokens_used": 1600, "cost_usd": 0.0048, "success": True},
+    {"thread_id": "demo-thread-002", "event_type": "tool_call", "agent_name": "refund_agent", "tool_name": "process_refund", "tokens_used": 0, "cost_usd": 0.0, "success": True},
+    {"thread_id": "demo-thread-003", "event_type": "message", "agent_name": "general_agent", "tokens_used": 800, "cost_usd": 0.0024, "success": True},
+    {"thread_id": "demo-thread-004", "event_type": "message", "agent_name": "order_agent", "tokens_used": 2000, "cost_usd": 0.006, "success": True},
+    {"thread_id": "demo-thread-004", "event_type": "escalation", "agent_name": "general_agent", "tokens_used": 2500, "cost_usd": 0.0075, "success": False},
+    {"thread_id": "demo-thread-005", "event_type": "message", "agent_name": "refund_agent", "tokens_used": 2100, "cost_usd": 0.0063, "success": True},
+]
+
+_INSERT_CONVERSATION = """
+INSERT INTO conversations
+    (thread_id, started_at, last_activity, turn_count, agents_used,
+     total_tokens, total_cost_usd, resolution_type, ended_at)
+VALUES
+    (%(thread_id)s, %(started_at)s, %(last_activity)s, %(turn_count)s,
+     %(agents_used)s, %(total_tokens)s, %(total_cost_usd)s,
+     %(resolution_type)s, %(ended_at)s)
+ON CONFLICT (thread_id) DO NOTHING
+"""
+
+_INSERT_EVENT = """
+INSERT INTO analytics_events
+    (thread_id, event_type, agent_name, tool_name, tokens_used, cost_usd, success)
+VALUES
+    (%(thread_id)s, %(event_type)s, %(agent_name)s, %(tool_name)s,
+     %(tokens_used)s, %(cost_usd)s, %(success)s)
+"""
+
+
+async def seed() -> None:
+    now = datetime.now(tz=timezone.utc)
+
+    async with await psycopg.AsyncConnection.connect(DATABASE_URL) as conn:
+        print("Seeding conversations...")
+        for conv in SAMPLE_CONVERSATIONS:
+            started_at = now - timedelta(minutes=conv["minutes_ago"])
+            last_activity = started_at + timedelta(minutes=conv["turn_count"] * 2)
+            ended_at = last_activity if conv["resolution_type"] else None
+
+            await conn.execute(
+                _INSERT_CONVERSATION,
+                {
+                    "thread_id": conv["thread_id"],
+                    "started_at": started_at,
+                    "last_activity": last_activity,
+                    "turn_count": conv["turn_count"],
+                    "agents_used": conv["agents_used"],
+                    "total_tokens": conv["total_tokens"],
+                    "total_cost_usd": conv["total_cost_usd"],
+                    "resolution_type": conv["resolution_type"],
+                    "ended_at": ended_at,
+                },
+            )
+            print(f"  Inserted conversation {conv['thread_id']}")
+
+        print("Seeding analytics events...")
+        for event in SAMPLE_EVENTS:
+            await conn.execute(
+                _INSERT_EVENT,
+                {
+                    "thread_id": event["thread_id"],
+                    "event_type": event["event_type"],
+                    "agent_name": event.get("agent_name"),
+                    "tool_name": event.get("tool_name"),
+                    "tokens_used": event.get("tokens_used", 0),
+                    "cost_usd": event.get("cost_usd", 0.0),
+                    "success": event.get("success"),
+                },
+            )
+            print(f"  Inserted event {event['event_type']} for {event['thread_id']}")
+
+        await conn.commit()
+
+    print("Done. Demo data seeded successfully.")
+
+
+if __name__ == "__main__":
+    asyncio.run(seed())
--- a/backend/fixtures/sample_openapi.yaml
+++ b/backend/fixtures/sample_openapi.yaml
@@ -0,0 +1,238 @@
+openapi: "3.0.3"
+info:
+  title: "E-Commerce API"
+  description: "Sample e-commerce API for Smart Support demo."
+  version: "1.0.0"
+
+servers:
+  - url: "https://api.example-shop.com/v1"
+    description: "Production server"
+
+paths:
+  /orders/{order_id}:
+    get:
+      operationId: getOrder
+      summary: "Get order details"
+      description: "Retrieve the full details of a specific order."
+      parameters:
+        - name: order_id
+          in: path
+          required: true
+          schema:
+            type: string
+      responses:
+        "200":
+          description: "Order details"
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/Order"
+
+  /orders/{order_id}/cancel:
+    post:
+      operationId: cancelOrder
+      summary: "Cancel an order"
+      description: "Cancel an order that has not yet been shipped."
+      parameters:
+        - name: order_id
+          in: path
+          required: true
+          schema:
+            type: string
+      requestBody:
+        required: true
+        content:
+          application/json:
+            schema:
+              type: object
+              properties:
+                reason:
+                  type: string
+      responses:
+        "200":
+          description: "Order cancelled"
+        "400":
+          description: "Order cannot be cancelled (already shipped)"
+
+  /orders/{order_id}/refund:
+    post:
+      operationId: refundOrder
+      summary: "Request a refund"
+      description: "Submit a refund request for a completed order."
+      parameters:
+        - name: order_id
+          in: path
+          required: true
+          schema:
+            type: string
+      requestBody:
+        required: true
+        content:
+          application/json:
+            schema:
+              type: object
+              properties:
+                amount:
+                  type: number
+                  description: "Refund amount in USD. Leave null for full refund."
+                reason:
+                  type: string
+      responses:
+        "200":
+          description: "Refund submitted"
+        "400":
+          description: "Invalid refund request"
+
+  /customers/{customer_id}:
+    get:
+      operationId: getCustomer
+      summary: "Get customer profile"
+      description: "Retrieve customer profile and account information."
+      parameters:
+        - name: customer_id
+          in: path
+          required: true
+          schema:
+            type: string
+      responses:
+        "200":
+          description: "Customer profile"
+          content:
+            application/json:
+              schema:
+                $ref: "#/components/schemas/Customer"
+
+  /customers/{customer_id}/orders:
+    get:
+      operationId: listCustomerOrders
+      summary: "List customer orders"
+      description: "Get a paginated list of orders for a customer."
+      parameters:
+        - name: customer_id
+          in: path
+          required: true
+          schema:
+            type: string
+        - name: page
+          in: query
+          schema:
+            type: integer
+            default: 1
+        - name: per_page
+          in: query
+          schema:
+            type: integer
+            default: 20
+      responses:
+        "200":
+          description: "List of orders"
+
+  /products/{product_id}:
+    get:
+      operationId: getProduct
+      summary: "Get product details"
+      description: "Retrieve product information including inventory status."
+      parameters:
+        - name: product_id
+          in: path
+          required: true
+          schema:
+            type: string
+      responses:
+        "200":
+          description: "Product details"
+
+  /support/tickets:
+    post:
+      operationId: createSupportTicket
+      summary: "Create support ticket"
+      description: "Open a new support ticket for a customer issue."
+      requestBody:
+        required: true
+        content:
+          application/json:
+            schema:
+              $ref: "#/components/schemas/CreateTicketRequest"
+      responses:
+        "201":
+          description: "Ticket created"
+
+  /support/tickets/{ticket_id}:
+    get:
+      operationId: getSupportTicket
+      summary: "Get support ticket"
+      description: "Retrieve a support ticket and its conversation history."
+      parameters:
+        - name: ticket_id
+          in: path
+          required: true
+          schema:
+            type: string
+      responses:
+        "200":
+          description: "Ticket details"
+
+components:
+  schemas:
+    Order:
+      type: object
+      properties:
+        order_id:
+          type: string
+        customer_id:
+          type: string
+        status:
+          type: string
+          enum: [pending, processing, shipped, delivered, cancelled, refunded]
+        items:
+          type: array
+          items:
+            $ref: "#/components/schemas/OrderItem"
+        total_usd:
+          type: number
+        created_at:
+          type: string
+          format: date-time
+
+    OrderItem:
+      type: object
+      properties:
+        product_id:
+          type: string
+        name:
+          type: string
+        quantity:
+          type: integer
+        unit_price_usd:
+          type: number
+
+    Customer:
+      type: object
+      properties:
+        customer_id:
+          type: string
+        email:
+          type: string
+        name:
+          type: string
+        tier:
+          type: string
+          enum: [standard, premium, vip]
+        created_at:
+          type: string
+          format: date-time
+
+    CreateTicketRequest:
+      type: object
+      required: [customer_id, subject, description]
+      properties:
+        customer_id:
+          type: string
+        subject:
+          type: string
+        description:
+          type: string
+        priority:
+          type: string
+          enum: [low, medium, high, urgent]
+          default: medium
--- a/backend/pyproject.toml
+++ b/backend/pyproject.toml
@@ -6,18 +6,23 @@ requires-python = ">=3.11"
 dependencies = [
    "fastapi>=0.115,<1.0",
    "uvicorn[standard]>=0.34,<1.0",
-    "langgraph>=0.4,<1.0",
-    "langgraph-supervisor>=0.0.12,<1.0",
+    "langgraph>=1.0,<2.0",
+    "langgraph-supervisor>=0.0.30,<1.0",
    "langgraph-checkpoint-postgres>=3.0,<4.0",
-    "langchain-core>=0.3,<1.0",
-    "langchain-anthropic>=0.3,<2.0",
-    "langchain-openai>=0.3,<1.0",
+    "langchain>=1.0,<2.0",
+    "langchain-core>=1.0,<2.0",
+    "langchain-anthropic>=1.0,<2.0",
+    "langchain-openai>=1.0,<2.0",
    "langchain-google-genai>=2.1,<3.0",
    "psycopg[binary,pool]>=3.2,<4.0",
    "pydantic>=2.10,<3.0",
    "pydantic-settings>=2.7,<3.0",
    "pyyaml>=6.0,<7.0",
    "python-dotenv>=1.0,<2.0",
+    "httpx>=0.28,<1.0",
+    "openapi-spec-validator>=0.7,<1.0",
+    "alembic>=1.13,<2.0",
+    "structlog>=24.0,<26.0",
 ]

 [project.optional-dependencies]
@@ -27,6 +32,7 @@ dev = [
    "pytest-cov>=6.0,<7.0",
    "httpx>=0.28,<1.0",
    "ruff>=0.9,<1.0",
+    "pytest-httpx>=0.35,<1.0",
 ]

 [build-system]
--- a/backend/templates/e-commerce.yaml
+++ b/backend/templates/e-commerce.yaml
@@ -0,0 +1,42 @@
+agents:
+  - name: order_lookup
+    description: "Looks up order status and tracking information. Use for queries about order status, shipping, and delivery."
+    permission: read
+    personality:
+      tone: "friendly and informative"
+      greeting: "I can help you check your order status!"
+      escalation_message: "Let me connect you with our support team for more details."
+    tools:
+      - get_order_status
+      - get_tracking_info
+
+  - name: order_actions
+    description: "Performs order modifications like cancellations. Use when the customer wants to cancel, modify, or change an order."
+    permission: write
+    personality:
+      tone: "careful and reassuring"
+      greeting: "I can help you with order changes."
+      escalation_message: "I'll connect you with a specialist who can assist further."
+    tools:
+      - cancel_order
+
+  - name: discount
+    description: "Applies discounts and generates coupon codes. Use when the customer asks for discounts, promotions, or coupon codes."
+    permission: write
+    personality:
+      tone: "generous and accommodating"
+      greeting: "I can help you with discounts and coupons!"
+      escalation_message: "Let me connect you with our promotions team."
+    tools:
+      - apply_discount
+      - generate_coupon
+
+  - name: fallback
+    description: "Handles general questions, unclear requests, and conversations that don't match other agents."
+    permission: read
+    personality:
+      tone: "professional and helpful"
+      greeting: "Hello! How can I help you today?"
+      escalation_message: "Let me connect you with a human agent who can better assist you."
+    tools:
+      - fallback_respond
--- a/backend/templates/fintech.yaml
+++ b/backend/templates/fintech.yaml
@@ -0,0 +1,31 @@
+agents:
+  - name: transaction_lookup
+    description: "Looks up transaction history, balances, and payment details. Use for queries about transactions and account activity."
+    permission: read
+    personality:
+      tone: "precise and trustworthy"
+      greeting: "I can help you review your transaction history."
+      escalation_message: "Let me connect you with our financial support team."
+    tools:
+      - get_transaction_history
+
+  - name: dispute_handler
+    description: "Files and manages transaction disputes. Use when the customer wants to dispute a charge or check dispute status."
+    permission: write
+    personality:
+      tone: "empathetic and thorough"
+      greeting: "I can help you with transaction disputes."
+      escalation_message: "Let me connect you with our disputes resolution team."
+    tools:
+      - file_dispute
+      - check_dispute_status
+
+  - name: fallback
+    description: "Handles general questions, unclear requests, and conversations that don't match other agents."
+    permission: read
+    personality:
+      tone: "professional and helpful"
+      greeting: "Hello! How can I help you today?"
+      escalation_message: "Let me connect you with a human agent who can better assist you."
+    tools:
+      - fallback_respond
--- a/backend/templates/saas.yaml
+++ b/backend/templates/saas.yaml
@@ -0,0 +1,31 @@
+agents:
+  - name: account_lookup
+    description: "Looks up account status, subscription details, and billing history. Use for queries about account information."
+    permission: read
+    personality:
+      tone: "professional and clear"
+      greeting: "I can help you with your account information!"
+      escalation_message: "Let me connect you with our account support team."
+    tools:
+      - get_account_status
+
+  - name: subscription_management
+    description: "Manages subscription changes like plan upgrades, downgrades, and cancellations. Use when the customer wants to change their subscription."
+    permission: write
+    personality:
+      tone: "helpful and consultative"
+      greeting: "I can help you manage your subscription."
+      escalation_message: "Let me connect you with our billing specialist."
+    tools:
+      - change_plan
+      - cancel_subscription
+
+  - name: fallback
+    description: "Handles general questions, unclear requests, and conversations that don't match other agents."
+    permission: read
+    personality:
+      tone: "professional and helpful"
+      greeting: "Hello! How can I help you today?"
+      escalation_message: "Let me connect you with a human agent who can better assist you."
+    tools:
+      - fallback_respond
--- a/backend/tests/conftest.py
+++ b/backend/tests/conftest.py
@@ -15,6 +15,16 @@ if TYPE_CHECKING:
    from pathlib import Path


+@pytest.fixture(autouse=True)
+def clear_rate_limit_state() -> None:
+    """Clear module-level rate limit state between tests to prevent leakage."""
+    import app.ws_handler as ws_handler
+
+    ws_handler._thread_timestamps.clear()
+    yield
+    ws_handler._thread_timestamps.clear()
+
+
@pytest.fixture
 def test_settings() -> Settings:
    return Settings(
--- a/backend/tests/e2e/conftest.py
+++ b/backend/tests/e2e/conftest.py
@@ -0,0 +1,230 @@
+"""E2E test fixtures -- full FastAPI app with mocked LLM and database."""
+
+from __future__ import annotations
+
+import asyncio
+from contextlib import asynccontextmanager
+from typing import Any
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+from fastapi import FastAPI, WebSocket, WebSocketDisconnect
+from httpx import ASGITransport, AsyncClient
+
+from app.analytics.api import router as analytics_router
+from app.callbacks import TokenUsageCallbackHandler
+from app.graph_context import GraphContext
+from app.interrupt_manager import InterruptManager
+from app.openapi.review_api import _job_store, router as openapi_router
+from app.replay.api import router as replay_router
+from app.session_manager import SessionManager
+from app.ws_context import WebSocketContext
+from app.ws_handler import dispatch_message
+
+
+# ---------------------------------------------------------------------------
+# Graph helpers -- simulate LangGraph streaming behaviour
+# ---------------------------------------------------------------------------
+
+
+class AsyncIterHelper:
+    """Make a list behave as an async iterator."""
+
+    def __init__(self, items: list) -> None:
+        self._items = list(items)
+
+    def __aiter__(self):
+        return self
+
+    async def __anext__(self):
+        if not self._items:
+            raise StopAsyncIteration
+        return self._items.pop(0)
+
+
+def make_chunk(content: str, node: str = "order_lookup") -> tuple:
+    c = MagicMock()
+    c.content = content
+    c.tool_calls = []
+    return (c, {"langgraph_node": node})
+
+
+def make_tool_chunk(name: str, args: dict, node: str = "order_lookup") -> tuple:
+    c = MagicMock()
+    c.content = ""
+    c.tool_calls = [{"name": name, "args": args}]
+    return (c, {"langgraph_node": node})
+
+
+def make_state(*, interrupt: bool = False, data: dict | None = None) -> Any:
+    s = MagicMock()
+    if interrupt:
+        obj = MagicMock()
+        obj.value = data or {"action": "cancel_order", "order_id": "1042"}
+        t = MagicMock()
+        t.interrupts = (obj,)
+        s.tasks = (t,)
+    else:
+        s.tasks = ()
+    return s
+
+
+def make_graph(
+    chunks: list | None = None,
+    state: Any = None,
+    resume_chunks: list | None = None,
+) -> MagicMock:
+    """Build a mock LangGraph CompiledStateGraph."""
+    g = MagicMock()
+
+    if state is None:
+        state = make_state()
+
+    streams = [chunks or [], resume_chunks or []]
+    idx = {"n": 0}
+
+    def astream_side_effect(*a, **kw):
+        i = min(idx["n"], len(streams) - 1)
+        idx["n"] += 1
+        return AsyncIterHelper(list(streams[i]))
+
+    g.astream = MagicMock(side_effect=astream_side_effect)
+    g.aget_state = AsyncMock(return_value=state)
+    return g
+
+
+def make_graph_ctx(graph: MagicMock | None = None) -> GraphContext:
+    """Build a GraphContext wrapping a mock graph."""
+    g = graph or make_graph()
+    registry = MagicMock()
+    registry.list_agents = MagicMock(return_value=())
+    return GraphContext(graph=g, registry=registry, intent_classifier=None)
+
+
+# ---------------------------------------------------------------------------
+# Fake database pool
+# ---------------------------------------------------------------------------
+
+
+class FakeCursor:
+    """Minimal async cursor returning pre-configured rows."""
+
+    def __init__(self, rows: list[dict]) -> None:
+        self._rows = rows
+
+    async def fetchall(self) -> list[dict]:
+        return self._rows
+
+    async def fetchone(self) -> tuple | dict | None:
+        return self._rows[0] if self._rows else None
+
+
+class FakeConnection:
+    """Fake async connection that returns a FakeCursor."""
+
+    def __init__(self, rows: list[dict]) -> None:
+        self._rows = rows
+
+    async def execute(self, query: str, params: dict | None = None) -> FakeCursor:
+        return FakeCursor(self._rows)
+
+
+class FakePool:
+    """Minimal pool that yields a fake connection."""
+
+    def __init__(self, rows: list[dict] | None = None) -> None:
+        self._rows = rows or []
+
+    @asynccontextmanager
+    async def connection(self):
+        yield FakeConnection(self._rows)
+
+    async def close(self) -> None:
+        pass
+
+
+# ---------------------------------------------------------------------------
+# App factory
+# ---------------------------------------------------------------------------
+
+
+def create_e2e_app(
+    graph: MagicMock | None = None,
+    pool: FakePool | None = None,
+    session_ttl: int = 3600,
+    interrupt_ttl: int = 1800,
+) -> FastAPI:
+    """Create a FastAPI app wired with mocked dependencies for E2E testing."""
+    g = graph or make_graph()
+    graph_ctx = make_graph_ctx(g)
+    p = pool or FakePool()
+    sm = SessionManager(session_ttl_seconds=session_ttl)
+    im = InterruptManager(ttl_seconds=interrupt_ttl)
+
+    app = FastAPI(title="Smart Support E2E Test")
+    app.include_router(openapi_router)
+    app.include_router(replay_router)
+    app.include_router(analytics_router)
+
+    app.state.graph_ctx = graph_ctx
+    app.state.session_manager = sm
+    app.state.interrupt_manager = im
+    app.state.pool = p
+    app.state.settings = MagicMock(llm_model="test-model")
+    app.state.analytics_recorder = AsyncMock()
+    app.state.conversation_tracker = AsyncMock()
+
+    @app.get("/api/v1/health")
+    def health_check() -> dict:
+        return {"status": "ok", "version": "test"}
+
+    @app.websocket("/ws")
+    async def websocket_endpoint(ws: WebSocket) -> None:
+        await ws.accept()
+        try:
+            while True:
+                raw_data = await ws.receive_text()
+                ws_ctx = WebSocketContext(
+                    graph_ctx=app.state.graph_ctx,
+                    session_manager=app.state.session_manager,
+                    callback_handler=TokenUsageCallbackHandler(model_name="test-model"),
+                    interrupt_manager=app.state.interrupt_manager,
+                    analytics_recorder=app.state.analytics_recorder,
+                    conversation_tracker=app.state.conversation_tracker,
+                    pool=app.state.pool,
+                )
+                await dispatch_message(ws, ws_ctx, raw_data)
+        except WebSocketDisconnect:
+            pass
+
+    return app
+
+
+@pytest.fixture
+def e2e_graph():
+    """Default graph fixture -- returns tokens and message_complete."""
+    return make_graph(
+        chunks=[make_chunk("Order 1042 is "), make_chunk("shipped.")]
+    )
+
+
+@pytest.fixture
+def e2e_app(e2e_graph):
+    """Default E2E app fixture."""
+    return create_e2e_app(graph=e2e_graph)
+
+
+@pytest.fixture
+async def e2e_client(e2e_app):
+    """Async HTTP client for E2E tests."""
+    transport = ASGITransport(app=e2e_app)
+    async with AsyncClient(transport=transport, base_url="http://test") as client:
+        yield client
+
+
+@pytest.fixture(autouse=True)
+def clear_openapi_job_store():
+    """Clear the in-memory job store between tests."""
+    _job_store.clear()
+    yield
+    _job_store.clear()
--- a/backend/tests/e2e/test_chat_flows.py
+++ b/backend/tests/e2e/test_chat_flows.py
@@ -0,0 +1,384 @@
+"""E2E tests for critical chat user flows (flows 1-4).
+
+Flow 1: Happy path -- query order, get answer
+Flow 2: Approval flow -- write operation, interrupt, approve, execute
+Flow 3: Rejection flow -- write operation, interrupt, reject, no execution
+Flow 4: Multi-turn context -- sequential messages in same session
+"""
+
+from __future__ import annotations
+
+import json
+
+import pytest
+from starlette.testclient import TestClient
+
+from tests.e2e.conftest import (
+    create_e2e_app,
+    make_chunk,
+    make_graph,
+    make_state,
+    make_tool_chunk,
+)
+
+pytestmark = pytest.mark.e2e
+
+
+class TestFlow1HappyPath:
+    """Flow 1: query order -> get answer with streaming tokens."""
+
+    def test_websocket_happy_path_order_query(self) -> None:
+        graph = make_graph(
+            chunks=[
+                make_tool_chunk("get_order_status", {"order_id": "1042"}),
+                make_chunk("Order 1042 has been shipped and is on its way."),
+            ],
+        )
+        app = create_e2e_app(graph=graph)
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-happy-1",
+                    "content": "What is the status of order 1042?",
+                })
+
+                messages = []
+                while True:
+                    msg = ws.receive_json()
+                    messages.append(msg)
+                    if msg["type"] in ("message_complete", "error"):
+                        break
+
+                tool_calls = [m for m in messages if m["type"] == "tool_call"]
+                assert len(tool_calls) == 1
+                assert tool_calls[0]["tool"] == "get_order_status"
+                assert tool_calls[0]["args"] == {"order_id": "1042"}
+
+                tokens = [m for m in messages if m["type"] == "token"]
+                assert len(tokens) == 1
+                assert "shipped" in tokens[0]["content"]
+
+                completes = [m for m in messages if m["type"] == "message_complete"]
+                assert len(completes) == 1
+                assert completes[0]["thread_id"] == "e2e-happy-1"
+
+    def test_websocket_multiple_token_stream(self) -> None:
+        """Verify streaming returns multiple token chunks."""
+        graph = make_graph(
+            chunks=[
+                make_chunk("Your order "),
+                make_chunk("1042 "),
+                make_chunk("was delivered "),
+                make_chunk("yesterday."),
+            ],
+        )
+        app = create_e2e_app(graph=graph)
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-stream-1",
+                    "content": "Where is my order?",
+                })
+
+                messages = _collect_until_complete(ws)
+
+                tokens = [m for m in messages if m["type"] == "token"]
+                assert len(tokens) == 4
+                full_text = "".join(t["content"] for t in tokens)
+                assert "1042" in full_text
+                assert "delivered" in full_text
+
+
+class TestFlow2ApprovalFlow:
+    """Flow 2: write operation -> interrupt -> approve -> execute."""
+
+    def test_interrupt_approve_executes_action(self) -> None:
+        interrupt_state = make_state(
+            interrupt=True,
+            data={"action": "cancel_order", "order_id": "1042"},
+        )
+        graph = make_graph(
+            chunks=[],
+            state=interrupt_state,
+            resume_chunks=[
+                make_chunk("Order 1042 has been cancelled successfully.", "order_actions"),
+            ],
+        )
+        app = create_e2e_app(graph=graph)
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                # Step 1: Send cancel request
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-approve-1",
+                    "content": "Cancel order 1042",
+                })
+
+                messages = _collect_until_type(ws, "interrupt")
+
+                interrupts = [m for m in messages if m["type"] == "interrupt"]
+                assert len(interrupts) == 1
+                assert interrupts[0]["action"] == "cancel_order"
+                assert interrupts[0]["thread_id"] == "e2e-approve-1"
+
+                # Step 2: Approve the interrupt
+                ws.send_json({
+                    "type": "interrupt_response",
+                    "thread_id": "e2e-approve-1",
+                    "approved": True,
+                })
+
+                resume_messages = _collect_until_complete(ws)
+
+                tokens = [m for m in resume_messages if m["type"] == "token"]
+                assert len(tokens) == 1
+                assert "cancelled" in tokens[0]["content"]
+                assert tokens[0]["agent"] == "order_actions"
+
+                completes = [m for m in resume_messages if m["type"] == "message_complete"]
+                assert len(completes) == 1
+
+
+class TestFlow3RejectionFlow:
+    """Flow 3: write operation -> interrupt -> reject -> no execution."""
+
+    def test_interrupt_reject_does_not_execute(self) -> None:
+        interrupt_state = make_state(
+            interrupt=True,
+            data={"action": "cancel_order", "order_id": "1042"},
+        )
+        graph = make_graph(
+            chunks=[],
+            state=interrupt_state,
+            resume_chunks=[
+                make_chunk("Understood. Order 1042 will remain active.", "order_actions"),
+            ],
+        )
+        app = create_e2e_app(graph=graph)
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                # Step 1: Trigger interrupt
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-reject-1",
+                    "content": "Cancel order 1042",
+                })
+
+                messages = _collect_until_type(ws, "interrupt")
+                assert any(m["type"] == "interrupt" for m in messages)
+
+                # Step 2: Reject
+                ws.send_json({
+                    "type": "interrupt_response",
+                    "thread_id": "e2e-reject-1",
+                    "approved": False,
+                })
+
+                resume_messages = _collect_until_complete(ws)
+
+                tokens = [m for m in resume_messages if m["type"] == "token"]
+                assert len(tokens) == 1
+                assert "remain active" in tokens[0]["content"]
+
+                # Verify graph.astream was called with resume=False
+                resume_call = graph.astream.call_args_list[-1]
+                command = resume_call[0][0]
+                assert command.resume is False
+
+
+class TestFlow4MultiTurnContext:
+    """Flow 4: multi-turn conversation in the same session."""
+
+    def test_multi_turn_messages_share_session(self) -> None:
+        """Multiple messages in the same thread_id maintain session context."""
+        graph = make_graph(
+            chunks=[make_chunk("Order 1042 status: shipped.")],
+        )
+        app = create_e2e_app(graph=graph)
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                # Turn 1: Query order
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-multi-1",
+                    "content": "What is the status of order 1042?",
+                })
+                turn1 = _collect_until_complete(ws)
+                assert any(m["type"] == "message_complete" for m in turn1)
+
+                # Turn 2: Follow-up in same thread
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-multi-1",
+                    "content": "When will it arrive?",
+                })
+                turn2 = _collect_until_complete(ws)
+                assert any(m["type"] == "message_complete" for m in turn2)
+
+                # Turn 3: Another follow-up
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-multi-1",
+                    "content": "Can you track it?",
+                })
+                turn3 = _collect_until_complete(ws)
+                assert any(m["type"] == "message_complete" for m in turn3)
+
+                # Verify all turns used the same thread_id in graph calls
+                for call in graph.astream.call_args_list:
+                    config = call[1].get("config", call[0][1] if len(call[0]) > 1 else {})
+                    assert config["configurable"]["thread_id"] == "e2e-multi-1"
+
+    def test_separate_threads_are_independent(self) -> None:
+        """Different thread_ids have independent sessions."""
+        graph = make_graph(
+            chunks=[make_chunk("Response.")],
+        )
+        app = create_e2e_app(graph=graph)
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                # Thread A
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-thread-a",
+                    "content": "Hello from thread A",
+                })
+                _collect_until_complete(ws)
+
+                # Thread B
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-thread-b",
+                    "content": "Hello from thread B",
+                })
+                _collect_until_complete(ws)
+
+                # Both threads should exist as separate sessions
+                sm = app.state.session_manager
+                assert sm.get_state("e2e-thread-a") is not None
+                assert sm.get_state("e2e-thread-b") is not None
+
+
+class TestChatEdgeCases:
+    """Edge cases and error handling for the chat WebSocket."""
+
+    def test_invalid_json_returns_error(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                ws.send_text("not valid json")
+                msg = ws.receive_json()
+                assert msg["type"] == "error"
+                assert "Invalid JSON" in msg["message"]
+
+    def test_missing_thread_id_returns_error(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                ws.send_json({"type": "message", "content": "hello"})
+                msg = ws.receive_json()
+                assert msg["type"] == "error"
+                assert "thread_id" in msg["message"]
+
+    def test_empty_content_returns_error(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-err-1",
+                    "content": "",
+                })
+                msg = ws.receive_json()
+                assert msg["type"] == "error"
+
+    def test_expired_session_returns_error(self) -> None:
+        graph = make_graph(chunks=[make_chunk("Response.")])
+        app = create_e2e_app(graph=graph, session_ttl=0)
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                # First message creates the session (TTL=0)
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-expired-1",
+                    "content": "hello",
+                })
+                _collect_until_complete_or_error(ws)
+
+                # Second message finds the session expired (TTL=0)
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-expired-1",
+                    "content": "hello again",
+                })
+                messages = _collect_until_complete_or_error(ws)
+                errors = [m for m in messages if m["type"] == "error"]
+                assert len(errors) >= 1
+                assert "expired" in errors[0]["message"].lower()
+
+    def test_oversized_message_returns_error(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            with client.websocket_connect("/ws") as ws:
+                ws.send_text("x" * 40_000)
+                msg = ws.receive_json()
+                assert msg["type"] == "error"
+                assert "too large" in msg["message"].lower()
+
+    def test_health_endpoint(self) -> None:
+        app = create_e2e_app()
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/health")
+            assert resp.status_code == 200
+            assert resp.json()["status"] == "ok"
+
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+
+def _collect_until_complete(ws, *, max_messages: int = 50) -> list[dict]:
+    """Receive WebSocket messages until message_complete or error."""
+    messages = []
+    for _ in range(max_messages):
+        msg = ws.receive_json()
+        messages.append(msg)
+        if msg["type"] in ("message_complete", "error"):
+            break
+    return messages
+
+
+def _collect_until_type(ws, msg_type: str, *, max_messages: int = 50) -> list[dict]:
+    """Receive until a specific message type is received."""
+    messages = []
+    for _ in range(max_messages):
+        msg = ws.receive_json()
+        messages.append(msg)
+        if msg["type"] == msg_type:
+            break
+    return messages
+
+
+def _collect_until_complete_or_error(ws, *, max_messages: int = 50) -> list[dict]:
+    """Receive until message_complete or error."""
+    messages = []
+    for _ in range(max_messages):
+        msg = ws.receive_json()
+        messages.append(msg)
+        if msg["type"] in ("message_complete", "error"):
+            break
+    return messages
--- a/backend/tests/e2e/test_openapi_import.py
+++ b/backend/tests/e2e/test_openapi_import.py
@@ -0,0 +1,201 @@
+"""E2E tests for OpenAPI import flow (flow 5).
+
+Flow 5: paste OpenAPI spec URL -> import job -> classify endpoints ->
+         review classifications -> approve -> tool generation.
+"""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, patch
+
+import pytest
+from starlette.testclient import TestClient
+
+from app.openapi.models import ClassificationResult, EndpointInfo
+from app.openapi.review_api import _job_store
+from tests.e2e.conftest import create_e2e_app
+
+pytestmark = pytest.mark.e2e
+
+
+def _fake_endpoint(
+    path: str = "/orders/{id}",
+    method: str = "GET",
+    operation_id: str = "getOrder",
+    summary: str = "Get order details",
+) -> EndpointInfo:
+    return EndpointInfo(
+        path=path,
+        method=method,
+        operation_id=operation_id,
+        summary=summary,
+        description="",
+        parameters=(),
+        request_body_schema=None,
+        response_schema=None,
+    )
+
+
+def _fake_classification(
+    endpoint: EndpointInfo | None = None,
+    access_type: str = "read",
+    needs_interrupt: bool = False,
+    agent_group: str = "order_lookup",
+) -> ClassificationResult:
+    return ClassificationResult(
+        endpoint=endpoint or _fake_endpoint(),
+        access_type=access_type,
+        customer_params=["order_id"],
+        agent_group=agent_group,
+        confidence=0.95,
+        needs_interrupt=needs_interrupt,
+    )
+
+
+class TestFlow5OpenAPIImport:
+    """Flow 5: full OpenAPI import lifecycle."""
+
+    def test_import_job_lifecycle(self) -> None:
+        """Start import -> check status -> review classifications -> approve."""
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            # Step 1: Start import job
+            resp = client.post(
+                "/api/v1/openapi/import",
+                json={"url": "https://api.example.com/openapi.json"},
+            )
+            assert resp.status_code == 202
+            body = resp.json()
+            assert body["status"] == "pending"
+            job_id = body["job_id"]
+
+            # Step 2: Check job status (still pending since background task hasn't run)
+            resp = client.get(f"/api/v1/openapi/jobs/{job_id}")
+            assert resp.status_code == 200
+            assert resp.json()["job_id"] == job_id
+
+    def test_import_job_with_classifications(self) -> None:
+        """Simulate completed import and review classified endpoints."""
+        app = create_e2e_app()
+
+        # Seed a completed job directly
+        ep_read = _fake_endpoint("/orders/{id}", "GET", "getOrder", "Get order")
+        ep_write = _fake_endpoint("/orders/{id}/cancel", "POST", "cancelOrder", "Cancel order")
+
+        clf_read = _fake_classification(ep_read, "read", False, "order_lookup")
+        clf_write = _fake_classification(ep_write, "write", True, "order_actions")
+
+        job_id = "test-job-001"
+        _job_store[job_id] = {
+            "job_id": job_id,
+            "status": "done",
+            "spec_url": "https://api.example.com/openapi.json",
+            "total_endpoints": 2,
+            "classified_count": 2,
+            "error_message": None,
+            "classifications": [clf_read, clf_write],
+        }
+
+        with TestClient(app) as client:
+            # Step 1: Get classifications
+            resp = client.get(f"/api/v1/openapi/jobs/{job_id}/classifications")
+            assert resp.status_code == 200
+            classifications = resp.json()
+            assert len(classifications) == 2
+
+            # Verify read endpoint
+            read_clf = classifications[0]
+            assert read_clf["access_type"] == "read"
+            assert read_clf["needs_interrupt"] is False
+            assert read_clf["endpoint"]["path"] == "/orders/{id}"
+
+            # Verify write endpoint
+            write_clf = classifications[1]
+            assert write_clf["access_type"] == "write"
+            assert write_clf["needs_interrupt"] is True
+            assert write_clf["endpoint"]["path"] == "/orders/{id}/cancel"
+
+            # Step 2: Update a classification
+            resp = client.put(
+                f"/api/v1/openapi/jobs/{job_id}/classifications/0",
+                json={
+                    "access_type": "write",
+                    "needs_interrupt": True,
+                    "agent_group": "order_actions",
+                },
+            )
+            assert resp.status_code == 200
+            updated = resp.json()
+            assert updated["access_type"] == "write"
+            assert updated["needs_interrupt"] is True
+            assert updated["agent_group"] == "order_actions"
+
+            # Step 3: Approve the job
+            resp = client.post(f"/api/v1/openapi/jobs/{job_id}/approve")
+            assert resp.status_code == 200
+            assert resp.json()["status"] == "approved"
+
+    def test_import_nonexistent_job_returns_404(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/openapi/jobs/nonexistent")
+            assert resp.status_code == 404
+
+    def test_import_invalid_url_returns_422(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            resp = client.post("/api/v1/openapi/import", json={"url": "not-a-url"})
+            assert resp.status_code == 422
+
+    def test_classification_index_out_of_range(self) -> None:
+        app = create_e2e_app()
+
+        job_id = "test-job-range"
+        _job_store[job_id] = {
+            "job_id": job_id,
+            "status": "done",
+            "spec_url": "https://example.com/spec.json",
+            "total_endpoints": 1,
+            "classified_count": 1,
+            "error_message": None,
+            "classifications": [_fake_classification()],
+        }
+
+        with TestClient(app) as client:
+            resp = client.put(
+                f"/api/v1/openapi/jobs/{job_id}/classifications/99",
+                json={
+                    "access_type": "read",
+                    "needs_interrupt": False,
+                    "agent_group": "order_lookup",
+                },
+            )
+            assert resp.status_code == 404
+
+    def test_update_classification_invalid_agent_group(self) -> None:
+        app = create_e2e_app()
+
+        job_id = "test-job-invalid"
+        _job_store[job_id] = {
+            "job_id": job_id,
+            "status": "done",
+            "spec_url": "https://example.com/spec.json",
+            "total_endpoints": 1,
+            "classified_count": 1,
+            "error_message": None,
+            "classifications": [_fake_classification()],
+        }
+
+        with TestClient(app) as client:
+            resp = client.put(
+                f"/api/v1/openapi/jobs/{job_id}/classifications/0",
+                json={
+                    "access_type": "read",
+                    "needs_interrupt": False,
+                    "agent_group": "invalid group!",  # spaces and special chars
+                },
+            )
+            assert resp.status_code == 422
--- a/backend/tests/e2e/test_replay_analytics.py
+++ b/backend/tests/e2e/test_replay_analytics.py
@@ -0,0 +1,230 @@
+"""E2E tests for replay and analytics flows (flow 6).
+
+Flow 6: list conversations -> select one -> step-by-step replay.
+Also tests the analytics dashboard endpoint.
+"""
+
+from __future__ import annotations
+
+from datetime import datetime, timezone
+
+import pytest
+from starlette.testclient import TestClient
+
+from tests.e2e.conftest import FakePool, create_e2e_app
+
+pytestmark = pytest.mark.e2e
+
+
+# ---------------------------------------------------------------------------
+# Custom pool that returns specific data per query
+# ---------------------------------------------------------------------------
+
+
+class ReplayPool(FakePool):
+    """Pool that returns different data depending on the SQL query."""
+
+    def __init__(
+        self,
+        conversations: list[dict] | None = None,
+        checkpoints: list[dict] | None = None,
+        analytics_rows: list[dict] | None = None,
+    ) -> None:
+        super().__init__()
+        self._conversations = conversations or []
+        self._checkpoints = checkpoints or []
+        self._analytics = analytics_rows or []
+
+    class _Conn:
+        def __init__(self, convos, checkpoints, analytics):
+            self._convos = convos
+            self._checkpoints = checkpoints
+            self._analytics = analytics
+
+        async def execute(self, query: str, params=None):
+            from tests.e2e.conftest import FakeCursor
+
+            if "COUNT" in query and "conversations" in query:
+                return FakeCursor([(len(self._convos),)])
+            if "conversations" in query and "SELECT" in query:
+                # Respect LIMIT/OFFSET from params if provided
+                rows = self._convos
+                if params:
+                    offset = params.get("offset", 0)
+                    limit = params.get("limit", len(rows))
+                    rows = rows[offset : offset + limit]
+                return FakeCursor(rows)
+            if "checkpoints" in query:
+                return FakeCursor(self._checkpoints)
+            # Analytics queries
+            return FakeCursor(self._analytics)
+
+    def connection(self):
+        from contextlib import asynccontextmanager
+
+        conn = self._Conn(self._conversations, self._checkpoints, self._analytics)
+
+        @asynccontextmanager
+        async def _ctx():
+            yield conn
+
+        return _ctx()
+
+
+class TestFlow6ReplayConversation:
+    """Flow 6: list conversations -> select one -> step replay."""
+
+    def test_list_conversations(self) -> None:
+        now = datetime.now(tz=timezone.utc).isoformat()
+        conversations = [
+            {
+                "thread_id": "conv-001",
+                "created_at": now,
+                "last_activity": now,
+                "status": "active",
+                "total_tokens": 150,
+                "total_cost_usd": 0.003,
+            },
+            {
+                "thread_id": "conv-002",
+                "created_at": now,
+                "last_activity": now,
+                "status": "completed",
+                "total_tokens": 300,
+                "total_cost_usd": 0.006,
+            },
+        ]
+        pool = ReplayPool(conversations=conversations)
+        app = create_e2e_app(pool=pool)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/conversations")
+            assert resp.status_code == 200
+            body = resp.json()
+            assert body["success"] is True
+            data = body["data"]
+            assert len(data["conversations"]) == 2
+            assert data["conversations"][0]["thread_id"] == "conv-001"
+            assert data["conversations"][1]["thread_id"] == "conv-002"
+            assert data["total"] == 2
+
+    def test_list_conversations_pagination(self) -> None:
+        conversations = [
+            {
+                "thread_id": f"conv-{i:03d}",
+                "created_at": "2026-04-01T00:00:00Z",
+                "last_activity": "2026-04-01T00:00:00Z",
+                "status": "active",
+                "total_tokens": 100,
+                "total_cost_usd": 0.001,
+            }
+            for i in range(5)
+        ]
+        pool = ReplayPool(conversations=conversations)
+        app = create_e2e_app(pool=pool)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/conversations", params={"page": 1, "per_page": 2})
+            assert resp.status_code == 200
+            body = resp.json()
+            assert body["success"] is True
+            data = body["data"]
+            assert data["total"] == 5
+            assert data["page"] == 1
+            assert data["per_page"] == 2
+            assert len(data["conversations"]) == 2
+
+    def test_replay_thread_not_found(self) -> None:
+        pool = ReplayPool(checkpoints=[])
+        app = create_e2e_app(pool=pool)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/replay/nonexistent-thread")
+            assert resp.status_code == 404
+
+    def test_replay_invalid_thread_id_format(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            # Thread ID with special chars fails regex validation
+            resp = client.get("/api/v1/replay/invalid%20thread%21%40")
+            assert resp.status_code == 400
+
+
+class TestAnalyticsDashboard:
+    """Analytics endpoint tests."""
+
+    def test_analytics_invalid_range_format(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/analytics", params={"range": "invalid"})
+            assert resp.status_code == 400
+
+    def test_analytics_range_too_large(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/analytics", params={"range": "999d"})
+            assert resp.status_code == 400
+
+    def test_analytics_range_zero_rejected(self) -> None:
+        app = create_e2e_app()
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/analytics", params={"range": "0d"})
+            assert resp.status_code == 400
+
+
+class TestFullUserJourney:
+    """End-to-end journey: chat -> then check replay list shows the conversation."""
+
+    def test_chat_then_check_conversations_endpoint(self) -> None:
+        """After chatting via WebSocket, the conversations endpoint is reachable."""
+        from tests.e2e.conftest import make_chunk, make_graph
+
+        graph = make_graph(chunks=[make_chunk("Your order is shipped.")])
+        now = datetime.now(tz=timezone.utc).isoformat()
+        pool = ReplayPool(
+            conversations=[
+                {
+                    "thread_id": "e2e-journey-1",
+                    "created_at": now,
+                    "last_activity": now,
+                    "status": "active",
+                    "total_tokens": 50,
+                    "total_cost_usd": 0.001,
+                },
+            ],
+        )
+        app = create_e2e_app(graph=graph, pool=pool)
+
+        with TestClient(app) as client:
+            # Step 1: Chat via WebSocket
+            with client.websocket_connect("/ws") as ws:
+                ws.send_json({
+                    "type": "message",
+                    "thread_id": "e2e-journey-1",
+                    "content": "Where is my order?",
+                })
+                messages = []
+                for _ in range(20):
+                    msg = ws.receive_json()
+                    messages.append(msg)
+                    if msg["type"] in ("message_complete", "error"):
+                        break
+                assert any(m["type"] == "message_complete" for m in messages)
+
+            # Step 2: Check conversations endpoint
+            resp = client.get("/api/v1/conversations")
+            assert resp.status_code == 200
+            body = resp.json()
+            assert body["success"] is True
+            assert any(
+                c["thread_id"] == "e2e-journey-1"
+                for c in body["data"]["conversations"]
+            )
+
+            # Step 3: Health check still works
+            resp = client.get("/api/v1/health")
+            assert resp.status_code == 200
--- a/backend/tests/integration/test_analytics_api.py
+++ b/backend/tests/integration/test_analytics_api.py
@@ -0,0 +1,183 @@
+"""Integration tests for the /api/v1/analytics endpoint.
+
+Tests the full API layer (routing, parameter validation, serialization,
+error handling) with a mocked database pool.
+"""
+
+from __future__ import annotations
+
+from dataclasses import asdict
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+from httpx import ASGITransport, AsyncClient
+
+from app.analytics.models import AnalyticsResult, InterruptStats
+
+pytestmark = pytest.mark.integration
+
+_SAMPLE_RESULT = AnalyticsResult(
+    range="7d",
+    total_conversations=42,
+    resolution_rate=0.85,
+    escalation_rate=0.05,
+    avg_turns_per_conversation=3.2,
+    avg_cost_per_conversation_usd=0.012,
+    agent_usage=(),
+    interrupt_stats=InterruptStats(total=10, approved=7, rejected=2, expired=1),
+)
+
+
+def _build_app():
+    """Build a minimal FastAPI app with the analytics router and mocked deps."""
+    from fastapi import FastAPI
+    from fastapi.exceptions import RequestValidationError
+    from fastapi.responses import JSONResponse
+
+    from app.analytics.api import router as analytics_router
+    from app.api_utils import envelope
+
+    test_app = FastAPI()
+    test_app.include_router(analytics_router)
+
+    @test_app.exception_handler(Exception)
+    async def _catch_all(request, exc):
+        return JSONResponse(
+            status_code=500,
+            content=envelope(None, success=False, error="Internal server error"),
+        )
+
+    from fastapi import HTTPException
+
+    @test_app.exception_handler(HTTPException)
+    async def _http_exc(request, exc):
+        return JSONResponse(
+            status_code=exc.status_code,
+            content=envelope(None, success=False, error=exc.detail),
+        )
+
+    @test_app.exception_handler(RequestValidationError)
+    async def _validation_exc(request, exc):
+        return JSONResponse(
+            status_code=422,
+            content=envelope(None, success=False, error=str(exc)),
+        )
+
+    # No admin_api_key set -> auth is skipped
+    test_app.state.settings = MagicMock(admin_api_key="")
+    test_app.state.pool = MagicMock()
+
+    return test_app
+
+
+class TestAnalyticsValidRange:
+    """Test analytics endpoint with valid range parameters."""
+
+    async def test_valid_range_7d_returns_envelope(self) -> None:
+        """GET /api/v1/analytics?range=7d returns success envelope with data."""
+        test_app = _build_app()
+        with patch(
+            "app.analytics.api.get_analytics",
+            new_callable=AsyncMock,
+            return_value=_SAMPLE_RESULT,
+        ):
+            async with AsyncClient(
+                transport=ASGITransport(app=test_app), base_url="http://test"
+            ) as client:
+                resp = await client.get("/api/v1/analytics", params={"range": "7d"})
+
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["success"] is True
+        assert body["error"] is None
+        assert body["data"]["total_conversations"] == 42
+        assert body["data"]["resolution_rate"] == 0.85
+
+    async def test_default_range_returns_success(self) -> None:
+        """GET /api/v1/analytics with no range param defaults to 7d."""
+        test_app = _build_app()
+        with patch(
+            "app.analytics.api.get_analytics",
+            new_callable=AsyncMock,
+            return_value=_SAMPLE_RESULT,
+        ) as mock_get:
+            async with AsyncClient(
+                transport=ASGITransport(app=test_app), base_url="http://test"
+            ) as client:
+                resp = await client.get("/api/v1/analytics")
+
+        assert resp.status_code == 200
+        # Verify default range of 7 days was passed
+        mock_get.assert_called_once()
+        call_args = mock_get.call_args
+        assert call_args[1].get("range_days", call_args[0][1] if len(call_args[0]) > 1 else None) in (7, None) or call_args[0][1] == 7
+
+    async def test_large_range_365d_works(self) -> None:
+        """GET /api/v1/analytics?range=365d is accepted (max boundary)."""
+        test_app = _build_app()
+        result = AnalyticsResult(
+            range="365d",
+            total_conversations=1000,
+            resolution_rate=0.9,
+            escalation_rate=0.02,
+            avg_turns_per_conversation=4.0,
+            avg_cost_per_conversation_usd=0.01,
+            agent_usage=(),
+            interrupt_stats=InterruptStats(),
+        )
+        with patch(
+            "app.analytics.api.get_analytics",
+            new_callable=AsyncMock,
+            return_value=result,
+        ):
+            async with AsyncClient(
+                transport=ASGITransport(app=test_app), base_url="http://test"
+            ) as client:
+                resp = await client.get("/api/v1/analytics", params={"range": "365d"})
+
+        assert resp.status_code == 200
+        assert resp.json()["success"] is True
+
+
+class TestAnalyticsInvalidRange:
+    """Test analytics endpoint with invalid range parameters."""
+
+    async def test_invalid_range_format_returns_400(self) -> None:
+        """GET /api/v1/analytics?range=abc returns 400 error envelope."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/analytics", params={"range": "abc"})
+
+        assert resp.status_code == 400
+        body = resp.json()
+        assert body["success"] is False
+        assert body["data"] is None
+        assert "Invalid range format" in body["error"]
+
+    async def test_zero_day_range_returns_400(self) -> None:
+        """GET /api/v1/analytics?range=0d returns 400 because 0 is below minimum."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/analytics", params={"range": "0d"})
+
+        assert resp.status_code == 400
+        body = resp.json()
+        assert body["success"] is False
+        assert "between 1 and 365" in body["error"]
+
+    async def test_range_exceeding_max_returns_400(self) -> None:
+        """GET /api/v1/analytics?range=999d returns 400 because it exceeds 365."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/analytics", params={"range": "999d"})
+
+        assert resp.status_code == 400
+        body = resp.json()
+        assert body["success"] is False
+        assert "between 1 and 365" in body["error"]
--- a/backend/tests/integration/test_error_responses.py
+++ b/backend/tests/integration/test_error_responses.py
@@ -0,0 +1,128 @@
+"""Integration tests for global error handling and envelope format consistency.
+
+Tests that all error responses from the FastAPI app conform to the
+standard envelope: {"success": false, "data": null, "error": "..."}.
+"""
+
+from __future__ import annotations
+
+from unittest.mock import MagicMock
+
+import pytest
+from httpx import ASGITransport, AsyncClient
+
+pytestmark = pytest.mark.integration
+
+
+def _build_app():
+    """Build the actual FastAPI app with exception handlers but mocked state."""
+    from fastapi import FastAPI, HTTPException
+    from fastapi.exceptions import RequestValidationError
+    from fastapi.responses import JSONResponse
+
+    from app.analytics.api import router as analytics_router
+    from app.api_utils import envelope
+    from app.replay.api import router as replay_router
+
+    test_app = FastAPI()
+    test_app.include_router(analytics_router)
+    test_app.include_router(replay_router)
+
+    @test_app.exception_handler(HTTPException)
+    async def _http_exc(request, exc):
+        return JSONResponse(
+            status_code=exc.status_code,
+            content=envelope(None, success=False, error=exc.detail),
+        )
+
+    @test_app.exception_handler(RequestValidationError)
+    async def _validation_exc(request, exc):
+        return JSONResponse(
+            status_code=422,
+            content=envelope(None, success=False, error=str(exc)),
+        )
+
+    @test_app.exception_handler(Exception)
+    async def _catch_all(request, exc):
+        return JSONResponse(
+            status_code=500,
+            content=envelope(None, success=False, error="Internal server error"),
+        )
+
+    @test_app.get("/api/v1/health")
+    def health_check():
+        return {"status": "ok", "version": "0.6.0"}
+
+    test_app.state.settings = MagicMock(admin_api_key="")
+    test_app.state.pool = MagicMock()
+
+    return test_app
+
+
+class TestEnvelopeFormat:
+    """Tests that error responses consistently follow envelope format."""
+
+    async def test_http_400_produces_envelope(self) -> None:
+        """A 400 error returns standard envelope with success=false."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/analytics", params={"range": "invalid"})
+
+        assert resp.status_code == 400
+        body = resp.json()
+        assert body["success"] is False
+        assert body["data"] is None
+        assert isinstance(body["error"], str)
+        assert len(body["error"]) > 0
+
+    async def test_validation_error_produces_422_envelope(self) -> None:
+        """Invalid query param type returns 422 with envelope format."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            # page must be >= 1; passing 0 triggers validation error
+            resp = await client.get("/api/v1/conversations", params={"page": 0})
+
+        assert resp.status_code == 422
+        body = resp.json()
+        assert body["success"] is False
+        assert body["data"] is None
+        assert isinstance(body["error"], str)
+
+    async def test_all_error_fields_present(self) -> None:
+        """Error envelope contains exactly success, data, and error keys."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/analytics", params={"range": "bad"})
+
+        body = resp.json()
+        assert set(body.keys()) == {"success", "data", "error"}
+
+    async def test_health_endpoint_returns_200(self) -> None:
+        """Health check returns 200 with status ok."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/health")
+
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["status"] == "ok"
+        assert "version" in body
+
+    async def test_unknown_endpoint_returns_404(self) -> None:
+        """Requesting a non-existent path returns 404."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/nonexistent-path")
+
+        # FastAPI returns 404 for unknown routes; may or may not be wrapped
+        assert resp.status_code == 404
--- a/backend/tests/integration/test_import_pipeline.py
+++ b/backend/tests/integration/test_import_pipeline.py
@@ -0,0 +1,203 @@
+"""Integration tests for the OpenAPI import pipeline orchestrator.
+
+Tests the full pipeline: fetch -> validate -> parse -> classify.
+Uses mocked HTTP and mocked LLM classifier.
+
+RED phase: written before implementation.
+"""
+
+from __future__ import annotations
+
+from unittest.mock import patch
+
+import pytest
+
+from app.openapi.models import ImportJob
+
+pytestmark = pytest.mark.integration
+
+_VALID_SPEC_JSON = """{
+  "openapi": "3.0.0",
+  "info": {"title": "Test API", "version": "1.0.0"},
+  "paths": {
+    "/orders": {
+      "get": {
+        "operationId": "list_orders",
+        "summary": "List orders",
+        "description": "Returns all orders",
+        "responses": {"200": {"description": "OK"}}
+      }
+    },
+    "/orders/{id}": {
+      "delete": {
+        "operationId": "delete_order",
+        "summary": "Delete order",
+        "description": "Deletes an order",
+        "parameters": [
+          {"name": "id", "in": "path", "required": true, "schema": {"type": "string"}}
+        ],
+        "responses": {"204": {"description": "Deleted"}}
+      }
+    }
+  }
+}"""
+
+_INVALID_SPEC_JSON = '{"not": "a valid openapi spec"}'
+
+_PUBLIC_IP = "93.184.216.34"
+
+
+@pytest.fixture
+def mock_classifier():
+    """A mock classifier that classifies using heuristics."""
+    from app.openapi.classifier import HeuristicClassifier
+
+    return HeuristicClassifier()
+
+
+@pytest.fixture
+def orchestrator(mock_classifier):
+    """Create an ImportOrchestrator with the mock classifier."""
+    from app.openapi.importer import ImportOrchestrator
+
+    return ImportOrchestrator(classifier=mock_classifier)
+
+
+class TestImportOrchestratorSuccess:
+    """Tests for successful import pipeline flows."""
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_full_pipeline_succeeds(self, orchestrator, httpx_mock) -> None:
+        """Full pipeline with valid spec and mocked HTTP succeeds."""
+        httpx_mock.add_response(
+            url="https://example.com/api/spec.json",
+            text=_VALID_SPEC_JSON,
+            headers={"content-type": "application/json"},
+        )
+        job = await orchestrator.start_import(
+            url="https://example.com/api/spec.json",
+            job_id="test-job-1",
+            on_progress=None,
+        )
+        assert isinstance(job, ImportJob)
+        assert job.status == "done"
+        assert job.job_id == "test-job-1"
+        assert job.total_endpoints == 2
+        assert job.classified_count == 2
+        assert job.error_message is None
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_progress_callback_called_at_stages(self, orchestrator, httpx_mock) -> None:
+        """on_progress callback is called at each pipeline stage."""
+        httpx_mock.add_response(
+            url="https://example.com/api/spec.json",
+            text=_VALID_SPEC_JSON,
+            headers={"content-type": "application/json"},
+        )
+        stages_seen: list[str] = []
+
+        def on_progress(stage: str, job: ImportJob) -> None:
+            stages_seen.append(stage)
+
+        await orchestrator.start_import(
+            url="https://example.com/api/spec.json",
+            job_id="test-job-2",
+            on_progress=on_progress,
+        )
+        assert "fetching" in stages_seen
+        assert "validating" in stages_seen
+        assert "parsing" in stages_seen
+        assert "classifying" in stages_seen
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_none_progress_callback_does_not_raise(
+        self, orchestrator, httpx_mock
+    ) -> None:
+        """Passing None as on_progress does not raise."""
+        httpx_mock.add_response(
+            url="https://example.com/api/spec.json",
+            text=_VALID_SPEC_JSON,
+            headers={"content-type": "application/json"},
+        )
+        job = await orchestrator.start_import(
+            url="https://example.com/api/spec.json",
+            job_id="test-job-3",
+            on_progress=None,
+        )
+        assert job.status == "done"
+
+
+class TestImportOrchestratorFailures:
+    """Tests for error handling in the import pipeline."""
+
+    async def test_fetch_failure_sets_failed_status(self, orchestrator) -> None:
+        """When HTTP fetch fails, job status is 'failed'."""
+        with patch("app.openapi.ssrf.resolve_hostname", return_value=["10.0.0.1"]):
+            job = await orchestrator.start_import(
+                url="http://internal.corp/spec.json",
+                job_id="test-job-fail-1",
+                on_progress=None,
+            )
+        assert job.status == "failed"
+        assert job.error_message is not None
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_validation_failure_sets_failed_status(
+        self, orchestrator, httpx_mock
+    ) -> None:
+        """When spec validation fails, job status is 'failed'."""
+        httpx_mock.add_response(
+            url="https://example.com/api/bad.json",
+            text=_INVALID_SPEC_JSON,
+            headers={"content-type": "application/json"},
+        )
+        job = await orchestrator.start_import(
+            url="https://example.com/api/bad.json",
+            job_id="test-job-fail-2",
+            on_progress=None,
+        )
+        assert job.status == "failed"
+        assert job.error_message is not None
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_error_message_is_descriptive(self, orchestrator, httpx_mock) -> None:
+        """Error message contains useful context."""
+        httpx_mock.add_response(
+            url="https://example.com/api/bad.json",
+            text=_INVALID_SPEC_JSON,
+            headers={"content-type": "application/json"},
+        )
+        job = await orchestrator.start_import(
+            url="https://example.com/api/bad.json",
+            job_id="test-job-fail-3",
+            on_progress=None,
+        )
+        assert len(job.error_message) > 0
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_failed_status_progress_called_with_failed(
+        self, orchestrator, httpx_mock
+    ) -> None:
+        """When pipeline fails, on_progress is called with 'failed' stage."""
+        httpx_mock.add_response(
+            url="https://example.com/api/bad.json",
+            text=_INVALID_SPEC_JSON,
+            headers={"content-type": "application/json"},
+        )
+        stages_seen: list[str] = []
+
+        def on_progress(stage: str, job: ImportJob) -> None:
+            stages_seen.append(stage)
+
+        await orchestrator.start_import(
+            url="https://example.com/api/bad.json",
+            job_id="test-job-fail-4",
+            on_progress=on_progress,
+        )
+        assert "failed" in stages_seen
+
+
+@pytest.fixture
+def _mock_public_dns():
+    with patch("app.openapi.ssrf.resolve_hostname", return_value=[_PUBLIC_IP]):
+        yield
--- a/backend/tests/integration/test_openapi_api.py
+++ b/backend/tests/integration/test_openapi_api.py
@@ -0,0 +1,164 @@
+"""Integration tests for /api/v1/openapi/ endpoints.
+
+Tests the full API layer for the OpenAPI import review workflow,
+including job creation, status retrieval, classification updates,
+and approval triggering.
+"""
+
+from __future__ import annotations
+
+from unittest.mock import MagicMock, patch
+
+import pytest
+from httpx import ASGITransport, AsyncClient
+
+pytestmark = pytest.mark.integration
+
+
+def _build_app():
+    """Build a minimal FastAPI app with the openapi router and mocked deps."""
+    from fastapi import FastAPI, HTTPException
+    from fastapi.exceptions import RequestValidationError
+    from fastapi.responses import JSONResponse
+
+    from app.api_utils import envelope
+    from app.openapi.review_api import router as openapi_router
+
+    test_app = FastAPI()
+    test_app.include_router(openapi_router)
+
+    @test_app.exception_handler(HTTPException)
+    async def _http_exc(request, exc):
+        return JSONResponse(
+            status_code=exc.status_code,
+            content=envelope(None, success=False, error=exc.detail),
+        )
+
+    @test_app.exception_handler(RequestValidationError)
+    async def _validation_exc(request, exc):
+        return JSONResponse(
+            status_code=422,
+            content=envelope(None, success=False, error=str(exc)),
+        )
+
+    test_app.state.settings = MagicMock(admin_api_key="")
+
+    return test_app
+
+
+@pytest.fixture(autouse=True)
+def _clear_job_store():
+    """Clear the in-memory job store between tests."""
+    from app.openapi.review_api import _job_store
+
+    _job_store.clear()
+    yield
+    _job_store.clear()
+
+
+class TestImportEndpoint:
+    """Tests for POST /api/v1/openapi/import."""
+
+    async def test_import_returns_202_with_job_id(self) -> None:
+        """Starting an import returns 202 with a job_id."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.post(
+                "/api/v1/openapi/import",
+                json={"url": "https://example.com/api/spec.json"},
+            )
+
+        assert resp.status_code == 202
+        body = resp.json()
+        assert "job_id" in body
+        assert body["status"] == "pending"
+        assert body["spec_url"] == "https://example.com/api/spec.json"
+
+    async def test_import_invalid_url_returns_422(self) -> None:
+        """POST with invalid URL (no http/https) returns 422."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.post(
+                "/api/v1/openapi/import",
+                json={"url": "ftp://example.com/spec.json"},
+            )
+
+        assert resp.status_code == 422
+        body = resp.json()
+        assert body["success"] is False
+
+
+class TestJobStatusEndpoint:
+    """Tests for GET /api/v1/openapi/jobs/{job_id}."""
+
+    async def test_get_existing_job_returns_status(self) -> None:
+        """Retrieving an existing job returns its status."""
+        from app.openapi.review_api import _job_store
+
+        _job_store["test-job-1"] = {
+            "job_id": "test-job-1",
+            "status": "done",
+            "spec_url": "https://example.com/spec.json",
+            "total_endpoints": 5,
+            "classified_count": 5,
+            "error_message": None,
+            "classifications": [],
+        }
+
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/openapi/jobs/test-job-1")
+
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["job_id"] == "test-job-1"
+        assert body["status"] == "done"
+        assert body["total_endpoints"] == 5
+
+    async def test_get_unknown_job_returns_404(self) -> None:
+        """Retrieving a non-existent job returns 404 error envelope."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/openapi/jobs/unknown-id-999")
+
+        assert resp.status_code == 404
+        body = resp.json()
+        assert body["success"] is False
+        assert "not found" in body["error"].lower()
+
+
+class TestApproveEndpoint:
+    """Tests for POST /api/v1/openapi/jobs/{job_id}/approve."""
+
+    async def test_approve_with_no_classifications_returns_400(self) -> None:
+        """Approving a job with no classifications returns 400."""
+        from app.openapi.review_api import _job_store
+
+        _job_store["empty-job"] = {
+            "job_id": "empty-job",
+            "status": "done",
+            "spec_url": "https://example.com/spec.json",
+            "total_endpoints": 0,
+            "classified_count": 0,
+            "error_message": None,
+            "classifications": [],
+        }
+
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.post("/api/v1/openapi/jobs/empty-job/approve")
+
+        assert resp.status_code == 400
+        body = resp.json()
+        assert body["success"] is False
+        assert "no classifications" in body["error"].lower()
--- a/backend/tests/integration/test_phase2_checkpoints.py
+++ b/backend/tests/integration/test_phase2_checkpoints.py
@@ -0,0 +1,512 @@
+"""Phase 2 checkpoint acceptance tests.
+
+Each test maps to one checkpoint criterion from DEVELOPMENT-PLAN.md:
+1. "查询订单 1042" -> routes to order_lookup agent
+2. "取消订单 1042 并给我一个 10% 折扣" -> sequential multi-agent execution
+3. Ambiguous message -> fallback asks for clarification
+4. Interrupt > 30 min TTL -> auto-cancel + retry prompt
+5. Agent escalation -> Webhook POST succeeds (or logs after retries)
+6. E-commerce template -> 4 pre-configured agents work
+7. pytest --cov >= 80% (verified separately)
+"""
+
+from __future__ import annotations
+
+import json
+from pathlib import Path
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+
+from app.callbacks import TokenUsageCallbackHandler
+from app.escalation import EscalationPayload, NoOpEscalator, WebhookEscalator
+from app.graph_context import GraphContext
+from app.intent import ClassificationResult, IntentTarget, LLMIntentClassifier
+from app.interrupt_manager import InterruptManager
+from app.registry import AgentConfig, AgentRegistry
+from app.session_manager import SessionManager
+from app.ws_context import WebSocketContext
+from app.ws_handler import dispatch_message
+
+TEMPLATES_DIR = Path(__file__).parent.parent.parent / "templates"
+
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+class AsyncIterHelper:
+    def __init__(self, items: list) -> None:
+        self._items = list(items)
+
+    def __aiter__(self):
+        return self
+
+    async def __anext__(self):
+        if not self._items:
+            raise StopAsyncIteration
+        return self._items.pop(0)
+
+
+class FakeWS:
+    def __init__(self) -> None:
+        self.sent: list[dict] = []
+
+    async def send_json(self, data: dict) -> None:
+        self.sent.append(data)
+
+
+def _chunk(content: str, node: str) -> tuple:
+    c = MagicMock()
+    c.content = content
+    c.tool_calls = []
+    return (c, {"langgraph_node": node})
+
+
+def _tool_chunk(name: str, args: dict, node: str) -> tuple:
+    c = MagicMock()
+    c.content = ""
+    c.tool_calls = [{"name": name, "args": args}]
+    return (c, {"langgraph_node": node})
+
+
+def _state(*, interrupt: bool = False, data: dict | None = None):
+    s = MagicMock()
+    if interrupt:
+        obj = MagicMock()
+        obj.value = data or {"action": "cancel_order", "order_id": "1042"}
+        t = MagicMock()
+        t.interrupts = (obj,)
+        s.tasks = (t,)
+    else:
+        s.tasks = ()
+    return s
+
+
+def _agent(name: str, desc: str, perm: str = "read") -> AgentConfig:
+    return AgentConfig(name=name, description=desc, permission=perm, tools=["fallback_respond"])
+
+
+# ---------------------------------------------------------------------------
+# Checkpoint 1: "查询订单 1042" -> 路由到订单查询 Agent
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestCheckpoint1OrderQueryRouting:
+    """Verify intent classifier routes order queries to order_lookup."""
+
+    @pytest.mark.asyncio
+    async def test_order_query_classified_to_order_lookup(self) -> None:
+        expected = ClassificationResult(
+            intents=(
+                IntentTarget(agent_name="order_lookup", confidence=0.95, reasoning="order query"),
+            ),
+        )
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(return_value=expected)
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        agents = (
+            _agent("order_lookup", "Looks up order status and tracking"),
+            _agent("order_actions", "Modifies orders", "write"),
+            _agent("discount", "Applies discounts", "write"),
+            _agent("fallback", "Handles unclear requests"),
+        )
+
+        result = await classifier.classify("查询订单 1042", agents)
+        assert len(result.intents) == 1
+        assert result.intents[0].agent_name == "order_lookup"
+        assert result.intents[0].confidence >= 0.9
+        assert not result.is_ambiguous
+
+    @pytest.mark.asyncio
+    async def test_order_query_streams_from_order_lookup_agent(self) -> None:
+        """Full dispatch: classify -> route -> stream from order_lookup."""
+        graph = MagicMock()
+        # Classifier returns order_lookup
+        mock_classifier = AsyncMock()
+        mock_classifier.classify = AsyncMock(return_value=ClassificationResult(
+            intents=(IntentTarget(agent_name="order_lookup", confidence=0.95, reasoning="query"),),
+        ))
+        mock_registry = MagicMock()
+        mock_registry.list_agents = MagicMock(return_value=())
+
+        # Graph streams order_lookup response
+        graph.astream = MagicMock(return_value=AsyncIterHelper([
+            _tool_chunk("get_order_status", {"order_id": "1042"}, "order_lookup"),
+            _chunk("Order 1042 is shipped.", "order_lookup"),
+        ]))
+        graph.aget_state = AsyncMock(return_value=_state())
+
+        graph_ctx = GraphContext(
+            graph=graph, registry=mock_registry, intent_classifier=mock_classifier,
+        )
+        sm = SessionManager()
+        sm.touch("t1")
+        im = InterruptManager()
+        cb = TokenUsageCallbackHandler()
+        ws = FakeWS()
+        ws_ctx = WebSocketContext(
+            graph_ctx=graph_ctx, session_manager=sm,
+            callback_handler=cb, interrupt_manager=im,
+        )
+
+        raw = json.dumps({"type": "message", "thread_id": "t1", "content": "查询订单 1042"})
+        await dispatch_message(ws, ws_ctx, raw)
+
+        tool_msgs = [m for m in ws.sent if m["type"] == "tool_call"]
+        assert any(m["tool"] == "get_order_status" for m in tool_msgs)
+
+        token_msgs = [m for m in ws.sent if m["type"] == "token"]
+        assert any(m["agent"] == "order_lookup" for m in token_msgs)
+
+
+# ---------------------------------------------------------------------------
+# Checkpoint 2: Multi-intent -> sequential execution
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestCheckpoint2MultiIntentSequential:
+    """Verify multi-intent classified and hint injected for sequential execution."""
+
+    @pytest.mark.asyncio
+    async def test_multi_intent_classification(self) -> None:
+        expected = ClassificationResult(
+            intents=(
+                IntentTarget(agent_name="order_actions", confidence=0.9, reasoning="cancel"),
+                IntentTarget(agent_name="discount", confidence=0.85, reasoning="discount"),
+            ),
+        )
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(return_value=expected)
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        agents = (
+            _agent("order_actions", "Modifies orders", "write"),
+            _agent("discount", "Applies discounts", "write"),
+            _agent("fallback", "Handles unclear requests"),
+        )
+
+        result = await classifier.classify("取消订单 1042 并给我一个 10% 折扣", agents)
+        assert len(result.intents) == 2
+        assert result.intents[0].agent_name == "order_actions"
+        assert result.intents[1].agent_name == "discount"
+        assert not result.is_ambiguous
+
+    @pytest.mark.asyncio
+    async def test_multi_intent_injects_routing_hint(self) -> None:
+        """When multi-intent detected, a [System: ...] hint is appended to the message."""
+        graph = MagicMock()
+        mock_classifier = AsyncMock()
+        mock_classifier.classify = AsyncMock(return_value=ClassificationResult(
+            intents=(
+                IntentTarget(agent_name="order_actions", confidence=0.9, reasoning="cancel"),
+                IntentTarget(agent_name="discount", confidence=0.85, reasoning="discount"),
+            ),
+        ))
+        mock_registry = MagicMock()
+        mock_registry.list_agents = MagicMock(return_value=())
+        graph.astream = MagicMock(return_value=AsyncIterHelper([]))
+        graph.aget_state = AsyncMock(return_value=_state())
+
+        graph_ctx = GraphContext(
+            graph=graph, registry=mock_registry, intent_classifier=mock_classifier,
+        )
+        sm = SessionManager()
+        sm.touch("t1")
+        im = InterruptManager()
+        cb = TokenUsageCallbackHandler()
+        ws = FakeWS()
+        ws_ctx = WebSocketContext(
+            graph_ctx=graph_ctx, session_manager=sm,
+            callback_handler=cb, interrupt_manager=im,
+        )
+
+        raw = json.dumps({
+            "type": "message",
+            "thread_id": "t1",
+            "content": "取消订单 1042 并给我一个 10% 折扣",
+        })
+        await dispatch_message(ws, ws_ctx, raw)
+
+        # Verify the graph was called with the routing hint in the message
+        call_args = graph.astream.call_args
+        input_msg = call_args[0][0]
+        msg_content = input_msg["messages"][0].content
+        assert "[System:" in msg_content
+        assert "order_actions" in msg_content
+        assert "discount" in msg_content
+
+
+# ---------------------------------------------------------------------------
+# Checkpoint 3: Ambiguous message -> clarification
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestCheckpoint3AmbiguousClarification:
+    """Verify ambiguous messages trigger clarification prompt."""
+
+    @pytest.mark.asyncio
+    async def test_ambiguous_intent_returns_clarification(self) -> None:
+        expected = ClassificationResult(
+            intents=(IntentTarget(agent_name="fallback", confidence=0.3, reasoning="unclear"),),
+            is_ambiguous=False,  # low confidence will trigger ambiguity threshold
+        )
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(return_value=expected)
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        agents = (_agent("order_lookup", "Orders"), _agent("fallback", "Fallback"))
+
+        result = await classifier.classify("嗯...", agents)
+        assert result.is_ambiguous
+        assert result.clarification_question is not None
+
+    @pytest.mark.asyncio
+    async def test_ambiguous_sends_clarification_via_websocket(self) -> None:
+        graph = MagicMock()
+        mock_classifier = AsyncMock()
+        mock_classifier.classify = AsyncMock(return_value=ClassificationResult(
+            intents=(),
+            is_ambiguous=True,
+            clarification_question=(
+                "Could you please provide more details about what you need help with?"
+            ),
+        ))
+        mock_registry = MagicMock()
+        mock_registry.list_agents = MagicMock(return_value=())
+        graph.astream = MagicMock(return_value=AsyncIterHelper([]))
+        graph.aget_state = AsyncMock(return_value=_state())
+
+        graph_ctx = GraphContext(
+            graph=graph, registry=mock_registry, intent_classifier=mock_classifier,
+        )
+        sm = SessionManager()
+        sm.touch("t1")
+        im = InterruptManager()
+        cb = TokenUsageCallbackHandler()
+        ws = FakeWS()
+        ws_ctx = WebSocketContext(
+            graph_ctx=graph_ctx, session_manager=sm,
+            callback_handler=cb, interrupt_manager=im,
+        )
+
+        raw = json.dumps({"type": "message", "thread_id": "t1", "content": "嗯..."})
+        await dispatch_message(ws, ws_ctx, raw)
+
+        clarifications = [m for m in ws.sent if m["type"] == "clarification"]
+        assert len(clarifications) == 1
+        assert "more details" in clarifications[0]["message"]
+
+        # Should NOT call graph.astream since we returned early
+        graph.astream.assert_not_called()
+
+
+# ---------------------------------------------------------------------------
+# Checkpoint 4: Interrupt > 30 min -> auto-cancel + retry
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestCheckpoint4InterruptTTLAutoCancel:
+    """Verify interrupt TTL expiration triggers auto-cancel and retry prompt."""
+
+    @pytest.mark.asyncio
+    async def test_30min_expired_interrupt_auto_cancels(self) -> None:
+        st = _state(interrupt=True, data={"action": "cancel_order", "order_id": "1042"})
+        graph = MagicMock()
+        graph.astream = MagicMock(return_value=AsyncIterHelper([]))
+        graph.aget_state = AsyncMock(return_value=st)
+
+        mock_registry = MagicMock()
+        mock_registry.list_agents = MagicMock(return_value=())
+        graph_ctx = GraphContext(graph=graph, registry=mock_registry, intent_classifier=None)
+
+        sm = SessionManager()
+        sm.touch("t1")
+        im = InterruptManager(ttl_seconds=1800)  # 30 minutes
+        cb = TokenUsageCallbackHandler()
+        ws = FakeWS()
+        ws_ctx = WebSocketContext(
+            graph_ctx=graph_ctx, session_manager=sm,
+            callback_handler=cb, interrupt_manager=im,
+        )
+
+        # Trigger interrupt
+        raw = json.dumps({"type": "message", "thread_id": "t1", "content": "Cancel order 1042"})
+        await dispatch_message(ws, ws_ctx, raw)
+
+        interrupts = [m for m in ws.sent if m["type"] == "interrupt"]
+        assert len(interrupts) == 1
+
+        # Simulate 31 minutes passing
+        record = im._interrupts["t1"]
+        ws.sent.clear()
+
+        with patch("app.interrupt_manager.time") as mock_time:
+            mock_time.time.return_value = record.created_at + 1860  # 31 min
+
+            raw = json.dumps({
+                "type": "interrupt_response",
+                "thread_id": "t1",
+                "approved": True,
+            })
+            await dispatch_message(ws, ws_ctx, raw)
+
+        # Should get retry prompt, NOT resume the graph
+        expired_msgs = [m for m in ws.sent if m["type"] == "interrupt_expired"]
+        assert len(expired_msgs) == 1
+        assert "30 minutes" in expired_msgs[0]["message"]
+        assert expired_msgs[0]["action"] == "cancel_order"
+        assert expired_msgs[0]["thread_id"] == "t1"
+
+    def test_cleanup_expired_returns_records(self) -> None:
+        im = InterruptManager(ttl_seconds=1800)
+        im.register("t1", "cancel_order", {"order_id": "1042"})
+        im.register("t2", "apply_discount", {"order_id": "1043"})
+
+        with patch("app.interrupt_manager.time") as mock_time:
+            record = im._interrupts["t1"]
+            mock_time.time.return_value = record.created_at + 1860
+            expired = im.cleanup_expired()
+
+        assert len(expired) == 2
+        actions = {r.action for r in expired}
+        assert "cancel_order" in actions
+        assert "apply_discount" in actions
+
+
+# ---------------------------------------------------------------------------
+# Checkpoint 5: Agent escalation -> Webhook POST
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestCheckpoint5WebhookEscalation:
+    """Verify webhook escalation sends POST and retries on failure."""
+
+    @pytest.mark.asyncio
+    async def test_webhook_post_success(self) -> None:
+        mock_response = AsyncMock()
+        mock_response.status_code = 200
+
+        mock_client = AsyncMock()
+        mock_client.post = AsyncMock(return_value=mock_response)
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        with patch("app.escalation.httpx.AsyncClient", return_value=mock_client):
+            escalator = WebhookEscalator(url="https://support.example.com/escalate")
+            payload = EscalationPayload(
+                thread_id="t1",
+                reason="Agent cannot resolve customer issue",
+                conversation_summary="Customer asked about refund policy",
+                metadata={"customer_id": "C-123"},
+            )
+            result = await escalator.escalate(payload)
+
+        assert result.success
+        assert result.status_code == 200
+        assert result.attempts == 1
+
+        # Verify POST was called with correct payload
+        call_args = mock_client.post.call_args
+        assert call_args[0][0] == "https://support.example.com/escalate"
+        posted_data = call_args[1]["json"]
+        assert posted_data["thread_id"] == "t1"
+        assert posted_data["reason"] == "Agent cannot resolve customer issue"
+
+    @pytest.mark.asyncio
+    async def test_webhook_retries_then_logs(self) -> None:
+        fail_response = AsyncMock()
+        fail_response.status_code = 503
+
+        mock_client = AsyncMock()
+        mock_client.post = AsyncMock(return_value=fail_response)
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        with (
+            patch("app.escalation.httpx.AsyncClient", return_value=mock_client),
+            patch("app.escalation.asyncio.sleep", new_callable=AsyncMock),
+        ):
+            escalator = WebhookEscalator(
+                url="https://support.example.com/escalate",
+                max_retries=3,
+            )
+            payload = EscalationPayload(
+                thread_id="t1",
+                reason="Escalation needed",
+                conversation_summary="Summary",
+            )
+            result = await escalator.escalate(payload)
+
+        assert not result.success
+        assert result.attempts == 3
+        assert "503" in result.error
+
+    @pytest.mark.asyncio
+    async def test_noop_escalator_when_disabled(self) -> None:
+        escalator = NoOpEscalator()
+        payload = EscalationPayload(
+            thread_id="t1",
+            reason="Test",
+            conversation_summary="Test",
+        )
+        result = await escalator.escalate(payload)
+        assert not result.success
+        assert "disabled" in result.error.lower()
+
+
+# ---------------------------------------------------------------------------
+# Checkpoint 6: E-commerce template -> pre-configured agents
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestCheckpoint6EcommerceTemplate:
+    """Verify e-commerce template loads with correct agents."""
+
+    def test_ecommerce_template_loads_4_agents(self) -> None:
+        registry = AgentRegistry.load_template("e-commerce", TEMPLATES_DIR)
+        assert len(registry) == 4
+
+    def test_ecommerce_template_has_correct_agents(self) -> None:
+        registry = AgentRegistry.load_template("e-commerce", TEMPLATES_DIR)
+        agents = registry.list_agents()
+        names = {a.name for a in agents}
+        assert names == {"order_lookup", "order_actions", "discount", "fallback"}
+
+    def test_ecommerce_order_lookup_is_read(self) -> None:
+        registry = AgentRegistry.load_template("e-commerce", TEMPLATES_DIR)
+        agent = registry.get_agent("order_lookup")
+        assert agent.permission == "read"
+        assert "get_order_status" in agent.tools
+        assert "get_tracking_info" in agent.tools
+
+    def test_ecommerce_order_actions_is_write(self) -> None:
+        registry = AgentRegistry.load_template("e-commerce", TEMPLATES_DIR)
+        agent = registry.get_agent("order_actions")
+        assert agent.permission == "write"
+        assert "cancel_order" in agent.tools
+
+    def test_ecommerce_discount_is_write(self) -> None:
+        registry = AgentRegistry.load_template("e-commerce", TEMPLATES_DIR)
+        agent = registry.get_agent("discount")
+        assert agent.permission == "write"
+        assert "apply_discount" in agent.tools
+        assert "generate_coupon" in agent.tools
+
+    def test_ecommerce_fallback_is_read(self) -> None:
+        registry = AgentRegistry.load_template("e-commerce", TEMPLATES_DIR)
+        agent = registry.get_agent("fallback")
+        assert agent.permission == "read"
+
+    def test_all_three_templates_available(self) -> None:
+        templates = AgentRegistry.list_templates(TEMPLATES_DIR)
+        assert "e-commerce" in templates
+        assert "saas" in templates
+        assert "fintech" in templates
--- a/backend/tests/integration/test_replay_api.py
+++ b/backend/tests/integration/test_replay_api.py
@@ -0,0 +1,213 @@
+"""Integration tests for /api/v1/conversations and /api/v1/replay/{thread_id}.
+
+Tests the full API layer with a mocked database pool, verifying routing,
+serialization, pagination, and error handling in envelope format.
+"""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+from httpx import ASGITransport, AsyncClient
+
+pytestmark = pytest.mark.integration
+
+
+def _make_fake_cursor(rows, *, fetchone_value=None):
+    """Build a fake async cursor returning the given rows on fetchall."""
+    cursor = AsyncMock()
+    cursor.fetchall = AsyncMock(return_value=rows)
+    if fetchone_value is not None:
+        cursor.fetchone = AsyncMock(return_value=fetchone_value)
+    return cursor
+
+
+class _FakeConnection:
+    """Fake async connection that returns pre-configured cursors in order."""
+
+    def __init__(self, cursors: list) -> None:
+        self._cursors = list(cursors)
+        self._idx = 0
+
+    async def execute(self, sql, params=None):
+        cursor = self._cursors[self._idx]
+        self._idx += 1
+        return cursor
+
+    async def __aenter__(self):
+        return self
+
+    async def __aexit__(self, *args):
+        pass
+
+
+class _FakePool:
+    """Fake connection pool that yields a fake connection."""
+
+    def __init__(self, conn: _FakeConnection) -> None:
+        self._conn = conn
+
+    def connection(self):
+        return self._conn
+
+
+def _build_app(pool=None):
+    """Build a minimal FastAPI app with the replay router and mocked deps."""
+    from fastapi import FastAPI, HTTPException
+    from fastapi.exceptions import RequestValidationError
+    from fastapi.responses import JSONResponse
+
+    from app.api_utils import envelope
+    from app.replay.api import router as replay_router
+
+    test_app = FastAPI()
+    test_app.include_router(replay_router)
+
+    @test_app.exception_handler(HTTPException)
+    async def _http_exc(request, exc):
+        return JSONResponse(
+            status_code=exc.status_code,
+            content=envelope(None, success=False, error=exc.detail),
+        )
+
+    @test_app.exception_handler(RequestValidationError)
+    async def _validation_exc(request, exc):
+        return JSONResponse(
+            status_code=422,
+            content=envelope(None, success=False, error=str(exc)),
+        )
+
+    test_app.state.settings = MagicMock(admin_api_key="")
+    test_app.state.pool = pool or MagicMock()
+
+    return test_app
+
+
+class TestListConversations:
+    """Tests for GET /api/v1/conversations endpoint."""
+
+    async def test_returns_paginated_envelope(self) -> None:
+        """Conversations list returns envelope with pagination metadata."""
+        count_cursor = _make_fake_cursor([], fetchone_value=(3,))
+        rows = [
+            {"thread_id": "t1", "created_at": "2026-01-01", "last_activity": "2026-01-01",
+             "status": "active", "total_tokens": 100, "total_cost_usd": 0.01},
+            {"thread_id": "t2", "created_at": "2026-01-02", "last_activity": "2026-01-02",
+             "status": "resolved", "total_tokens": 200, "total_cost_usd": 0.02},
+        ]
+        list_cursor = _make_fake_cursor(rows)
+        conn = _FakeConnection([count_cursor, list_cursor])
+        pool = _FakePool(conn)
+        test_app = _build_app(pool)
+
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/conversations")
+
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["success"] is True
+        assert body["data"]["total"] == 3
+        assert len(body["data"]["conversations"]) == 2
+        assert body["data"]["page"] == 1
+        assert body["data"]["per_page"] == 20
+
+    async def test_custom_page_and_per_page(self) -> None:
+        """Custom page/per_page params are reflected in the response."""
+        count_cursor = _make_fake_cursor([], fetchone_value=(50,))
+        list_cursor = _make_fake_cursor([])
+        conn = _FakeConnection([count_cursor, list_cursor])
+        pool = _FakePool(conn)
+        test_app = _build_app(pool)
+
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/conversations", params={"page": 3, "per_page": 10})
+
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["data"]["page"] == 3
+        assert body["data"]["per_page"] == 10
+
+    async def test_invalid_page_returns_422(self) -> None:
+        """page=0 violates ge=1 constraint and returns 422 error envelope."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/conversations", params={"page": 0})
+
+        assert resp.status_code == 422
+        body = resp.json()
+        assert body["success"] is False
+
+
+class TestReplayEndpoint:
+    """Tests for GET /api/v1/replay/{thread_id} endpoint."""
+
+    async def test_valid_thread_returns_timeline(self) -> None:
+        """Replay with valid thread_id returns steps in envelope format."""
+        checkpoint_rows = [
+            {
+                "thread_id": "abc123",
+                "checkpoint_id": "cp1",
+                "checkpoint": {
+                    "channel_values": {
+                        "messages": [
+                            {"type": "human", "content": "Hello", "created_at": "2026-01-01T00:00:00Z"},
+                            {"type": "ai", "content": "Hi there!", "created_at": "2026-01-01T00:00:01Z"},
+                        ]
+                    }
+                },
+                "metadata": {},
+            }
+        ]
+        cursor = _make_fake_cursor(checkpoint_rows)
+        conn = _FakeConnection([cursor])
+        pool = _FakePool(conn)
+        test_app = _build_app(pool)
+
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/replay/abc123")
+
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["success"] is True
+        assert body["data"]["thread_id"] == "abc123"
+        assert body["data"]["total_steps"] == 2
+        assert len(body["data"]["steps"]) == 2
+        assert body["data"]["steps"][0]["type"] == "user_message"
+        assert body["data"]["steps"][1]["type"] == "agent_response"
+
+    async def test_invalid_thread_id_format_returns_400(self) -> None:
+        """Thread IDs with path traversal characters are rejected with 400."""
+        test_app = _build_app()
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/replay/../../etc/passwd")
+
+        # FastAPI may return 400 from our handler or 404 from routing
+        assert resp.status_code in (400, 404, 422)
+
+    async def test_nonexistent_thread_returns_404(self) -> None:
+        """Replay with a thread_id that has no checkpoints returns 404."""
+        cursor = _make_fake_cursor([])
+        conn = _FakeConnection([cursor])
+        pool = _FakePool(conn)
+        test_app = _build_app(pool)
+
+        async with AsyncClient(
+            transport=ASGITransport(app=test_app), base_url="http://test"
+        ) as client:
+            resp = await client.get("/api/v1/replay/nonexistent-thread")
+
+        assert resp.status_code == 404
+        body = resp.json()
+        assert body["success"] is False
+        assert "not found" in body["error"].lower()
--- a/backend/tests/integration/test_routing.py
+++ b/backend/tests/integration/test_routing.py
@@ -0,0 +1,371 @@
+"""Integration tests for multi-agent routing flow.
+
+Tests the full pipeline: intent classification -> supervisor routing ->
+agent execution -> response streaming, exercising cross-module integration
+with mocked LLM.
+
+Required by Phase 2 test plan:
+- Unit: intent classification accuracy
+- Unit: multi-intent sequential execution
+- Integration: complete multi-agent routing flow
+"""
+
+from __future__ import annotations
+
+import json
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+from app.callbacks import TokenUsageCallbackHandler
+from app.graph_context import GraphContext
+from app.intent import ClassificationResult, IntentTarget, LLMIntentClassifier
+from app.interrupt_manager import InterruptManager
+from app.registry import AgentConfig
+from app.session_manager import SessionManager
+from app.ws_context import WebSocketContext
+from app.ws_handler import dispatch_message
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+class AsyncIterHelper:
+    def __init__(self, items: list) -> None:
+        self._items = list(items)
+
+    def __aiter__(self):
+        return self
+
+    async def __anext__(self):
+        if not self._items:
+            raise StopAsyncIteration
+        return self._items.pop(0)
+
+
+class FakeWS:
+    def __init__(self) -> None:
+        self.sent: list[dict] = []
+
+    async def send_json(self, data: dict) -> None:
+        self.sent.append(data)
+
+
+def _chunk(content: str, node: str) -> tuple:
+    c = MagicMock()
+    c.content = content
+    c.tool_calls = []
+    return (c, {"langgraph_node": node})
+
+
+def _tool_chunk(name: str, args: dict, node: str) -> tuple:
+    c = MagicMock()
+    c.content = ""
+    c.tool_calls = [{"name": name, "args": args}]
+    return (c, {"langgraph_node": node})
+
+
+def _state(*, interrupt: bool = False, data: dict | None = None):
+    s = MagicMock()
+    if interrupt:
+        obj = MagicMock()
+        obj.value = data or {}
+        t = MagicMock()
+        t.interrupts = (obj,)
+        s.tasks = (t,)
+    else:
+        s.tasks = ()
+    return s
+
+
+AGENTS = (
+    AgentConfig(
+        name="order_lookup", description="Looks up orders",
+        permission="read", tools=["get_order_status", "get_tracking_info"],
+    ),
+    AgentConfig(
+        name="order_actions", description="Modifies orders",
+        permission="write", tools=["cancel_order"],
+    ),
+    AgentConfig(
+        name="discount", description="Applies discounts",
+        permission="write", tools=["apply_discount", "generate_coupon"],
+    ),
+    AgentConfig(
+        name="fallback", description="Handles unclear requests",
+        permission="read", tools=["fallback_respond"],
+    ),
+)
+
+
+def _make_classifier(result: ClassificationResult) -> AsyncMock:
+    """Create a mock classifier returning the given result."""
+    classifier = AsyncMock()
+    classifier.classify = AsyncMock(return_value=result)
+    return classifier
+
+
+def _make_graph_and_ctx(
+    classifier_result: ClassificationResult | None,
+    chunks: list,
+    state=None,
+) -> tuple[MagicMock, GraphContext]:
+    """Build a graph mock and GraphContext with optional intent classifier."""
+    graph = MagicMock()
+    graph.astream = MagicMock(return_value=AsyncIterHelper(list(chunks)))
+    graph.aget_state = AsyncMock(return_value=state or _state())
+
+    if classifier_result is not None:
+        classifier = _make_classifier(classifier_result)
+        mock_registry = MagicMock()
+        mock_registry.list_agents = MagicMock(return_value=AGENTS)
+        graph_ctx = GraphContext(
+            graph=graph, registry=mock_registry, intent_classifier=classifier,
+        )
+    else:
+        mock_registry = MagicMock()
+        mock_registry.list_agents = MagicMock(return_value=())
+        graph_ctx = GraphContext(
+            graph=graph, registry=mock_registry, intent_classifier=None,
+        )
+
+    return graph, graph_ctx
+
+
+async def _dispatch(graph_ctx: GraphContext, content: str, thread_id: str = "t1") -> list[dict]:
+    sm = SessionManager()
+    sm.touch(thread_id)
+    im = InterruptManager()
+    cb = TokenUsageCallbackHandler()
+    ws = FakeWS()
+    ws_ctx = WebSocketContext(
+        graph_ctx=graph_ctx, session_manager=sm,
+        callback_handler=cb, interrupt_manager=im,
+    )
+    raw = json.dumps({"type": "message", "thread_id": thread_id, "content": content})
+    await dispatch_message(ws, ws_ctx, raw)
+    return ws.sent
+
+
+# ---------------------------------------------------------------------------
+# Single-intent routing to each agent
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestSingleIntentRouting:
+    """Verify single-intent messages route to the correct agent."""
+
+    @pytest.mark.asyncio
+    async def test_routes_to_order_lookup(self) -> None:
+        result = ClassificationResult(
+            intents=(IntentTarget(
+                agent_name="order_lookup", confidence=0.95, reasoning="status query",
+            ),),
+        )
+        graph, graph_ctx = _make_graph_and_ctx(result, [
+            _tool_chunk("get_order_status", {"order_id": "1042"}, "order_lookup"),
+            _chunk("Order 1042 is shipped.", "order_lookup"),
+        ])
+
+        msgs = await _dispatch(graph_ctx, "What is the status of order 1042?")
+
+        tools = [m for m in msgs if m["type"] == "tool_call"]
+        assert len(tools) == 1
+        assert tools[0]["tool"] == "get_order_status"
+        assert tools[0]["agent"] == "order_lookup"
+
+        tokens = [m for m in msgs if m["type"] == "token"]
+        assert any("shipped" in t["content"] for t in tokens)
+
+    @pytest.mark.asyncio
+    async def test_routes_to_order_actions(self) -> None:
+        result = ClassificationResult(
+            intents=(IntentTarget(agent_name="order_actions", confidence=0.9, reasoning="cancel"),),
+        )
+        graph, graph_ctx = _make_graph_and_ctx(
+            result,
+            [_tool_chunk("cancel_order", {"order_id": "1042"}, "order_actions")],
+            state=_state(interrupt=True, data={"action": "cancel_order", "order_id": "1042"}),
+        )
+
+        msgs = await _dispatch(graph_ctx, "Cancel order 1042")
+
+        tools = [m for m in msgs if m["type"] == "tool_call"]
+        assert tools[0]["tool"] == "cancel_order"
+        assert tools[0]["agent"] == "order_actions"
+
+        interrupts = [m for m in msgs if m["type"] == "interrupt"]
+        assert len(interrupts) == 1
+
+    @pytest.mark.asyncio
+    async def test_routes_to_discount(self) -> None:
+        result = ClassificationResult(
+            intents=(IntentTarget(agent_name="discount", confidence=0.88, reasoning="coupon"),),
+        )
+        graph, graph_ctx = _make_graph_and_ctx(result, [
+            _tool_chunk("generate_coupon", {"discount_percent": 15, "expiry_days": 30}, "discount"),
+            _chunk("Here is your coupon: SAVE15-ABC12345", "discount"),
+        ])
+
+        msgs = await _dispatch(graph_ctx, "Give me a 15% coupon")
+
+        tools = [m for m in msgs if m["type"] == "tool_call"]
+        assert tools[0]["tool"] == "generate_coupon"
+        assert tools[0]["agent"] == "discount"
+
+    @pytest.mark.asyncio
+    async def test_routes_to_fallback(self) -> None:
+        result = ClassificationResult(
+            intents=(IntentTarget(agent_name="fallback", confidence=0.7, reasoning="general"),),
+        )
+        graph, graph_ctx = _make_graph_and_ctx(result, [
+            _chunk("I can help with order inquiries.", "fallback"),
+        ])
+
+        msgs = await _dispatch(graph_ctx, "What can you do?")
+
+        tokens = [m for m in msgs if m["type"] == "token"]
+        assert tokens[0]["agent"] == "fallback"
+
+
+# ---------------------------------------------------------------------------
+# Multi-intent routing
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestMultiIntentRouting:
+    """Verify multi-intent triggers sequential execution hint."""
+
+    @pytest.mark.asyncio
+    async def test_two_intents_inject_routing_hint(self) -> None:
+        result = ClassificationResult(
+            intents=(
+                IntentTarget(agent_name="order_actions", confidence=0.9, reasoning="cancel"),
+                IntentTarget(agent_name="discount", confidence=0.85, reasoning="discount"),
+            ),
+        )
+        graph, graph_ctx = _make_graph_and_ctx(result, [
+            _tool_chunk("cancel_order", {"order_id": "1042"}, "order_actions"),
+            _tool_chunk("apply_discount", {"order_id": "1042", "discount_percent": 10}, "discount"),
+        ])
+
+        sm = SessionManager()
+        sm.touch("t1")
+        im = InterruptManager()
+        cb = TokenUsageCallbackHandler()
+        ws = FakeWS()
+        ws_ctx = WebSocketContext(
+            graph_ctx=graph_ctx, session_manager=sm,
+            callback_handler=cb, interrupt_manager=im,
+        )
+
+        raw = json.dumps({
+            "type": "message",
+            "thread_id": "t1",
+            "content": "取消订单 1042 并给我一个 10% 折扣",
+        })
+        await dispatch_message(ws, ws_ctx, raw)
+
+        # Verify routing hint was injected
+        call_args = graph.astream.call_args[0][0]
+        msg_content = call_args["messages"][0].content
+        assert "[System:" in msg_content
+        assert "order_actions" in msg_content
+        assert "discount" in msg_content
+
+        # Both tool calls should appear
+        tools = [m for m in ws.sent if m["type"] == "tool_call"]
+        tool_names = {t["tool"] for t in tools}
+        assert "cancel_order" in tool_names
+        assert "apply_discount" in tool_names
+
+    @pytest.mark.asyncio
+    async def test_single_intent_no_routing_hint(self) -> None:
+        result = ClassificationResult(
+            intents=(IntentTarget(agent_name="order_lookup", confidence=0.95, reasoning="query"),),
+        )
+        graph, graph_ctx = _make_graph_and_ctx(result, [_chunk("Order shipped.", "order_lookup")])
+
+        sm = SessionManager()
+        sm.touch("t1")
+        im = InterruptManager()
+        cb = TokenUsageCallbackHandler()
+        ws = FakeWS()
+        ws_ctx = WebSocketContext(
+            graph_ctx=graph_ctx, session_manager=sm,
+            callback_handler=cb, interrupt_manager=im,
+        )
+
+        raw = json.dumps({"type": "message", "thread_id": "t1", "content": "查询订单 1042"})
+        await dispatch_message(ws, ws_ctx, raw)
+
+        msg_content = graph.astream.call_args[0][0]["messages"][0].content
+        assert "[System:" not in msg_content
+
+
+# ---------------------------------------------------------------------------
+# Ambiguity routing
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestAmbiguityRouting:
+    """Verify ambiguous intents produce clarification, not agent calls."""
+
+    @pytest.mark.asyncio
+    async def test_ambiguous_skips_graph_returns_clarification(self) -> None:
+        result = ClassificationResult(
+            intents=(),
+            is_ambiguous=True,
+            clarification_question="Could you please clarify what you need?",
+        )
+        graph, graph_ctx = _make_graph_and_ctx(result, [])
+
+        msgs = await _dispatch(graph_ctx, "嗯...")
+
+        clarifications = [m for m in msgs if m["type"] == "clarification"]
+        assert len(clarifications) == 1
+        assert "clarify" in clarifications[0]["message"]
+
+        # Graph should NOT have been called
+        graph.astream.assert_not_called()
+
+    @pytest.mark.asyncio
+    async def test_low_confidence_triggers_ambiguity(self) -> None:
+        """LLMIntentClassifier applies threshold -- low confidence -> ambiguous."""
+        raw_result = ClassificationResult(
+            intents=(IntentTarget(agent_name="fallback", confidence=0.2, reasoning="unclear"),),
+            is_ambiguous=False,
+        )
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(return_value=raw_result)
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        result = await classifier.classify("hmm", AGENTS)
+
+        assert result.is_ambiguous
+        assert result.clarification_question is not None
+
+
+# ---------------------------------------------------------------------------
+# No classifier fallback
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestNoClassifierFallback:
+    """Verify system works without intent classifier (falls back to supervisor prompt)."""
+
+    @pytest.mark.asyncio
+    async def test_no_classifier_routes_via_supervisor(self) -> None:
+        graph, graph_ctx = _make_graph_and_ctx(
+            classifier_result=None,
+            chunks=[_chunk("Order 1042 is shipped.", "order_lookup")],
+        )
+
+        msgs = await _dispatch(graph_ctx, "What is order 1042 status?")
+
+        tokens = [m for m in msgs if m["type"] == "token"]
+        assert len(tokens) == 1
+        completes = [m for m in msgs if m["type"] == "message_complete"]
+        assert len(completes) == 1
--- a/backend/tests/integration/test_session_interrupt_lifecycle.py
+++ b/backend/tests/integration/test_session_interrupt_lifecycle.py
@@ -0,0 +1,159 @@
+"""Integration tests for SessionManager + InterruptManager lifecycle.
+
+These tests exercise the in-memory managers together, verifying the full
+lifecycle of sessions and interrupts: creation, TTL sliding, interrupt
+registration/resolution, and expired-interrupt cleanup.
+
+No database required -- both managers are in-memory.
+"""
+
+from __future__ import annotations
+
+import time
+from unittest.mock import patch
+
+import pytest
+
+from app.interrupt_manager import InterruptManager
+from app.session_manager import SessionManager
+
+pytestmark = pytest.mark.integration
+
+
+class TestSessionInterruptLifecycle:
+    """Tests for the combined session + interrupt lifecycle."""
+
+    def test_create_session_register_interrupt_check_status(self) -> None:
+        """Full lifecycle: create session, register interrupt, verify both states."""
+        sm = SessionManager(session_ttl_seconds=3600)
+        im = InterruptManager(ttl_seconds=300)
+
+        # Create a session
+        state = sm.touch("thread-1")
+        assert state.thread_id == "thread-1"
+        assert not state.has_pending_interrupt
+        assert not sm.is_expired("thread-1")
+
+        # Register an interrupt
+        record = im.register("thread-1", "cancel_order", {"order_id": "1042"})
+        sm.extend_for_interrupt("thread-1")
+
+        assert im.has_pending("thread-1")
+        session_state = sm.get_state("thread-1")
+        assert session_state is not None
+        assert session_state.has_pending_interrupt
+
+        # Session should not expire while interrupt is pending
+        assert not sm.is_expired("thread-1")
+
+    def test_interrupt_expiry_after_ttl(self) -> None:
+        """Interrupt expires when TTL elapses, even if session is alive."""
+        im = InterruptManager(ttl_seconds=5)
+
+        record = im.register("thread-2", "refund", {"amount": 50})
+        assert im.has_pending("thread-2")
+
+        # Simulate time passing beyond TTL
+        with patch("app.interrupt_manager.time") as mock_time:
+            mock_time.time.return_value = record.created_at + 10
+            assert not im.has_pending("thread-2")
+
+            status = im.check_status("thread-2")
+            assert status is not None
+            assert status.is_expired
+            assert status.remaining_seconds == 0.0
+
+    def test_interrupt_resolve_flow(self) -> None:
+        """Resolving an interrupt removes it from pending and resets session."""
+        sm = SessionManager(session_ttl_seconds=3600)
+        im = InterruptManager(ttl_seconds=300)
+
+        sm.touch("thread-3")
+        im.register("thread-3", "delete_account", {"user_id": "u1"})
+        sm.extend_for_interrupt("thread-3")
+
+        # Verify pending state
+        assert im.has_pending("thread-3")
+        assert sm.get_state("thread-3").has_pending_interrupt
+
+        # Resolve
+        im.resolve("thread-3")
+        sm.resolve_interrupt("thread-3")
+
+        assert not im.has_pending("thread-3")
+        session_state = sm.get_state("thread-3")
+        assert session_state is not None
+        assert not session_state.has_pending_interrupt
+
+    def test_cleanup_expired_removes_old_interrupts(self) -> None:
+        """cleanup_expired removes only expired interrupts, keeping active ones."""
+        im = InterruptManager(ttl_seconds=10)
+
+        # Register two interrupts at different times
+        old_record = im.register("thread-old", "action_old", {})
+        new_record = im.register("thread-new", "action_new", {})
+
+        # Simulate time where only old one expired
+        with patch("app.interrupt_manager.time") as mock_time:
+            # Move old record's creation to the past
+            im._interrupts["thread-old"] = old_record.__class__(
+                interrupt_id=old_record.interrupt_id,
+                thread_id=old_record.thread_id,
+                action=old_record.action,
+                params=old_record.params,
+                created_at=time.time() - 20,
+                ttl_seconds=old_record.ttl_seconds,
+            )
+            mock_time.time.return_value = time.time()
+
+        expired = im.cleanup_expired()
+        assert len(expired) == 1
+        assert expired[0].thread_id == "thread-old"
+
+        # New one should still be pending
+        assert im.has_pending("thread-new")
+        assert not im.has_pending("thread-old")
+
+    def test_session_ttl_sliding_window(self) -> None:
+        """Touching a session resets the sliding window TTL."""
+        sm = SessionManager(session_ttl_seconds=3600)
+
+        state1 = sm.touch("thread-5")
+        first_activity = state1.last_activity
+
+        time.sleep(0.01)
+        state2 = sm.touch("thread-5")
+        second_activity = state2.last_activity
+
+        assert second_activity > first_activity
+        assert not sm.is_expired("thread-5")
+
+    def test_session_expires_after_ttl_without_activity(self) -> None:
+        """Session expires when TTL passes without a touch or interrupt."""
+        sm = SessionManager(session_ttl_seconds=0)
+        sm.touch("thread-6")
+
+        # TTL is 0 so session is immediately expired
+        assert sm.is_expired("thread-6")
+
+    def test_pending_interrupt_prevents_session_expiry(self) -> None:
+        """A session with pending interrupt does not expire even with TTL=0."""
+        sm = SessionManager(session_ttl_seconds=0)
+        sm.touch("thread-7")
+        sm.extend_for_interrupt("thread-7")
+
+        # Even with TTL=0, session should not expire because of pending interrupt
+        assert not sm.is_expired("thread-7")
+
+    def test_retry_prompt_for_expired_interrupt(self) -> None:
+        """InterruptManager generates a retry prompt for expired interrupts."""
+        im = InterruptManager(ttl_seconds=300)
+        record = im.register("thread-8", "cancel_order", {"order_id": "1042"})
+
+        prompt = im.generate_retry_prompt(record)
+
+        assert prompt["type"] == "interrupt_expired"
+        assert prompt["thread_id"] == "thread-8"
+        assert "cancel_order" in prompt["action"]
+        assert "cancel_order" in prompt["message"]
+        assert "expired" in prompt["message"].lower()
--- a/backend/tests/integration/test_websocket.py
+++ b/backend/tests/integration/test_websocket.py
@@ -0,0 +1,360 @@
+"""Integration tests for WebSocket message flow.
+
+These tests exercise dispatch_message end-to-end with a mocked LangGraph
+graph, verifying streaming, interrupt approval/rejection, session TTL,
+and interrupt TTL expiration through the full message handling pipeline.
+"""
+
+from __future__ import annotations
+
+import json
+import time
+from typing import Any
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+
+from app.callbacks import TokenUsageCallbackHandler
+from app.graph_context import GraphContext
+from app.interrupt_manager import InterruptManager
+from app.session_manager import SessionManager
+from app.ws_context import WebSocketContext
+from app.ws_handler import dispatch_message
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+class AsyncIterHelper:
+    """Make a list behave as an async iterator."""
+
+    def __init__(self, items: list) -> None:
+        self._items = list(items)
+
+    def __aiter__(self):
+        return self
+
+    async def __anext__(self):
+        if not self._items:
+            raise StopAsyncIteration
+        return self._items.pop(0)
+
+
+class FakeWS:
+    """Fake WebSocket that records sent messages."""
+
+    def __init__(self) -> None:
+        self.sent: list[dict] = []
+
+    async def send_json(self, data: dict) -> None:
+        self.sent.append(data)
+
+
+def _chunk(content: str, node: str = "order_lookup") -> tuple:
+    c = MagicMock()
+    c.content = content
+    c.tool_calls = []
+    return (c, {"langgraph_node": node})
+
+
+def _tool_chunk(name: str, args: dict, node: str = "order_lookup") -> tuple:
+    c = MagicMock()
+    c.content = ""
+    c.tool_calls = [{"name": name, "args": args}]
+    return (c, {"langgraph_node": node})
+
+
+def _state(*, interrupt: bool = False, data: dict | None = None) -> Any:
+    s = MagicMock()
+    if interrupt:
+        obj = MagicMock()
+        obj.value = data or {"action": "cancel_order", "order_id": "1042"}
+        t = MagicMock()
+        t.interrupts = (obj,)
+        s.tasks = (t,)
+    else:
+        s.tasks = ()
+    return s
+
+
+def _graph(
+    chunks: list | None = None,
+    st: Any = None,
+    resume_chunks: list | None = None,
+) -> MagicMock:
+    g = MagicMock()
+
+    if st is None:
+        st = _state()
+
+    streams = [chunks or [], resume_chunks or []]
+    idx = {"n": 0}
+
+    def make_stream(*a, **kw):
+        i = min(idx["n"], len(streams) - 1)
+        idx["n"] += 1
+        return AsyncIterHelper(list(streams[i]))
+
+    g.astream = MagicMock(side_effect=make_stream)
+    g.aget_state = AsyncMock(return_value=st)
+    return g
+
+
+def _make_graph_ctx(graph: MagicMock | None = None) -> GraphContext:
+    g = graph or _graph()
+    registry = MagicMock()
+    registry.list_agents = MagicMock(return_value=())
+    return GraphContext(graph=g, registry=registry, intent_classifier=None)
+
+
+def _setup(
+    graph=None,
+    session_ttl: int = 1800,
+    interrupt_ttl: int = 1800,
+    thread_id: str = "t1",
+    touch: bool = True,
+):
+    """Create test dependencies. Pre-touches session by default."""
+    g = graph or _graph()
+    graph_ctx = _make_graph_ctx(g)
+    sm = SessionManager(session_ttl_seconds=session_ttl)
+    im = InterruptManager(ttl_seconds=interrupt_ttl)
+    cb = TokenUsageCallbackHandler()
+    ws = FakeWS()
+    ws_ctx = WebSocketContext(
+        graph_ctx=graph_ctx, session_manager=sm,
+        callback_handler=cb, interrupt_manager=im,
+    )
+    if touch:
+        sm.touch(thread_id)
+    return g, sm, im, cb, ws, ws_ctx
+
+
+async def _send(ws, ws_ctx, *, thread_id="t1", content="hello", msg_type="message"):
+    raw = json.dumps({"type": msg_type, "thread_id": thread_id, "content": content})
+    await dispatch_message(ws, ws_ctx, raw)
+
+
+async def _respond(ws, ws_ctx, *, thread_id="t1", approved=True):
+    raw = json.dumps({"type": "interrupt_response", "thread_id": thread_id, "approved": approved})
+    await dispatch_message(ws, ws_ctx, raw)
+
+
+# ---------------------------------------------------------------------------
+# Tests
+# ---------------------------------------------------------------------------
+
+@pytest.mark.integration
+class TestWebSocketHappyPath:
+    @pytest.mark.asyncio
+    async def test_send_message_receives_tokens_and_complete(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup(
+            graph=_graph(chunks=[_chunk("Order 1042 is "), _chunk("shipped.")])
+        )
+        await _send(ws, ws_ctx, content="What is the status of order 1042?")
+
+        tokens = [m for m in ws.sent if m["type"] == "token"]
+        assert len(tokens) == 2
+        assert tokens[0]["content"] == "Order 1042 is "
+        assert tokens[0]["agent"] == "order_lookup"
+        assert tokens[1]["content"] == "shipped."
+
+        completes = [m for m in ws.sent if m["type"] == "message_complete"]
+        assert len(completes) == 1
+        assert completes[0]["thread_id"] == "t1"
+
+    @pytest.mark.asyncio
+    async def test_tool_call_streamed(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup(
+            graph=_graph(chunks=[
+                _tool_chunk("get_order_status", {"order_id": "1042"}),
+                _chunk("Order shipped."),
+            ])
+        )
+        await _send(ws, ws_ctx, content="Check order 1042")
+
+        tools = [m for m in ws.sent if m["type"] == "tool_call"]
+        assert len(tools) == 1
+        assert tools[0]["tool"] == "get_order_status"
+        assert tools[0]["args"] == {"order_id": "1042"}
+
+    @pytest.mark.asyncio
+    async def test_multiple_messages_same_session(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup()
+        for i in range(3):
+            await _send(ws, ws_ctx, content=f"msg {i}")
+
+        completes = [m for m in ws.sent if m["type"] == "message_complete"]
+        assert len(completes) == 3
+
+
+@pytest.mark.integration
+class TestWebSocketInterruptApproval:
+    @pytest.mark.asyncio
+    async def test_interrupt_then_approve(self) -> None:
+        st_int = _state(interrupt=True, data={"action": "cancel_order", "order_id": "1042"})
+        resume = [_chunk("Order 1042 cancelled.", "order_actions")]
+        g = _graph(chunks=[], st=st_int, resume_chunks=resume)
+        g_, sm, im, cb, ws, ws_ctx = _setup(graph=g)
+
+        # Send message -> triggers interrupt
+        await _send(ws, ws_ctx, content="Cancel order 1042")
+
+        interrupts = [m for m in ws.sent if m["type"] == "interrupt"]
+        assert len(interrupts) == 1
+        assert interrupts[0]["action"] == "cancel_order"
+        assert interrupts[0]["thread_id"] == "t1"
+        assert im.has_pending("t1")
+
+        # Approve
+        ws.sent.clear()
+        await _respond(ws, ws_ctx, approved=True)
+
+        tokens = [m for m in ws.sent if m["type"] == "token"]
+        assert len(tokens) == 1
+        assert "cancelled" in tokens[0]["content"]
+
+        completes = [m for m in ws.sent if m["type"] == "message_complete"]
+        assert len(completes) == 1
+        assert not im.has_pending("t1")
+
+    @pytest.mark.asyncio
+    async def test_interrupt_then_reject(self) -> None:
+        st_int = _state(interrupt=True)
+        resume = [_chunk("Order remains active.", "order_actions")]
+        g = _graph(chunks=[], st=st_int, resume_chunks=resume)
+        g_, sm, im, cb, ws, ws_ctx = _setup(graph=g)
+
+        await _send(ws, ws_ctx, content="Cancel order 1042")
+        ws.sent.clear()
+
+        await _respond(ws, ws_ctx, approved=False)
+
+        tokens = [m for m in ws.sent if m["type"] == "token"]
+        assert "remains active" in tokens[0]["content"]
+
+
+@pytest.mark.integration
+class TestWebSocketSessionTTL:
+    @pytest.mark.asyncio
+    async def test_expired_session_returns_error(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup(session_ttl=0)
+        # Session was touched in _setup, but TTL is 0 so it's already expired
+        await _send(ws, ws_ctx, content="hello")
+        assert ws.sent[0]["type"] == "error"
+        assert "expired" in ws.sent[0]["message"].lower()
+
+    @pytest.mark.asyncio
+    async def test_new_session_not_expired(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup(session_ttl=3600)
+        await _send(ws, ws_ctx, content="hello")
+        completes = [m for m in ws.sent if m["type"] == "message_complete"]
+        assert len(completes) == 1
+
+    @pytest.mark.asyncio
+    async def test_sliding_window_resets_on_message(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup(session_ttl=3600)
+
+        await _send(ws, ws_ctx, content="hello")
+        first_activity = sm.get_state("t1").last_activity
+
+        time.sleep(0.01)
+        await _send(ws, ws_ctx, content="hello again")
+        second_activity = sm.get_state("t1").last_activity
+
+        assert second_activity > first_activity
+
+    @pytest.mark.asyncio
+    async def test_interrupt_extends_session_ttl(self) -> None:
+        st_int = _state(interrupt=True)
+        g = _graph(chunks=[], st=st_int)
+        g_, sm, im, cb, ws, ws_ctx = _setup(graph=g, session_ttl=3600)
+
+        await _send(ws, ws_ctx, content="cancel order")
+
+        state = sm.get_state("t1")
+        assert state is not None
+        assert state.has_pending_interrupt
+        assert not sm.is_expired("t1")
+
+
+@pytest.mark.integration
+class TestWebSocketValidation:
+    @pytest.mark.asyncio
+    async def test_invalid_json(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup()
+        await dispatch_message(ws, ws_ctx, "not json")
+        assert ws.sent[0]["type"] == "error"
+        assert "Invalid JSON" in ws.sent[0]["message"]
+
+    @pytest.mark.asyncio
+    async def test_missing_thread_id(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup()
+        raw = json.dumps({"type": "message", "content": "hi"})
+        await dispatch_message(ws, ws_ctx, raw)
+        assert ws.sent[0]["type"] == "error"
+        assert "thread_id" in ws.sent[0]["message"]
+
+    @pytest.mark.asyncio
+    async def test_invalid_thread_id_format(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup()
+        raw = json.dumps({"type": "message", "thread_id": "../../etc/passwd", "content": "hi"})
+        await dispatch_message(ws, ws_ctx, raw)
+        assert ws.sent[0]["type"] == "error"
+
+    @pytest.mark.asyncio
+    async def test_missing_content(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup()
+        raw = json.dumps({"type": "message", "thread_id": "t1"})
+        await dispatch_message(ws, ws_ctx, raw)
+        assert ws.sent[0]["type"] == "error"
+
+    @pytest.mark.asyncio
+    async def test_unknown_message_type(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup()
+        raw = json.dumps({"type": "foobar", "thread_id": "t1"})
+        await dispatch_message(ws, ws_ctx, raw)
+        assert ws.sent[0]["type"] == "error"
+        assert "Unknown" in ws.sent[0]["message"]
+
+    @pytest.mark.asyncio
+    async def test_message_too_large(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup()
+        await dispatch_message(ws, ws_ctx, "x" * 40_000)
+        assert ws.sent[0]["type"] == "error"
+        assert "too large" in ws.sent[0]["message"].lower()
+
+    @pytest.mark.asyncio
+    async def test_content_too_long(self) -> None:
+        g, sm, im, cb, ws, ws_ctx = _setup()
+        raw = json.dumps({"type": "message", "thread_id": "t1", "content": "x" * 10001})
+        await dispatch_message(ws, ws_ctx, raw)
+        assert ws.sent[0]["type"] == "error"
+        assert "too long" in ws.sent[0]["message"].lower()
+
+
+@pytest.mark.integration
+class TestWebSocketInterruptTTL:
+    @pytest.mark.asyncio
+    async def test_expired_interrupt_sends_retry_prompt(self) -> None:
+        st_int = _state(interrupt=True, data={"action": "cancel_order", "order_id": "1042"})
+        g = _graph(chunks=[], st=st_int)
+        g_, sm, im, cb, ws, ws_ctx = _setup(graph=g, interrupt_ttl=5)
+
+        # Trigger interrupt
+        await _send(ws, ws_ctx, content="Cancel order 1042")
+
+        interrupts = [m for m in ws.sent if m["type"] == "interrupt"]
+        assert len(interrupts) == 1
+
+        # Expire the interrupt
+        record = im._interrupts["t1"]
+        ws.sent.clear()
+
+        with patch("app.interrupt_manager.time") as mock_time:
+            mock_time.time.return_value = record.created_at + 10
+            await _respond(ws, ws_ctx, approved=True)
+
+        assert ws.sent[0]["type"] == "interrupt_expired"
+        assert "cancel_order" in ws.sent[0]["message"]
+        assert ws.sent[0]["thread_id"] == "t1"
--- a/backend/tests/unit/analytics/init.py
+++ b/backend/tests/unit/analytics/init.py
@@ -0,0 +1 @@
+"""Unit tests for app.analytics module."""
--- a/backend/tests/unit/analytics/test_api.py
+++ b/backend/tests/unit/analytics/test_api.py
@@ -0,0 +1,149 @@
+"""Unit tests for app.analytics.api."""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+from fastapi import FastAPI
+from fastapi.testclient import TestClient
+
+pytestmark = pytest.mark.unit
+
+
+def _build_app() -> FastAPI:
+    from app.analytics.api import router
+
+    app = FastAPI()
+    app.include_router(router)
+    return app
+
+
+def _make_mock_pool() -> MagicMock:
+    mock_conn = AsyncMock()
+    mock_ctx = AsyncMock()
+    mock_ctx.__aenter__ = AsyncMock(return_value=mock_conn)
+    mock_ctx.__aexit__ = AsyncMock(return_value=None)
+    mock_pool = MagicMock()
+    mock_pool.connection.return_value = mock_ctx
+    return mock_pool
+
+
+def _make_analytics_result() -> object:
+    from app.analytics.models import AgentUsage, AnalyticsResult, InterruptStats
+
+    return AnalyticsResult(
+        range="7d",
+        total_conversations=50,
+        resolution_rate=0.8,
+        escalation_rate=0.1,
+        avg_turns_per_conversation=3.5,
+        avg_cost_per_conversation_usd=0.02,
+        agent_usage=(AgentUsage(agent="order_agent", count=30, percentage=60.0),),
+        interrupt_stats=InterruptStats(total=5, approved=4, rejected=1, expired=0),
+    )
+
+
+def _get_analytics(app: FastAPI, path: str = "/api/v1/analytics", **patch_kwargs: object) -> object:
+    """Helper: patch get_analytics, make request, return (response, mock)."""
+    analytics_result = _make_analytics_result()
+    with (
+        patch("app.analytics.api.get_analytics", return_value=analytics_result) as mock_ga,
+        TestClient(app) as client,
+    ):
+        resp = client.get(path)
+    return resp, mock_ga
+
+
+class TestAnalyticsEndpoint:
+    def test_returns_200_with_default_range(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool()
+        resp, _ = _get_analytics(app)
+
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["success"] is True
+        assert body["error"] is None
+        assert body["data"]["range"] == "7d"
+
+    def test_returns_correct_analytics_structure(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool()
+        resp, _ = _get_analytics(app)
+
+        data = resp.json()["data"]
+        assert "total_conversations" in data
+        assert "resolution_rate" in data
+        assert "escalation_rate" in data
+        assert "avg_turns_per_conversation" in data
+        assert "avg_cost_per_conversation_usd" in data
+        assert "agent_usage" in data
+        assert "interrupt_stats" in data
+
+    def test_custom_range_7d(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool()
+        resp, mock_ga = _get_analytics(app, "/api/v1/analytics?range=7d")
+
+        assert resp.status_code == 200
+        mock_ga.assert_called_once()
+        call_kwargs = mock_ga.call_args
+        assert call_kwargs[1]["range_days"] == 7 or call_kwargs[0][1] == 7
+
+    def test_custom_range_30d(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool()
+        resp, mock_ga = _get_analytics(app, "/api/v1/analytics?range=30d")
+
+        assert resp.status_code == 200
+        call_kwargs = mock_ga.call_args
+        assert call_kwargs[1].get("range_days") == 30 or (
+            len(call_kwargs[0]) > 1 and call_kwargs[0][1] == 30
+        )
+
+    def test_invalid_range_format_returns_400(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool()
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/analytics?range=invalid")
+
+        assert resp.status_code == 400
+
+    def test_range_without_d_suffix_returns_400(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool()
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/analytics?range=7")
+
+        assert resp.status_code == 400
+
+    def test_agent_usage_in_response(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool()
+        resp, _ = _get_analytics(app)
+
+        data = resp.json()["data"]
+        assert len(data["agent_usage"]) == 1
+        assert data["agent_usage"][0]["agent"] == "order_agent"
+
+    def test_interrupt_stats_in_response(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool()
+        resp, _ = _get_analytics(app)
+
+        data = resp.json()["data"]
+        assert data["interrupt_stats"]["total"] == 5
+        assert data["interrupt_stats"]["approved"] == 4
+
+    def test_envelope_format(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool()
+        resp, _ = _get_analytics(app)
+
+        body = resp.json()
+        assert "success" in body
+        assert "data" in body
+        assert "error" in body
--- a/backend/tests/unit/analytics/test_event_recorder.py
+++ b/backend/tests/unit/analytics/test_event_recorder.py
@@ -0,0 +1,155 @@
+"""Unit tests for app.analytics.event_recorder."""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+pytestmark = pytest.mark.unit
+
+
+class TestAnalyticsRecorderProtocol:
+    def test_postgres_recorder_implements_protocol(self) -> None:
+        from app.analytics.event_recorder import PostgresAnalyticsRecorder
+
+        mock_pool = MagicMock()
+        recorder = PostgresAnalyticsRecorder(pool=mock_pool)
+        # Runtime check: has record method
+        assert hasattr(recorder, "record")
+        assert callable(recorder.record)
+
+    def test_noop_recorder_implements_protocol(self) -> None:
+        from app.analytics.event_recorder import NoOpAnalyticsRecorder
+
+        recorder = NoOpAnalyticsRecorder()
+        assert hasattr(recorder, "record")
+        assert callable(recorder.record)
+
+
+class TestNoOpAnalyticsRecorder:
+    @pytest.mark.asyncio
+    async def test_record_does_nothing(self) -> None:
+        from app.analytics.event_recorder import NoOpAnalyticsRecorder
+
+        recorder = NoOpAnalyticsRecorder()
+        # Should not raise
+        await recorder.record(
+            thread_id="t1",
+            event_type="tool_call",
+            agent_name="order_agent",
+            tool_name="get_order",
+            tokens_used=50,
+            cost_usd=0.001,
+        )
+
+    @pytest.mark.asyncio
+    async def test_record_with_all_params(self) -> None:
+        from app.analytics.event_recorder import NoOpAnalyticsRecorder
+
+        recorder = NoOpAnalyticsRecorder()
+        await recorder.record(
+            thread_id="t1",
+            event_type="agent_response",
+            agent_name="fallback",
+            tool_name=None,
+            tokens_used=100,
+            cost_usd=0.002,
+            duration_ms=150,
+            success=True,
+            error_message=None,
+            metadata={"extra": "data"},
+        )
+
+    @pytest.mark.asyncio
+    async def test_record_minimal_params(self) -> None:
+        from app.analytics.event_recorder import NoOpAnalyticsRecorder
+
+        recorder = NoOpAnalyticsRecorder()
+        # Only required params
+        await recorder.record(thread_id="t1", event_type="conversation_start")
+
+
+class TestPostgresAnalyticsRecorder:
+    @pytest.mark.asyncio
+    async def test_record_executes_insert(self) -> None:
+        from app.analytics.event_recorder import PostgresAnalyticsRecorder
+
+        mock_conn = AsyncMock()
+        mock_ctx = AsyncMock()
+        mock_ctx.__aenter__ = AsyncMock(return_value=mock_conn)
+        mock_ctx.__aexit__ = AsyncMock(return_value=None)
+        mock_pool = MagicMock()
+        mock_pool.connection.return_value = mock_ctx
+
+        recorder = PostgresAnalyticsRecorder(pool=mock_pool)
+        await recorder.record(
+            thread_id="t1",
+            event_type="tool_call",
+            agent_name="order_agent",
+            tokens_used=50,
+            cost_usd=0.001,
+        )
+        mock_conn.execute.assert_awaited_once()
+        call_args = mock_conn.execute.call_args
+        sql = call_args[0][0]
+        assert "INSERT INTO analytics_events" in sql
+
+    @pytest.mark.asyncio
+    async def test_record_passes_correct_params(self) -> None:
+        from app.analytics.event_recorder import PostgresAnalyticsRecorder
+
+        mock_conn = AsyncMock()
+        mock_ctx = AsyncMock()
+        mock_ctx.__aenter__ = AsyncMock(return_value=mock_conn)
+        mock_ctx.__aexit__ = AsyncMock(return_value=None)
+        mock_pool = MagicMock()
+        mock_pool.connection.return_value = mock_ctx
+
+        recorder = PostgresAnalyticsRecorder(pool=mock_pool)
+        await recorder.record(
+            thread_id="thread-xyz",
+            event_type="agent_response",
+            agent_name="discount_agent",
+            tool_name="apply_discount",
+            tokens_used=75,
+            cost_usd=0.002,
+            duration_ms=300,
+            success=True,
+            error_message=None,
+            metadata={"promo": "10PCT"},
+        )
+        call_args = mock_conn.execute.call_args
+        params = call_args[0][1]
+        assert params["thread_id"] == "thread-xyz"
+        assert params["event_type"] == "agent_response"
+        assert params["agent_name"] == "discount_agent"
+        assert params["tokens_used"] == 75
+
+    @pytest.mark.asyncio
+    async def test_record_stores_metadata_as_dict(self) -> None:
+        from app.analytics.event_recorder import PostgresAnalyticsRecorder
+
+        mock_conn = AsyncMock()
+        mock_ctx = AsyncMock()
+        mock_ctx.__aenter__ = AsyncMock(return_value=mock_conn)
+        mock_ctx.__aexit__ = AsyncMock(return_value=None)
+        mock_pool = MagicMock()
+        mock_pool.connection.return_value = mock_ctx
+
+        recorder = PostgresAnalyticsRecorder(pool=mock_pool)
+        await recorder.record(
+            thread_id="t1",
+            event_type="tool_call",
+            metadata={"key": "val"},
+        )
+        call_args = mock_conn.execute.call_args
+        params = call_args[0][1]
+        # PostgresAnalyticsRecorder wraps metadata with psycopg Json() adapter.
+        # Unwrap to compare the inner dict.
+        from psycopg.types.json import Json
+
+        meta = params["metadata"]
+        if isinstance(meta, Json):
+            meta = meta.obj
+        assert meta == {"key": "val"}
--- a/backend/tests/unit/analytics/test_models.py
+++ b/backend/tests/unit/analytics/test_models.py
@@ -0,0 +1,106 @@
+"""Unit tests for app.analytics.models."""
+
+from __future__ import annotations
+
+import pytest
+
+pytestmark = pytest.mark.unit
+
+
+class TestAgentUsage:
+    def test_agent_usage_construction(self) -> None:
+        from app.analytics.models import AgentUsage
+
+        au = AgentUsage(agent="order_agent", count=10, percentage=50.0)
+        assert au.agent == "order_agent"
+        assert au.count == 10
+        assert au.percentage == 50.0
+
+    def test_agent_usage_is_frozen(self) -> None:
+        from app.analytics.models import AgentUsage
+
+        au = AgentUsage(agent="a", count=1, percentage=100.0)
+        with pytest.raises((AttributeError, TypeError)):
+            au.count = 2  # type: ignore[misc]
+
+
+class TestInterruptStats:
+    def test_interrupt_stats_defaults(self) -> None:
+        from app.analytics.models import InterruptStats
+
+        stats = InterruptStats()
+        assert stats.total == 0
+        assert stats.approved == 0
+        assert stats.rejected == 0
+        assert stats.expired == 0
+
+    def test_interrupt_stats_custom_values(self) -> None:
+        from app.analytics.models import InterruptStats
+
+        stats = InterruptStats(total=10, approved=7, rejected=2, expired=1)
+        assert stats.total == 10
+        assert stats.approved == 7
+        assert stats.rejected == 2
+        assert stats.expired == 1
+
+    def test_interrupt_stats_is_frozen(self) -> None:
+        from app.analytics.models import InterruptStats
+
+        stats = InterruptStats()
+        with pytest.raises((AttributeError, TypeError)):
+            stats.total = 5  # type: ignore[misc]
+
+
+class TestAnalyticsResult:
+    def test_analytics_result_construction(self) -> None:
+        from app.analytics.models import AgentUsage, AnalyticsResult, InterruptStats
+
+        result = AnalyticsResult(
+            range="7d",
+            total_conversations=100,
+            resolution_rate=0.85,
+            escalation_rate=0.05,
+            avg_turns_per_conversation=4.2,
+            avg_cost_per_conversation_usd=0.03,
+            agent_usage=(AgentUsage(agent="order_agent", count=60, percentage=60.0),),
+            interrupt_stats=InterruptStats(total=5, approved=4, rejected=1, expired=0),
+        )
+        assert result.range == "7d"
+        assert result.total_conversations == 100
+        assert result.resolution_rate == 0.85
+        assert result.escalation_rate == 0.05
+        assert result.avg_turns_per_conversation == 4.2
+        assert result.avg_cost_per_conversation_usd == 0.03
+        assert len(result.agent_usage) == 1
+        assert result.interrupt_stats.total == 5
+
+    def test_analytics_result_is_frozen(self) -> None:
+        from app.analytics.models import AnalyticsResult, InterruptStats
+
+        result = AnalyticsResult(
+            range="7d",
+            total_conversations=0,
+            resolution_rate=0.0,
+            escalation_rate=0.0,
+            avg_turns_per_conversation=0.0,
+            avg_cost_per_conversation_usd=0.0,
+            agent_usage=(),
+            interrupt_stats=InterruptStats(),
+        )
+        with pytest.raises((AttributeError, TypeError)):
+            result.range = "30d"  # type: ignore[misc]
+
+    def test_analytics_result_empty_agent_usage(self) -> None:
+        from app.analytics.models import AnalyticsResult, InterruptStats
+
+        result = AnalyticsResult(
+            range="7d",
+            total_conversations=0,
+            resolution_rate=0.0,
+            escalation_rate=0.0,
+            avg_turns_per_conversation=0.0,
+            avg_cost_per_conversation_usd=0.0,
+            agent_usage=(),
+            interrupt_stats=InterruptStats(),
+        )
+        assert result.agent_usage == ()
--- a/backend/tests/unit/analytics/test_queries.py
+++ b/backend/tests/unit/analytics/test_queries.py
@@ -0,0 +1,249 @@
+"""Unit tests for app.analytics.queries."""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+pytestmark = pytest.mark.unit
+
+
+def _make_pool_with_fetchone(result: dict | None) -> MagicMock:
+    mock_cursor = AsyncMock()
+    mock_cursor.fetchone = AsyncMock(return_value=result)
+    mock_conn = AsyncMock()
+    mock_conn.execute = AsyncMock(return_value=mock_cursor)
+    mock_ctx = AsyncMock()
+    mock_ctx.__aenter__ = AsyncMock(return_value=mock_conn)
+    mock_ctx.__aexit__ = AsyncMock(return_value=None)
+    mock_pool = MagicMock()
+    mock_pool.connection.return_value = mock_ctx
+    return mock_pool
+
+
+def _make_pool_with_fetchall(result: list[dict]) -> MagicMock:
+    mock_cursor = AsyncMock()
+    mock_cursor.fetchall = AsyncMock(return_value=result)
+    mock_conn = AsyncMock()
+    mock_conn.execute = AsyncMock(return_value=mock_cursor)
+    mock_ctx = AsyncMock()
+    mock_ctx.__aenter__ = AsyncMock(return_value=mock_conn)
+    mock_ctx.__aexit__ = AsyncMock(return_value=None)
+    mock_pool = MagicMock()
+    mock_pool.connection.return_value = mock_ctx
+    return mock_pool
+
+
+class TestResolutionRate:
+    @pytest.mark.asyncio
+    async def test_returns_float(self) -> None:
+        from app.analytics.queries import resolution_rate
+
+        pool = _make_pool_with_fetchone({"rate": 0.85})
+        result = await resolution_rate(pool, range_days=7)
+        assert isinstance(result, float)
+
+    @pytest.mark.asyncio
+    async def test_zero_state_returns_zero(self) -> None:
+        from app.analytics.queries import resolution_rate
+
+        pool = _make_pool_with_fetchone(None)
+        result = await resolution_rate(pool, range_days=7)
+        assert result == 0.0
+
+    @pytest.mark.asyncio
+    async def test_returns_correct_value(self) -> None:
+        from app.analytics.queries import resolution_rate
+
+        pool = _make_pool_with_fetchone({"rate": 0.75})
+        result = await resolution_rate(pool, range_days=7)
+        assert result == 0.75
+
+
+class TestAgentUsageQuery:
+    @pytest.mark.asyncio
+    async def test_returns_tuple(self) -> None:
+        from app.analytics.queries import agent_usage
+
+        pool = _make_pool_with_fetchall([])
+        result = await agent_usage(pool, range_days=7)
+        assert isinstance(result, tuple)
+
+    @pytest.mark.asyncio
+    async def test_empty_state_returns_empty_tuple(self) -> None:
+        from app.analytics.queries import agent_usage
+
+        pool = _make_pool_with_fetchall([])
+        result = await agent_usage(pool, range_days=7)
+        assert result == ()
+
+    @pytest.mark.asyncio
+    async def test_maps_rows_to_agent_usage_objects(self) -> None:
+        from app.analytics.models import AgentUsage
+        from app.analytics.queries import agent_usage
+
+        pool = _make_pool_with_fetchall([
+            {"agent": "order_agent", "count": 10, "percentage": 66.7},
+            {"agent": "discount_agent", "count": 5, "percentage": 33.3},
+        ])
+        result = await agent_usage(pool, range_days=7)
+        assert len(result) == 2
+        assert isinstance(result[0], AgentUsage)
+        assert result[0].agent == "order_agent"
+        assert result[0].count == 10
+
+
+class TestEscalationRate:
+    @pytest.mark.asyncio
+    async def test_returns_float(self) -> None:
+        from app.analytics.queries import escalation_rate
+
+        pool = _make_pool_with_fetchone({"rate": 0.05})
+        result = await escalation_rate(pool, range_days=7)
+        assert isinstance(result, float)
+
+    @pytest.mark.asyncio
+    async def test_zero_state_returns_zero(self) -> None:
+        from app.analytics.queries import escalation_rate
+
+        pool = _make_pool_with_fetchone(None)
+        result = await escalation_rate(pool, range_days=7)
+        assert result == 0.0
+
+
+class TestCostPerConversation:
+    @pytest.mark.asyncio
+    async def test_returns_float(self) -> None:
+        from app.analytics.queries import cost_per_conversation
+
+        pool = _make_pool_with_fetchone({"avg_cost": 0.03})
+        result = await cost_per_conversation(pool, range_days=7)
+        assert isinstance(result, float)
+
+    @pytest.mark.asyncio
+    async def test_zero_state_returns_zero(self) -> None:
+        from app.analytics.queries import cost_per_conversation
+
+        pool = _make_pool_with_fetchone(None)
+        result = await cost_per_conversation(pool, range_days=7)
+        assert result == 0.0
+
+
+class TestInterruptStatsQuery:
+    @pytest.mark.asyncio
+    async def test_returns_interrupt_stats(self) -> None:
+        from app.analytics.models import InterruptStats
+        from app.analytics.queries import interrupt_stats
+
+        pool = _make_pool_with_fetchone(
+            {"total": 10, "approved": 7, "rejected": 2, "expired": 1}
+        )
+        result = await interrupt_stats(pool, range_days=7)
+        assert isinstance(result, InterruptStats)
+        assert result.total == 10
+        assert result.approved == 7
+
+    @pytest.mark.asyncio
+    async def test_zero_state_returns_zeros(self) -> None:
+        from app.analytics.models import InterruptStats
+        from app.analytics.queries import interrupt_stats
+
+        pool = _make_pool_with_fetchone(None)
+        result = await interrupt_stats(pool, range_days=7)
+        assert isinstance(result, InterruptStats)
+        assert result.total == 0
+        assert result.approved == 0
+        assert result.rejected == 0
+        assert result.expired == 0
+
+
+class TestTotalConversations:
+    @pytest.mark.asyncio
+    async def test_returns_count(self) -> None:
+        from app.analytics.queries import _total_conversations
+
+        pool = _make_pool_with_fetchone({"total": 42})
+        result = await _total_conversations(pool, range_days=7)
+        assert result == 42
+
+    @pytest.mark.asyncio
+    async def test_zero_state_returns_zero(self) -> None:
+        from app.analytics.queries import _total_conversations
+
+        pool = _make_pool_with_fetchone(None)
+        result = await _total_conversations(pool, range_days=7)
+        assert result == 0
+
+
+class TestAvgTurns:
+    @pytest.mark.asyncio
+    async def test_returns_float(self) -> None:
+        from app.analytics.queries import _avg_turns
+
+        pool = _make_pool_with_fetchone({"avg_turns": 3.5})
+        result = await _avg_turns(pool, range_days=7)
+        assert result == 3.5
+
+    @pytest.mark.asyncio
+    async def test_zero_state_returns_zero(self) -> None:
+        from app.analytics.queries import _avg_turns
+
+        pool = _make_pool_with_fetchone(None)
+        result = await _avg_turns(pool, range_days=7)
+        assert result == 0.0
+
+
+class TestGetAnalytics:
+    @pytest.mark.asyncio
+    async def test_returns_analytics_result(self) -> None:
+        from unittest.mock import patch
+
+        from app.analytics.models import AnalyticsResult, InterruptStats
+        from app.analytics.queries import get_analytics
+
+        mock_pool = MagicMock()
+
+        with (
+            patch("app.analytics.queries.resolution_rate", return_value=0.85),
+            patch("app.analytics.queries.escalation_rate", return_value=0.05),
+            patch("app.analytics.queries.cost_per_conversation", return_value=0.03),
+            patch("app.analytics.queries.agent_usage", return_value=()),
+            patch(
+                "app.analytics.queries.interrupt_stats",
+                return_value=InterruptStats(),
+            ),
+            patch("app.analytics.queries._total_conversations", return_value=100),
+            patch("app.analytics.queries._avg_turns", return_value=4.2),
+        ):
+            result = await get_analytics(mock_pool, range_days=7)
+
+        assert isinstance(result, AnalyticsResult)
+        assert result.range == "7d"
+        assert result.total_conversations == 100
+        assert result.resolution_rate == 0.85
+
+    @pytest.mark.asyncio
+    async def test_zero_state_returns_zeros(self) -> None:
+        from unittest.mock import patch
+
+        from app.analytics.models import AnalyticsResult, InterruptStats
+        from app.analytics.queries import get_analytics
+
+        mock_pool = MagicMock()
+
+        with (
+            patch("app.analytics.queries.resolution_rate", return_value=0.0),
+            patch("app.analytics.queries.escalation_rate", return_value=0.0),
+            patch("app.analytics.queries.cost_per_conversation", return_value=0.0),
+            patch("app.analytics.queries.agent_usage", return_value=()),
+            patch("app.analytics.queries.interrupt_stats", return_value=InterruptStats()),
+            patch("app.analytics.queries._total_conversations", return_value=0),
+            patch("app.analytics.queries._avg_turns", return_value=0.0),
+        ):
+            result = await get_analytics(mock_pool, range_days=7)
+
+        assert isinstance(result, AnalyticsResult)
+        assert result.total_conversations == 0
+        assert result.resolution_rate == 0.0
+        assert result.agent_usage == ()
--- a/backend/tests/unit/openapi/init.py
+++ b/backend/tests/unit/openapi/init.py
--- a/backend/tests/unit/openapi/test_classifier.py
+++ b/backend/tests/unit/openapi/test_classifier.py
@@ -0,0 +1,249 @@
+"""Tests for OpenAPI endpoint classifier module.
+
+RED phase: written before implementation.
+"""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+from app.openapi.models import EndpointInfo, ParameterInfo
+
+pytestmark = pytest.mark.unit
+
+
+def _make_endpoint(
+    path: str = "/items",
+    method: str = "GET",
+    operation_id: str = "list_items",
+    summary: str = "List items",
+    description: str = "",
+    parameters: tuple[ParameterInfo, ...] = (),
+) -> EndpointInfo:
+    return EndpointInfo(
+        path=path,
+        method=method,
+        operation_id=operation_id,
+        summary=summary,
+        description=description,
+        parameters=parameters,
+    )
+
+
+_ORDER_PARAM = ParameterInfo(
+    name="order_id", location="path", required=True, schema_type="string"
+)
+_CUSTOMER_PARAM = ParameterInfo(
+    name="customer_id", location="query", required=False, schema_type="string"
+)
+
+
+class TestHeuristicClassifier:
+    """Tests for the rule-based HeuristicClassifier."""
+
+    async def test_get_classified_as_read(self) -> None:
+        """GET endpoints are classified as read access."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint(method="GET")
+        results = await clf.classify((ep,))
+        assert len(results) == 1
+        assert results[0].access_type == "read"
+
+    async def test_post_classified_as_write(self) -> None:
+        """POST endpoints are classified as write access."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint(method="POST")
+        results = await clf.classify((ep,))
+        assert results[0].access_type == "write"
+
+    async def test_post_needs_interrupt(self) -> None:
+        """POST endpoints require interrupt/approval."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint(method="POST")
+        results = await clf.classify((ep,))
+        assert results[0].needs_interrupt is True
+
+    async def test_put_classified_as_write(self) -> None:
+        """PUT endpoints are classified as write access."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint(method="PUT")
+        results = await clf.classify((ep,))
+        assert results[0].access_type == "write"
+
+    async def test_delete_classified_as_write_with_interrupt(self) -> None:
+        """DELETE endpoints are classified as write and require interrupt."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint(method="DELETE")
+        results = await clf.classify((ep,))
+        assert results[0].access_type == "write"
+        assert results[0].needs_interrupt is True
+
+    async def test_get_does_not_need_interrupt(self) -> None:
+        """GET endpoints do not require interrupt."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint(method="GET")
+        results = await clf.classify((ep,))
+        assert results[0].needs_interrupt is False
+
+    async def test_empty_endpoints_returns_empty_tuple(self) -> None:
+        """Empty input yields empty output."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        results = await clf.classify(())
+        assert results == ()
+
+    async def test_customer_params_detected_order_id(self) -> None:
+        """Parameters named order_id are recognized as customer params."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint(method="GET", parameters=(_ORDER_PARAM,))
+        results = await clf.classify((ep,))
+        assert "order_id" in results[0].customer_params
+
+    async def test_customer_params_detected_customer_id(self) -> None:
+        """Parameters named customer_id are recognized as customer params."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint(method="GET", parameters=(_CUSTOMER_PARAM,))
+        results = await clf.classify((ep,))
+        assert "customer_id" in results[0].customer_params
+
+    async def test_result_is_tuple(self) -> None:
+        """classify returns a tuple (immutable)."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint()
+        results = await clf.classify((ep,))
+        assert isinstance(results, tuple)
+
+    async def test_classification_has_confidence(self) -> None:
+        """Heuristic results have a confidence value between 0 and 1."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint()
+        results = await clf.classify((ep,))
+        assert 0.0 <= results[0].confidence <= 1.0
+
+    async def test_patch_classified_as_write(self) -> None:
+        """PATCH endpoints are classified as write access."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        ep = _make_endpoint(method="PATCH")
+        results = await clf.classify((ep,))
+        assert results[0].access_type == "write"
+
+
+class TestLLMClassifier:
+    """Tests for the LLM-backed classifier."""
+
+    def _make_mock_llm(self, classifications: list[dict]) -> MagicMock:
+        """Create a mock LLM that returns structured classification data."""
+        mock_llm = MagicMock()
+        mock_response = MagicMock()
+        mock_response.content = str(classifications)
+        mock_llm.ainvoke = AsyncMock(return_value=mock_response)
+        return mock_llm
+
+    async def test_llm_classifier_classifies_endpoints(self) -> None:
+        """LLM classifier returns ClassificationResult for each endpoint."""
+        from app.openapi.classifier import LLMClassifier
+
+        ep = _make_endpoint(method="GET")
+
+        mock_llm = MagicMock()
+        mock_response = MagicMock()
+        mock_response.content = (
+            '[{"access_type": "read", "agent_group": "support",'
+            ' "needs_interrupt": false, "customer_params": [], "confidence": 0.9}]'
+        )
+        mock_llm.ainvoke = AsyncMock(return_value=mock_response)
+
+        clf = LLMClassifier(llm=mock_llm)
+        results = await clf.classify((ep,))
+        assert len(results) == 1
+        assert results[0].access_type == "read"
+
+    async def test_llm_failure_falls_back_to_heuristic(self) -> None:
+        """When LLM raises an exception, falls back to heuristic classifier."""
+        from app.openapi.classifier import LLMClassifier
+
+        ep = _make_endpoint(method="GET")
+
+        mock_llm = MagicMock()
+        mock_llm.ainvoke = AsyncMock(side_effect=RuntimeError("LLM unavailable"))
+
+        clf = LLMClassifier(llm=mock_llm)
+        results = await clf.classify((ep,))
+        # Falls back to heuristic: GET = read
+        assert len(results) == 1
+        assert results[0].access_type == "read"
+
+    async def test_llm_invalid_json_falls_back_to_heuristic(self) -> None:
+        """When LLM returns unparseable output, falls back to heuristic."""
+        from app.openapi.classifier import LLMClassifier
+
+        ep = _make_endpoint(method="DELETE")
+
+        mock_llm = MagicMock()
+        mock_response = MagicMock()
+        mock_response.content = "this is not valid json at all"
+        mock_llm.ainvoke = AsyncMock(return_value=mock_response)
+
+        clf = LLMClassifier(llm=mock_llm)
+        results = await clf.classify((ep,))
+        # Fallback: DELETE = write with interrupt
+        assert results[0].access_type == "write"
+        assert results[0].needs_interrupt is True
+
+    async def test_llm_empty_endpoints_returns_empty(self) -> None:
+        """Empty input yields empty output without calling LLM."""
+        from app.openapi.classifier import LLMClassifier
+
+        mock_llm = MagicMock()
+        mock_llm.ainvoke = AsyncMock()
+
+        clf = LLMClassifier(llm=mock_llm)
+        results = await clf.classify(())
+        assert results == ()
+        mock_llm.ainvoke.assert_not_called()
+
+
+class TestClassifierProtocol:
+    """Verify both classifiers conform to ClassifierProtocol."""
+
+    def test_heuristic_has_classify_method(self) -> None:
+        """HeuristicClassifier exposes classify method."""
+        from app.openapi.classifier import HeuristicClassifier
+
+        clf = HeuristicClassifier()
+        assert hasattr(clf, "classify")
+        assert callable(clf.classify)
+
+    def test_llm_has_classify_method(self) -> None:
+        """LLMClassifier exposes classify method."""
+        from app.openapi.classifier import LLMClassifier
+
+        mock_llm = MagicMock()
+        clf = LLMClassifier(llm=mock_llm)
+        assert hasattr(clf, "classify")
+        assert callable(clf.classify)
--- a/backend/tests/unit/openapi/test_fetcher.py
+++ b/backend/tests/unit/openapi/test_fetcher.py
@@ -0,0 +1,120 @@
+"""Tests for OpenAPI spec fetcher module.
+
+RED phase: written before implementation.
+"""
+
+from __future__ import annotations
+
+from unittest.mock import patch
+
+import pytest
+
+from app.openapi.ssrf import SSRFError
+
+pytestmark = pytest.mark.unit
+
+_SAMPLE_JSON = '{"openapi": "3.0.0", "info": {"title": "Test", "version": "1.0"}, "paths": {}}'
+_SAMPLE_YAML = "openapi: '3.0.0'\ninfo:\n  title: Test\n  version: '1.0'\npaths: {}\n"
+_PUBLIC_IP = "93.184.216.34"
+
+
+@pytest.fixture
+def _mock_public_dns():
+    with patch("app.openapi.ssrf.resolve_hostname", return_value=[_PUBLIC_IP]):
+        yield
+
+
+class TestFetchSpec:
+    """Tests for fetch_spec function."""
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_fetch_json_spec_succeeds(self, httpx_mock) -> None:
+        """Fetch a JSON spec and return parsed dict."""
+        from app.openapi.fetcher import fetch_spec
+
+        httpx_mock.add_response(
+            url="https://example.com/spec.json",
+            text=_SAMPLE_JSON,
+            headers={"content-type": "application/json"},
+        )
+        result = await fetch_spec("https://example.com/spec.json")
+        assert isinstance(result, dict)
+        assert result["openapi"] == "3.0.0"
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_fetch_yaml_spec_succeeds(self, httpx_mock) -> None:
+        """Fetch a YAML spec and return parsed dict."""
+        from app.openapi.fetcher import fetch_spec
+
+        httpx_mock.add_response(
+            url="https://example.com/spec.yaml",
+            text=_SAMPLE_YAML,
+            headers={"content-type": "application/x-yaml"},
+        )
+        result = await fetch_spec("https://example.com/spec.yaml")
+        assert isinstance(result, dict)
+        assert result["openapi"] == "3.0.0"
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_fetch_yaml_by_url_extension(self, httpx_mock) -> None:
+        """Auto-detect YAML format from .yaml URL extension."""
+        from app.openapi.fetcher import fetch_spec
+
+        httpx_mock.add_response(
+            url="https://example.com/api.yaml",
+            text=_SAMPLE_YAML,
+            headers={"content-type": "text/plain"},
+        )
+        result = await fetch_spec("https://example.com/api.yaml")
+        assert isinstance(result, dict)
+        assert result["openapi"] == "3.0.0"
+
+    async def test_ssrf_blocked_url_raises(self) -> None:
+        """SSRF-blocked URL raises SSRFError."""
+        from app.openapi.fetcher import fetch_spec
+
+        with (
+            patch("app.openapi.ssrf.resolve_hostname", return_value=["10.0.0.1"]),
+            pytest.raises(SSRFError),
+        ):
+            await fetch_spec("http://internal.corp/spec.json")
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_oversized_response_raises(self, httpx_mock) -> None:
+        """Response exceeding 10MB raises ValueError."""
+        from app.openapi.fetcher import fetch_spec
+
+        big_content = "x" * (10 * 1024 * 1024 + 1)
+        httpx_mock.add_response(
+            url="https://example.com/huge.json",
+            text=big_content,
+            headers={"content-type": "application/json"},
+        )
+        with pytest.raises(ValueError, match="too large"):
+            await fetch_spec("https://example.com/huge.json")
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_invalid_json_raises(self, httpx_mock) -> None:
+        """Non-parseable JSON raises ValueError."""
+        from app.openapi.fetcher import fetch_spec
+
+        httpx_mock.add_response(
+            url="https://example.com/bad.json",
+            text="not valid json {{{",
+            headers={"content-type": "application/json"},
+        )
+        with pytest.raises(ValueError, match="[Pp]arse|[Ii]nvalid|[Dd]ecode"):
+            await fetch_spec("https://example.com/bad.json")
+
+    @pytest.mark.usefixtures("_mock_public_dns")
+    async def test_invalid_yaml_raises(self, httpx_mock) -> None:
+        """Non-parseable YAML raises ValueError."""
+        from app.openapi.fetcher import fetch_spec
+
+        httpx_mock.add_response(
+            url="https://example.com/bad.yaml",
+            text=": invalid: yaml: {\n",
+            headers={"content-type": "application/x-yaml"},
+        )
+        with pytest.raises(ValueError, match="[Pp]arse|[Ii]nvalid|[Yy]AML"):
+            await fetch_spec("https://example.com/bad.yaml")
--- a/backend/tests/unit/openapi/test_generator.py
+++ b/backend/tests/unit/openapi/test_generator.py
@@ -0,0 +1,258 @@
+"""Tests for OpenAPI tool generator module.
+
+RED phase: written before implementation.
+"""
+
+from __future__ import annotations
+
+import pytest
+
+from app.openapi.models import ClassificationResult, EndpointInfo, ParameterInfo
+
+pytestmark = pytest.mark.unit
+
+_BASE_URL = "https://api.example.com"
+
+
+def _make_endpoint(
+    path: str = "/items",
+    method: str = "GET",
+    operation_id: str = "list_items",
+    summary: str = "List items",
+    description: str = "Returns all items",
+    parameters: tuple[ParameterInfo, ...] = (),
+    request_body_schema: dict | None = None,
+) -> EndpointInfo:
+    return EndpointInfo(
+        path=path,
+        method=method,
+        operation_id=operation_id,
+        summary=summary,
+        description=description,
+        parameters=parameters,
+        request_body_schema=request_body_schema,
+    )
+
+
+def _make_classification(
+    endpoint: EndpointInfo,
+    access_type: str = "read",
+    needs_interrupt: bool = False,
+    agent_group: str = "read_agent",
+) -> ClassificationResult:
+    return ClassificationResult(
+        endpoint=endpoint,
+        access_type=access_type,
+        customer_params=(),
+        agent_group=agent_group,
+        confidence=0.9,
+        needs_interrupt=needs_interrupt,
+    )
+
+
+_PATH_PARAM = ParameterInfo(
+    name="item_id", location="path", required=True, schema_type="string"
+)
+_QUERY_PARAM = ParameterInfo(
+    name="filter", location="query", required=False, schema_type="string"
+)
+
+
+class TestGenerateToolCode:
+    """Tests for generate_tool_code function."""
+
+    def test_generate_tool_for_get_endpoint(self) -> None:
+        """Generated tool for GET endpoint is a GeneratedTool with non-empty code."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint(method="GET")
+        clf = _make_classification(ep)
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        assert tool.function_name == "list_items"
+        assert tool.code != ""
+        assert "@tool" in tool.code
+
+    def test_generate_tool_contains_function_name(self) -> None:
+        """Generated code contains the function name."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint(operation_id="get_order", method="GET")
+        clf = _make_classification(ep)
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        assert "get_order" in tool.code
+
+    def test_generate_tool_contains_base_url(self) -> None:
+        """Generated code contains the base URL."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint()
+        clf = _make_classification(ep)
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        assert _BASE_URL in tool.code
+
+    def test_generate_tool_contains_http_method(self) -> None:
+        """Generated code uses the correct HTTP method."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint(method="POST")
+        clf = _make_classification(ep, access_type="write")
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        assert "post" in tool.code.lower()
+
+    def test_generate_tool_for_post_with_body(self) -> None:
+        """Generated tool for POST includes body parameter."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint(
+            method="POST",
+            request_body_schema={"type": "object", "properties": {"name": {"type": "string"}}},
+        )
+        clf = _make_classification(ep, access_type="write")
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        assert tool.code != ""
+        assert "POST" in tool.code or "post" in tool.code
+
+    def test_generate_tool_with_path_params(self) -> None:
+        """Generated tool includes path parameter in function signature."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint(
+            path="/items/{item_id}",
+            operation_id="get_item",
+            parameters=(_PATH_PARAM,),
+        )
+        clf = _make_classification(ep)
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        assert "item_id" in tool.code
+
+    def test_write_tool_includes_interrupt_marker(self) -> None:
+        """Write tools that need interrupt include a marker comment."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint(method="DELETE", operation_id="delete_item")
+        clf = _make_classification(ep, access_type="write", needs_interrupt=True)
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        assert "interrupt" in tool.code.lower() or "approval" in tool.code.lower()
+
+    def test_generated_code_is_executable(self) -> None:
+        """Generated code can be exec'd without syntax errors."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint(
+            path="/items/{item_id}",
+            operation_id="fetch_item",
+            parameters=(_PATH_PARAM,),
+        )
+        clf = _make_classification(ep)
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        # Must be valid Python syntax
+        compile(tool.code, "<generated>", "exec")
+
+    def test_generated_tool_code_exec_imports(self) -> None:
+        """Generated code exec'd with required imports does not raise."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint()
+        clf = _make_classification(ep)
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        namespace: dict = {}
+        try:
+            import httpx
+            from langchain_core.tools import tool as lc_tool
+
+            namespace = {"httpx": httpx, "tool": lc_tool}
+            exec(tool.code, namespace)  # noqa: S102
+        except ImportError:
+            pytest.skip("langchain_core not available for exec test")
+
+    def test_returns_generated_tool_instance(self) -> None:
+        """generate_tool_code returns a GeneratedTool instance."""
+        from app.openapi.generator import generate_tool_code
+        from app.openapi.models import GeneratedTool
+
+        ep = _make_endpoint()
+        clf = _make_classification(ep)
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        assert isinstance(tool, GeneratedTool)
+
+    def test_generated_tool_is_frozen(self) -> None:
+        """GeneratedTool instance is immutable."""
+        from app.openapi.generator import generate_tool_code
+
+        ep = _make_endpoint()
+        clf = _make_classification(ep)
+        tool = generate_tool_code(clf, _BASE_URL)
+
+        with pytest.raises((AttributeError, TypeError)):
+            tool.code = "new code"  # type: ignore[misc]
+
+
+class TestGenerateAgentYaml:
+    """Tests for generate_agent_yaml function."""
+
+    def test_generate_yaml_is_valid_string(self) -> None:
+        """generate_agent_yaml returns a non-empty string."""
+        from app.openapi.generator import generate_agent_yaml
+
+        ep = _make_endpoint()
+        clf = _make_classification(ep)
+        result = generate_agent_yaml((clf,), _BASE_URL)
+
+        assert isinstance(result, str)
+        assert len(result) > 0
+
+    def test_generated_yaml_is_parseable(self) -> None:
+        """Output can be parsed as YAML."""
+        import yaml
+
+        from app.openapi.generator import generate_agent_yaml
+
+        ep = _make_endpoint()
+        clf = _make_classification(ep)
+        result = generate_agent_yaml((clf,), _BASE_URL)
+
+        parsed = yaml.safe_load(result)
+        assert isinstance(parsed, dict)
+
+    def test_generated_yaml_contains_agents_key(self) -> None:
+        """Generated YAML has an 'agents' key matching AgentConfig format."""
+        import yaml
+
+        from app.openapi.generator import generate_agent_yaml
+
+        ep = _make_endpoint()
+        clf = _make_classification(ep)
+        result = generate_agent_yaml((clf,), _BASE_URL)
+
+        parsed = yaml.safe_load(result)
+        assert "agents" in parsed
+
+    def test_generated_yaml_contains_tool_name(self) -> None:
+        """Generated YAML references the tool function name."""
+        from app.openapi.generator import generate_agent_yaml
+
+        ep = _make_endpoint(operation_id="list_orders")
+        clf = _make_classification(ep)
+        result = generate_agent_yaml((clf,), _BASE_URL)
+
+        assert "list_orders" in result
+
+    def test_empty_classifications_returns_empty_agents(self) -> None:
+        """No classifications yields YAML with empty agents list."""
+        import yaml
+
+        from app.openapi.generator import generate_agent_yaml
+
+        result = generate_agent_yaml((), _BASE_URL)
+        parsed = yaml.safe_load(result)
+        assert parsed.get("agents") == [] or parsed.get("agents") is None
--- a/backend/tests/unit/openapi/test_parser.py
+++ b/backend/tests/unit/openapi/test_parser.py
@@ -0,0 +1,290 @@
+"""Tests for OpenAPI endpoint parser module.
+
+RED phase: written before implementation.
+"""
+
+from __future__ import annotations
+
+import pytest
+
+pytestmark = pytest.mark.unit
+
+_MINIMAL_SPEC = {
+    "openapi": "3.0.0",
+    "info": {"title": "Test API", "version": "1.0.0"},
+    "paths": {},
+}
+
+_GET_SPEC = {
+    "openapi": "3.0.0",
+    "info": {"title": "Orders API", "version": "1.0.0"},
+    "paths": {
+        "/orders/{order_id}": {
+            "get": {
+                "operationId": "get_order",
+                "summary": "Get an order",
+                "description": "Retrieves a single order by ID",
+                "parameters": [
+                    {
+                        "name": "order_id",
+                        "in": "path",
+                        "required": True,
+                        "schema": {"type": "string"},
+                        "description": "The order identifier",
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "Order found",
+                        "content": {
+                            "application/json": {
+                                "schema": {
+                                    "type": "object",
+                                    "properties": {"id": {"type": "string"}},
+                                }
+                            }
+                        },
+                    }
+                },
+            }
+        }
+    },
+}
+
+_POST_SPEC = {
+    "openapi": "3.0.0",
+    "info": {"title": "Orders API", "version": "1.0.0"},
+    "paths": {
+        "/orders": {
+            "post": {
+                "operationId": "create_order",
+                "summary": "Create an order",
+                "description": "Creates a new order",
+                "requestBody": {
+                    "required": True,
+                    "content": {
+                        "application/json": {
+                            "schema": {
+                                "type": "object",
+                                "properties": {
+                                    "item": {"type": "string"},
+                                    "quantity": {"type": "integer"},
+                                },
+                            }
+                        }
+                    },
+                },
+                "responses": {"201": {"description": "Created"}},
+            }
+        }
+    },
+}
+
+_MULTI_PARAM_SPEC = {
+    "openapi": "3.0.0",
+    "info": {"title": "Items API", "version": "1.0.0"},
+    "paths": {
+        "/items/{item_id}": {
+            "get": {
+                "operationId": "get_item",
+                "summary": "Get item",
+                "description": "",
+                "parameters": [
+                    {
+                        "name": "item_id",
+                        "in": "path",
+                        "required": True,
+                        "schema": {"type": "integer"},
+                    },
+                    {
+                        "name": "include_details",
+                        "in": "query",
+                        "required": False,
+                        "schema": {"type": "boolean"},
+                    },
+                ],
+                "responses": {"200": {"description": "OK"}},
+            }
+        }
+    },
+}
+
+_REF_SPEC = {
+    "openapi": "3.0.0",
+    "info": {"title": "Ref API", "version": "1.0.0"},
+    "components": {
+        "schemas": {
+            "Item": {
+                "type": "object",
+                "properties": {"id": {"type": "string"}},
+            }
+        }
+    },
+    "paths": {
+        "/items": {
+            "get": {
+                "operationId": "list_items",
+                "summary": "List items",
+                "description": "",
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "content": {
+                            "application/json": {
+                                "schema": {"$ref": "#/components/schemas/Item"}
+                            }
+                        },
+                    }
+                },
+            }
+        }
+    },
+}
+
+_MULTI_ENDPOINT_SPEC = {
+    "openapi": "3.0.0",
+    "info": {"title": "Multi API", "version": "1.0.0"},
+    "paths": {
+        "/users": {
+            "get": {
+                "operationId": "list_users",
+                "summary": "List users",
+                "description": "",
+                "responses": {"200": {"description": "OK"}},
+            },
+            "post": {
+                "operationId": "create_user",
+                "summary": "Create user",
+                "description": "",
+                "responses": {"201": {"description": "Created"}},
+            },
+        },
+        "/users/{id}": {
+            "delete": {
+                "operationId": "delete_user",
+                "summary": "Delete user",
+                "description": "",
+                "parameters": [
+                    {"name": "id", "in": "path", "required": True, "schema": {"type": "string"}}
+                ],
+                "responses": {"204": {"description": "Deleted"}},
+            }
+        },
+    },
+}
+
+
+class TestParseEndpoints:
+    """Tests for parse_endpoints function."""
+
+    def test_empty_paths_returns_empty_tuple(self) -> None:
+        """Spec with no paths yields no endpoints."""
+        from app.openapi.parser import parse_endpoints
+
+        result = parse_endpoints(_MINIMAL_SPEC)
+        assert result == ()
+
+    def test_parse_get_endpoint(self) -> None:
+        """Parse a GET endpoint with path parameter."""
+        from app.openapi.parser import parse_endpoints
+
+        result = parse_endpoints(_GET_SPEC)
+        assert len(result) == 1
+        ep = result[0]
+        assert ep.path == "/orders/{order_id}"
+        assert ep.method == "GET"
+        assert ep.operation_id == "get_order"
+        assert ep.summary == "Get an order"
+
+    def test_parse_get_endpoint_parameters(self) -> None:
+        """Path parameters are extracted correctly."""
+        from app.openapi.parser import parse_endpoints
+
+        result = parse_endpoints(_GET_SPEC)
+        ep = result[0]
+        assert len(ep.parameters) == 1
+        param = ep.parameters[0]
+        assert param.name == "order_id"
+        assert param.location == "path"
+        assert param.required is True
+        assert param.schema_type == "string"
+
+    def test_parse_post_with_request_body(self) -> None:
+        """POST endpoint with request body is extracted."""
+        from app.openapi.parser import parse_endpoints
+
+        result = parse_endpoints(_POST_SPEC)
+        assert len(result) == 1
+        ep = result[0]
+        assert ep.method == "POST"
+        assert ep.request_body_schema is not None
+        assert ep.request_body_schema["type"] == "object"
+
+    def test_parse_path_and_query_params(self) -> None:
+        """Both path and query parameters are extracted."""
+        from app.openapi.parser import parse_endpoints
+
+        result = parse_endpoints(_MULTI_PARAM_SPEC)
+        ep = result[0]
+        locations = {p.location for p in ep.parameters}
+        assert "path" in locations
+        assert "query" in locations
+
+    def test_autogenerate_operation_id_when_missing(self) -> None:
+        """Auto-generate operation_id when not provided in spec."""
+        from app.openapi.parser import parse_endpoints
+
+        spec = {
+            "openapi": "3.0.0",
+            "info": {"title": "Test", "version": "1.0"},
+            "paths": {
+                "/things/{id}": {
+                    "get": {
+                        "summary": "Get thing",
+                        "description": "",
+                        "responses": {"200": {"description": "OK"}},
+                    }
+                }
+            },
+        }
+        result = parse_endpoints(spec)
+        ep = result[0]
+        assert ep.operation_id != ""
+        assert len(ep.operation_id) > 0
+
+    def test_multiple_endpoints_extracted(self) -> None:
+        """Multiple path+method combinations are all extracted."""
+        from app.openapi.parser import parse_endpoints
+
+        result = parse_endpoints(_MULTI_ENDPOINT_SPEC)
+        assert len(result) == 3
+        methods = {ep.method for ep in result}
+        assert "GET" in methods
+        assert "POST" in methods
+        assert "DELETE" in methods
+
+    def test_ref_in_response_schema_resolved(self) -> None:
+        """$ref in response schema is resolved to the target schema."""
+        from app.openapi.parser import parse_endpoints
+
+        result = parse_endpoints(_REF_SPEC)
+        ep = result[0]
+        assert ep.response_schema is not None
+        # Resolved ref should contain the properties
+        assert "properties" in ep.response_schema or "$ref" not in ep.response_schema
+
+    def test_result_is_tuple(self) -> None:
+        """parse_endpoints returns a tuple (immutable)."""
+        from app.openapi.parser import parse_endpoints
+
+        result = parse_endpoints(_GET_SPEC)
+        assert isinstance(result, tuple)
+
+    def test_endpoint_info_is_frozen(self) -> None:
+        """EndpointInfo instances are frozen/immutable."""
+        from app.openapi.parser import parse_endpoints
+
+        result = parse_endpoints(_GET_SPEC)
+        ep = result[0]
+        with pytest.raises((AttributeError, TypeError)):
+            ep.method = "POST"  # type: ignore[misc]
--- a/backend/tests/unit/openapi/test_review_api.py
+++ b/backend/tests/unit/openapi/test_review_api.py
@@ -0,0 +1,219 @@
+"""Tests for OpenAPI review API endpoints.
+
+RED phase: written before implementation.
+"""
+
+from __future__ import annotations
+
+import pytest
+from fastapi.testclient import TestClient
+
+pytestmark = pytest.mark.unit
+
+_SAMPLE_URL = "https://example.com/api/spec.json"
+
+
+@pytest.fixture
+def client():
+    """Create TestClient for the review API app."""
+    from fastapi import FastAPI
+
+    from app.openapi.review_api import router
+
+    app = FastAPI()
+    app.include_router(router)
+    return TestClient(app)
+
+
+@pytest.fixture
+def job_id(client):
+    """Create a job and return its ID."""
+    response = client.post("/api/v1/openapi/import", json={"url": _SAMPLE_URL})
+    assert response.status_code == 202
+    return response.json()["job_id"]
+
+
+@pytest.fixture
+def job_with_classifications(client, job_id):
+    """Return job_id for a job that has mock classifications injected."""
+    from app.openapi.models import ClassificationResult, EndpointInfo
+    from app.openapi.review_api import _job_store
+
+    ep = EndpointInfo(
+        path="/orders",
+        method="GET",
+        operation_id="list_orders",
+        summary="List orders",
+        description="",
+    )
+    clf = ClassificationResult(
+        endpoint=ep,
+        access_type="read",
+        customer_params=(),
+        agent_group="read_agent",
+        confidence=0.9,
+        needs_interrupt=False,
+    )
+    # Inject classifications directly into the store
+    job = _job_store[job_id]
+    _job_store[job_id] = {**job, "classifications": [clf]}
+    return job_id
+
+
+class TestImportEndpoint:
+    """Tests for POST /api/v1/openapi/import."""
+
+    def test_post_import_returns_job_id(self, client) -> None:
+        """POST /import returns 202 with a job_id."""
+        response = client.post("/api/v1/openapi/import", json={"url": _SAMPLE_URL})
+        assert response.status_code == 202
+        data = response.json()
+        assert "job_id" in data
+        assert len(data["job_id"]) > 0
+
+    def test_post_import_empty_url_returns_422(self, client) -> None:
+        """POST /import with empty URL returns 422 validation error."""
+        response = client.post("/api/v1/openapi/import", json={"url": ""})
+        assert response.status_code == 422
+
+    def test_post_import_missing_url_returns_422(self, client) -> None:
+        """POST /import with missing URL field returns 422."""
+        response = client.post("/api/v1/openapi/import", json={})
+        assert response.status_code == 422
+
+    def test_post_import_invalid_scheme_returns_422(self, client) -> None:
+        """POST /import with non-http URL returns 422."""
+        response = client.post("/api/v1/openapi/import", json={"url": "ftp://evil.com/spec"})
+        assert response.status_code == 422
+
+    def test_post_import_returns_pending_status(self, client) -> None:
+        """Newly created job has pending status."""
+        response = client.post("/api/v1/openapi/import", json={"url": _SAMPLE_URL})
+        data = response.json()
+        assert data["status"] == "pending"
+
+    def test_post_import_returns_spec_url(self, client) -> None:
+        """Response includes the original spec URL."""
+        response = client.post("/api/v1/openapi/import", json={"url": _SAMPLE_URL})
+        data = response.json()
+        assert data["spec_url"] == _SAMPLE_URL
+
+
+class TestGetJobEndpoint:
+    """Tests for GET /api/v1/openapi/jobs/{job_id}."""
+
+    def test_get_job_returns_status(self, client, job_id) -> None:
+        """GET /jobs/{id} returns job status."""
+        response = client.get(f"/api/v1/openapi/jobs/{job_id}")
+        assert response.status_code == 200
+        data = response.json()
+        assert "status" in data
+        assert "job_id" in data
+
+    def test_get_unknown_job_returns_404(self, client) -> None:
+        """GET /jobs/nonexistent returns 404."""
+        response = client.get("/api/v1/openapi/jobs/nonexistent-id")
+        assert response.status_code == 404
+
+    def test_get_job_includes_spec_url(self, client, job_id) -> None:
+        """Job response includes the spec URL."""
+        response = client.get(f"/api/v1/openapi/jobs/{job_id}")
+        data = response.json()
+        assert data["spec_url"] == _SAMPLE_URL
+
+
+class TestGetClassificationsEndpoint:
+    """Tests for GET /api/v1/openapi/jobs/{job_id}/classifications."""
+
+    def test_get_classifications_returns_list(self, client, job_with_classifications) -> None:
+        """GET /classifications returns a list."""
+        response = client.get(
+            f"/api/v1/openapi/jobs/{job_with_classifications}/classifications"
+        )
+        assert response.status_code == 200
+        data = response.json()
+        assert isinstance(data, list)
+        assert len(data) == 1
+
+    def test_get_classifications_unknown_job_returns_404(self, client) -> None:
+        """GET /classifications for unknown job returns 404."""
+        response = client.get("/api/v1/openapi/jobs/unknown/classifications")
+        assert response.status_code == 404
+
+    def test_classification_has_expected_fields(self, client, job_with_classifications) -> None:
+        """Each classification item has access_type and endpoint fields."""
+        response = client.get(
+            f"/api/v1/openapi/jobs/{job_with_classifications}/classifications"
+        )
+        item = response.json()[0]
+        assert "access_type" in item
+        assert "endpoint" in item
+        assert "needs_interrupt" in item
+
+
+class TestUpdateClassificationEndpoint:
+    """Tests for PUT /api/v1/openapi/jobs/{job_id}/classifications/{idx}."""
+
+    def test_update_classification_succeeds(self, client, job_with_classifications) -> None:
+        """PUT /classifications/0 updates the classification."""
+        response = client.put(
+            f"/api/v1/openapi/jobs/{job_with_classifications}/classifications/0",
+            json={"access_type": "write", "needs_interrupt": True, "agent_group": "write_agent"},
+        )
+        assert response.status_code == 200
+
+    def test_update_unknown_job_returns_404(self, client) -> None:
+        """PUT /classifications/0 for unknown job returns 404."""
+        response = client.put(
+            "/api/v1/openapi/jobs/unknown/classifications/0",
+            json={"access_type": "write", "needs_interrupt": True, "agent_group": "write_agent"},
+        )
+        assert response.status_code == 404
+
+    def test_update_invalid_access_type_returns_422(self, client, job_with_classifications) -> None:
+        """PUT /classifications/0 with invalid access_type returns 422."""
+        response = client.put(
+            f"/api/v1/openapi/jobs/{job_with_classifications}/classifications/0",
+            json={"access_type": "admin", "needs_interrupt": True, "agent_group": "x"},
+        )
+        assert response.status_code == 422
+
+    def test_update_invalid_agent_group_returns_422(self, client, job_with_classifications) -> None:
+        """PUT /classifications/0 with invalid agent_group returns 422."""
+        response = client.put(
+            f"/api/v1/openapi/jobs/{job_with_classifications}/classifications/0",
+            json={"access_type": "read", "needs_interrupt": False, "agent_group": "evil group!"},
+        )
+        assert response.status_code == 422
+
+    def test_update_out_of_range_index_returns_404(self, client, job_with_classifications) -> None:
+        """PUT /classifications/999 returns 404 for out-of-range index."""
+        response = client.put(
+            f"/api/v1/openapi/jobs/{job_with_classifications}/classifications/999",
+            json={"access_type": "read", "needs_interrupt": False, "agent_group": "read_agent"},
+        )
+        assert response.status_code == 404
+
+
+class TestApproveEndpoint:
+    """Tests for POST /api/v1/openapi/jobs/{job_id}/approve."""
+
+    def test_approve_job_succeeds(self, client, job_with_classifications) -> None:
+        """POST /approve transitions job to approved status."""
+        response = client.post(
+            f"/api/v1/openapi/jobs/{job_with_classifications}/approve"
+        )
+        assert response.status_code == 200
+
+    def test_approve_unknown_job_returns_404(self, client) -> None:
+        """POST /approve for unknown job returns 404."""
+        response = client.post("/api/v1/openapi/jobs/unknown/approve")
+        assert response.status_code == 404
+
+    def test_approve_returns_job_status(self, client, job_with_classifications) -> None:
+        """POST /approve returns updated job status."""
+        response = client.post(
+            f"/api/v1/openapi/jobs/{job_with_classifications}/approve"
+        )
+        data = response.json()
+        assert "status" in data
--- a/backend/tests/unit/openapi/test_validator.py
+++ b/backend/tests/unit/openapi/test_validator.py
@@ -0,0 +1,93 @@
+"""Tests for OpenAPI spec validator module.
+
+RED phase: written before implementation.
+"""
+
+from __future__ import annotations
+
+import pytest
+
+pytestmark = pytest.mark.unit
+
+_VALID_SPEC = {
+    "openapi": "3.0.0",
+    "info": {"title": "Test API", "version": "1.0.0"},
+    "paths": {
+        "/items": {
+            "get": {
+                "summary": "List items",
+                "responses": {"200": {"description": "OK"}},
+            }
+        }
+    },
+}
+
+
+class TestValidateSpec:
+    """Tests for validate_spec function."""
+
+    def test_valid_minimal_spec_passes(self) -> None:
+        """A valid minimal spec returns empty error list."""
+        from app.openapi.validator import validate_spec
+
+        errors = validate_spec(_VALID_SPEC)
+        assert errors == []
+
+    def test_missing_openapi_key_returns_error(self) -> None:
+        """Missing 'openapi' field returns an error."""
+        from app.openapi.validator import validate_spec
+
+        spec = {k: v for k, v in _VALID_SPEC.items() if k != "openapi"}
+        errors = validate_spec(spec)
+        assert len(errors) > 0
+        assert any("openapi" in e.lower() for e in errors)
+
+    def test_missing_info_returns_error(self) -> None:
+        """Missing 'info' field returns an error."""
+        from app.openapi.validator import validate_spec
+
+        spec = {k: v for k, v in _VALID_SPEC.items() if k != "info"}
+        errors = validate_spec(spec)
+        assert len(errors) > 0
+        assert any("info" in e.lower() for e in errors)
+
+    def test_missing_paths_returns_error(self) -> None:
+        """Missing 'paths' field returns an error."""
+        from app.openapi.validator import validate_spec
+
+        spec = {k: v for k, v in _VALID_SPEC.items() if k != "paths"}
+        errors = validate_spec(spec)
+        assert len(errors) > 0
+        assert any("paths" in e.lower() for e in errors)
+
+    def test_non_dict_input_returns_error(self) -> None:
+        """Non-dict input returns an error without raising."""
+        from app.openapi.validator import validate_spec
+
+        errors = validate_spec("not a dict")  # type: ignore[arg-type]
+        assert len(errors) > 0
+
+    def test_empty_dict_returns_multiple_errors(self) -> None:
+        """Empty dict returns errors for all required fields."""
+        from app.openapi.validator import validate_spec
+
+        errors = validate_spec({})
+        # Should have at least one error for each required field
+        assert len(errors) >= 3
+
+    def test_invalid_openapi_version_returns_error(self) -> None:
+        """Unsupported openapi version string returns an error."""
+        from app.openapi.validator import validate_spec
+
+        spec = {**_VALID_SPEC, "openapi": "1.0.0"}
+        errors = validate_spec(spec)
+        assert len(errors) > 0
+
+    def test_errors_are_descriptive_strings(self) -> None:
+        """All returned errors are non-empty strings."""
+        from app.openapi.validator import validate_spec
+
+        errors = validate_spec({})
+        for e in errors:
+            assert isinstance(e, str)
+            assert len(e) > 0
--- a/backend/tests/unit/replay/init.py
+++ b/backend/tests/unit/replay/init.py
@@ -0,0 +1 @@
+"""Unit tests for app.replay module."""
--- a/backend/tests/unit/replay/test_api.py
+++ b/backend/tests/unit/replay/test_api.py
@@ -0,0 +1,217 @@
+"""Unit tests for app.replay.api."""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+from fastapi import FastAPI, HTTPException
+from fastapi.responses import JSONResponse
+from fastapi.testclient import TestClient
+
+from app.api_utils import envelope
+
+pytestmark = pytest.mark.unit
+
+
+def _build_app() -> FastAPI:
+    from app.replay.api import router
+
+    app = FastAPI()
+    app.include_router(router)
+
+    @app.exception_handler(HTTPException)
+    async def _http_exc(request, exc):  # type: ignore[no-untyped-def]
+        return JSONResponse(
+            status_code=exc.status_code,
+            content=envelope(None, success=False, error=exc.detail),
+        )
+
+    return app
+
+
+def _make_mock_pool(
+    fetchall_result: list[dict],
+    *,
+    count: int | None = None,
+) -> MagicMock:
+    """Build a mock pool that returns the given rows from fetchall.
+
+    When *count* is provided, the first execute() call returns a cursor
+    whose fetchone() yields ``(count,)`` (for the COUNT query) and the
+    second call returns the rows via fetchall().  When *count* is None
+    (the default), a single cursor backed by *fetchall_result* is used
+    for all calls.
+    """
+    if count is not None:
+        count_cursor = AsyncMock()
+        count_cursor.fetchone = AsyncMock(return_value=(count,))
+
+        rows_cursor = AsyncMock()
+        rows_cursor.fetchall = AsyncMock(return_value=fetchall_result)
+
+        mock_conn = AsyncMock()
+        mock_conn.execute = AsyncMock(side_effect=[count_cursor, rows_cursor])
+    else:
+        mock_cursor = AsyncMock()
+        mock_cursor.fetchall = AsyncMock(return_value=fetchall_result)
+        mock_cursor.fetchone = AsyncMock(return_value=None)
+
+        mock_conn = AsyncMock()
+        mock_conn.execute = AsyncMock(return_value=mock_cursor)
+
+    mock_ctx = AsyncMock()
+    mock_ctx.__aenter__ = AsyncMock(return_value=mock_conn)
+    mock_ctx.__aexit__ = AsyncMock(return_value=None)
+
+    mock_pool = MagicMock()
+    mock_pool.connection.return_value = mock_ctx
+    return mock_pool
+
+
+class TestListConversations:
+    def test_returns_200_with_empty_list(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool([], count=0)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/conversations")
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["success"] is True
+        data = body["data"]
+        assert isinstance(data["conversations"], list)
+        assert data["total"] == 0
+        assert data["page"] == 1
+        assert body["error"] is None
+
+    def test_returns_conversations_list(self) -> None:
+        app = _build_app()
+        mock_rows = [
+            {
+                "thread_id": "t1",
+                "created_at": "2026-01-01T00:00:00",
+                "last_activity": "2026-01-01T00:01:00",
+                "status": "active",
+                "total_tokens": 100,
+                "total_cost_usd": 0.01,
+            }
+        ]
+        app.state.pool = _make_mock_pool(mock_rows, count=1)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/conversations")
+        body = resp.json()
+        assert resp.status_code == 200
+        data = body["data"]
+        assert len(data["conversations"]) == 1
+        assert data["conversations"][0]["thread_id"] == "t1"
+        assert data["total"] == 1
+
+    def test_pagination_defaults(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool([], count=0)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/conversations")
+        assert resp.status_code == 200
+
+    def test_pagination_custom_params(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool([], count=0)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/conversations?page=2&per_page=10")
+        assert resp.status_code == 200
+
+    def test_per_page_max_capped_at_100(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool([], count=0)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/conversations?per_page=200")
+        # FastAPI Query(le=100) rejects values > 100
+        assert resp.status_code == 422
+
+
+class TestGetReplay:
+    def test_thread_not_found_returns_404(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool([])
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/replay/nonexistent-thread")
+        assert resp.status_code == 404
+
+    def test_returns_replay_page_for_existing_thread(self) -> None:
+        app = _build_app()
+        mock_rows = [
+            {
+                "thread_id": "thread-123",
+                "checkpoint_id": "cp-001",
+                "checkpoint": {
+                    "channel_values": {
+                        "messages": [{"type": "human", "content": "Hello"}]
+                    }
+                },
+                "metadata": {},
+            }
+        ]
+        app.state.pool = _make_mock_pool(mock_rows)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/replay/thread-123")
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["success"] is True
+        assert body["data"]["thread_id"] == "thread-123"
+        assert "steps" in body["data"]
+        assert "total_steps" in body["data"]
+        assert "page" in body["data"]
+        assert "per_page" in body["data"]
+
+    def test_replay_pagination_params(self) -> None:
+        app = _build_app()
+        mock_rows = [
+            {
+                "thread_id": "t1",
+                "checkpoint_id": "cp-001",
+                "checkpoint": {
+                    "channel_values": {"messages": [{"type": "human", "content": "Hi"}]}
+                },
+                "metadata": {},
+            }
+        ]
+        app.state.pool = _make_mock_pool(mock_rows)
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/replay/t1?page=1&per_page=5")
+        assert resp.status_code == 200
+
+    def test_error_response_has_envelope(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool([])
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/replay/missing")
+        assert resp.status_code == 404
+        body = resp.json()
+        assert body["success"] is False
+        assert body["data"] is None
+        assert body["error"] is not None
+
+    def test_invalid_thread_id_returns_400(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool([])
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/replay/id%20with%20spaces")
+        assert resp.status_code == 400
+
+    def test_thread_id_special_chars_returns_400(self) -> None:
+        app = _build_app()
+        app.state.pool = _make_mock_pool([])
+
+        with TestClient(app) as client:
+            resp = client.get("/api/v1/replay/id;DROP TABLE")
+        assert resp.status_code == 400
--- a/backend/tests/unit/replay/test_models.py
+++ b/backend/tests/unit/replay/test_models.py
@@ -0,0 +1,134 @@
+"""Unit tests for app.replay.models."""
+
+from __future__ import annotations
+
+import pytest
+
+pytestmark = pytest.mark.unit
+
+
+class TestStepType:
+    def test_all_step_types_exist(self) -> None:
+        from app.replay.models import StepType
+
+        assert StepType.user_message
+        assert StepType.supervisor_routing
+        assert StepType.tool_call
+        assert StepType.tool_result
+        assert StepType.agent_response
+        assert StepType.interrupt
+
+    def test_step_type_values(self) -> None:
+        from app.replay.models import StepType
+
+        assert StepType.user_message.value == "user_message"
+        assert StepType.tool_call.value == "tool_call"
+        assert StepType.agent_response.value == "agent_response"
+
+
+class TestReplayStep:
+    def test_minimal_replay_step(self) -> None:
+        from app.replay.models import ReplayStep, StepType
+
+        step = ReplayStep(step=1, type=StepType.user_message, timestamp="2026-01-01T00:00:00Z")
+        assert step.step == 1
+        assert step.type == StepType.user_message
+        assert step.timestamp == "2026-01-01T00:00:00Z"
+        assert step.content == ""
+        assert step.agent is None
+        assert step.tool is None
+        assert step.params is None
+        assert step.result is None
+        assert step.reasoning is None
+        assert step.tokens is None
+        assert step.duration_ms is None
+
+    def test_full_replay_step(self) -> None:
+        from app.replay.models import ReplayStep, StepType
+
+        step = ReplayStep(
+            step=2,
+            type=StepType.tool_call,
+            timestamp="2026-01-01T00:00:01Z",
+            content="calling get_order",
+            agent="order_agent",
+            tool="get_order_status",
+            params={"order_id": "ORD-123"},
+            result={"status": "shipped"},
+            reasoning="user asked about order",
+            tokens=50,
+            duration_ms=200,
+        )
+        assert step.step == 2
+        assert step.agent == "order_agent"
+        assert step.tool == "get_order_status"
+        assert step.params == {"order_id": "ORD-123"}
+        assert step.tokens == 50
+
+    def test_replay_step_is_frozen(self) -> None:
+        from app.replay.models import ReplayStep, StepType
+
+        step = ReplayStep(step=1, type=StepType.user_message, timestamp="2026-01-01T00:00:00Z")
+        with pytest.raises((AttributeError, TypeError)):
+            step.step = 99  # type: ignore[misc]
+
+    def test_replay_step_params_is_immutable_copy(self) -> None:
+        from app.replay.models import ReplayStep, StepType
+
+        params = {"key": "value"}
+        step = ReplayStep(
+            step=1,
+            type=StepType.tool_call,
+            timestamp="2026-01-01T00:00:00Z",
+            params=params,
+        )
+        # Modifying original dict should not affect step
+        params["new_key"] = "new_value"
+        assert "new_key" not in (step.params or {})
+
+
+class TestReplayPage:
+    def test_replay_page_construction(self) -> None:
+        from app.replay.models import ReplayPage, ReplayStep, StepType
+
+        steps = (
+            ReplayStep(step=1, type=StepType.user_message, timestamp="2026-01-01T00:00:00Z"),
+            ReplayStep(step=2, type=StepType.agent_response, timestamp="2026-01-01T00:00:01Z"),
+        )
+        page = ReplayPage(
+            thread_id="thread-123",
+            total_steps=2,
+            page=1,
+            per_page=20,
+            steps=steps,
+        )
+        assert page.thread_id == "thread-123"
+        assert page.total_steps == 2
+        assert page.page == 1
+        assert page.per_page == 20
+        assert len(page.steps) == 2
+
+    def test_replay_page_is_frozen(self) -> None:
+        from app.replay.models import ReplayPage
+
+        page = ReplayPage(
+            thread_id="t1",
+            total_steps=0,
+            page=1,
+            per_page=20,
+            steps=(),
+        )
+        with pytest.raises((AttributeError, TypeError)):
+            page.page = 2  # type: ignore[misc]
+
+    def test_replay_page_empty_steps(self) -> None:
+        from app.replay.models import ReplayPage
+
+        page = ReplayPage(
+            thread_id="t1",
+            total_steps=0,
+            page=1,
+            per_page=20,
+            steps=(),
+        )
+        assert page.steps == ()
--- a/backend/tests/unit/replay/test_transformer.py
+++ b/backend/tests/unit/replay/test_transformer.py
@@ -0,0 +1,257 @@
+"""Unit tests for app.replay.transformer."""
+
+from __future__ import annotations
+
+import pytest
+
+pytestmark = pytest.mark.unit
+
+
+def _make_row(messages: list[dict], metadata: dict | None = None) -> dict:
+    """Helper to build a checkpoint row with the given messages."""
+    return {
+        "thread_id": "thread-abc",
+        "checkpoint_id": "cp-001",
+        "checkpoint": {"channel_values": {"messages": messages}},
+        "metadata": metadata or {},
+    }
+
+
+class TestTransformCheckpoints:
+    def test_empty_rows_returns_empty_list(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        result = transform_checkpoints([])
+        assert result == []
+
+    def test_human_message_produces_user_message_step(self) -> None:
+        from app.replay.models import StepType
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [_make_row([{"type": "human", "content": "Hello, I need help"}])]
+        steps = transform_checkpoints(rows)
+        assert len(steps) == 1
+        assert steps[0].type == StepType.user_message
+        assert steps[0].content == "Hello, I need help"
+        assert steps[0].step == 1
+
+    def test_ai_message_with_content_produces_agent_response(self) -> None:
+        from app.replay.models import StepType
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            _make_row(
+                [{"type": "ai", "content": "I can help you with that.", "tool_calls": []}],
+                metadata={"writes": {"some_agent": "response"}},
+            )
+        ]
+        steps = transform_checkpoints(rows)
+        assert len(steps) == 1
+        assert steps[0].type == StepType.agent_response
+        assert steps[0].content == "I can help you with that."
+
+    def test_ai_message_with_tool_calls_produces_tool_call_step(self) -> None:
+        from app.replay.models import StepType
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            _make_row(
+                [
+                    {
+                        "type": "ai",
+                        "content": "",
+                        "tool_calls": [
+                            {
+                                "name": "get_order_status",
+                                "args": {"order_id": "ORD-123"},
+                                "id": "call_abc",
+                            }
+                        ],
+                    }
+                ]
+            )
+        ]
+        steps = transform_checkpoints(rows)
+        assert len(steps) == 1
+        assert steps[0].type == StepType.tool_call
+        assert steps[0].tool == "get_order_status"
+        assert steps[0].params == {"order_id": "ORD-123"}
+
+    def test_tool_message_produces_tool_result_step(self) -> None:
+        from app.replay.models import StepType
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            _make_row(
+                [
+                    {
+                        "type": "tool",
+                        "content": '{"status": "shipped"}',
+                        "name": "get_order_status",
+                    }
+                ]
+            )
+        ]
+        steps = transform_checkpoints(rows)
+        assert len(steps) == 1
+        assert steps[0].type == StepType.tool_result
+        assert steps[0].tool == "get_order_status"
+
+    def test_multiple_messages_sequential_steps(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            _make_row(
+                [
+                    {"type": "human", "content": "Help"},
+                    {"type": "ai", "content": "Sure!", "tool_calls": []},
+                ]
+            )
+        ]
+        steps = transform_checkpoints(rows)
+        assert len(steps) == 2
+        assert steps[0].step == 1
+        assert steps[1].step == 2
+
+    def test_unknown_message_type_skipped(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [_make_row([{"type": "unknown_type", "content": "test"}])]
+        steps = transform_checkpoints(rows)
+        # Should not crash; unknown types may be skipped
+        assert isinstance(steps, list)
+
+    def test_row_missing_checkpoint_skipped(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [{"thread_id": "t1", "checkpoint_id": "cp1", "checkpoint": None, "metadata": {}}]
+        steps = transform_checkpoints(rows)
+        assert isinstance(steps, list)
+
+    def test_row_missing_messages_key_skipped(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [{"thread_id": "t1", "checkpoint_id": "cp1", "checkpoint": {}, "metadata": {}}]
+        steps = transform_checkpoints(rows)
+        assert isinstance(steps, list)
+
+    def test_multiple_rows_steps_are_continuous(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            _make_row([{"type": "human", "content": "Q1"}]),
+            _make_row([{"type": "ai", "content": "A1", "tool_calls": []}]),
+        ]
+        steps = transform_checkpoints(rows)
+        assert len(steps) == 2
+        assert steps[0].step == 1
+        assert steps[1].step == 2
+
+    def test_timestamps_are_strings(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [_make_row([{"type": "human", "content": "Hi"}])]
+        steps = transform_checkpoints(rows)
+        assert isinstance(steps[0].timestamp, str)
+
+    def test_list_content_joined_to_string(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            _make_row(
+                [
+                    {
+                        "type": "human",
+                        "content": [
+                            {"text": "Hello"},
+                            {"text": " world"},
+                        ],
+                    }
+                ]
+            )
+        ]
+        steps = transform_checkpoints(rows)
+        assert len(steps) == 1
+        assert steps[0].content == "Hello  world"
+
+    def test_checkpoint_as_string_skipped(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            {
+                "thread_id": "t1",
+                "checkpoint_id": "cp1",
+                "checkpoint": "not-a-dict",
+                "metadata": {},
+            }
+        ]
+        steps = transform_checkpoints(rows)
+        assert steps == []
+
+    def test_channel_values_not_dict_skipped(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            {
+                "thread_id": "t1",
+                "checkpoint_id": "cp1",
+                "checkpoint": {"channel_values": "bad"},
+                "metadata": {},
+            }
+        ]
+        steps = transform_checkpoints(rows)
+        assert steps == []
+
+    def test_tool_result_valid_json_parsed(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            _make_row(
+                [
+                    {
+                        "type": "tool",
+                        "content": '{"order_id": "123", "status": "shipped"}',
+                        "name": "get_order_status",
+                    }
+                ]
+            )
+        ]
+        steps = transform_checkpoints(rows)
+        assert len(steps) == 1
+        assert steps[0].result == {"order_id": "123", "status": "shipped"}
+
+    def test_tool_result_invalid_json_wrapped(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            _make_row(
+                [
+                    {
+                        "type": "tool",
+                        "content": "not valid json",
+                        "name": "some_tool",
+                    }
+                ]
+            )
+        ]
+        steps = transform_checkpoints(rows)
+        assert len(steps) == 1
+        assert steps[0].result == {"raw": "not valid json"}
+
+    def test_malformed_message_skipped_gracefully(self) -> None:
+        from app.replay.transformer import transform_checkpoints
+
+        rows = [
+            _make_row(
+                [
+                    {"type": "human", "content": "Good message"},
+                    42,  # not a dict -- will raise in _step_from_message
+                    {"type": "ai", "content": "Response", "tool_calls": []},
+                ]
+            )
+        ]
+        steps = transform_checkpoints(rows)
+        # The malformed message is skipped; the other two produce steps.
+        assert len(steps) == 2
+        assert steps[0].step == 1
+        assert steps[1].step == 2
--- a/backend/tests/unit/test_config.py
+++ b/backend/tests/unit/test_config.py
@@ -7,10 +7,41 @@ import pytest
 from app.config import Settings


+def _isolated_settings(**kwargs: object) -> Settings:
+    """Create a Settings instance that ignores .env files and process env vars.
+
+    pydantic-settings reads from env_file and environment by default, which
+    causes test results to depend on the machine they run on.  We override
+    model_config at the class level temporarily so that every test gets
+    deterministic results.
+    """
+    # Build a throwaway subclass that disables env-file and env-var loading.
+    class _IsolatedSettings(Settings):
+        model_config = Settings.model_config.copy()
+        model_config["env_file"] = None  # type: ignore[assignment]
+        model_config["env_ignore_empty"] = True
+
+    # _env_parse_none_str makes pydantic-settings treat missing env vars as
+    # absent rather than empty-string, so required fields will raise.
+    import os
+
+    env_backup = os.environ.copy()
+    # Strip all env vars that Settings knows about so they can't leak in.
+    settings_fields = set(Settings.model_fields)
+    for key in list(os.environ):
+        if key.lower() in settings_fields:
+            del os.environ[key]
+    try:
+        return _IsolatedSettings(**kwargs)  # type: ignore[return-value]
+    finally:
+        os.environ.clear()
+        os.environ.update(env_backup)
+
+
@pytest.mark.unit
 class TestSettings:
    def test_default_values(self) -> None:
-        settings = Settings(
+        settings = _isolated_settings(
            database_url="postgresql://x:x@localhost/db",
            anthropic_api_key="key",
        )
@@ -20,7 +51,7 @@ class TestSettings:
        assert settings.interrupt_ttl_minutes == 30

    def test_custom_values(self) -> None:
-        settings = Settings(
+        settings = _isolated_settings(
            database_url="postgresql://x:x@localhost/db",
            llm_provider="openai",
            llm_model="gpt-4o",
@@ -33,18 +64,18 @@ class TestSettings:

    def test_invalid_provider_rejected(self) -> None:
        with pytest.raises(Exception):
-            Settings(
+            _isolated_settings(
                database_url="postgresql://x:x@localhost/db",
                llm_provider="invalid",
            )

    def test_missing_database_url_rejected(self) -> None:
        with pytest.raises(Exception):
-            Settings(anthropic_api_key="key")
+            _isolated_settings(anthropic_api_key="key")

    def test_empty_api_key_for_provider_rejected(self) -> None:
        with pytest.raises(ValueError, match="API key"):
-            Settings(
+            _isolated_settings(
                database_url="postgresql://x:x@localhost/db",
                llm_provider="anthropic",
                anthropic_api_key="",
@@ -52,9 +83,27 @@ class TestSettings:

    def test_wrong_provider_key_rejected(self) -> None:
        with pytest.raises(ValueError, match="API key"):
-            Settings(
+            _isolated_settings(
                database_url="postgresql://x:x@localhost/db",
                llm_provider="openai",
                anthropic_api_key="key",
                openai_api_key="",
            )
+
+    def test_azure_openai_missing_endpoint_rejected(self) -> None:
+        with pytest.raises(ValueError, match="AZURE_OPENAI_ENDPOINT"):
+            _isolated_settings(
+                database_url="postgresql://x:x@localhost/db",
+                llm_provider="azure_openai",
+                azure_openai_api_key="key",
+                azure_openai_deployment="my-deploy",
+            )
+
+    def test_azure_openai_missing_deployment_rejected(self) -> None:
+        with pytest.raises(ValueError, match="AZURE_OPENAI_DEPLOYMENT"):
+            _isolated_settings(
+                database_url="postgresql://x:x@localhost/db",
+                llm_provider="azure_openai",
+                azure_openai_api_key="key",
+                azure_openai_endpoint="https://example.openai.azure.com",
+            )
--- a/backend/tests/unit/test_conversation_tracker.py
+++ b/backend/tests/unit/test_conversation_tracker.py
@@ -0,0 +1,156 @@
+"""Tests for app.conversation_tracker module."""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+from app.conversation_tracker import (
+    ConversationTrackerProtocol,
+    NoOpConversationTracker,
+    PostgresConversationTracker,
+)
+
+pytestmark = pytest.mark.unit
+
+
+def _make_pool() -> AsyncMock:
+    """Create a mock async connection pool."""
+    pool = AsyncMock()
+    conn = AsyncMock()
+    conn.execute = AsyncMock()
+    pool.connection = MagicMock(return_value=_AsyncContextManager(conn))
+    return pool, conn
+
+
+class _AsyncContextManager:
+    """Async context manager helper."""
+
+    def __init__(self, value: object) -> None:
+        self._value = value
+
+    async def __aenter__(self) -> object:
+        return self._value
+
+    async def __aexit__(self, *args: object) -> None:
+        pass
+
+
+class TestConversationTrackerProtocol:
+    def test_noop_satisfies_protocol(self) -> None:
+        tracker = NoOpConversationTracker()
+        assert isinstance(tracker, ConversationTrackerProtocol)
+
+    def test_postgres_satisfies_protocol(self) -> None:
+        tracker = PostgresConversationTracker()
+        assert isinstance(tracker, ConversationTrackerProtocol)
+
+
+class TestNoOpConversationTracker:
+    @pytest.mark.asyncio
+    async def test_ensure_conversation_does_nothing(self) -> None:
+        tracker = NoOpConversationTracker()
+        pool = AsyncMock()
+        # Should not raise
+        await tracker.ensure_conversation(pool, "thread-1")
+
+    @pytest.mark.asyncio
+    async def test_record_turn_does_nothing(self) -> None:
+        tracker = NoOpConversationTracker()
+        pool = AsyncMock()
+        await tracker.record_turn(pool, "thread-1", "agent_a", 100, 0.05)
+
+    @pytest.mark.asyncio
+    async def test_resolve_does_nothing(self) -> None:
+        tracker = NoOpConversationTracker()
+        pool = AsyncMock()
+        await tracker.resolve(pool, "thread-1", "resolved")
+
+    @pytest.mark.asyncio
+    async def test_accepts_none_agent_name(self) -> None:
+        tracker = NoOpConversationTracker()
+        pool = AsyncMock()
+        await tracker.record_turn(pool, "thread-1", None, 0, 0.0)
+
+
+class TestPostgresConversationTracker:
+    @pytest.mark.asyncio
+    async def test_ensure_conversation_executes_insert(self) -> None:
+        tracker = PostgresConversationTracker()
+        pool, conn = _make_pool()
+
+        await tracker.ensure_conversation(pool, "thread-abc")
+
+        conn.execute.assert_awaited_once()
+        sql, params = conn.execute.call_args[0]
+        assert "INSERT" in sql
+        assert "ON CONFLICT" in sql
+        assert params["thread_id"] == "thread-abc"
+
+    @pytest.mark.asyncio
+    async def test_record_turn_executes_update(self) -> None:
+        tracker = PostgresConversationTracker()
+        pool, conn = _make_pool()
+
+        await tracker.record_turn(pool, "thread-abc", "order_agent", 250, 0.12)
+
+        conn.execute.assert_awaited_once()
+        sql, params = conn.execute.call_args[0]
+        assert "UPDATE" in sql
+        assert params["thread_id"] == "thread-abc"
+        assert params["agent_name"] == "order_agent"
+        assert params["tokens"] == 250
+        assert params["cost"] == 0.12
+
+    @pytest.mark.asyncio
+    async def test_record_turn_accepts_none_agent_name(self) -> None:
+        tracker = PostgresConversationTracker()
+        pool, conn = _make_pool()
+
+        await tracker.record_turn(pool, "thread-abc", None, 0, 0.0)
+
+        conn.execute.assert_awaited_once()
+        sql, params = conn.execute.call_args[0]
+        assert params["agent_name"] is None
+
+    @pytest.mark.asyncio
+    async def test_resolve_executes_update(self) -> None:
+        tracker = PostgresConversationTracker()
+        pool, conn = _make_pool()
+
+        await tracker.resolve(pool, "thread-abc", "resolved")
+
+        conn.execute.assert_awaited_once()
+        sql, params = conn.execute.call_args[0]
+        assert "UPDATE" in sql
+        assert params["thread_id"] == "thread-abc"
+        assert params["resolution_type"] == "resolved"
+
+    @pytest.mark.asyncio
+    async def test_resolve_sets_ended_at(self) -> None:
+        tracker = PostgresConversationTracker()
+        pool, conn = _make_pool()
+
+        await tracker.resolve(pool, "thread-abc", "escalated")
+
+        sql, params = conn.execute.call_args[0]
+        assert "ended_at" in sql.lower()
+
+    @pytest.mark.asyncio
+    async def test_ensure_conversation_with_special_thread_id(self) -> None:
+        tracker = PostgresConversationTracker()
+        pool, conn = _make_pool()
+
+        await tracker.ensure_conversation(pool, "thread-123-abc-XYZ")
+
+        conn.execute.assert_awaited_once()
+
+    @pytest.mark.asyncio
+    async def test_record_turn_with_zero_cost(self) -> None:
+        tracker = PostgresConversationTracker()
+        pool, conn = _make_pool()
+
+        await tracker.record_turn(pool, "t1", "agent", 0, 0.0)
+
+        conn.execute.assert_awaited_once()
--- a/backend/tests/unit/test_db.py
+++ b/backend/tests/unit/test_db.py
@@ -55,7 +55,7 @@ class TestDbModule:
        from app.db import setup_app_tables

        await setup_app_tables(mock_pool)
-        assert mock_conn.execute.await_count == 2
+        assert mock_conn.execute.await_count == 5

    def test_ddl_statements_valid(self) -> None:
        assert "CREATE TABLE IF NOT EXISTS conversations" in _CONVERSATIONS_DDL
--- a/backend/tests/unit/test_db_phase4.py
+++ b/backend/tests/unit/test_db_phase4.py
@@ -0,0 +1,55 @@
+"""Phase 4 DB migration tests -- analytics_events table and conversation columns."""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+pytestmark = pytest.mark.unit
+
+
+class TestAnalyticsEventsDDL:
+    def test_analytics_events_ddl_exists(self) -> None:
+        from app.db import _ANALYTICS_EVENTS_DDL
+
+        assert "CREATE TABLE IF NOT EXISTS analytics_events" in _ANALYTICS_EVENTS_DDL
+
+    def test_analytics_events_ddl_has_required_columns(self) -> None:
+        from app.db import _ANALYTICS_EVENTS_DDL
+
+        assert "thread_id" in _ANALYTICS_EVENTS_DDL
+        assert "event_type" in _ANALYTICS_EVENTS_DDL
+        assert "agent_name" in _ANALYTICS_EVENTS_DDL
+        assert "tool_name" in _ANALYTICS_EVENTS_DDL
+        assert "tokens_used" in _ANALYTICS_EVENTS_DDL
+        assert "cost_usd" in _ANALYTICS_EVENTS_DDL
+        assert "duration_ms" in _ANALYTICS_EVENTS_DDL
+        assert "success" in _ANALYTICS_EVENTS_DDL
+        assert "error_message" in _ANALYTICS_EVENTS_DDL
+        assert "metadata" in _ANALYTICS_EVENTS_DDL
+
+    def test_conversations_migration_ddl_exists(self) -> None:
+        from app.db import _CONVERSATIONS_MIGRATION_DDL
+
+        assert "ALTER TABLE" in _CONVERSATIONS_MIGRATION_DDL
+        assert "resolution_type" in _CONVERSATIONS_MIGRATION_DDL
+        assert "agents_used" in _CONVERSATIONS_MIGRATION_DDL
+        assert "turn_count" in _CONVERSATIONS_MIGRATION_DDL
+        assert "ended_at" in _CONVERSATIONS_MIGRATION_DDL
+        assert "IF NOT EXISTS" in _CONVERSATIONS_MIGRATION_DDL
+
+    @pytest.mark.asyncio
+    async def test_setup_app_tables_executes_analytics_ddl(self) -> None:
+        mock_conn = AsyncMock()
+        mock_ctx = AsyncMock()
+        mock_ctx.__aenter__ = AsyncMock(return_value=mock_conn)
+        mock_ctx.__aexit__ = AsyncMock(return_value=None)
+        mock_pool = MagicMock()
+        mock_pool.connection.return_value = mock_ctx
+
+        from app.db import setup_app_tables
+
+        await setup_app_tables(mock_pool)
+        # Now expects 5 statements: conversations, interrupts, sessions, analytics_events, migrations
+        assert mock_conn.execute.await_count == 5
--- a/backend/tests/unit/test_discount.py
+++ b/backend/tests/unit/test_discount.py
@@ -0,0 +1,79 @@
+"""Tests for app.agents.discount module."""
+
+from __future__ import annotations
+
+from unittest.mock import patch
+
+import pytest
+
+from app.agents.discount import apply_discount, generate_coupon
+
+
+@pytest.mark.unit
+class TestApplyDiscount:
+    def test_invalid_discount_zero(self) -> None:
+        result = apply_discount.invoke({"order_id": "1042", "discount_percent": 0})
+        assert result["status"] == "error"
+        assert "Invalid" in result["message"]
+
+    def test_invalid_discount_over_100(self) -> None:
+        result = apply_discount.invoke({"order_id": "1042", "discount_percent": 101})
+        assert result["status"] == "error"
+
+    def test_invalid_discount_negative(self) -> None:
+        result = apply_discount.invoke({"order_id": "1042", "discount_percent": -5})
+        assert result["status"] == "error"
+
+    @patch("app.agents.discount.interrupt", return_value=True)
+    def test_approved_discount(self, mock_interrupt) -> None:
+        result = apply_discount.invoke({"order_id": "1042", "discount_percent": 10})
+        assert result["status"] == "applied"
+        assert result["discount_percent"] == 10
+        assert "1042" in result["message"]
+
+    @patch("app.agents.discount.interrupt", return_value=False)
+    def test_rejected_discount(self, mock_interrupt) -> None:
+        result = apply_discount.invoke({"order_id": "1042", "discount_percent": 10})
+        assert result["status"] == "declined"
+
+    @patch("app.agents.discount.interrupt", return_value={"approved": True})
+    def test_approved_via_dict(self, mock_interrupt) -> None:
+        result = apply_discount.invoke({"order_id": "1042", "discount_percent": 50})
+        assert result["status"] == "applied"
+
+    @patch("app.agents.discount.interrupt", return_value={"approved": False})
+    def test_rejected_via_dict(self, mock_interrupt) -> None:
+        result = apply_discount.invoke({"order_id": "1042", "discount_percent": 50})
+        assert result["status"] == "declined"
+
+
+@pytest.mark.unit
+class TestGenerateCoupon:
+    def test_valid_coupon(self) -> None:
+        result = generate_coupon.invoke({"discount_percent": 15, "expiry_days": 7})
+        assert result["status"] == "generated"
+        assert result["discount_percent"] == 15
+        assert result["expiry_days"] == 7
+        assert result["coupon_code"].startswith("SAVE15-")
+
+    def test_default_expiry(self) -> None:
+        result = generate_coupon.invoke({"discount_percent": 20})
+        assert result["status"] == "generated"
+        assert result["expiry_days"] == 30
+
+    def test_invalid_discount_zero(self) -> None:
+        result = generate_coupon.invoke({"discount_percent": 0})
+        assert result["status"] == "error"
+
+    def test_invalid_discount_over_100(self) -> None:
+        result = generate_coupon.invoke({"discount_percent": 101})
+        assert result["status"] == "error"
+
+    def test_invalid_expiry(self) -> None:
+        result = generate_coupon.invoke({"discount_percent": 10, "expiry_days": 0})
+        assert result["status"] == "error"
+
+    def test_coupon_codes_unique(self) -> None:
+        r1 = generate_coupon.invoke({"discount_percent": 10})
+        r2 = generate_coupon.invoke({"discount_percent": 10})
+        assert r1["coupon_code"] != r2["coupon_code"]
--- a/backend/tests/unit/test_edge_cases.py
+++ b/backend/tests/unit/test_edge_cases.py
@@ -0,0 +1,210 @@
+"""Edge case tests for ws_handler input validation and rate limiting."""
+
+from __future__ import annotations
+
+import json
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+from app.callbacks import TokenUsageCallbackHandler
+from app.graph_context import GraphContext
+from app.session_manager import SessionManager
+from app.ws_context import WebSocketContext
+from app.ws_handler import dispatch_message
+
+pytestmark = pytest.mark.unit
+
+
+def _make_ws() -> AsyncMock:
+    ws = AsyncMock()
+    ws.send_json = AsyncMock()
+    return ws
+
+
+def _make_graph() -> MagicMock:
+    graph = AsyncMock()
+
+    class AsyncIterHelper:
+        def __aiter__(self):
+            return self
+
+        async def __anext__(self):
+            raise StopAsyncIteration
+
+    graph.astream = MagicMock(return_value=AsyncIterHelper())
+    state = MagicMock()
+    state.tasks = ()
+    graph.aget_state = AsyncMock(return_value=state)
+    return graph
+
+
+def _make_ws_ctx(sm: SessionManager | None = None) -> WebSocketContext:
+    graph = _make_graph()
+    registry = MagicMock()
+    registry.list_agents = MagicMock(return_value=())
+    graph_ctx = GraphContext(graph=graph, registry=registry, intent_classifier=None)
+    return WebSocketContext(
+        graph_ctx=graph_ctx,
+        session_manager=sm or SessionManager(),
+        callback_handler=TokenUsageCallbackHandler(),
+    )
+
+
+@pytest.mark.unit
+class TestEmptyMessageHandling:
+    @pytest.mark.asyncio
+    async def test_empty_message_content_returns_error(self) -> None:
+        ws = _make_ws()
+        sm = SessionManager()
+        ws_ctx = _make_ws_ctx(sm=sm)
+
+        sm.touch("t1")
+        msg = json.dumps({"type": "message", "thread_id": "t1", "content": ""})
+        await dispatch_message(ws, ws_ctx, msg)
+
+        call_data = ws.send_json.call_args[0][0]
+        assert call_data["type"] == "error"
+        msg_lower = call_data["message"].lower()
+        assert "content" in msg_lower or "missing" in msg_lower
+
+    @pytest.mark.asyncio
+    async def test_whitespace_only_message_treated_as_empty(self) -> None:
+        ws = _make_ws()
+        sm = SessionManager()
+        ws_ctx = _make_ws_ctx(sm=sm)
+
+        sm.touch("t1")
+        msg = json.dumps({"type": "message", "thread_id": "t1", "content": "   "})
+        await dispatch_message(ws, ws_ctx, msg)
+
+        call_data = ws.send_json.call_args[0][0]
+        assert call_data["type"] == "error"
+
+
+@pytest.mark.unit
+class TestOversizedMessageHandling:
+    @pytest.mark.asyncio
+    async def test_content_over_10000_chars_returns_error(self) -> None:
+        ws = _make_ws()
+        sm = SessionManager()
+        ws_ctx = _make_ws_ctx(sm=sm)
+
+        sm.touch("t1")
+        content = "x" * 10001
+        msg = json.dumps({"type": "message", "thread_id": "t1", "content": content})
+        await dispatch_message(ws, ws_ctx, msg)
+
+        call_data = ws.send_json.call_args[0][0]
+        assert call_data["type"] == "error"
+        assert "too long" in call_data["message"].lower()
+
+    @pytest.mark.asyncio
+    async def test_content_exactly_10000_chars_is_accepted(self) -> None:
+        ws = _make_ws()
+        sm = SessionManager()
+        ws_ctx = _make_ws_ctx(sm=sm)
+
+        sm.touch("t1")
+        content = "x" * 10000
+        msg = json.dumps({"type": "message", "thread_id": "t1", "content": content})
+        await dispatch_message(ws, ws_ctx, msg)
+
+        last_call = ws.send_json.call_args[0][0]
+        # Should be processed, not an error about length
+        msg_text = last_call.get("message", "").lower()
+        assert last_call["type"] != "error" or "too long" not in msg_text
+
+    @pytest.mark.asyncio
+    async def test_raw_message_over_32kb_returns_error(self) -> None:
+        ws = _make_ws()
+        ws_ctx = _make_ws_ctx()
+
+        large_msg = "x" * 40_000
+        await dispatch_message(ws, ws_ctx, large_msg)
+
+        call_data = ws.send_json.call_args[0][0]
+        assert call_data["type"] == "error"
+        assert "too large" in call_data["message"].lower()
+
+
+@pytest.mark.unit
+class TestInvalidJsonHandling:
+    @pytest.mark.asyncio
+    async def test_invalid_json_returns_error(self) -> None:
+        ws = _make_ws()
+        ws_ctx = _make_ws_ctx()
+
+        await dispatch_message(ws, ws_ctx, "not valid json {{")
+
+        call_data = ws.send_json.call_args[0][0]
+        assert call_data["type"] == "error"
+        assert "invalid json" in call_data["message"].lower()
+
+    @pytest.mark.asyncio
+    async def test_empty_string_returns_json_error(self) -> None:
+        ws = _make_ws()
+        ws_ctx = _make_ws_ctx()
+
+        await dispatch_message(ws, ws_ctx, "")
+
+        call_data = ws.send_json.call_args[0][0]
+        assert call_data["type"] == "error"
+
+    @pytest.mark.asyncio
+    async def test_json_array_not_object_returns_error(self) -> None:
+        ws = _make_ws()
+        ws_ctx = _make_ws_ctx()
+
+        await dispatch_message(ws, ws_ctx, '["not", "an", "object"]')
+
+        call_data = ws.send_json.call_args[0][0]
+        assert call_data["type"] == "error"
+
+
+@pytest.mark.unit
+class TestRateLimiting:
+    @pytest.mark.asyncio
+    async def test_rapid_fire_messages_rate_limited(self) -> None:
+        ws = _make_ws()
+        sm = SessionManager()
+
+        sm.touch("t1")
+
+        # Simulate 11 rapid messages (exceeds 10 per 10 seconds limit)
+        rate_limit_triggered = False
+        for i in range(11):
+            ws_ctx = _make_ws_ctx(sm=sm)
+            await dispatch_message(ws, ws_ctx, json.dumps({
+                "type": "message",
+                "thread_id": "t1",
+                "content": f"message {i}",
+            }))
+            last_call = ws.send_json.call_args[0][0]
+            if last_call["type"] == "error" and "rate" in last_call.get("message", "").lower():
+                rate_limit_triggered = True
+                break
+
+        assert rate_limit_triggered, "Rate limiting should trigger after 10 rapid messages"
+
+    @pytest.mark.asyncio
+    async def test_different_threads_have_separate_rate_limits(self) -> None:
+        ws = _make_ws()
+        sm = SessionManager()
+
+        sm.touch("t1")
+        sm.touch("t2")
+
+        # Send 5 messages on t1 and 5 on t2 -- neither should be rate limited
+        for i in range(5):
+            ws_ctx1 = _make_ws_ctx(sm=sm)
+            ws_ctx2 = _make_ws_ctx(sm=sm)
+            await dispatch_message(ws, ws_ctx1, json.dumps({
+                "type": "message", "thread_id": "t1", "content": f"msg {i}",
+            }))
+            await dispatch_message(ws, ws_ctx2, json.dumps({
+                "type": "message", "thread_id": "t2", "content": f"msg {i}",
+            }))
+
+        last_call = ws.send_json.call_args[0][0]
+        assert "rate" not in last_call.get("message", "").lower()
--- a/backend/tests/unit/test_error_handler.py
+++ b/backend/tests/unit/test_error_handler.py
@@ -0,0 +1,175 @@
+"""Tests for app.tools.error_handler module."""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, patch
+
+import httpx
+import pytest
+
+from app.tools.error_handler import (
+    ErrorCategory,
+    classify_error,
+    with_retry,
+)
+
+pytestmark = pytest.mark.unit
+
+
+class TestErrorClassification:
+    def test_timeout_exception_is_timeout(self) -> None:
+        exc = httpx.TimeoutException("timed out")
+        assert classify_error(exc) == ErrorCategory.TIMEOUT
+
+    def test_connect_error_is_network(self) -> None:
+        exc = httpx.ConnectError("connection refused")
+        assert classify_error(exc) == ErrorCategory.NETWORK
+
+    def test_401_is_auth_failure(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(401, request=request)
+        exc = httpx.HTTPStatusError("401", request=request, response=response)
+        assert classify_error(exc) == ErrorCategory.AUTH_FAILURE
+
+    def test_403_is_auth_failure(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(403, request=request)
+        exc = httpx.HTTPStatusError("403", request=request, response=response)
+        assert classify_error(exc) == ErrorCategory.AUTH_FAILURE
+
+    def test_429_is_retryable(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(429, request=request)
+        exc = httpx.HTTPStatusError("429", request=request, response=response)
+        assert classify_error(exc) == ErrorCategory.RETRYABLE
+
+    def test_500_is_retryable(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(500, request=request)
+        exc = httpx.HTTPStatusError("500", request=request, response=response)
+        assert classify_error(exc) == ErrorCategory.RETRYABLE
+
+    def test_502_is_retryable(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(502, request=request)
+        exc = httpx.HTTPStatusError("502", request=request, response=response)
+        assert classify_error(exc) == ErrorCategory.RETRYABLE
+
+    def test_503_is_retryable(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(503, request=request)
+        exc = httpx.HTTPStatusError("503", request=request, response=response)
+        assert classify_error(exc) == ErrorCategory.RETRYABLE
+
+    def test_404_is_non_retryable(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(404, request=request)
+        exc = httpx.HTTPStatusError("404", request=request, response=response)
+        assert classify_error(exc) == ErrorCategory.NON_RETRYABLE
+
+    def test_400_is_non_retryable(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(400, request=request)
+        exc = httpx.HTTPStatusError("400", request=request, response=response)
+        assert classify_error(exc) == ErrorCategory.NON_RETRYABLE
+
+    def test_generic_exception_is_non_retryable(self) -> None:
+        exc = ValueError("bad value")
+        assert classify_error(exc) == ErrorCategory.NON_RETRYABLE
+
+    def test_runtime_error_is_non_retryable(self) -> None:
+        exc = RuntimeError("boom")
+        assert classify_error(exc) == ErrorCategory.NON_RETRYABLE
+
+
+class TestWithRetry:
+    @pytest.mark.asyncio
+    async def test_succeeds_on_first_try(self) -> None:
+        fn = AsyncMock(return_value="ok")
+        result = await with_retry(fn, max_retries=3, base_delay=0.0)
+        assert result == "ok"
+        assert fn.call_count == 1
+
+    @pytest.mark.asyncio
+    async def test_retries_on_retryable_error(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(503, request=request)
+        retryable_exc = httpx.HTTPStatusError("503", request=request, response=response)
+
+        fn = AsyncMock(side_effect=[retryable_exc, retryable_exc, "success"])
+
+        with patch("app.tools.error_handler.asyncio.sleep", new_callable=AsyncMock):
+            result = await with_retry(fn, max_retries=3, base_delay=0.0)
+
+        assert result == "success"
+        assert fn.call_count == 3
+
+    @pytest.mark.asyncio
+    async def test_does_not_retry_non_retryable_error(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(404, request=request)
+        non_retryable_exc = httpx.HTTPStatusError("404", request=request, response=response)
+
+        fn = AsyncMock(side_effect=non_retryable_exc)
+
+        with pytest.raises(httpx.HTTPStatusError):
+            await with_retry(fn, max_retries=3, base_delay=0.0)
+
+        assert fn.call_count == 1
+
+    @pytest.mark.asyncio
+    async def test_does_not_retry_auth_failure(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(401, request=request)
+        auth_exc = httpx.HTTPStatusError("401", request=request, response=response)
+
+        fn = AsyncMock(side_effect=auth_exc)
+
+        with pytest.raises(httpx.HTTPStatusError):
+            await with_retry(fn, max_retries=3, base_delay=0.0)
+
+        assert fn.call_count == 1
+
+    @pytest.mark.asyncio
+    async def test_raises_after_max_retries_exhausted(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(500, request=request)
+        retryable_exc = httpx.HTTPStatusError("500", request=request, response=response)
+
+        fn = AsyncMock(side_effect=retryable_exc)
+
+        with (
+            patch("app.tools.error_handler.asyncio.sleep", new_callable=AsyncMock),
+            pytest.raises(httpx.HTTPStatusError),
+        ):
+            await with_retry(fn, max_retries=3, base_delay=0.0)
+
+        assert fn.call_count == 3
+
+    @pytest.mark.asyncio
+    async def test_does_not_retry_timeout(self) -> None:
+        """TimeoutException is TIMEOUT category -- not retried by default."""
+        fn = AsyncMock(side_effect=httpx.TimeoutException("timed out"))
+
+        with pytest.raises(httpx.TimeoutException):
+            await with_retry(fn, max_retries=3, base_delay=0.0)
+
+        assert fn.call_count == 1
+
+    @pytest.mark.asyncio
+    async def test_exponential_backoff_increases_delay(self) -> None:
+        request = httpx.Request("GET", "http://example.com")
+        response = httpx.Response(503, request=request)
+        retryable_exc = httpx.HTTPStatusError("503", request=request, response=response)
+
+        fn = AsyncMock(side_effect=[retryable_exc, retryable_exc, "done"])
+        sleep_delays: list[float] = []
+
+        async def capture_sleep(delay: float) -> None:
+            sleep_delays.append(delay)
+
+        with patch("app.tools.error_handler.asyncio.sleep", side_effect=capture_sleep):
+            await with_retry(fn, max_retries=3, base_delay=1.0)
+
+        assert len(sleep_delays) == 2
+        assert sleep_delays[1] > sleep_delays[0]
--- a/backend/tests/unit/test_error_responses.py
+++ b/backend/tests/unit/test_error_responses.py
@@ -0,0 +1,142 @@
+"""Tests for standardized error response envelope format."""
+
+from __future__ import annotations
+
+import pytest
+from fastapi import FastAPI, HTTPException
+from fastapi.exceptions import RequestValidationError
+from fastapi.responses import JSONResponse
+from fastapi.testclient import TestClient
+from pydantic import BaseModel, Field
+
+from app.api_utils import envelope
+
+pytestmark = pytest.mark.unit
+
+
+def _build_test_app() -> FastAPI:
+    """Build a minimal FastAPI app with the standard exception handlers."""
+    app = FastAPI()
+
+    @app.exception_handler(HTTPException)
+    async def http_exception_handler(request, exc):  # type: ignore[no-untyped-def]
+        return JSONResponse(
+            status_code=exc.status_code,
+            content=envelope(None, success=False, error=exc.detail),
+        )
+
+    @app.exception_handler(RequestValidationError)
+    async def validation_exception_handler(request, exc):  # type: ignore[no-untyped-def]
+        return JSONResponse(
+            status_code=422,
+            content=envelope(None, success=False, error=str(exc)),
+        )
+
+    @app.exception_handler(Exception)
+    async def general_exception_handler(request, exc):  # type: ignore[no-untyped-def]
+        return JSONResponse(
+            status_code=500,
+            content=envelope(None, success=False, error="Internal server error"),
+        )
+
+    class ItemRequest(BaseModel):
+        name: str = Field(..., min_length=1)
+        count: int = Field(..., gt=0)
+
+    @app.get("/items/{item_id}")
+    def get_item(item_id: int) -> dict:
+        if item_id == 0:
+            raise HTTPException(status_code=400, detail="Invalid item ID")
+        if item_id == 999:
+            raise HTTPException(status_code=404, detail="Item not found")
+        if item_id == 401:
+            raise HTTPException(status_code=401, detail="Not authenticated")
+        return envelope({"id": item_id, "name": "test"})
+
+    @app.post("/items")
+    def create_item(item: ItemRequest) -> dict:
+        return envelope({"id": 1, "name": item.name})
+
+    @app.get("/crash")
+    def crash() -> dict:
+        msg = "unexpected failure"
+        raise RuntimeError(msg)
+
+    return app
+
+
+class TestHttpExceptionEnvelope:
+    """HTTPException responses use the standard envelope format."""
+
+    def test_400_returns_envelope(self) -> None:
+        app = _build_test_app()
+        with TestClient(app, raise_server_exceptions=False) as client:
+            resp = client.get("/items/0")
+        assert resp.status_code == 400
+        body = resp.json()
+        assert body["success"] is False
+        assert body["data"] is None
+        assert body["error"] == "Invalid item ID"
+
+    def test_404_returns_envelope(self) -> None:
+        app = _build_test_app()
+        with TestClient(app, raise_server_exceptions=False) as client:
+            resp = client.get("/items/999")
+        assert resp.status_code == 404
+        body = resp.json()
+        assert body["success"] is False
+        assert body["data"] is None
+        assert body["error"] == "Item not found"
+
+    def test_401_returns_envelope(self) -> None:
+        app = _build_test_app()
+        with TestClient(app, raise_server_exceptions=False) as client:
+            resp = client.get("/items/401")
+        assert resp.status_code == 401
+        body = resp.json()
+        assert body["success"] is False
+        assert body["data"] is None
+        assert body["error"] == "Not authenticated"
+
+
+class TestValidationErrorEnvelope:
+    """Validation errors return 422 with envelope format."""
+
+    def test_validation_error_returns_envelope(self) -> None:
+        app = _build_test_app()
+        with TestClient(app, raise_server_exceptions=False) as client:
+            resp = client.post("/items", json={"name": "", "count": -1})
+        assert resp.status_code == 422
+        body = resp.json()
+        assert body["success"] is False
+        assert body["data"] is None
+        assert isinstance(body["error"], str)
+        assert len(body["error"]) > 0
+
+
+class TestGeneralExceptionEnvelope:
+    """Unhandled exceptions return 500 with safe envelope."""
+
+    def test_unhandled_exception_returns_500_envelope(self) -> None:
+        app = _build_test_app()
+        with TestClient(app, raise_server_exceptions=False) as client:
+            resp = client.get("/crash")
+        assert resp.status_code == 500
+        body = resp.json()
+        assert body["success"] is False
+        assert body["data"] is None
+        assert body["error"] == "Internal server error"
+
+
+class TestSuccessResponseUnchanged:
+    """Success responses still work normally."""
+
+    def test_success_returns_envelope(self) -> None:
+        app = _build_test_app()
+        with TestClient(app) as client:
+            resp = client.get("/items/42")
+        assert resp.status_code == 200
+        body = resp.json()
+        assert body["success"] is True
+        assert body["data"]["id"] == 42
+        assert body["error"] is None
--- a/backend/tests/unit/test_escalation.py
+++ b/backend/tests/unit/test_escalation.py
@@ -0,0 +1,169 @@
+"""Tests for app.escalation module."""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, patch
+
+import httpx
+import pytest
+
+from app.escalation import (
+    EscalationPayload,
+    EscalationResult,
+    NoOpEscalator,
+    WebhookEscalator,
+)
+
+
+def _make_payload(**kwargs) -> EscalationPayload:
+    defaults = {
+        "thread_id": "t1",
+        "reason": "Agent cannot resolve",
+        "conversation_summary": "User asked about refund policy",
+    }
+    defaults.update(kwargs)
+    return EscalationPayload(**defaults)
+
+
+@pytest.mark.unit
+class TestEscalationPayload:
+    def test_frozen(self) -> None:
+        payload = _make_payload()
+        with pytest.raises(Exception):
+            payload.thread_id = "t2"  # type: ignore[misc]
+
+    def test_default_metadata(self) -> None:
+        payload = _make_payload()
+        assert payload.metadata == {}
+
+    def test_model_dump(self) -> None:
+        payload = _make_payload(metadata={"key": "val"})
+        data = payload.model_dump()
+        assert data["thread_id"] == "t1"
+        assert data["metadata"] == {"key": "val"}
+
+
+@pytest.mark.unit
+class TestEscalationResult:
+    def test_frozen(self) -> None:
+        result = EscalationResult(success=True, status_code=200, attempts=1, error=None)
+        assert result.success
+        assert result.status_code == 200
+
+
+@pytest.mark.unit
+class TestWebhookEscalator:
+    @pytest.mark.asyncio
+    async def test_empty_url_returns_failure(self) -> None:
+        escalator = WebhookEscalator(url="", max_retries=3)
+        result = await escalator.escalate(_make_payload())
+        assert not result.success
+        assert result.attempts == 0
+        assert "not configured" in result.error
+
+    @pytest.mark.asyncio
+    async def test_successful_post(self) -> None:
+        mock_response = AsyncMock()
+        mock_response.status_code = 200
+
+        mock_client = AsyncMock()
+        mock_client.post = AsyncMock(return_value=mock_response)
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        with patch("app.escalation.httpx.AsyncClient", return_value=mock_client):
+            escalator = WebhookEscalator(url="https://example.com/hook")
+            result = await escalator.escalate(_make_payload())
+
+        assert result.success
+        assert result.status_code == 200
+        assert result.attempts == 1
+
+    @pytest.mark.asyncio
+    async def test_retry_on_server_error(self) -> None:
+        fail_response = AsyncMock()
+        fail_response.status_code = 500
+        success_response = AsyncMock()
+        success_response.status_code = 200
+
+        mock_client = AsyncMock()
+        mock_client.post = AsyncMock(side_effect=[fail_response, fail_response, success_response])
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        with (
+            patch("app.escalation.httpx.AsyncClient", return_value=mock_client),
+            patch("app.escalation.asyncio.sleep", new_callable=AsyncMock),
+        ):
+            escalator = WebhookEscalator(url="https://example.com/hook", max_retries=3)
+            result = await escalator.escalate(_make_payload())
+
+        assert result.success
+        assert result.attempts == 3
+
+    @pytest.mark.asyncio
+    async def test_all_retries_exhausted(self) -> None:
+        fail_response = AsyncMock()
+        fail_response.status_code = 500
+
+        mock_client = AsyncMock()
+        mock_client.post = AsyncMock(return_value=fail_response)
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        with (
+            patch("app.escalation.httpx.AsyncClient", return_value=mock_client),
+            patch("app.escalation.asyncio.sleep", new_callable=AsyncMock),
+        ):
+            escalator = WebhookEscalator(url="https://example.com/hook", max_retries=3)
+            result = await escalator.escalate(_make_payload())
+
+        assert not result.success
+        assert result.attempts == 3
+        assert "500" in result.error
+
+    @pytest.mark.asyncio
+    async def test_timeout_error(self) -> None:
+        mock_client = AsyncMock()
+        mock_client.post = AsyncMock(side_effect=httpx.TimeoutException("timeout"))
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        with (
+            patch("app.escalation.httpx.AsyncClient", return_value=mock_client),
+            patch("app.escalation.asyncio.sleep", new_callable=AsyncMock),
+        ):
+            escalator = WebhookEscalator(url="https://example.com/hook", max_retries=2)
+            result = await escalator.escalate(_make_payload())
+
+        assert not result.success
+        assert "timed out" in result.error
+
+    @pytest.mark.asyncio
+    async def test_request_error(self) -> None:
+        mock_client = AsyncMock()
+        mock_client.post = AsyncMock(
+            side_effect=httpx.RequestError("connection refused")
+        )
+        mock_client.__aenter__ = AsyncMock(return_value=mock_client)
+        mock_client.__aexit__ = AsyncMock(return_value=False)
+
+        with (
+            patch("app.escalation.httpx.AsyncClient", return_value=mock_client),
+            patch("app.escalation.asyncio.sleep", new_callable=AsyncMock),
+        ):
+            escalator = WebhookEscalator(url="https://example.com/hook", max_retries=1)
+            result = await escalator.escalate(_make_payload())
+
+        assert not result.success
+
+
+@pytest.mark.unit
+class TestNoOpEscalator:
+    @pytest.mark.asyncio
+    async def test_returns_disabled(self) -> None:
+        escalator = NoOpEscalator()
+        result = await escalator.escalate(_make_payload())
+        assert not result.success
+        assert result.attempts == 0
+        assert "disabled" in result.error.lower()
--- a/backend/tests/unit/test_graph.py
+++ b/backend/tests/unit/test_graph.py
@@ -6,8 +6,11 @@ from typing import TYPE_CHECKING
 from unittest.mock import AsyncMock, MagicMock

 import pytest
+from langgraph.checkpoint.memory import InMemorySaver

-from app.graph import SUPERVISOR_PROMPT, build_agent_nodes, build_graph
+from app.graph import build_agent_nodes, build_graph
+from app.graph_context import GraphContext
+from app.intent import ClassificationResult, IntentTarget

 if TYPE_CHECKING:
    from app.registry import AgentRegistry
@@ -33,12 +36,59 @@ class TestBuildGraph:
        mock_llm = MagicMock()
        mock_llm.bind_tools = MagicMock(return_value=mock_llm)
        mock_llm.with_structured_output = MagicMock(return_value=mock_llm)
-        mock_checkpointer = AsyncMock()
+        checkpointer = InMemorySaver()

-        graph = build_graph(sample_registry, mock_llm, mock_checkpointer)
-        assert graph is not None
+        graph_ctx = build_graph(sample_registry, mock_llm, checkpointer)
+        assert graph_ctx is not None
+        assert graph_ctx.graph is not None

-    def test_supervisor_prompt_contains_routing_info(self) -> None:
-        assert "order_lookup" in SUPERVISOR_PROMPT
-        assert "order_actions" in SUPERVISOR_PROMPT
-        assert "fallback" in SUPERVISOR_PROMPT
+    def test_graph_has_classifier_attached(self, sample_registry: AgentRegistry) -> None:
+        mock_llm = MagicMock()
+        mock_llm.bind_tools = MagicMock(return_value=mock_llm)
+        mock_llm.with_structured_output = MagicMock(return_value=mock_llm)
+        checkpointer = InMemorySaver()
+        mock_classifier = MagicMock()
+
+        graph_ctx = build_graph(
+            sample_registry, mock_llm, checkpointer, intent_classifier=mock_classifier
+        )
+        assert graph_ctx.intent_classifier is mock_classifier
+        assert graph_ctx.registry is sample_registry
+
+    def test_graph_without_classifier(self, sample_registry: AgentRegistry) -> None:
+        mock_llm = MagicMock()
+        mock_llm.bind_tools = MagicMock(return_value=mock_llm)
+        mock_llm.with_structured_output = MagicMock(return_value=mock_llm)
+        checkpointer = InMemorySaver()
+
+        graph_ctx = build_graph(sample_registry, mock_llm, checkpointer)
+        assert graph_ctx.intent_classifier is None
+
+
+@pytest.mark.unit
+class TestClassifyIntent:
+    @pytest.mark.asyncio
+    async def test_returns_none_without_classifier(self) -> None:
+        mock_registry = MagicMock()
+        mock_registry.list_agents = MagicMock(return_value=())
+        graph_ctx = GraphContext(graph=MagicMock(), registry=mock_registry, intent_classifier=None)
+        result = await graph_ctx.classify_intent("hello")
+        assert result is None
+
+    @pytest.mark.asyncio
+    async def test_calls_classifier(self) -> None:
+        expected = ClassificationResult(
+            intents=(IntentTarget(agent_name="order_lookup", confidence=0.9, reasoning="test"),),
+        )
+        mock_classifier = AsyncMock()
+        mock_classifier.classify = AsyncMock(return_value=expected)
+
+        mock_registry = MagicMock()
+        mock_registry.list_agents = MagicMock(return_value=())
+        graph_ctx = GraphContext(
+            graph=MagicMock(), registry=mock_registry, intent_classifier=mock_classifier,
+        )
+
+        result = await graph_ctx.classify_intent("check order")
+        assert result is not None
+        assert result.intents[0].agent_name == "order_lookup"
--- a/backend/tests/unit/test_intent.py
+++ b/backend/tests/unit/test_intent.py
@@ -0,0 +1,177 @@
+"""Tests for app.intent module."""
+
+from __future__ import annotations
+
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+from app.intent import (
+    AMBIGUITY_THRESHOLD,
+    ClassificationResult,
+    IntentTarget,
+    LLMIntentClassifier,
+    _build_agent_list,
+)
+from app.registry import AgentConfig
+
+
+def _make_agent(name: str, desc: str = "test", perm: str = "read") -> AgentConfig:
+    return AgentConfig(
+        name=name, description=desc, permission=perm, tools=["fallback_respond"],
+    )
+
+
+@pytest.mark.unit
+class TestIntentModels:
+    def test_intent_target_frozen(self) -> None:
+        target = IntentTarget(agent_name="order_lookup", confidence=0.9, reasoning="order query")
+        with pytest.raises(Exception):
+            target.agent_name = "other"  # type: ignore[misc]
+
+    def test_classification_result_frozen(self) -> None:
+        result = ClassificationResult(
+            intents=(IntentTarget(agent_name="a", confidence=0.9, reasoning="r"),),
+        )
+        assert not result.is_ambiguous
+        assert result.clarification_question is None
+
+    def test_classification_result_ambiguous(self) -> None:
+        result = ClassificationResult(
+            intents=(),
+            is_ambiguous=True,
+            clarification_question="What do you mean?",
+        )
+        assert result.is_ambiguous
+
+    def test_multi_intent(self) -> None:
+        result = ClassificationResult(
+            intents=(
+                IntentTarget(agent_name="order_actions", confidence=0.85, reasoning="cancel"),
+                IntentTarget(agent_name="discount", confidence=0.8, reasoning="discount"),
+            ),
+        )
+        assert len(result.intents) == 2
+
+
+@pytest.mark.unit
+class TestBuildAgentList:
+    def test_formats_agents(self) -> None:
+        agents = (
+            _make_agent("order_lookup", "Looks up orders", "read"),
+            _make_agent("order_actions", "Modifies orders", "write"),
+        )
+        text = _build_agent_list(agents)
+        assert "order_lookup" in text
+        assert "order_actions" in text
+        assert "read" in text
+        assert "write" in text
+
+
+@pytest.mark.unit
+class TestLLMIntentClassifier:
+    @pytest.mark.asyncio
+    async def test_single_intent_classification(self) -> None:
+        expected = ClassificationResult(
+            intents=(IntentTarget(agent_name="order_lookup", confidence=0.95, reasoning="query"),),
+        )
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(return_value=expected)
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        agents = (_make_agent("order_lookup"), _make_agent("fallback"))
+
+        result = await classifier.classify("What is order 1042 status?", agents)
+        assert len(result.intents) == 1
+        assert result.intents[0].agent_name == "order_lookup"
+        assert not result.is_ambiguous
+
+    @pytest.mark.asyncio
+    async def test_multi_intent_classification(self) -> None:
+        expected = ClassificationResult(
+            intents=(
+                IntentTarget(agent_name="order_actions", confidence=0.9, reasoning="cancel"),
+                IntentTarget(agent_name="discount", confidence=0.85, reasoning="discount"),
+            ),
+        )
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(return_value=expected)
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        agents = (_make_agent("order_actions"), _make_agent("discount"), _make_agent("fallback"))
+
+        result = await classifier.classify("Cancel order 1042 and give me 10% off", agents)
+        assert len(result.intents) == 2
+        assert not result.is_ambiguous
+
+    @pytest.mark.asyncio
+    async def test_ambiguous_classification(self) -> None:
+        expected = ClassificationResult(
+            intents=(IntentTarget(agent_name="fallback", confidence=0.3, reasoning="unclear"),),
+            is_ambiguous=False,
+        )
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(return_value=expected)
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        agents = (_make_agent("order_lookup"), _make_agent("fallback"))
+
+        result = await classifier.classify("hmm", agents)
+        # Low confidence triggers ambiguity
+        assert result.is_ambiguous
+        assert result.clarification_question is not None
+
+    @pytest.mark.asyncio
+    async def test_llm_error_returns_ambiguous(self) -> None:
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(side_effect=RuntimeError("LLM error"))
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        agents = (_make_agent("fallback"),)
+
+        result = await classifier.classify("test", agents)
+        assert result.is_ambiguous
+        assert result.clarification_question is not None
+
+    @pytest.mark.asyncio
+    async def test_non_result_type_returns_ambiguous(self) -> None:
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(return_value="not a ClassificationResult")
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        agents = (_make_agent("fallback"),)
+
+        result = await classifier.classify("test", agents)
+        assert result.is_ambiguous
+
+    @pytest.mark.asyncio
+    async def test_high_confidence_not_ambiguous(self) -> None:
+        expected = ClassificationResult(
+            intents=(
+                IntentTarget(
+                    agent_name="order_lookup",
+                    confidence=AMBIGUITY_THRESHOLD + 0.1,
+                    reasoning="clear",
+                ),
+            ),
+        )
+        mock_structured = MagicMock()
+        mock_structured.ainvoke = AsyncMock(return_value=expected)
+        mock_llm = MagicMock()
+        mock_llm.with_structured_output = MagicMock(return_value=mock_structured)
+
+        classifier = LLMIntentClassifier(mock_llm)
+        agents = (_make_agent("order_lookup"),)
+
+        result = await classifier.classify("order status 1042", agents)
+        assert not result.is_ambiguous
--- a/Show More
+++ b/Show More
Author	SHA1	Message	Date
Yaojia Wang	f0699436c5	refactor: engineering improvements -- API versioning, structured logging, Alembic, error standardization, test coverage - API versioning: all REST endpoints prefixed with /api/v1/ - Structured logging: replaced stdlib logging with structlog (console/JSON modes) - Alembic migrations: versioned DB schema with initial migration - Error standardization: global exception handlers for consistent envelope format - Interrupt cleanup: asyncio background task for expired interrupt removal - Integration tests: +30 tests (analytics, replay, openapi, error, session APIs) - Frontend tests: +57 tests (all components, pages, useWebSocket hook) - Backend: 557 tests, 89.75% coverage \| Frontend: 80 tests, 16 test files	2026-04-06 23:19:29 +02:00
Yaojia Wang	af53111928	refactor: fix architectural issues across frontend and backend Address all architecture review findings: P0 fixes: - Add API key authentication for admin endpoints (analytics, replay, openapi) and WebSocket connections via ADMIN_API_KEY env var - Add PostgreSQL-backed PgSessionManager and PgInterruptManager for multi-worker production deployments (in-memory defaults preserved) P1 fixes: - Implement actual tool generation in OpenAPI approve_job endpoint using generate_tool_code() and generate_agent_yaml() - Add missing clarification, interrupt_expired, and tool_result message handlers in frontend ChatPage P2 fixes: - Replace monkey-patching on CompiledStateGraph with typed GraphContext - Replace 9-param dispatch_message with WebSocketContext dataclass - Extract duplicate _envelope() into shared app/api_utils.py - Replace mutable module-level counter with crypto.randomUUID() - Remove hardcoded mock data from ReviewPage, use api.ts wrappers - Remove `as any` type escape from ReplayPage All 516 tests passing, 0 TypeScript errors.	2026-04-06 15:59:14 +02:00
Yaojia Wang	b8654aa31f	feat: upgrade LangGraph to 1.x and migrate deprecated APIs - Bump langgraph from 0.4 to 1.0+, langgraph-supervisor from 0.0.12 to 0.0.30+ - Bump langchain-core, langchain-anthropic, langchain-openai to 1.x - Add langchain>=1.0 dependency for new create_agent location - Migrate create_react_agent -> create_agent (prompt -> system_prompt) - Fix create_supervisor positional arg to named agents= parameter - Replace AsyncMock checkpointer with InMemorySaver in tests (v1 type validation) - Update version references in README, ARCHITECTURE, eng-review-plan	2026-04-06 14:51:51 +02:00
Yaojia Wang	be5c84bcff	docs: reconcile README and docs with actual codebase README: - Remove duplicated agent config, safety, security sections (covered by docs) - Add ux_design_system.md and safety.py to project structure and doc links - Convert doc links to descriptive table agent-config-guide.md: - Replace fictional agents/tools with real ones from agents.yaml - Remove nonexistent 'admin' permission level (only read/write) - Fix template names (e-commerce, saas, fintech) - List all available built-in tools openapi-import-guide.md: - Fix /result -> /classifications endpoint - Fix POST /approve to show no request body - Remove nonexistent 'admin' access type - Update response examples to match actual API demo-script.md: - Fix agent names (order_agent -> order_lookup) - Replace fictional refund scenario with real lookup+cancel flow ARCHITECTURE.md: - Fix langgraph-supervisor version (v1.1 -> 0.0.12+) docker-compose.yml: - Expose postgres on port 5433 for local dev	2026-04-06 13:55:45 +02:00
Yaojia Wang	19fc9f3289	test: close coverage gaps and add frontend test infrastructure Backend (516 tests, 94% coverage): - Add azure_openai endpoint/deployment validation tests (config.py -> 100%) - Add _total_conversations and _avg_turns direct tests (queries.py -> 100%) - Add transformer edge cases: list content, string checkpoint, invalid JSON, malformed message graceful skip (transformer.py -> 93%) - Add safety combined status_code+error_message interaction tests - Fix ambiguous 200/422 assertion to strict 422 - Add E2E pagination shape assertions (total, page, per_page, row count) - Fix ReplayPool mock to respect LIMIT/OFFSET params Frontend (23 tests, vitest + happy-dom + @testing-library/react): - Add vitest infrastructure with happy-dom environment - Add api.ts tests: success, HTTP error, success=false, URL encoding - Add DashboardPage tests: loading, data, error, empty states - Add ReplayListPage tests: loading, empty, data, error, status badge classes - Add ReplayPage tests: loading, steps, empty, error states	2026-04-06 13:32:10 +02:00
Yaojia Wang	036e12349d	refactor: formalize safety rules, extract shared styles, reconcile docs (P2) - Add backend/app/safety.py with explicit confirmation policy, multi-intent semantics, and MCP error taxonomy with retry classification - Add 26 unit tests for safety module (confirmation rules, error taxonomy) - Extract repeated inline styles into shared CSS classes in index.css (section-card, stat-label, status-badge, data-table, empty/error-state, pagination-bar) - Refactor DashboardPage, ReplayListPage, ReplayPage to use shared classes - Update README: add missing API endpoints, document safety/confirmation rules - Use proper HTML entities for arrow/dash characters to fix encoding glitches	2026-04-05 23:10:50 +02:00
Yaojia Wang	e0931daece	feat: wire frontend pages to live APIs and standardize response contracts (P1) - Backend: Add COUNT query and paginated response shape to conversations endpoint Returns { conversations: [...], total, page, per_page } instead of flat array - Frontend: Replace mock data in DashboardPage with fetchAnalytics() API calls - Frontend: Replace mock data in ReplayListPage with fetchConversations() API calls - Frontend: Replace mock data in ReplayPage with fetchReplay() API calls - Add proper loading, empty, and error states to all three pages - Align ConversationSummary type with actual DB columns (created_at, status) - Update unit and E2E tests for new paginated conversation response shape - Add fetchone() to FakeCursor for COUNT query support in E2E tests	2026-04-05 23:06:00 +02:00
Yaojia Wang	e55ec42ae5	fix: restore green builds and align frontend-backend contracts (P0) - Isolate Settings tests from .env and process env leakage - Fix analytics metadata test to unwrap psycopg Json wrapper - Remove unused state variables causing frontend build failures - Fix ReviewPage to use /classifications endpoint instead of nonexistent /result - Normalize ReviewPage status enums (failed not error) and access_type values - Align api.ts types with backend response shapes (ReplayPage, AnalyticsData, AgentUsage)	2026-04-05 23:00:39 +02:00
Yaojia Wang	189a0fad34	feat(ui): implement premium beige design system and ux refinements	2026-04-05 22:35:48 +02:00
Yaojia Wang	d2b4610df9	fix: address code and security review findings for Phase 5 - Add nginx security headers (X-Frame-Options, X-Content-Type-Options, etc.) - Fix postgres networking: add to app_network, comment out host port exposure - Fix rate limit memory leak: add bounded eviction for stale thread entries - Use immutable update pattern in rate limit check (no .append mutation) - Extract _VERSION constant to avoid duplicate hardcoded version string	2026-03-31 21:35:13 +02:00
Yaojia Wang	0e78e5b06b	feat: complete phase 5 -- error hardening, frontend, Docker, demo, docs Backend: - ConversationTracker: Protocol + PostgresConversationTracker for lifecycle tracking - Error handler: ErrorCategory enum, classify_error(), with_retry() exponential backoff - Wire PostgresAnalyticsRecorder + ConversationTracker into ws_handler - Rate limiting (10 msg/10s per thread), edge case hardening - Health endpoint GET /api/health, version 0.5.0 - Demo seed data script + sample OpenAPI spec Frontend (all new): - React Router with NavBar (Chat / Replay / Dashboard / Review) - ReplayListPage + ReplayPage with ReplayTimeline component - DashboardPage with MetricCard, range selector, zero-state - ReviewPage for OpenAPI classification review - ErrorBanner for WebSocket disconnect handling - API client (api.ts) with typed fetch wrappers Infrastructure: - Frontend Dockerfile (multi-stage node -> nginx) - nginx.conf with SPA routing + API/WS proxy - docker-compose.yml with frontend service + healthchecks - .env.example files (root + backend) Documentation: - README.md with quick start and architecture - Agent configuration guide - OpenAPI import guide - Deployment guide - Demo script 48 new tests, 449 total passing, 92.87% coverage	2026-03-31 21:20:06 +02:00
Yaojia Wang	38644594d2	test: add thread_id validation tests for replay API - Test invalid thread_id with spaces returns 400 - Test thread_id with special chars returns 400 - Tighten existing 404 test assertion	2026-03-31 13:44:04 +02:00
Yaojia Wang	ef6e5ac2be	fix: address security findings in Phase 4 analytics and replay - Fix CRITICAL: use parameterized INTERVAL arithmetic (%(days)s * INTERVAL '1 day') instead of string interpolation inside SQL literal - Use asyncio.gather() for parallel query execution in get_analytics() - Add range upper bound (max 365 days) to prevent DoS via full-table scans - Add thread_id validation (alphanumeric, max 128 chars) in replay API - Sanitize error messages to not reflect user input	2026-03-31 13:38:09 +02:00
Yaojia Wang	33db5aeb10	feat: complete phase 4 -- conversation replay API + analytics dashboard - Replay models: StepType enum, ReplayStep, ReplayPage frozen dataclasses - Checkpoint transformer: PostgresSaver JSONB -> structured timeline steps - Replay API: GET /api/conversations (paginated), GET /api/replay/{thread_id} - Analytics models: AgentUsage, InterruptStats, AnalyticsResult - Analytics event recorder: Protocol + PostgresAnalyticsRecorder + NoOp - Analytics queries: resolution_rate, agent_usage, escalation_rate, cost, interrupts - Analytics API: GET /api/analytics?range=Xd with envelope response - DB migration: analytics_events table + conversations column additions - 74 new tests, 399 total passing, 92.87% coverage	2026-03-31 13:35:45 +02:00
Yaojia Wang	a2f750269d	fix: address critical security and code review findings in Phase 3 - Wire ImportOrchestrator into review_api start_import via BackgroundTasks - Sanitize docstrings in generated tool code to prevent code injection - Add Literal["read", "write"] validation for access_type - Add regex validation for agent_group - Validate URL scheme (http/https only) in ImportRequest - Validate LLM output fields (clamp confidence, validate access_type) - Use dataclasses.replace instead of manual reconstruction in importer - Expand SSRF blocked networks (Carrier-Grade NAT, IPv4-mapped IPv6, etc.) - Make _BLOCKED_NETWORKS immutable tuple - Use yaml.safe_dump instead of yaml.dump - Fix _to_snake_case for empty strings and Python keywords	2026-03-31 00:28:28 +02:00
Yaojia Wang	a54eb224e0	feat: complete phase 3 -- OpenAPI auto-discovery, SSRF protection, tool generation - SSRF protection: private IP blocking, DNS rebinding defense, redirect validation - OpenAPI fetcher with SSRF guard, JSON/YAML auto-detection, 10MB limit - Structural spec validator (3.0.x/3.1.x) - Endpoint parser with $ref resolution, auto-generated operation IDs - Heuristic + LLM endpoint classifier with Protocol interface - Review API at /api/openapi (import, job status, classification CRUD, approve) - @tool code generator + Agent YAML generator - Import orchestrator (fetch -> validate -> parse -> classify pipeline) - 125 new tests, 322 total passing, 93.23% coverage	2026-03-31 00:10:44 +02:00
Yaojia Wang	006b4ee5d7	fix: resolve ruff lint errors in Phase 2 code - Move intent imports to TYPE_CHECKING block in graph.py (TC001) - Rename test classes to CapWords convention (N801) - Fix line length violations across test files (E501) - Auto-fix import sorting (I001)	2026-03-30 21:44:47 +02:00
Yaojia Wang	b861ff055f	test: add routing integration tests for Phase 2 test requirements 9 tests covering the complete multi-agent routing flow: - Single-intent routing to each agent (order_lookup, order_actions, discount, fallback) - Multi-intent routing hint injection for sequential execution - Ambiguity detection skips graph and returns clarification - Low confidence threshold triggers ambiguity - No-classifier fallback to supervisor prompt routing Fills Phase 2 test requirement for integration-level routing coverage. Total: 197 tests, 92.60% coverage.	2026-03-30 21:41:01 +02:00
Yaojia Wang	512f988dd0	test: add Phase 2 checkpoint acceptance tests 18 integration tests validating all 7 Phase 2 checkpoint criteria: 1. Order query routes to order_lookup agent 2. Multi-intent classification with routing hint injection 3. Ambiguous message triggers clarification prompt 4. 30-min interrupt TTL auto-cancel with retry prompt 5. Webhook POST escalation with retry on failure 6. E-commerce template loads 4 correctly configured agents 7. Coverage at 92.60% (188 tests total)	2026-03-30 21:38:25 +02:00
Yaojia Wang	6e7b824b64	test: add integration tests for WebSocket message flow 17 integration tests covering: - Happy path: token streaming, tool calls, multi-message sessions - Interrupt flow: approve and reject paths with manager tracking - Session TTL: expiration, sliding window reset, interrupt extension - Validation: invalid JSON, missing fields, size limits - Interrupt TTL: expired interrupt sends retry prompt Fills Phase 1 test gap for integration-level WebSocket coverage. Total: 170 tests, 92.15% coverage.	2026-03-30 21:24:31 +02:00
Yaojia Wang	1050df780d	feat: complete phase 2 -- multi-agent routing, interrupt TTL, escalation, templates - Intent classification with LLM structured output (single/multi/ambiguous) - Discount agent with apply_discount and generate_coupon tools - Interrupt manager with 30-min TTL auto-expiration and retry prompts - Webhook escalation module with exponential backoff retry (max 3) - Three vertical industry templates (e-commerce, SaaS, fintech) - Template loading in AgentRegistry - Enhanced supervisor prompt with dynamic agent descriptions - 153 tests passing, 90.18% coverage	2026-03-30 21:04:39 +02:00
Yaojia Wang	7c3571b47d	chore: update local Claude Code permission settings Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>	2026-03-30 15:14:16 +02:00