nexus/.planning/phases/21-chat-foundation/21-03-PLAN.md

phase	plan	type	wave	depends_on	files_modified	autonomous	requirements	must_haves
21-chat-foundation	03	execute	2	21-00 21-01	server/src/services/chat.ts server/src/routes/chat.ts server/src/app.ts	true	CHAT-04 CHAT-05 CHAT-06 HIST-05	truths artifacts key_links A user on any device on the network can create a conversation and retrieve it from another browser session POST /api/companies/:companyId/conversations creates a conversation row in DB GET /api/companies/:companyId/conversations returns paginated list sorted by updatedAt DESC POST /api/conversations/:id/messages creates a message and bumps conversation updatedAt First message on a title-less conversation auto-sets the title to the first 60 chars PATCH /api/conversations/:id can set pinnedAt, archivedAt, and title DELETE /api/conversations/:id soft-deletes by setting deletedAt path provides exports server/src/services/chat.ts chatService factory with all CRUD methods chatService path provides exports server/src/routes/chat.ts chatRoutes factory returning Express Router chatRoutes from to via pattern server/src/routes/chat.ts server/src/services/chat.ts chatService(db) instantiation chatService(db) from to via pattern server/src/app.ts server/src/routes/chat.ts api.use(chatRoutes(db)) chatRoutes(db) from to via pattern server/src/services/chat.ts packages/db/src/schema/chat_conversations.ts Drizzle query on chatConversations table chatConversations

Build the server-side chat service and REST API routes.

Purpose: Provide the backend for conversation CRUD (create, list, update, pin, archive, soft-delete) and message CRUD (create, list) with cursor-based pagination. This is the data layer the UI consumes. HIST-05 (cross-device sync) is satisfied by these API endpoints being network-accessible. Output: Working API endpoints mounted on the Express app.

<execution_context> @$HOME/.claude/get-shit-done/workflows/execute-plan.md @$HOME/.claude/get-shit-done/templates/summary.md </execution_context>

@.planning/PROJECT.md @.planning/ROADMAP.md @.planning/phases/21-chat-foundation/21-RESEARCH.md @.planning/phases/21-chat-foundation/21-01-SUMMARY.md From packages/db/src/schema/chat_conversations.ts (created in Plan 01): ```typescript export const chatConversations = pgTable("chat_conversations", { id: uuid("id").primaryKey().defaultRandom(), companyId: uuid("company_id").notNull().references(() => companies.id), title: text("title"), agentId: uuid("agent_id").references(() => agents.id, { onDelete: "set null" }), pinnedAt: timestamp("pinned_at", { withTimezone: true }), archivedAt: timestamp("archived_at", { withTimezone: true }), deletedAt: timestamp("deleted_at", { withTimezone: true }), createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(), updatedAt: timestamp("updated_at", { withTimezone: true }).notNull().defaultNow(), }); ```

From packages/db/src/schema/chat_messages.ts (created in Plan 01):

export const chatMessages = pgTable("chat_messages", {
  id: uuid("id").primaryKey().defaultRandom(),
  conversationId: uuid("conversation_id").notNull().references(() => chatConversations.id, { onDelete: "cascade" }),
  role: text("role").notNull(),
  content: text("content").notNull(),
  agentId: uuid("agent_id"),
  createdAt: timestamp("created_at", { withTimezone: true }).notNull().defaultNow(),
});

From packages/shared/src/validators/chat.ts (created in Plan 01):

export const createConversationSchema = z.object({ title: z.string().max(200).optional(), agentId: z.string().uuid().optional() });
export const updateConversationSchema = z.object({ title: z.string().max(200).optional(), agentId: z.string().uuid().nullable().optional(), pinnedAt: z.string().datetime().nullable().optional(), archivedAt: z.string().datetime().nullable().optional() });
export const createMessageSchema = z.object({ role: z.enum(["user", "assistant", "system"]), content: z.string().min(1).max(100_000), agentId: z.string().uuid().optional() });

From server/src/routes/authz.ts:

export function assertBoard(req: Request): void;
export function assertCompanyAccess(req: Request, companyId: string): void;

From server/src/errors.ts:

export function notFound(message?: string): HttpError;
export function unprocessable(message: string, issues?: unknown): HttpError;

Task 1: Create chat service with CRUD operations server/src/services/chat.ts, server/src/__tests__/chat-service.test.ts - createConversation inserts a row and returns it with id + timestamps - listConversations returns items sorted by updatedAt DESC, excludes deleted, supports cursor pagination with hasMore - getConversation returns row by id, throws notFound for missing/deleted - updateConversation sets provided fields and bumps updatedAt - softDeleteConversation sets deletedAt, throws notFound if already deleted - addMessage inserts message, bumps conversation updatedAt, auto-sets title on first user message when title IS NULL - listMessages returns items sorted by createdAt DESC with cursor pagination - server/src/services/documents.ts (reference for service factory pattern, Drizzle query patterns) - server/src/services/activity.ts (reference for simpler service pattern) - server/src/__tests__/chat-service.test.ts (test stub from Plan 00 -- fill in test implementations) - packages/db/src/schema/chat_conversations.ts (table definition -- will exist from Plan 01) - packages/db/src/schema/chat_messages.ts (table definition -- will exist from Plan 01) First, update `server/src/__tests__/chat-service.test.ts` to replace `.todo` stubs with real test implementations using the vi.mock pattern from activity-routes.test.ts. Mock the db object and verify: - createConversation calls db.insert with correct table and returns result - listConversations calls db.select with correct where/orderBy/limit - addMessage calls db.insert for the message AND db.update for conversation updatedAt - addMessage calls db.update with `isNull(title)` condition for auto-title

Then create server/src/services/chat.ts following the function chatService(db: Db) factory pattern:

import { and, asc, desc, eq, isNull, lt, sql, count } from "drizzle-orm";
import type { Db } from "@paperclipai/db";
import { chatConversations, chatMessages } from "@paperclipai/db";
import { notFound } from "../errors.js";

export function chatService(db: Db) {
  return {
    async listConversations(companyId: string, opts: { cursor?: string; limit?: number; includeArchived?: boolean }) {
      // ...
    },
    async createConversation(companyId: string, data: { title?: string; agentId?: string }) {
      // ...
    },
    async getConversation(id: string) {
      // ...
    },
    async updateConversation(id: string, data: { title?: string; agentId?: string | null; pinnedAt?: string | null; archivedAt?: string | null }) {
      // ...
    },
    async softDeleteConversation(id: string) {
      // ...
    },
    async listMessages(conversationId: string, opts: { cursor?: string; limit?: number }) {
      // ...
    },
    async addMessage(conversationId: string, data: { role: string; content: string; agentId?: string }) {
      // ...
    },
  };
}

Implementation details for each method:

listConversations:

• limit defaults to 30, max 100: const limit = Math.min(opts.limit ?? 30, 100);
• Filter: companyId matches, deletedAt IS NULL. If includeArchived is false (default), also filter archivedAt IS NULL.
• Cursor: if opts.cursor provided, add lt(chatConversations.updatedAt, new Date(opts.cursor))
• Order: desc(chatConversations.updatedAt)
• Pagination: fetch limit + 1, if rows.length > limit then hasMore = true, return rows.slice(0, limit)
• Also do a lateral subquery or second query to get lastMessagePreview: for each conversation, get the most recent message content truncated to 100 chars. If that's too complex, return lastMessagePreview: null for now and add it in a follow-up.

createConversation:

• Insert into chatConversations with companyId, optional title, optional agentId
• Return the inserted row

getConversation:

• Select where id matches and deletedAt IS NULL
• Throw notFound("Conversation not found") if no row

updateConversation:

• Build a partial update object from provided fields
• For pinnedAt and archivedAt: if value is a string, convert to new Date(value). If value is null, set column to null.
• Also set updatedAt: new Date() on every update
• Use RETURNING * to get the updated row

softDeleteConversation:

• UPDATE chat_conversations SET deleted_at = now(), updated_at = now() WHERE id = $id AND deleted_at IS NULL
• Return the updated row or throw notFound

listMessages:

• limit defaults to 50, max 200
• Filter: conversationId matches
• Cursor: if opts.cursor provided, add lt(chatMessages.createdAt, new Date(opts.cursor))
• Order: desc(chatMessages.createdAt) (most recent first)
• Same pagination pattern as conversations

addMessage:

• Insert into chatMessages with conversationId, role, content, optional agentId
• CRITICAL (Pitfall 3 from RESEARCH.md): After inserting the message, also UPDATE the conversation's updatedAt to now():

  await db.update(chatConversations)
    .set({ updatedAt: new Date() })
    .where(eq(chatConversations.id, conversationId));
  

• CRITICAL (Pitfall 5 from RESEARCH.md): Auto-title generation -- if this is the first message (role === "user") and the conversation has no title:

  await db.update(chatConversations)
    .set({ title: data.content.slice(0, 60), updatedAt: new Date() })
    .where(and(eq(chatConversations.id, conversationId), isNull(chatConversations.title)));
  

  Use WHERE title IS NULL to make it idempotent.
• Return the inserted message row

Run tests after implementation:

pnpm vitest run server/src/__tests__/chat-service.test.ts

cd /opt/nexus && pnpm vitest run server/src/__tests__/chat-service.test.ts 2>&1 | tail -5 - server/src/services/chat.ts contains `export function chatService(db: Db)` - Contains methods: listConversations, createConversation, getConversation, updateConversation, softDeleteConversation, listMessages, addMessage - addMessage updates `chatConversations.updatedAt` after inserting message (Pitfall 3) - addMessage auto-sets title when `title IS NULL` using `data.content.slice(0, 60)` (Pitfall 5) - listConversations filters `isNull(chatConversations.deletedAt)` - listConversations uses `desc(chatConversations.updatedAt)` ordering - Pagination uses `limit + 1` pattern with `hasMore` boolean - chat-service tests pass via vitest Chat service exports a factory function with 7 CRUD methods covering conversation lifecycle (create, list, get, update, soft-delete) and message operations (list, add), including auto-title generation and updatedAt bumping. Tests pass. Task 2: Create chat routes and mount in app.ts server/src/routes/chat.ts, server/src/app.ts, server/src/__tests__/chat-routes.test.ts - POST /companies/:companyId/conversations creates a conversation and returns 201 - GET /companies/:companyId/conversations returns paginated list - GET /conversations/:id returns conversation, 404 for missing - PATCH /conversations/:id updates fields - DELETE /conversations/:id soft-deletes and returns 204 - POST /conversations/:id/messages creates message and returns 201 - GET /conversations/:id/messages returns paginated messages - server/src/routes/activity.ts (reference route factory pattern: function activityRoutes(db: Db): Router) - server/src/routes/authz.ts (assertBoard, assertCompanyAccess imports) - server/src/app.ts (existing route mounting pattern: api.use(fooRoutes(db))) - server/src/middleware/validate.ts (if exists -- validation middleware pattern) - server/src/__tests__/chat-routes.test.ts (test stub from Plan 00 -- fill in test implementations) First, update `server/src/__tests__/chat-routes.test.ts` to replace `.todo` stubs with real test implementations using the supertest + vi.mock pattern from activity-routes.test.ts. Mock chatService, create an express app with mock actor middleware, and verify: - POST /companies/:companyId/conversations returns 201 with created conversation - GET /companies/:companyId/conversations returns 200 with list - GET /conversations/:id returns 200 - DELETE /conversations/:id returns 204 - POST /conversations/:id/messages returns 201

Then create server/src/routes/chat.ts:

import { Router } from "express";
import type { Db } from "@paperclipai/db";
import { assertBoard, assertCompanyAccess } from "./authz.js";
import { chatService } from "../services/chat.js";
import { createConversationSchema, updateConversationSchema, createMessageSchema } from "@paperclipai/shared";

export function chatRoutes(db: Db): Router {
  const router = Router();
  const svc = chatService(db);

  // GET /api/companies/:companyId/conversations
  router.get("/companies/:companyId/conversations", async (req, res) => {
    assertBoard(req);
    assertCompanyAccess(req, req.params.companyId!);
    const { cursor, limit, includeArchived } = req.query;
    const result = await svc.listConversations(req.params.companyId!, {
      cursor: cursor as string | undefined,
      limit: limit ? Number(limit) : undefined,
      includeArchived: includeArchived === "true",
    });
    res.json(result);
  });

  // POST /api/companies/:companyId/conversations
  router.post("/companies/:companyId/conversations", async (req, res) => {
    assertBoard(req);
    assertCompanyAccess(req, req.params.companyId!);
    const data = createConversationSchema.parse(req.body);
    const conversation = await svc.createConversation(req.params.companyId!, data);
    res.status(201).json(conversation);
  });

  // GET /api/conversations/:id
  router.get("/conversations/:id", async (req, res) => {
    assertBoard(req);
    const conversation = await svc.getConversation(req.params.id!);
    res.json(conversation);
  });

  // PATCH /api/conversations/:id
  router.patch("/conversations/:id", async (req, res) => {
    assertBoard(req);
    const data = updateConversationSchema.parse(req.body);
    const conversation = await svc.updateConversation(req.params.id!, data);
    res.json(conversation);
  });

  // DELETE /api/conversations/:id
  router.delete("/conversations/:id", async (req, res) => {
    assertBoard(req);
    await svc.softDeleteConversation(req.params.id!);
    res.status(204).end();
  });

  // GET /api/conversations/:id/messages
  router.get("/conversations/:id/messages", async (req, res) => {
    assertBoard(req);
    const { cursor, limit } = req.query;
    const result = await svc.listMessages(req.params.id!, {
      cursor: cursor as string | undefined,
      limit: limit ? Number(limit) : undefined,
    });
    res.json(result);
  });

  // POST /api/conversations/:id/messages
  router.post("/conversations/:id/messages", async (req, res) => {
    assertBoard(req);
    const data = createMessageSchema.parse(req.body);
    const message = await svc.addMessage(req.params.id!, data);
    res.status(201).json(message);
  });

  return router;
}

NOTE: Check if existing routes wrap async handlers with a try/catch or rely on Express 5's built-in async error handling. Express 5.1.0 natively handles rejected promises in async route handlers, so no manual try/catch wrapper is needed unless the existing pattern uses one.

Mount in server/src/app.ts:

1. Add import at the top with the other route imports: import { chatRoutes } from "./routes/chat.js";
2. Add api.use(chatRoutes(db)); in the route mounting section, after the activityRoutes line (around line 158).

Run tests after implementation:

pnpm vitest run server/src/__tests__/chat-routes.test.ts

cd /opt/nexus && pnpm vitest run server/src/__tests__/chat-routes.test.ts 2>&1 | tail -5 - server/src/routes/chat.ts contains `export function chatRoutes(db: Db): Router` - server/src/routes/chat.ts contains all 7 route handlers - server/src/routes/chat.ts calls `assertBoard(req)` on every route - server/src/routes/chat.ts calls `assertCompanyAccess(req, req.params.companyId!)` on company-scoped routes - server/src/app.ts contains `import { chatRoutes } from "./routes/chat.js"` - server/src/app.ts contains `chatRoutes(db)` - chat-routes tests pass via vitest Chat API routes are mounted on the Express app with 7 endpoints covering conversation CRUD and message CRUD, all gated by assertBoard auth. Tests pass. - `cd /opt/nexus && pnpm --filter @paperclipai/server exec -- tsc --noEmit` passes - `pnpm vitest run server/src/__tests__/chat-service.test.ts` passes - `pnpm vitest run server/src/__tests__/chat-routes.test.ts` passes - Routes follow the factory pattern used by all other route files - Service correctly handles all pitfalls from RESEARCH.md (updatedAt bump, auto-title, soft delete)

<success_criteria>

• Chat service has 7 methods covering full conversation + message CRUD
• Chat routes mounted in app.ts with proper auth
• Pagination uses cursor-based approach with hasMore
• Auto-title and updatedAt bump implemented per RESEARCH.md pitfalls
• Both server test files pass </success_criteria>

After completion, create `.planning/phases/21-chat-foundation/21-03-SUMMARY.md`