fix(slack): retain DM thread tasks after completion (#19486)

## Thinking Path > - Paperclip manages AI agents and their work. > - Slack conversations store that work in tasks and comments. > - A native thread must keep its task when work finishes. > - The server treated all DMs as linear conversations. > - A reply in a completed DM thread therefore started a new task without its earlier comments. > - This pull request uses the native thread identity for task continuity. > - People can continue the same work with its saved context. ## Linked Issues or Issue Description **What happened?** A reply in a Slack DM thread created a new task after the preceding task was Done or Cancelled. It also created a new task when the saved conversation was completed. The new task lacked earlier comments. **Expected behavior** A native Slack thread keeps one task in channels and DMs. Later replies retain earlier user and agent comments. Top-level DMs keep their existing task generation rules. **Steps to reproduce** 1. Start work in a Slack DM thread. 2. Mark its task Done. 3. Reply in the same thread. 4. Before this fix, the reply creates another task. **Paperclip version or commit** Reproduced from master at eb5c24b61c. **Deployment mode** Built from source. Tests use local PostgreSQL and provider fixtures. Related PR: #16151 covers the DM mention exemption. This fix preserves that behavior. GitHub searches found no duplicate fix for completion routing. ## What Changed - Detect Slack native thread roots in the Slack module. - Classify native DM threads as persistent threads for task routing. - Select the resource type from the actual DM destination. Keep DM access checks. - Preserve DM task controls. Select the latest DM task even after completion. Require a delivered control receipt before an explicit new task generation. - Add completion, duplicate, saved-history, separate-root, Idle, and explicit-control regressions. - Document the task boundary. Correct only the inaccurate DM-thread statement in the existing feature recipe. ## Verification - Before the production edit, the new PostgreSQL regression failed in all three threaded-DM completion cases: two conversations existed instead of one. The channel-thread and top-level-DM controls passed. - The initial eight routing cases passed. CI then found five existing slash-control failures. All five reproduced locally. Greptile reported the same regression at 4/5. - The first correction passed all 16 focused PostgreSQL cases. Secondary review then found that slash commands skipped Done, Cancelled, and completed DM tasks. Four new cases failed before the lookup change. Commit 23ff4f04f passed all 20 focused cases, including status, explicit new/close, delivered receipts, and a new task generation. The original same-thread continuity cases still pass. - Command: `pnpm exec vitest run server/src/__tests__/chat-channels.integration.test.ts -t 'preserves Slack thread history across completion|keeps separate Slack DM thread roots|returns two answered Slack turns to Idle|binds Slack DM slash controls|treats D-prefixed Slack status|serializes duplicate Slack admission with an owned provider-reply settlement|suppresses a queued provider reply when destination reach|continues to accept authenticated Slack slash close/new'`. - Map validation and `git diff --check` passed. Map validation proves structure only. - All 107 neighboring Slack adapter, SDK runtime, and receipt tests passed across three files. - The initial complete server typecheck passed with `PAPERCLIP_TYPECHECK_LOW_MEMORY=1 pnpm --filter @paperclipai/server typecheck`, including all three test-tree shards. - Full local recursive typecheck and build stopped because this workspace has no `cargo`. A separate default server typecheck was killed under concurrent memory load; its lower-memory rerun passed. The broad local test run was interrupted to free memory, so no full-local-suite pass is claimed. The complete server typecheck passed again for correction 367b6f9b3, including all three test-tree shards. The [full CI pipeline](https://github.com/paperclipai/paperclip/actions/runs/42250458200) passed for exact head 367b6f9b3f. This includes typecheck, build, all chat and other test lanes, browser E2E, Runner, and aggregate verify. The first CI run passed broad typecheck, build, E2E, Runner, and other test groups, but its chat failures remain recorded above. - The initial regression launch could not load the unbuilt plugin SDK. It ran after building the required workspace dependencies. A test-only resource assertion was corrected to read persisted DM resources, which the settings list omits. The completed-conversation case preserves an existing review status. - The initial correction test used a follow-up timestamp older than the delivered control. The chronology gate correctly rejected it. A current provider timestamp now verifies the new generation without weakening that gate. - Greptile's map finding was addressed by removing recipe expansions and all agent-access map changes. Both review threads have replies and are resolved. Greptile reviewed exact head 367b6f9b3f at [5/5 with zero new findings](https://github.com/paperclipai/paperclip/pull/19486#issuecomment-6689117840). The secondary Paperclip Review rated that head 4/5 and found the completed-task slash lookup error. Commit 23ff4f04f fixes this finding. Greptile and Paperclip Review both rate head 23ff4f04f6 at 5/5. All three review threads are resolved. The [full CI pipeline](https://github.com/paperclipai/paperclip/actions/runs/42255926149) now passes on this exact head. This includes typecheck, build, all test lanes, browser E2E, Runner checks, Canary Dry Run, and aggregate verify. All checks are terminal: 54 success, 1 neutral, and 3 skipped. Snyk also passes. The PR has no merge conflict. - The complete server typecheck passed again on 23ff4f04f, including all three test-tree shards. - The new test first asserted the conversation-list state. That API displays terminal tasks as completed before the control is sent. The test now reads stored binding state to check that completion waits for the delivered receipt. - No live Slack send or deployment was performed. ## Risks - Native DM threads now reopen the existing task after Done or Cancelled. Explicit new/close controls still release the binding after their response is delivered. Top-level DMs still start new generations after completion. - Existing split tasks stay separate. Future replies use the latest saved binding. This change does not merge old tasks or copy surrounding DM history into a newly created thread. - No schema, credential, provider scope, or permission changes are required. ## Model Used OpenAI Codex, based on GPT-6, with reasoning, tool use, repository editing, and code execution. The runtime does not expose a more precise serving model ID or context-window size. ## Checklist - [x] I have included a thinking path that traces from project context to this change - [x] I have specified the model used (with version and capability details) - [x] I have checked ROADMAP.md and confirmed this PR does not duplicate planned core work - [x] I have searched GitHub for duplicate or related PRs and linked them above - [x] I have either (a) linked existing issues with `Fixes: #` / `Closes #` / `Refs #` OR (b) described the issue in-PR following the relevant issue template - [x] I have not referenced internal/instance-local Paperclip issues or links (only public GitHub `#NNN` / `github.com/paperclipai/paperclip` URLs) - [x] My branch name describes the change (e.g. `docs/...`, `fix/...`) and contains no internal Paperclip ticket id or instance-derived details - [x] I have run tests locally and they pass - [x] I have added or updated tests where applicable - [x] I have updated relevant documentation to reflect my changes - [x] I have considered and documented any risks above - [x] All Paperclip CI gates are green - [x] Greptile is 5/5 with no open P2s, recommendations, or follow-ups - [x] I will address all Greptile and reviewer comments before requesting merge --------- Co-authored-by: Paperclip <[email protected]>
2026-11-07 06:16:06 -10:00 · 2026-11-07 08:35:29 -06:00
1 parent c740cb9ded
commit 2e52dfa864
@@ -102,6 +102,16 @@ subscribes to the Slack thread, and starts the agent; later replies in that thre
 continue the same task without another mention. Normal account and channel access
 rules still apply, and repeated Slack deliveries do not create duplicate tasks.

+A native Slack thread keeps the same task in channels and DMs, including after
+the task is Done or Cancelled. A new reply reopens that task with its saved
+comments. DM access settings and task controls still apply to threads inside DMs.
+An explicit `/new` or `/close` starts the next task generation only after its
+control response is delivered. Task completion alone does not release the binding.
+Top-level DMs keep their linear lifecycle and can start a new task after completion.
+For a thread that was split before this fix, later replies continue its latest
+saved task. Earlier tasks remain separate; this change does not merge history
+or copy messages from the surrounding DM into a new thread.
+
 Agents can ask interactive questions in Slack through Paperclip's saved
 `ask_user_questions` interactions. Native runners use `request_human_input`;
 legacy adapters use the issue-interactions API documented in the injected
@@ -101,9 +101,9 @@ cover the database and prompt contracts; they do not prove live provider deliver

 For Slack, enable **Require at-mention** and **Allow direct messages**. Send a
 plain DM and follow up without a mention: both should reach the agent, with
-top-level replies to top-level DMs. Channel messages and thread replies still
+top-level replies to top-level DMs. Channel messages and channel thread replies still
 require a mention when that setting is enabled. Disable direct messages and
-confirm a plain DM is rejected. Use a private channel for threaded conversations.
+confirm a plain DM is rejected. Threads also work in DMs.

 For Slack acknowledgement latency, mention the bot with and without an attachment.
 Eyes should appear after authorized task/comment persistence, independently of
@@ -30541,6 +30541,82 @@ describeEmbeddedPostgres("chat channel control-plane integration", () => {
    await service.shutdown();
  });

+  it.each([
+    { isDM: true, threaded: true, status: "done", state: "active" },
+    { isDM: true, threaded: true, status: "cancelled", state: "active" },
+    { isDM: true, threaded: true, status: "in_review", state: "completed" },
+    { isDM: false, threaded: true, status: "done", state: "completed" },
+    { isDM: true, threaded: false, status: "done", state: "completed" },
+  ] as const)(
+    "preserves Slack thread history across completion ($isDM, $threaded, $status, $state)",
+    async ({ isDM, threaded, status, state }) => {
+      const fixture = await seedCompany();
+      const { callbacks, endpoint, service, wakeup } = await configuredSlackEndpoint(fixture, { linkedBoardUser: true });
+      const channelId = isDM ? "D-HISTORY" : "C-HISTORY";
+      const thread = makeThread({
+        channelId,
+        id: `slack:${channelId}:${threaded ? "1000.1" : ""}`,
+        isDM,
+      }).thread;
+      const send = (id: string, text: string) => deliverMessage({
+        callbacks, endpointId: endpoint.id, thread,
+        message: makeMessage({ id, text, mentioned: !isDM, userId: "UBOARD" }),
+        trigger: isDM ? "direct_message" : "mention",
+      });
+      await send("1000.1", "Keep this context for my next request");
+      const [original] = await readChatConversationsByEndpointId(endpoint.id);
+      await db.insert(issueComments).values({
+        companyId: fixture.companyId, issueId: original.issueId,
+        authorType: "agent", authorAgentId: fixture.assignedAgentId,
+        body: "I kept the original request.",
+      });
+      await db.update(issues).set({ status }).where(eq(issues.id, original.issueId));
+      await db.update(chatConversations).set({ state }).where(eq(chatConversations.id, original.id));
+
+      await send("1000.2", "Is it done?");
+      await send("1000.2", "Is it done?");
+      const conversations = await readChatConversationsByEndpointId(endpoint.id);
+      expect(conversations).toHaveLength(threaded ? 1 : 2);
+      const generation = threaded ? original.sessionGeneration : original.sessionGeneration + 1;
+      const continued = conversations.find(row => row.sessionGeneration === generation)!;
+      expect(continued.issueId === original.issueId).toBe(threaded);
+      expect(continued.state).toBe("active");
+      expect((await issueService(db).getById(continued.issueId))?.status).toBe(status === "in_review" ? "in_review" : "todo");
+      const comments = await readIssueCommentsByIssueId(continued.issueId)
+        .orderBy(asc(issueComments.createdAt), asc(issueComments.id));
+      expect(comments.map(row => row.body)).toEqual(threaded
+        ? ["Keep this context for my next request", "I kept the original request.", "Is it done?"]
+        : ["Is it done?"]);
+      expect(wakeup).toHaveBeenCalledTimes(2);
+      const resources = await db.select().from(chatEndpointResources)
+        .where(eq(chatEndpointResources.endpointId, endpoint.id));
+      expect(resources.find(row => row.providerResourceId === channelId)?.type).toBe(isDM ? "direct_message" : "channel");
+      if (isDM) {
+        await service.update(endpoint.id, { allowDirectMessages: false });
+        await send("1000.3", "This must be rejected");
+        expect(wakeup).toHaveBeenCalledTimes(2);
+        expect(await readIssueCommentsByIssueId(continued.issueId)).toHaveLength(threaded ? 3 : 1);
+      }
+    },
+  );
+
+  it("keeps separate Slack DM thread roots on separate tasks", async () => {
+    const fixture = await seedCompany();
+    const { callbacks, endpoint } = await configuredSlackEndpoint(fixture);
+    for (const root of ["1000.1", "1000.2"]) {
+      await deliverMessage({
+        callbacks, endpointId: endpoint.id,
+        thread: makeThread({ channelId: "D-ROOTS", id: `slack:D-ROOTS:${root}`, isDM: true }).thread,
+        message: makeMessage({ id: root, text: "A separate request" }),
+        trigger: "direct_message",
+      });
+    }
+    const conversations = await readChatConversationsByEndpointId(endpoint.id);
+    expect(conversations).toHaveLength(2);
+    expect(new Set(conversations.map(row => row.issueId)).size).toBe(2);
+    expect(conversations.map(row => row.sessionGeneration)).toEqual([1, 1]);
+  });
+
  it("deduplicates inbound events, keeps one task per thread, and enables newly discovered Slack channels", async () => {
    const fixture = await seedCompany();
    const { callbacks, endpoint, runtime, service, wakeup } =
@@ -36300,10 +36376,11 @@ describeEmbeddedPostgres("chat channel control-plane integration", () => {
    await resumed.service.shutdown();
  });

-  it("returns two answered Slack turns to Idle in the same thread", async () => {
+  it.each([false, true])("returns two answered Slack turns to Idle in the same thread (DM=%s)", async (isDM) => {
    const fixture = await seedCompany();
    const { callbacks, endpoint, service } = await configuredSlackEndpoint(fixture);
-    const thread = makeThread({ channelId: "C-IDLE", id: "slack:C-IDLE:4049.1", name: "idle" });
+    const channelId = isDM ? "D-IDLE" : "C-IDLE";
+    const thread = makeThread({ channelId, id: `slack:${channelId}:4049.1`, name: "idle", isDM });
    let issueId: string | undefined;
    let conversationId: string | undefined;
    for (const [index, text] of ["@maya are you there?", "what is your name?"].entries()) {
@@ -58532,7 +58609,14 @@ describeEmbeddedPostgres("chat channel control-plane integration", () => {
    ]);
  });

-  it("binds Slack DM slash controls to the native root returned for the latest task", async () => {
+  it.each([
+    { control: "new", status: "todo", state: "active" },
+    { control: "close", status: "todo", state: "active" },
+    { control: "new", status: "done", state: "active" },
+    { control: "close", status: "cancelled", state: "active" },
+    { control: "new", status: "done", state: "completed" },
+    { control: "close", status: "cancelled", state: "completed" },
+  ] as const)("binds Slack DM slash controls to the latest task ($control, $status, $state)", async ({ control, status, state }) => {
    const fixture = await seedCompany();
    const { callbacks, endpoint, runtime, service } =
      await configuredSlackEndpoint(fixture);
@@ -58589,18 +58673,20 @@ describeEmbeddedPostgres("chat channel control-plane integration", () => {
    );
    const [conversation] = await service.listConversations(endpoint.id);
    expect(conversation.externalThreadId).toBe(starterThreadId);
+    await db.update(issues).set({ status }).where(eq(issues.id, conversation.issueId));
+    await db.update(chatConversations).set({ state }).where(eq(chatConversations.id, conversation.id));

    await invoke("status");
    await service.processPendingPublications();
    expect(runtime.endpoints.get(endpoint.id)?.posts.at(-1)).toMatchObject({
      threadId: starterThreadId,
-      text: expect.stringMatching(/— todo$/),
+      text: expect.stringMatching(new RegExp(`— ${status}$`)),
    });
-    await invoke("close");
-    await expect(service.listConversations(endpoint.id)).resolves.toEqual([
+    await invoke(control);
+    await expect(readChatConversationsByEndpointId(endpoint.id)).resolves.toEqual([
      expect.objectContaining({
        externalThreadId: starterThreadId,
-        state: "active",
+        state,
      }),
    ]);
    await service.processPendingPublications();
@@ -58610,9 +58696,26 @@ describeEmbeddedPostgres("chat channel control-plane integration", () => {
        state: "completed",
      }),
    ]);
-    expect(
-      await readIssuesByCompanyId(fixture.companyId),
-    ).toHaveLength(1);
+    const [completion] = await db.select().from(chatPublications).where(and(
+      eq(chatPublications.conversationId, conversation.id),
+      like(chatPublications.idempotencyKey, `control:${control}:%`),
+    ));
+    expect(completion?.state).toBe("published");
+    expect(await readIssuesByCompanyId(fixture.companyId)).toHaveLength(1);
+    const providerTime = Date.now();
+    const providerTimestamp = `${Math.floor(providerTime / 1_000)}.${String((providerTime % 1_000) * 1_000).padStart(6, "0")}`;
+    await deliverMessage({
+      callbacks, endpointId: endpoint.id,
+      thread: makeThread({ channelId: "D09SLASHTASK", id: starterThreadId, isDM: true }).thread,
+      message: makeMessage({ id: providerTimestamp, raw: { ts: providerTimestamp }, text: "An explicitly requested new task", userId: "U-DM-SLASH-TASK" }),
+      trigger: "direct_message",
+    });
+    const conversations = await service.listConversations(endpoint.id);
+    expect(conversations).toHaveLength(2);
+    expect(conversations.find(row => row.state === "active")).toMatchObject({
+      externalThreadId: starterThreadId, sessionGeneration: 2,
+    });
+    expect(await readIssuesByCompanyId(fixture.companyId)).toHaveLength(2);
  });

  it("acknowledges a Slack retry while one durable worker owns the unrecorded command root", async () => {
@@ -1755,13 +1755,17 @@ export function chatChannelService(db: Db, options: ChatChannelServiceOptions) {
      let { conversation: existingConversation, issue: existingIssue, latestConversation, isLinear } =
        await resolveInboundConversationBinding(db, {
          endpoint, thread,
-          isLinear: () => endpoint.provider === "speko" ? SPEKO_CONVERSATION_IS_LINEAR : surfaceKind !== "native_thread",
+          isLinear: () => endpoint.provider === "speko"
+            ? SPEKO_CONVERSATION_IS_LINEAR
+            : surfaceKind !== "native_thread" || (endpoint.provider === "slack" && thread.isDM),
          lookupConversation: endpoint.provider === "microsoft-teams"
            ? () => conversationForThread(endpoint.id, thread.id)
            : undefined,
          conversationIsComplete: endpoint.provider === "imessage-photon"
            ? (conversationId) => photonConversationBindingIsComplete(conversationId, hasCommittedTaskControlCompletion)
-            : undefined,
+            : endpoint.provider === "slack" && thread.isDM && surfaceKind === "native_thread"
+              ? async (conversationId, state) => state === "completed" && hasCommittedTaskControlCompletion(conversationId)
+              : undefined,
        });
      const telegramControls = endpoint.provider === "telegram"
        ? telegramInboundControls(message.text, surfaceKind)
@@ -373,6 +373,7 @@ export function createChatInboundAuthority(db: Db, options: InboundAuthorityOpti
    const type = providerResourceType(
      endpoint.provider,
      chatSurfaceKind(endpoint.provider, thread),
+      thread.isDM,
    );
    const providerResourceId = canonicalProviderResourceId(
      endpoint.provider,
@@ -9,7 +9,7 @@ type ConversationBindingInput = {
  thread: { id: string; channelId: string };
  isLinear: () => boolean;
  lookupConversation?: () => Promise<ConversationRow | null>;
-  conversationIsComplete?: (conversationId: string) => Promise<boolean>;
+  conversationIsComplete?: (conversationId: string, state: ConversationRow["state"]) => Promise<boolean>;
 };

 export async function resolveInboundConversationBinding(
@@ -54,7 +54,7 @@ export async function resolveInboundConversationBinding(
    isLinear &&
    existingConversation &&
    (conversationIsComplete
-      ? await conversationIsComplete(existingConversation.id)
+      ? await conversationIsComplete(existingConversation.id, existingConversation.state)
      : existingConversation.state === "completed" ||
        existingIssue?.status === "done" ||
        existingIssue?.status === "cancelled")
@@ -263,7 +263,7 @@ export function createInboundEnvelope(db: Db, options: InboundEnvelopeOptions) {
        handle: message.author.userName,
      },
      resource: {
-        type: providerResourceType(endpoint.provider, surfaceKind),
+        type: providerResourceType(endpoint.provider, surfaceKind, thread.isDM),
        providerResourceId: canonicalProviderResourceId(
          endpoint.provider,
          thread,
@@ -340,7 +340,7 @@ export function createInboundEnvelope(db: Db, options: InboundEnvelopeOptions) {
          }
        : {}),
      resource: {
-        type: providerResourceType(endpoint.provider, surfaceKind),
+        type: providerResourceType(endpoint.provider, surfaceKind, thread.isDM),
        providerResourceId: canonicalProviderResourceId(
          endpoint.provider,
          thread,
@@ -1,4 +1,4 @@
-import { slackThreadChannelId } from "../slack/messages.js";
+import { slackThreadChannelId, slackThreadRootMessageId } from "../slack/messages.js";

 import type { EndpointRow } from "../runtime-types.js";

@@ -30,8 +30,9 @@ type ChatSurfaceKind = "direct_message" | "linear_group" | "native_thread";
 function providerResourceType(
  provider: ChatProvider,
  surfaceKind: ChatSurfaceKind,
+  isDirectMessage: boolean,
 ): string {
-  if (surfaceKind === "direct_message") return "direct_message";
+  if (isDirectMessage) return "direct_message";
  if (provider === "github") return "repository";
  if (provider === "imessage-photon") return "group_chat";
  if (provider === "discord") return "channel";
@@ -116,6 +117,7 @@ function chatSurfaceKind(
  provider: ChatProvider,
  thread: Thread,
 ): ChatSurfaceKind {
+  if (provider === "slack" && slackThreadRootMessageId(thread.id)) return "native_thread";
  if (thread.isDM) return "direct_message";
  if (provider === "imessage-photon") return "linear_group";
  if (provider === "telegram") {
@@ -91,8 +91,12 @@ export function slackThreadChannelId(threadId: string): string | null {
  return channelId || null;
 }

+export function slackThreadRootMessageId(threadId: string): string | null {
+  return /^slack:[^:]+:([^:]+)$/.exec(threadId)?.[1] ?? null;
+}
+
 export function slackOrphanFollowUp(threadId: string, messageId: string): boolean {
-  const rootMessageId = /^slack:[^:]+:(.+)$/.exec(threadId)?.[1];
+  const rootMessageId = slackThreadRootMessageId(threadId);
  return Boolean(rootMessageId) && rootMessageId !== messageId;
 }

@@ -19,7 +19,6 @@ import {
  inArray,
  lte,
  ne,
-  notInArray,
  or,
  sql,
 } from "drizzle-orm";
@@ -173,8 +172,6 @@ export function createSlackTaskStart(db: Db, options: SlackTaskStartOptions) {
          eq(chatConversations.endpointId, endpointId),
          inArray(chatConversations.externalConversationId, conversationIds),
          eq(chatConversations.isDirectMessage, true),
-          inArray(chatConversations.state, ["active", "waiting"]),
-          notInArray(issues.status, ["done", "cancelled"]),
        ),
      )
      .orderBy(