PaperClipAI/server/src/__tests__/agent-conversations.test.ts

import { createLocalAgentJwt } from "../agent-auth-jwt.js";
import { applyRunnerGoalPrpEvent } from "../services/runner-goals.js";
import { mkdtemp, rm } from "node:fs/promises";
import { tmpdir } from "node:os";
import { join } from "node:path";
import { ensureHumanRoleDefaultGrants } from "../services/principal-access-compatibility.js";
import express from "express";
import request from "supertest";
import { issueRoutes } from "../routes/issues.js";
import { errorHandler } from "../middleware/index.js";
import { actorMiddleware } from "../middleware/auth.js";
import { randomUUID } from "node:crypto";
import { and, eq } from "drizzle-orm";
import { afterAll, beforeAll, describe, expect, it } from "vitest";
import {
  activityLog,
  authUsers,
  agents,
  agentTaskSessions,
  agentWakeupRequests,
  companyMemberships,
  companies,
  createDb,
  heartbeatRuns,
  issueComments,
  issueTreeHolds,
  issueThreadInteractions,
  issueRecoveryActions,
  issues,
} from "@paperclipai/db";
import {
  recoveryPostgresSupport as support,
  startRecoveryPostgres,
} from "./helpers/recovery-postgres.js";
import { issueService } from "../services/issues.js";
import { documentService } from "../services/documents.js";
import { getTaskPlanContext } from "../services/task-plan-context.js";
import { terminalizeLegacyExecution, LEGACY_RECOVERY_CAUSE } from "../services/legacy-execution-recovery.js";
import { settleUnrecoverableExecutions } from "../services/execution-recovery-resolution.js";
import { renderPaperclipWakePrompt } from "@paperclipai/adapter-utils/server-utils";
import { instanceSettingsService } from "../services/instance-settings.js";
import {
  AGENT_CHAT_DIRECTIVE,
  conversationNativeDecision,
  deliverConversationComments,
  conversationReplay,
  isWaitingConversation,
  isConversationExecutionWake,
  prepareConversationTurn,
  settleConversationTurn,
  undeliveredConversationComments,
} from "../services/agent-conversations.js";
import { classifyIssueGraphLiveness } from "../services/recovery/issue-graph-liveness.js";
import { NATIVE_STATUS_ARBITER_POLICY_VERSION } from "../services/native-runtime/status-arbiter.js";
import { runningProcesses } from "../adapters/index.js";
import {
  buildPaperclipTaskMarkdown,
  buildPaperclipWakePayload,
  heartbeatService,
} from "../services/heartbeat.js";

(support.supported ? describe : describe.skip)(
  "persistent agent conversations",
  () => {
    let database: Awaited<ReturnType<typeof startRecoveryPostgres>>;
    let db: ReturnType<typeof createDb>;
    let companyId: string;
    let agentId: string;
    beforeAll(async () => {
      database = await startRecoveryPostgres(
        "paperclip-agent-conversations-",
      );
      db = createDb(database.connectionString);
      companyId = randomUUID();
      agentId = randomUUID();
      await db
        .insert(authUsers)
        .values({
          id: "local-board",
          name: "Local Board",
          email: "local@paperclip.test",
          createdAt: new Date(),
          updatedAt: new Date(),
        })
        .onConflictDoNothing();
      await db
        .insert(companies)
        .values({
          id: companyId,
          name: "Chats",
          issuePrefix: "CHAT",
          requireBoardApprovalForNewAgents: false,
        });
      await db
        .insert(agents)
        .values({
          id: agentId,
          companyId,
          name: "Planner",
          role: "engineer",
          status: "idle",
          adapterType: "process",
        });
      await instanceSettingsService(db).updateExperimental({
        enableAgentChat: true,
      });
    }, 90000);
    afterAll(async () => {
      await db?.$client.end({ timeout: 0 });
      await database?.cleanup();
    });
    const create = (user = randomUUID()) =>
      issueService(db).create(companyId, {
        title: "Conversation",
        conversationAgentId: agentId,
        conversationUserId: user,
        assigneeAgentId: agentId,
        status: "in_review",
        conversationState: "waiting",
      });
    async function runFor(issueId: string, commentId: string, overrides = {}) {
      return (
        await db
          .insert(heartbeatRuns)
          .values({
            companyId,
            agentId,
            status: "running",
            contextSnapshot: {
              issueId,
              taskKey: issueId,
              wakeCommentId: commentId,
              commentId,
              ...overrides,
            },
          })
          .returning()
      )[0]!;
    }
    it("atomically resolves one task per person and agent and excludes it from ordinary lists", async () => {
      const user = randomUUID();
      expect(
        await issueService(db).getConversation(companyId, agentId, user),
      ).toBeNull();
      const results = await Promise.all(
        Array.from({ length: 6 }, () => create(user)),
      );
      expect(new Set(results.map((issue) => issue.id)).size).toBe(1);
      expect((await create()).id).not.toBe(results[0].id);
      expect(
        (await issueService(db).list(companyId)).some(
          (issue) => issue.id === results[0].id,
        ),
      ).toBe(false);
      expect(
        (
          await issueService(db).list(companyId, { q: results[0].identifier! })
        ).some((issue) => issue.id === results[0].id),
      ).toBe(true);
      expect(
        (await issueService(db).getById(results[0].id))?.conversationUserId,
      ).toBe(user);
      await expect(
        issueService(db).update(results[0].id, { status: "done" }),
      ).rejects.toThrow(/conversation/i);
      await expect(
        issueService(db).update(results[0].id, { assigneeAgentId: null }),
      ).rejects.toThrow(/conversation/i);
    });
    it("resolves through authenticated company routes, keeps opens read-only, and derives ownership", async () => {
      const appFor = (userId?: string, allowed = true) => {
        const app = express();
        app.use(express.json());
        if (!userId)
          app.use(actorMiddleware(db, { deploymentMode: "local_trusted" }));
        else
          app.use((req, _res, next) => {
            req.actor = {
              type: "board",
              source: "session",
              userId,
              companyIds: allowed ? [companyId] : [],
            };
            next();
          });
        app.use("/api", issueRoutes(db, { wakeup: async () => null } as never));
        app.use(errorHandler);
        return app;
      };
      const path = `/api/companies/${companyId}/chats/${agentId}`;
      const owner = randomUUID();
      const colleague = randomUUID();
      const app = appFor(owner);
      for (const userId of [owner, colleague]) {
        await db
          .insert(companyMemberships)
          .values({
            companyId,
            principalType: "user",
            principalId: userId,
            status: "active",
            membershipRole: "operator",
          });
        await ensureHumanRoleDefaultGrants(db, {
          companyId,
          principalId: userId,
          membershipRole: "operator",
          grantedByUserId: null,
        });
      }
      expect((await request(app).get(path)).body).toBeNull();
      expect(
        await issueService(db).getConversation(companyId, agentId, owner),
      ).toBeNull();
      const resolved = await Promise.all([
        request(app).post(path).send({ conversationUserId: "spoof" }),
        request(app).post(path),
      ]);
      expect(resolved.every((response) => response.status === 200)).toBe(true);
      expect(resolved[0].body.id).toBe(resolved[1].body.id);
      expect(resolved[0].body.conversationUserId).toBe(owner);
      const listPath = `/api/companies/${companyId}/chats`;
      const owned = await request(app).get(listPath);
      expect(owned.status).toBe(200);
      expect(owned.body.map((chat: { id: string }) => chat.id)).toEqual([resolved[0].body.id]);
      expect((await request(appFor(colleague)).get(listPath)).body).toEqual([]);
      expect((await request(appFor(randomUUID(), false)).get(listPath)).status).toBe(403);
      await instanceSettingsService(db).updateExperimental({ enableAgentChat: false });
      expect((await request(app).get(listPath)).status).toBe(200);
      await instanceSettingsService(db).updateExperimental({ enableAgentChat: true });
      expect(
        (
          await request(appFor(colleague)).get(
            `/api/issues/${resolved[0].body.id}`,
          )
        ).status,
      ).toBe(200);
      expect(
        (await request(appFor(randomUUID(), false)).get(path)).status,
      ).toBe(403);
      expect(
        (
          await request(app)
            .post(`/api/issues/${resolved[0].body.id}/comments`)
            .send({ body: "Hello" })
        ).status,
      ).toBe(422);
      const chatId = resolved[0].body.id;
      const queuedInterrupt = { queueId: randomUUID(), revision: "queue-revision", targetRunId: randomUUID() };
      expect((await request(appFor(colleague)).post(`/api/issues/${chatId}/queued-comments/interrupt`)
        .send(queuedInterrupt)).status).toBe(403);
      for (const body of ["Hello", "/new"]) {
        expect((await request(appFor(colleague)).post(`/api/issues/${chatId}/comments`)
          .send({ body, clientRequestId: randomUUID() })).status).toBe(403);
      }
      expect((await request(appFor(colleague))
        .post(`/api/companies/${companyId}/issues/${chatId}/attachments`)
        .attach("file", Buffer.from("foreign upload"), "note.txt")).status).toBe(403);

      const [planReview] = await db.insert(issueThreadInteractions).values({
        companyId, issueId: chatId, kind: "request_confirmation", status: "pending",
        continuationPolicy: "wake_assignee_on_accept", payload: { version: 1, prompt: "Hand off this plan?" },
      }).returning();
      expect((await request(appFor(colleague))
        .post(`/api/issues/${chatId}/interactions/${planReview.id}/accept`).send({})).status).toBe(403);
      expect((await db.select().from(issueThreadInteractions).where(eq(issueThreadInteractions.id, planReview.id)))[0].status).toBe("pending");
      const [pause] = await db.insert(issueTreeHolds).values({
        companyId, rootIssueId: chatId, mode: "pause", status: "active",
        createdByActorType: "user", createdByUserId: owner,
        releasePolicy: { strategy: "manual", note: "leaf_pause" },
      }).returning();
      const blockedSend = await request(app).post(`/api/issues/${chatId}/comments`)
        .send({ body: "Continue working", clientRequestId: randomUUID() });
      expect(blockedSend.status).toBe(409);
      expect(await db.select().from(issueComments).where(eq(issueComments.issueId, chatId))).toHaveLength(0);
      const resetRequest = { body: "/new", clientRequestId: randomUUID() };
      const reset = await request(app).post(`/api/issues/${chatId}/comments`).send(resetRequest);
      expect(reset.status).toBe(201);
      const retriedResets = await Promise.all(Array.from({ length: 3 }, () =>
        request(app).post(`/api/issues/${chatId}/comments`).send(resetRequest)));
      expect(retriedResets.every((response) => response.status === 201 && response.body.id === reset.body.id)).toBe(true);
      const addedEvents = await db.select().from(activityLog).where(and(
        eq(activityLog.entityId, chatId), eq(activityLog.action, "issue.comment_added"),
      ));
      expect(addedEvents).toHaveLength(1);

      expect((await db.select().from(issueTreeHolds).where(eq(issueTreeHolds.id, pause.id)))[0].status).toBe("released");
      const local = await request(appFor()).post(path);
      expect(local.body.conversationUserId).toBe("local-board");
      await instanceSettingsService(db).updateExperimental({
        enableAgentChat: false,
      });
      expect((await request(app).get(path)).status).toBe(200);
      expect(
        (await request(app).get(`/api/issues/${resolved[0].body.id}`)).status,
      ).toBe(200);
      await instanceSettingsService(db).updateExperimental({
        enableAgentChat: true,
      });
    });
    it("deduplicates concurrent message retries and preserves recoverable delivery", async () => {
      const issue = await create();
      const clientRequestId = randomUUID();
      const messages = await Promise.all(
        Array.from({ length: 4 }, () =>
          issueService(db).addComment(
            issue.id,
            "Help scope a project",
            { userId: "local-board" },
            { clientRequestId },
          ),
        ),
      );
      expect(new Set(messages.map((message) => message.id)).size).toBe(1);
      expect(
        await undeliveredConversationComments(db, companyId, issue.id),
      ).toHaveLength(1);
      await expect(
        issueService(db).addComment(
          issue.id,
          "Different",
          { userId: "local-board" },
          { clientRequestId },
        ),
      ).rejects.toThrow(/different content/);
    });
    it("resets only this task, keeps history, and fences stale replies and retries", async () => {
      const issue = await create();
      const other = await create();
      const before = await issueService(db).addComment(
        issue.id,
        "Old session secret context",
        { userId: "local-board" },
      );
      const oldRun = await runFor(issue.id, before.id);
      await prepareConversationTurn(db, oldRun);
      for (const target of [issue, other])
        await db
          .insert(agentTaskSessions)
          .values({
            companyId,
            agentId,
            adapterType: "process",
            taskKey: target.id,
            sessionDisplayId: "old-session",
          });
      const command = await issueService(db).addComment(issue.id, "/new", {
        userId: "local-board",
      });
      const resetRun = await runFor(issue.id, command.id);
      expect((await prepareConversationTurn(db, resetRun)).reset).toBe(true);
      expect(
        (
          await prepareConversationTurn(
            db,
            (
              await db
                .select()
                .from(heartbeatRuns)
                .where(eq(heartbeatRuns.id, resetRun.id))
            )[0]!,
          )
        ).reset,
      ).toBe(true);
      const [current] = await db
        .select()
        .from(issues)
        .where(eq(issues.id, issue.id));
      expect(current.conversationSessionGeneration).toBe(1);
      expect(current.conversationBoundaryCommentId).toBe(command.id);
      expect(
        await db
          .select()
          .from(agentTaskSessions)
          .where(eq(agentTaskSessions.taskKey, issue.id)),
      ).toHaveLength(0);
      expect(
        await db
          .select()
          .from(agentTaskSessions)
          .where(eq(agentTaskSessions.taskKey, other.id)),
      ).toHaveLength(1);
      expect(
        await db
          .select()
          .from(issueComments)
          .where(eq(issueComments.issueId, issue.id)),
      ).toHaveLength(2);
      await expect(
        issueService(db).addComment(issue.id, "Late old reply", {
          agentId,
          runId: oldRun.id,
        }),
      ).rejects.toThrow(/earlier session/);
      await expect(
        prepareConversationTurn(
          db,
          (
            await db
              .select()
              .from(heartbeatRuns)
              .where(eq(heartbeatRuns.id, oldRun.id))
          )[0]!,
        ),
      ).rejects.toThrow(/older turn/);
      expect(await applyRunnerGoalPrpEvent(db, { companyId, agentId, issueId: issue.id, adapterType: "process" }, {
        eventType: "session.capabilities.updated", sourceRunId: oldRun.id, sourceSeq: 500, payload: {},
      })).toBeNull();
      expect(await db.select().from(agentTaskSessions).where(eq(agentTaskSessions.taskKey, issue.id))).toHaveLength(0);
      const next = await issueService(db).addComment(
        issue.id,
        "Fresh context",
        { userId: "local-board" },
      );
      expect(
        await conversationReplay(db, companyId, issue.id, next.id),
      ).not.toContain("Old session");
      const payload = await buildPaperclipWakePayload({
        db, companyId,
        contextSnapshot: { issueId: issue.id, conversationMode: true, wakeCommentId: next.id },
        continuationSummary: { key: "summary", title: null, body: "Old session summary", updatedAt: new Date() },
        issueSummary: { ...issue, description: "Old session description" },
      });
      expect(JSON.stringify(payload)).not.toContain("Old session");
      expect(payload?.planReviewContext).toBeNull();
      expect(payload?.documentReviewContext).toBeNull();
      const later = await issueService(db).addComment(
        issue.id,
        "Following turn",
        { userId: "local-board" },
      );
      expect(
        await conversationReplay(db, companyId, issue.id, later.id),
      ).toContain("Fresh context");
      expect(
        await conversationReplay(db, companyId, issue.id, next.id),
      ).not.toContain("Following turn");
    });
    it("projects the resolved chat plan review into fresh and resumed prompts without replaying old reviews", async () => {
      const issue = await create();
      const { document } = await documentService(db).upsertIssueDocument({
        issueId: issue.id, key: "plan", title: "Plan", format: "markdown", body: "Draft plan",
      });
      const [interaction] = await db.insert(issueThreadInteractions).values({
        companyId, issueId: issue.id, kind: "request_confirmation", status: "rejected",
        payload: { version: 1, prompt: "Approve the plan?", target: { type: "issue_document", key: "plan", documentId: document.id,
          revisionId: document.latestRevisionId!, revisionNumber: document.latestRevisionNumber } },
        result: { version: 1, outcome: "rejected", reason: "Include CHAT_REVIEW_MARKER in the revised plan." },
      }).returning();
      const input = { db, companyId, issueSummary: { ...issue, workMode: "planning" },
        contextSnapshot: { issueId: issue.id, conversationMode: true, interactionId: interaction!.id,
          interactionKind: "request_confirmation", interactionStatus: "rejected" } };
      const payload = await buildPaperclipWakePayload(input);
      expect(payload?.planReviewContext?.interaction).toMatchObject({
        status: "rejected", acceptedTargetRevision: null,
        result: { outcome: "rejected", reason: "Include CHAT_REVIEW_MARKER in the revised plan." },
      });
      for (const resumedSession of [false, true]) {
        const prompt = renderPaperclipWakePrompt(payload, { resumedSession });
        expect(prompt).toContain("request_confirmation rejected");
        expect(prompt).toContain("Include CHAT_REVIEW_MARKER in the revised plan.");
        expect(prompt).toContain("not approval to implement or hand off execution tasks");
        expect(prompt).not.toContain("- accepted target:");
      }
      const later = await buildPaperclipWakePayload({ ...input,
        contextSnapshot: { issueId: issue.id, conversationMode: true } });
      expect(later?.planReviewContext).toBeNull();
      // An unrelated confirmation must not cause old plan context to be replayed.
      await db.update(issueThreadInteractions).set({ payload: { version: 1, prompt: "Proceed?" } })
        .where(eq(issueThreadInteractions.id, interaction!.id));
      expect((await buildPaperclipWakePayload(input))?.planReviewContext).toBeNull();
    });
    it("includes an initial handoff plan in the first execution prompt and pins approved revisions", async () => {
      const task = await issueService(db).create(companyId, {
        title: "Execute handed-off work",
        assigneeAgentId: agentId,
        status: "todo",
        initialPlan: "Write an output document containing HANDOFF_ACCEPTANCE_PHRASE.",
      });
      const initial = await getTaskPlanContext({ db, companyId, issueId: task.id });
      expect(task.description).toBeNull();
      expect(initial?.body).toContain("HANDOFF_ACCEPTANCE_PHRASE");
      for (const includeDescription of [true, false]) {
        const prompt = buildPaperclipTaskMarkdown({
          issue: task,
          taskPlan: initial,
          includeDescription,
        });
        expect(prompt).toContain("HANDOFF_ACCEPTANCE_PHRASE");
        expect(prompt).toContain(initial!.revisionId);
      }
      const { document: revision } = await documentService(db).upsertIssueDocument({
        issueId: task.id,
        key: "plan",
        format: "markdown",
        body: "A later unapproved draft.",
        baseRevisionId: initial!.revisionId,
      });
      expect((await getTaskPlanContext({ db, companyId, issueId: task.id }))?.revisionId)
        .toBe(revision.latestRevisionId);
      const approved = await getTaskPlanContext({
        db, companyId, issueId: task.id, approvedRevisionId: initial!.revisionId,
      });
      expect(approved?.body).toContain("HANDOFF_ACCEPTANCE_PHRASE");
      expect(approved?.body).not.toContain("unapproved");
      expect(await getTaskPlanContext({ db, companyId: randomUUID(), issueId: task.id })).toBeNull();
      expect(await getTaskPlanContext({
        db, companyId, issueId: task.id, approvedRevisionId: randomUUID(),
      })).toBeNull();
      const conversation = await create();
      await documentService(db).upsertIssueDocument({
        issueId: conversation.id, key: "plan", format: "markdown", body: "Pre-reset chat draft",
      });
      expect(await getTaskPlanContext({ db, companyId, issueId: conversation.id })).toBeNull();
      await documentService(db).upsertIssueDocument({
        issueId: task.id,
        key: "plan",
        format: "markdown",
        body: "QUARANTINED_PLAN_BODY",
        baseRevisionId: revision.latestRevisionId,
        sourceTrust: {
          preset: "low_trust_review",
          disposition: "quarantined",
          sourceIssueId: task.id,
          sourceRunId: randomUUID(),
          sourceAgentId: agentId,
        },
      });
      expect((await getTaskPlanContext({ db, companyId, issueId: task.id }))?.body)
        .not.toContain("QUARANTINED_PLAN_BODY");
      expect((await getTaskPlanContext({
        db, companyId, issueId: task.id, exposeLowTrustRaw: true,
      }))?.body).toBe("QUARANTINED_PLAN_BODY");
    });
    it("keeps concurrent delivery and multiple resets in separate ordered queue entries", async () => {
      const issue = await create();
      const first = await issueService(db).addComment(issue.id, "First", {
        userId: "local-board",
      });
      const active = await runFor(issue.id, first.id);
      await prepareConversationTurn(db, active);
      await db
        .update(issues)
        .set({ executionRunId: active.id, executionLockedAt: new Date() })
        .where(eq(issues.id, issue.id));
      runningProcesses.set(active.id, {
        child: {} as never,
        graceSec: 0,
        processGroupId: null,
      });
      try {
        const commands = [];
        for (const body of ["Before reset", "/new", "/new", "After reset"])
          commands.push(
            await issueService(db).addComment(
              issue.id,
              body,
              { userId: "local-board" },
              { clientRequestId: randomUUID() },
            ),
          );
        const heartbeat = heartbeatService(db);
        await Promise.all(
          Array.from({ length: 3 }, () =>
            deliverConversationComments(db, issue, heartbeat.wakeup),
          ),
        );
        const wakes = await db
          .select()
          .from(agentWakeupRequests)
          .where(eq(agentWakeupRequests.agentId, agentId));
        const queued = wakes.filter(
          (wake) =>
            (wake.payload as Record<string, unknown>)?.issueId === issue.id,
        );
        expect(queued).toHaveLength(4);
        expect(
          queued.every((wake) => wake.status === "deferred_issue_execution"),
        ).toBe(true);
        expect(
          queued.map(
            (wake) => (wake.payload as Record<string, unknown>).commentId,
          ),
        ).toEqual(commands.map((comment) => comment.id));
        expect(
          await undeliveredConversationComments(db, companyId, issue.id),
        ).toHaveLength(0);
        for (const command of commands.slice(1, 3)) {
          const reset = await runFor(issue.id, command.id);
          await prepareConversationTurn(db, reset);
        }
        const [current] = await db
          .select()
          .from(issues)
          .where(eq(issues.id, issue.id));
        expect(current.conversationSessionGeneration).toBe(2);
        expect(current.conversationBoundaryCommentId).toBe(commands[2].id);
      } finally {
        runningProcesses.delete(active.id);
      }
    });
    it.each([false, true])("runs real process turns and resets without replaying pre-Stop queued input (queued=%s)", async (queuedBeforeStop) => {
      const runtimeCompany = randomUUID();
      const runtimeAgent = randomUUID();
      await db
        .insert(companies)
        .values({
          id: runtimeCompany,
          name: "Runtime chat",
          issuePrefix: queuedBeforeStop ? "RCHATQ" : "RCHAT",
          requireBoardApprovalForNewAgents: false,
        });
      const generations: unknown[] = [];
      const app = express();
      app.use(express.json());
      app.post("/respond", async (req, res) => {
        const [run] = await db
          .select()
          .from(heartbeatRuns)
          .where(eq(heartbeatRuns.id, req.body.runId));
        generations.push(run.contextSnapshot?.conversationSessionGeneration);
        await issueService(db).addComment(
          String(run.contextSnapshot?.issueId),
          "What outcome should the task deliver?",
          { agentId: runtimeAgent, runId: run.id },
        );
        res.json({ ok: true });
      });
      const listener = app.listen(0, "127.0.0.1");
      await new Promise<void>((resolve) => listener.once("listening", resolve));
      const address = listener.address() as { port: number };
      const cwd = await mkdtemp(join(tmpdir(), "chat-runtime-"));
      const script = `fetch("http://127.0.0.1:${address.port}/respond", {method:"POST", headers:{"content-type":"application/json"}, body:JSON.stringify({runId:process.env.PAPERCLIP_RUN_ID})}).then(async r=>{if(!r.ok){console.error(r.status,await r.text());process.exitCode=1}})`;
      await db
        .insert(agents)
        .values({
          id: runtimeAgent,
          companyId: runtimeCompany,
          name: "Conversation runtime",
          role: "engineer",
          status: "idle",
          adapterType: "process",
          adapterConfig: {
            command: process.execPath,
            args: ["-e", script],
            cwd,
          },
          runtimeConfig: { heartbeat: { enabled: false, wakeOnDemand: true } },
        });
      const chat = await issueService(db).create(runtimeCompany, {
        title: "Runtime chat",
        conversationAgentId: runtimeAgent,
        conversationUserId: "local-board",
        assigneeAgentId: runtimeAgent,
        conversationState: "waiting",
        status: "in_review",
      });
      const heartbeat = heartbeatService(db);
      const send = async (body: string) => {
        await issueService(db).addComment(
          chat.id,
          body,
          { userId: "local-board" },
          { clientRequestId: randomUUID() },
        );
        await deliverConversationComments(db, chat, heartbeat.wakeup);
      };
      const waitIdle = async () => {
        for (let i = 0; i < 160; i += 1) {
          const current = await issueService(db).getById(chat.id);
          if (isWaitingConversation(current) && !current?.executionRunId)
            return;
          await new Promise((resolve) => setTimeout(resolve, 50));
        }
        const runs = await db
          .select()
          .from(heartbeatRuns)
          .where(eq(heartbeatRuns.agentId, runtimeAgent));
        throw new Error(
          JSON.stringify(
            runs.map((run) => ({
              status: run.status,
              error: run.error,
              result: run.resultJson,
            })),
          ),
        );
      };
      try {
        await send("Help clarify an idea");
        await waitIdle();
        expect(generations).toEqual([0]);
        // Stop leaves a pause and a no-replay recovery disposition. /new must
        // get through dispatch, release the chat pause, and reset in queue order.
        await db.insert(issueTreeHolds).values({ companyId: runtimeCompany,
          rootIssueId: chat.id, mode: "pause", status: "active", createdByActorType: "user",
          createdByUserId: "local-board", releasePolicy: { strategy: "manual", note: "leaf_pause" },
        });
        await db.insert(issueRecoveryActions).values({ companyId: runtimeCompany,
          sourceIssueId: chat.id, kind: "active_run_watchdog", ownerType: "board",
          cause: "uncertain_provider_action", status: "resolved", fingerprint: randomUUID(),
          evidence: { automaticRecovery: { replay: "blocked" } }, nextAction: "Do not replay the stopped turn.",
        });
        await db.insert(issueThreadInteractions).values({ companyId: runtimeCompany, issueId: chat.id,
          kind: "ask_user_questions", status: "pending", title: "Old topic", payload: { version: 1, questions: [{ id: "old", prompt: "Old topic?", options: [{ id: "yes", label: "Yes" }], selectionMode: "single", required: true }], supersedeOnUserComment: false },
        });
        let stoppedQueuedWakeId: string | null = null;
        if (queuedBeforeStop) {
          const [pending] = await db.insert(issueComments).values({ companyId: runtimeCompany,
            issueId: chat.id, authorUserId: "local-board", body: "Old topic queued before Stop",
          }).returning();
          const [stoppedQueuedWake] = await db.insert(agentWakeupRequests).values({ companyId: runtimeCompany, agentId: runtimeAgent,
            source: "on_demand", reason: "issue_execution_deferred", status: "deferred_issue_execution",
            requestedByActorType: "user", requestedByActorId: "local-board",
            payload: { issueId: chat.id, commentId: pending.id,
              _paperclipWakeContext: { issueId: chat.id, wakeReason: "issue_commented", wakeCommentId: pending.id, wakeCommentIds: [pending.id] } },
          }).returning();
          stoppedQueuedWakeId = stoppedQueuedWake.id;
        }
        await send("/new");
        await waitIdle();
        expect((await db.select().from(issueThreadInteractions).where(eq(issueThreadInteractions.issueId, chat.id)))[0].status).toBe("expired");
        expect((await db.select().from(issueTreeHolds).where(eq(issueTreeHolds.rootIssueId, chat.id)))[0].status).toBe("released");
        expect(generations).toEqual([0]);
        await send("A fresh idea");
        await waitIdle();
        expect(generations).toEqual([0, 1]);
        if (stoppedQueuedWakeId) {
          const [stoppedWake] = await db.select().from(agentWakeupRequests).where(eq(agentWakeupRequests.id, stoppedQueuedWakeId));
          expect(stoppedWake).toMatchObject({ status: "cancelled", runId: null });
        }

        expect(
          await heartbeat.wakeup(runtimeAgent, {
            source: "automation",
            contextSnapshot: { issueId: chat.id },
          }),
        ).toBeNull();
        const history = await db
          .select()
          .from(issueComments)
          .where(eq(issueComments.issueId, chat.id));
        expect(history).toHaveLength(queuedBeforeStop ? 6 : 5);
      } finally {
        await new Promise<void>((resolve) => listener.close(() => resolve()));
        await rm(cwd, { recursive: true, force: true });
      }
    }, 30000);
    it("parks successful native interaction-only turns without consuming unrelated or stale gates", async () => {
      const chat = await create();
      const message = await issueService(db).addComment(chat.id, "Plan the work", { userId: "local-board" });
      const run = await runFor(chat.id, message.id);
      const prepared = await prepareConversationTurn(db, run);
      const succeeded = { ...run, contextSnapshot: prepared.context, status: "succeeded" };
      const [interaction] = await db.insert(issueThreadInteractions).values({
        companyId, issueId: chat.id, sourceRunId: run.id, createdByAgentId: agentId,
        kind: "request_confirmation", status: "answered", payload: { version: 1, prompt: "Proceed?" },
      }).returning();
      expect(await settleConversationTurn(db, succeeded)).toBe(false);
      await db.update(issueThreadInteractions).set({ status: "pending", sourceRunId: null })
        .where(eq(issueThreadInteractions.id, interaction.id));
      expect(await settleConversationTurn(db, succeeded)).toBe(false);
      await db.update(issueThreadInteractions).set({ sourceRunId: run.id })
        .where(eq(issueThreadInteractions.id, interaction.id));
      for (const status of ["failed", "cancelled", "timed_out"]) {
        expect(await settleConversationTurn(db, { ...succeeded, status })).toBe(false);
      }
      await db.update(issueThreadInteractions).set({ createdByAgentId: null })
        .where(eq(issueThreadInteractions.id, interaction.id));
      expect(await settleConversationTurn(db, succeeded)).toBe(false);
      await db.update(issueThreadInteractions).set({ createdByAgentId: agentId })
        .where(eq(issueThreadInteractions.id, interaction.id));
      expect(await settleConversationTurn(db, { ...succeeded,
        contextSnapshot: { ...prepared.context, conversationSessionGeneration: -1 },
      })).toBe(false);
      expect(await settleConversationTurn(db, succeeded)).toBe(true);
      const [idle] = await db.select().from(issues).where(eq(issues.id, chat.id));
      expect(isWaitingConversation(idle)).toBe(true);
      const [pending] = await db.select().from(issueThreadInteractions)
        .where(eq(issueThreadInteractions.id, interaction.id));
      expect(pending.status).toBe("pending");
    });
    it("rejects late replies and session events from cancelled conversation turns", async () => {
      const chat = await create();
      const message = await issueService(db).addComment(chat.id, "Old topic", { userId: "local-board" });
      const run = await runFor(chat.id, message.id);
      await prepareConversationTurn(db, run);
      await db.update(heartbeatRuns).set({ status: "cancelled" }).where(eq(heartbeatRuns.id, run.id));
      const previousSecret = process.env.PAPERCLIP_AGENT_JWT_SECRET;
      process.env.PAPERCLIP_AGENT_JWT_SECRET = "test-conversation-cancellation-secret";
      try {
        const app = express();
        app.use(actorMiddleware(db, { deploymentMode: "local_trusted" }));
        app.post("/mutate", (_req, res) => res.sendStatus(204));
        const token = createLocalAgentJwt(agentId, companyId, "process", run.id)!;
        expect((await request(app).post("/mutate").set("Authorization", `Bearer ${token}`)).status).toBe(403);
      } finally {
        if (previousSecret === undefined) delete process.env.PAPERCLIP_AGENT_JWT_SECRET;
        else process.env.PAPERCLIP_AGENT_JWT_SECRET = previousSecret;
      }
      await expect(issueService(db).addComment(chat.id, "Late old reply", { agentId, runId: run.id }))
        .rejects.toThrow(/cancelled/);
      expect(await applyRunnerGoalPrpEvent(db, { companyId, agentId, issueId: chat.id, adapterType: "process" }, {
        eventType: "session.capabilities.updated", sourceRunId: run.id, sourceSeq: 500, payload: {},
      })).toBeNull();
    });
    it("ignores execution dependency wakes during active and idle chat turns", async () => {
      const chat = await create();
      const heartbeat = heartbeatService(db);
      const blocker = await issueService(db).create(companyId, { title: "Linked execution", status: "done" });
      await issueService(db).update(chat.id, { blockedByIssueIds: [blocker.id] });
      const ordinary = await issueService(db).create(companyId, {
        title: "Ordinary dependent",
        status: "in_review",
        assigneeAgentId: agentId,
        blockedByIssueIds: [blocker.id],
      });
      for (const state of [
        { status: "in_review", conversationState: "waiting" as const },
        { status: "blocked", conversationState: "active" as const },
      ]) {
        await db.update(issues).set(state).where(eq(issues.id, chat.id));
        for (const reason of ["issue_blockers_resolved", "issue_children_completed", "issue_unblock_requested"]) {
          expect(await heartbeat.wakeup(agentId, {
            source: "automation",
            reason,
            contextSnapshot: { issueId: chat.id, wakeReason: reason },
          })).toBeNull();
        }
        expect((await issueService(db).listWakeableBlockedDependents(blocker.id)).map((issue) => issue.id))
          .toEqual([ordinary.id]);
      }
      expect((await issueService(db).getDependencyReadiness(chat.id)).blockerIssueIds).toEqual([blocker.id]);
    });

    it.each([
      { name: "reset idle chat", generation: 1, sourceGeneration: 0, waiting: true, ordinary: false, superseded: true },
      { name: "reset active chat", generation: 1, sourceGeneration: 0, waiting: false, ordinary: false, superseded: true },
      { name: "newer reply in the same session", generation: 1, sourceGeneration: 1, waiting: true, ordinary: false, superseded: true },
      { name: "current unanswered chat turn", generation: 1, sourceGeneration: 1, waiting: false, ordinary: false, superseded: false },
      { name: "unprepared failure without a session generation", generation: 1, sourceGeneration: undefined, waiting: true, ordinary: false, superseded: false },
      { name: "ordinary review task", generation: 0, sourceGeneration: 0, waiting: true, ordinary: true, superseded: false },
    ])("guards delayed cancelled-run recovery for $name", async (scenario) => {
      const task = scenario.ordinary
        ? await issueService(db).create(companyId, { title: "Ordinary review", status: "in_review", assigneeAgentId: agentId })
        : await create();
      const status = scenario.waiting ? "in_review" : "in_progress";
      await db.update(issues).set({
        status,
        ...(scenario.ordinary ? {} : {
          conversationSessionGeneration: scenario.generation,
          conversationState: scenario.waiting ? "waiting" : "active",
        }),
      }).where(eq(issues.id, task.id));
      const run = await runFor(task.id, randomUUID(), {
        conversationSessionGeneration: scenario.sourceGeneration,
      });
      await terminalizeLegacyExecution({ db, run, status: "cancelled", patch: { finishedAt: new Date() } });
      let actions = await db.select().from(issueRecoveryActions).where(eq(issueRecoveryActions.sourceIssueId, task.id));
      expect(actions).toHaveLength(scenario.superseded ? 0 : 1);
      // Also exercise an action queued before /new or the newer reply settled.
      if (!actions.length) {
        actions = await db.insert(issueRecoveryActions).values({
          companyId, sourceIssueId: task.id, kind: "active_run_watchdog",
          ownerType: "board", returnOwnerAgentId: agentId,
          cause: LEGACY_RECOVERY_CAUSE, fingerprint: `legacy-execution:${run.id}`,
          evidence: { runId: run.id }, nextAction: "Reconcile stopped work",
        }).returning();
      }
      await settleUnrecoverableExecutions(db);
      const [after] = await db.select().from(issues).where(eq(issues.id, task.id));
      const [action] = await db.select().from(issueRecoveryActions).where(eq(issueRecoveryActions.id, actions[0]!.id));
      expect(after.status).toBe(scenario.superseded ? status : "blocked");
      expect(action).toMatchObject({ status: "resolved", outcome: scenario.superseded ? "cancelled" : "blocked" });
      expect((await db.select().from(heartbeatRuns).where(eq(heartbeatRuns.id, run.id)))[0].status).toBe("cancelled");
      if (!scenario.ordinary) expect(after.conversationSessionGeneration).toBe(scenario.generation);
    });

    it.each(["answered", "new-message", "response-less", "failed", "stale-session", "failed-gap", "missing-gap"])("settles a historical question using completed conversation progress (%s)", async scenario => {
      const chat = await create();
      const svc = issueService(db);
      const first = await svc.addComment(chat.id, "Which color?", { userId: "local-board" });
      const original = await runFor(chat.id, first.id);
      const [question] = await db.insert(issueThreadInteractions).values({ companyId, issueId: chat.id,
        kind: "ask_user_questions", status: "answered", continuationPolicy: "wake_assignee", sourceRunId: original.id,
        createdByAgentId: agentId, resolvedByUserId: "local-board", payload: { version: 1, questions: [] }, result: { version: 1, answers: [] } }).returning();
      if (scenario === "failed-gap" || scenario === "missing-gap") {
        const skipped = await svc.addComment(chat.id, "This request still needs an answer.", { userId: "local-board" });
        if (scenario === "failed-gap") {
          const failed = await runFor(chat.id, skipped.id, { conversationSessionGeneration: 0 });
          await db.update(heartbeatRuns).set({ status: "failed" }).where(eq(heartbeatRuns.id, failed.id));
        }
      }
      const newer = await svc.addComment(chat.id, "What is the capital of France?", { userId: "local-board" });
      const replyRun = await runFor(chat.id, newer.id, { conversationSessionGeneration: 0 });
      if (scenario !== "response-less") await svc.addComment(chat.id, "Paris.", { agentId, runId: replyRun.id });
      await db.update(heartbeatRuns).set({ status: scenario === "failed" ? "failed" : "succeeded",
        ...(scenario === "stale-session" ? { contextSnapshot: { ...replyRun.contextSnapshot, conversationSessionGeneration: 99 } } : {}) }).where(eq(heartbeatRuns.id, replyRun.id));
      const answerRun = await runFor(chat.id, first.id, { source: "issue.interaction.respond", interactionId: question.id,
        interactionKind: "ask_user_questions", interactionStatus: "answered" });
      const prepared = await prepareConversationTurn(db, answerRun);
      const preparedContext: Record<string, unknown> = prepared.context;
      expect(preparedContext.wakeCommentId).toBe(first.id);
      expect(preparedContext.conversationReplyBoundaryCommentId).toBe(["answered", "new-message"].includes(scenario) ? newer.id : first.id);
      // A retry reuses the frozen boundary, even if another message has arrived.
      if (scenario === "new-message") await svc.addComment(chat.id, "New instructions while you answer", { userId: "local-board" });
      const retry = await prepareConversationTurn(db, { ...answerRun, contextSnapshot: prepared.context });
      const retryContext: Record<string, unknown> = retry.context;
      expect(retryContext.conversationReplyBoundaryCommentId).toBe(preparedContext.conversationReplyBoundaryCommentId);
      await svc.addComment(chat.id, "You chose Blue.", { agentId, runId: answerRun.id });
      expect(await settleConversationTurn(db, { ...answerRun, status: "succeeded", contextSnapshot: prepared.context })).toBe(true);
      const [settled] = await db.select().from(issues).where(eq(issues.id, chat.id));
      expect(settled.conversationState).toBe(scenario === "answered" ? "waiting" : "active");
      expect(retryContext.conversationReplayThroughCommentId).toBe(preparedContext.conversationReplayThroughCommentId);
      const replay = await conversationReplay(db, companyId, chat.id, first.id,
        preparedContext.conversationReplayThroughCommentId as string);
      if (["answered", "new-message"].includes(scenario)) {
        expect(replay).toContain("What is the capital of France?");
        expect(replay).toContain("Paris.");
      } else {
        expect(replay).not.toContain("What is the capital of France?");
        expect(replay).not.toContain("Paris.");
      }
      expect(replay).not.toContain("This request still needs an answer.");
      expect(replay).not.toContain("New instructions while you answer");
      expect(replay).not.toContain("You chose Blue.");
    });

    it("only parks answered turns and preserves idle across recovery classification", async () => {
      const issue = await create();
      const message = await issueService(db).addComment(
        issue.id,
        "Which goal matters?",
        { userId: "local-board" },
      );
      const run = await runFor(issue.id, message.id);
      const prepared = await prepareConversationTurn(db, run);
      const succeeded = {
        ...run,
        contextSnapshot: prepared.context,
        status: "succeeded",
      };
      expect(await settleConversationTurn(db, succeeded)).toBe(false);
      await issueService(db).addComment(
        issue.id,
        "What outcome should the task deliver?",
        { agentId, runId: run.id },
      );
      expect(await settleConversationTurn(db, succeeded)).toBe(true);
      const [idle] = await db
        .select()
        .from(issues)
        .where(eq(issues.id, issue.id));
      expect(isWaitingConversation(idle)).toBe(true);
      expect(
        classifyIssueGraphLiveness({
          issues: [idle],
          relations: [],
          agents: [],
        }),
      ).toEqual([]);
      const child = await issueService(db).create(companyId, { title: "Execute work", status: "done" });
      await db.update(issues).set({ parentId: issue.id }).where(eq(issues.id, child.id));
      expect(
        await issueService(db).getWakeableParentAfterChildCompletion(issue.id, {
          issueId: child.id,
          summary: "Finished",
        }),
      ).toBeNull();
    });
  },
);

describe("conversation execution wake policy", () => {
  it.each(["issue_blockers_resolved", "issue_children_completed", "issue_unblock_requested"])(
    "suppresses %s only for conversation containers",
    (reason) => {
      expect(isConversationExecutionWake({ conversationAgentId: "agent", conversationUserId: "user" }, reason)).toBe(true);
      expect(isConversationExecutionWake({}, reason)).toBe(false);
    },
  );
  it.each(["issue_commented", "interaction_resolved", "run_failed", "issue_recovery_action_restored"])(
    "preserves %s handling for pending conversation turns",
    (reason) => expect(isConversationExecutionWake({ conversationAgentId: "agent", conversationUserId: "user" }, reason)).toBe(false),
  );
});

describe("chat prompt policy", () => {
  it("tells chat to link the profile of an agent it acted on without turning the link into a wake mention", () => {
    expect(AGENT_CHAT_DIRECTIVE).toContain("link its profile at /<prefix>/agents/<urlKey or id>");
    expect(AGENT_CHAT_DIRECTIVE).toContain("use agent:// only when you intend to notify that agent");
    const prompt = buildPaperclipTaskMarkdown({ issue: { id: "chat", identifier: null, title: "Chat", workMode: "ask", conversationAgentId: "agent" } });
    expect(prompt).toContain("/<prefix>/agents/<urlKey or id>");
  });

  it("preserves explicit plan approval while avoiding ritual confirmations for ordinary chat", () => {
    expect(AGENT_CHAT_DIRECTIVE).toContain("When the user asks to approve a plan before handoff");
    expect(AGENT_CHAT_DIRECTIVE).toContain('interactionKind: "confirmation"');
    expect(AGENT_CHAT_DIRECTIVE).toContain("targetRevisionId from the saved document's latestRevisionId");
    expect(AGENT_CHAT_DIRECTIVE).toContain('payload.target to { type: "issue_document", key: "plan", revisionId: latestRevisionId }');
    expect(AGENT_CHAT_DIRECTIVE).toContain("ordinary conversation replies and draft planning do not need confirmation");
    expect(AGENT_CHAT_DIRECTIVE).toContain("In Ask mode, discuss the plan without creating or revising documents or approval cards");
  });

  it("gives chat replies a usable route for both task and approval sources", () => {
    expect(AGENT_CHAT_DIRECTIVE).toContain("/<prefix>/issues/<identifier>");
    expect(AGENT_CHAT_DIRECTIVE).toContain("For approval links, use /<prefix>/approvals/<approvalId>");
    expect(AGENT_CHAT_DIRECTIVE).toContain("Never invent a hostname for a Paperclip link.");
  });

  it.each([true, false])("preserves rejected-plan changes in task markdown (includeDescription=%s)", (includeDescription) => {
    const prompt = buildPaperclipTaskMarkdown({
      issue: { id: "chat", identifier: null, title: "Chat", workMode: "planning", conversationAgentId: "agent" },
      interaction: { kind: "request_confirmation", status: "rejected" },
      planReview: { status: "rejected", reason: "Add CHAT_REVIEW_MARKER and a validation step." },
      acceptedPlanContinuation: true,
      acceptedPlan: { revisionId: "stale-approved-plan" },
      includeDescription,
    });
    expect(prompt).toContain("Rejected plan review directive:");
    expect(prompt).toContain("Add CHAT_REVIEW_MARKER and a validation step.");
    expect(prompt).toContain("not approval to implement or hand off execution tasks");
    expect(prompt).toContain("first GET /api/issues/{issueId}/documents/plan");
    expect(prompt).toContain("baseRevisionId set to that latestRevisionId");
    expect(prompt).toContain("Bind the new approval request to the revision returned by the successful update");
    expect(prompt).not.toContain("Accepted chat plan directive:");
    expect(prompt).not.toContain("stale-approved-plan");
  });
  it.each(["standard", "ask", "planning"])(
    "keeps handoff instructions in %s, including accepted plans and resumes",
    (workMode) => {
      const prompt = buildPaperclipTaskMarkdown({
        issue: {
          id: "chat",
          identifier: null,
          title: "Chat",
          workMode,
          conversationAgentId: "agent",
          description: "Pre-boundary summary that must not replay",
        },
        acceptedPlanContinuation: true,
        includeDescription: true,
        acceptedPlan: { revisionId: "old-approved-plan" },
      });
      expect(prompt).toContain(AGENT_CHAT_DIRECTIVE);
      expect(prompt).not.toContain("Pre-boundary summary");
      expect(prompt).not.toContain("old-approved-plan");
      expect(prompt).not.toContain("Implement the accepted plan on this issue");
      expect(prompt).toContain("Create and link each task before claiming it exists");
    },
  );
});

describe("native conversation finalization", () => {
  it("does not require execution completion or schedule a continuation after a successful chat turn", () => {
    const decision = {
      policyVersion: NATIVE_STATUS_ARBITER_POLICY_VERSION,
      statusAction: "in_progress",
      toStatus: "in_progress",
      reasonCode: "completion_evidence_incomplete",
      unblockDescriptor: null,
      effects: [
        {
          kind: "enqueue_continuation",
          continuationKind: "same_agent",
          summary: "Finish",
          idempotencyKey: "next",
          agentId: "agent",
        },
      ],
    } as Parameters<typeof conversationNativeDecision>[0]["decision"];
    const input = {
      conversation: true,
      terminalState: "succeeded",
      workspaceFinalizeStatus: "succeeded",
      hasGovernanceGate: false,
      priorStatus: "in_progress" as const,
      decision,
    };
    expect(conversationNativeDecision(input)).toMatchObject({
      statusAction: "preserve",
      effects: [],
    });
    expect(
      conversationNativeDecision({ ...input, hasGovernanceGate: true }),
    ).toBe(decision);
    expect(
      conversationNativeDecision({ ...input, terminalState: "failed" }),
    ).toBe(decision);
    expect(conversationNativeDecision({ ...input, conversation: false })).toBe(
      decision,
    );
  });
});