@vellumai/assistant 0.12.1-staging.1 → 0.12.1

package/src/__tests__/messaging-send-tool.test.ts

@@ -36,18 +36,25 @@ function makeProvider(id: string, displayName: string): MessagingProvider {
   };
 }
 
-// "phone" is a provider with a send of its own and no channel transport, so
-// its send stays tool-mediated; "outlook" drafts. A channel with a transport
-// (slack, telegram) never reaches a provider's send: the tool hands it to
-// the transport-backed send, which is what these tests prove.
+// "outlook" is a messaging provider but not a channel (it is not in
+// CHANNEL_IDS): a send through it has no chat conversation to record in.
+// "phone" and "telegram" are channels.
 const phoneProvider = makeProvider("phone", "Phone");
+const telegramProvider = makeProvider("telegram", "Telegram");
 const outlookProvider = makeProvider("outlook", "Outlook");
-const telegramProvider: MessagingProvider = {
-  ...makeProvider("telegram", "Telegram"),
-  sendMessage: undefined,
+// Slack's provider threads exactly where it is told and reports that thread
+// on the result; Telegram's ignores a requested thread and reports none.
+const slackProvider: MessagingProvider = {
+  ...makeProvider("slack", "Slack"),
+  sendMessage: async (_connection, conversationId, _text, options) => ({
+    id: "1700000000.000100",
+    timestamp: 123,
+    conversationId,
+    ...(options?.threadId ? { threadId: options.threadId } : {}),
+  }),
 };
-
 let provider: MessagingProvider = phoneProvider;
+
 let connection: OAuthConnection | undefined = undefined;
 
 /** Fires during provider resolution, the first await after the entry guard. */
@@ -67,24 +74,26 @@ mock.module("../config/bundled-skills/messaging/tools/shared.js", () => ({
   isMailboxAddress: (value: string) => value.includes("@"),
 }));
 
-// ── The transport-backed send ──
-
-const ADDRESSABLE = new Set(["slack", "telegram", "discord", "whatsapp"]);
-const sendChannelTextMock = mock(async (params: Record<string, unknown>) => ({
-  channel: params.channel,
-  chatId: (params.target as { chatId: string }).chatId,
-  ...((params.target as { threadId?: string }).threadId
-    ? { threadId: (params.target as { threadId?: string }).threadId }
-    : {}),
-  messageIds: ["1700000000.000100"],
-  lastMessageId: "1700000000.000100",
-  recordedIn: "home-1",
-}));
+// ── Sent-post record dependency mocks ──
 
-mock.module("../runtime/channel-send.js", () => ({
-  isProactivelyAddressable: (channel: string) => ADDRESSABLE.has(channel),
-  sendChannelText: sendChannelTextMock,
-}));
+const getConversationMock = mock(
+  (_id: string) => null as { id: string; createdAt: number } | null,
+);
+
+const syncMessageToDiskMock = mock(
+  (_conversationId: string, _messageId: string, _createdAtMs: number) => {},
+);
+
+const resolveProactiveHomeConversationMock = mock(
+  async (_params: Record<string, unknown>) => ({
+    conversationId: "home-1",
+    createdNewConversation: false,
+  }),
+);
+
+const recordDeliveredChannelPostMock = mock(
+  async (_post: Record<string, unknown>) => ({ messageId: "row-1" }),
+);
 
 const mockOutlookCreateDraft = mock(
   async (_conn: OAuthConnection, _draft: Record<string, unknown>) => ({
@@ -118,155 +127,155 @@ mock.module("../messaging/providers/outlook/client.js", () => ({
     })),
 }));
 
-import { run } from "../config/bundled-skills/messaging/tools/messaging-send.js";
+mock.module("../persistence/conversation-crud.js", () => ({
+  setConversationProcessingStartedAt: () => {},
+  isConversationProcessing: () => false,
+  getConversation: getConversationMock,
+  reserveMessage: mock(async () => ({ id: "msg-reserve" })),
+}));
 
-const turn = {
-  workingDir: "/tmp",
-  conversationId: "conv-A",
-  assistantId: "ast-1",
-  trustClass: "guardian" as const,
-  executionChannel: "slack",
-  requesterChatId: "D0123456789",
-  sourceThreadId: "1700000000.000001",
-};
+mock.module("../persistence/conversation-disk-view.js", () => ({
+  syncMessageToDisk: syncMessageToDiskMock,
+}));
+
+mock.module("../notifications/conversation-pairing.js", () => ({
+  resolveProactiveHomeConversation: resolveProactiveHomeConversationMock,
+}));
+
+mock.module("../persistence/external-conversation-store.js", () => ({
+  normalizeExternalThreadId: (value: string | null | undefined) => {
+    const trimmed = value?.trim();
+    return trimmed ? trimmed : null;
+  },
+}));
+
+mock.module("../notifications/delivered-post-record.js", () => ({
+  recordDeliveredChannelPost: recordDeliveredChannelPostMock,
+}));
+
+import { run } from "../config/bundled-skills/messaging/tools/messaging-send.js";
 
 describe("messaging-send tool", () => {
   beforeEach(() => {
     provider = phoneProvider;
     connection = undefined;
     sendMessageMock.mockClear();
-    sendChannelTextMock.mockClear();
     mockOutlookCreateDraft.mockClear();
     mockOutlookCreateReplyDraft.mockClear();
     onResolveProvider = null;
+    getConversationMock.mockClear();
+    syncMessageToDiskMock.mockClear();
+    resolveProactiveHomeConversationMock.mockClear();
+    resolveProactiveHomeConversationMock.mockImplementation(async () => ({
+      conversationId: "home-1",
+      createdNewConversation: false,
+    }));
+    recordDeliveredChannelPostMock.mockClear();
+    recordDeliveredChannelPostMock.mockImplementation(async () => ({
+      messageId: "row-1",
+    }));
   });
 
-  describe("a channel with a transport", () => {
-    test("is sent through the transport-backed send with the turn's snapshot, never a provider", async () => {
-      const result = await run(
-        {
-          platform: "slack",
-          conversation_id: "C123",
-          thread_id: "1700000000.000009",
-          text: "hello",
-        },
-        turn,
-      );
-
-      expect(result.isError).toBe(false);
-      expect(sendMessageMock).not.toHaveBeenCalled();
-      expect(sendChannelTextMock).toHaveBeenCalledTimes(1);
-      expect(sendChannelTextMock.mock.calls[0]![0]).toEqual({
-        channel: "slack",
-        target: {
-          kind: "chat",
-          chatId: "C123",
-          threadId: "1700000000.000009",
-        },
-        text: "hello",
-        renderRichly: true,
-        assistantId: "ast-1",
-        sender: {
-          conversationId: "conv-A",
-          executionChannel: "slack",
-          requesterChatId: "D0123456789",
-          sourceThreadId: "1700000000.000001",
-        },
-      });
-      expect(result.content).toBe(
-        'Message sent (ID: 1700000000.000100, "thread_id": "1700000000.000009").',
-      );
-    });
-
-    test("names the channel outright without resolving a provider, so a channel with no provider is reachable", async () => {
-      provider = outlookProvider;
-      const result = await run(
-        { platform: "discord", conversation_id: "C1", text: "hi" },
-        turn,
-      );
-      expect(result.isError).toBe(false);
-      expect(sendChannelTextMock.mock.calls[0]![0]).toMatchObject({
-        channel: "discord",
-        target: { kind: "chat", chatId: "C1" },
-      });
-    });
-
-    test("an auto-detected provider that is a channel goes through the transport too", async () => {
-      provider = telegramProvider;
-      const result = await run(
-        { conversation_id: "123456789", text: "hi" },
-        turn,
-      );
-      expect(result.isError).toBe(false);
-      expect(sendChannelTextMock.mock.calls[0]![0]).toMatchObject({
-        channel: "telegram",
-        target: { kind: "chat", chatId: "123456789" },
-      });
-    });
-
-    test("rejects attachments before any send", async () => {
-      const result = await run(
-        {
-          platform: "slack",
-          conversation_id: "C123",
-          text: "with a file",
-          attachment_paths: ["/tmp/does-not-matter.pdf"],
-        },
-        turn,
-      );
-      expect(result.isError).toBe(true);
-      expect(result.content).toContain("Gmail and Outlook");
-      expect(sendChannelTextMock).not.toHaveBeenCalled();
-    });
+  test("passes assistantId from tool context to provider send options", async () => {
+    const result = await run(
+      {
+        platform: "phone",
+        conversation_id: "+15550004444",
+        text: "test message",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-1",
+        assistantId: "ast-alpha",
+        trustClass: "guardian" as const,
+      },
+    );
+
+    expect(result.isError).toBe(false);
+    expect(sendMessageMock).toHaveBeenCalledWith(
+      undefined,
+      "+15550004444",
+      "test message",
+      {
+        subject: undefined,
+        inReplyTo: undefined,
+        threadId: undefined,
+        attachments: undefined,
+        assistantId: "ast-alpha",
+      },
+    );
+  });
 
-    test("refuses an account rather than sending from the channel's default identity", async () => {
-      const result = await run(
-        {
-          platform: "slack",
-          account: "workspace-b@example.com",
-          conversation_id: "C123",
-          text: "hi",
-        },
-        turn,
-      );
-      expect(result.isError).toBe(true);
-      expect(result.content).toContain("account does not apply to slack");
-      expect(sendChannelTextMock).not.toHaveBeenCalled();
-    });
+  test("passes threadId to provider when replying on non-Gmail platform", async () => {
+    const result = await run(
+      {
+        platform: "phone",
+        conversation_id: "conv-1",
+        text: "reply text",
+        thread_id: "thread-abc",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-1",
+        assistantId: "ast-alpha",
+        trustClass: "guardian" as const,
+      },
+    );
+
+    expect(result.isError).toBe(false);
+    expect(sendMessageMock).toHaveBeenCalledWith(
+      undefined,
+      "conv-1",
+      "reply text",
+      {
+        subject: undefined,
+        inReplyTo: undefined,
+        threadId: "thread-abc",
+        attachments: undefined,
+        assistantId: "ast-alpha",
+      },
+    );
+  });
 
-    test("a turn cancelled during provider resolution sends nothing", async () => {
-      provider = telegramProvider;
-      const controller = new AbortController();
-      onResolveProvider = () => controller.abort();
-      await expect(
-        run(
-          { conversation_id: "123456789", text: "never sent" },
-          { ...turn, signal: controller.signal },
-        ),
-      ).rejects.toThrow();
-      expect(sendChannelTextMock).not.toHaveBeenCalled();
-    });
+  test("rejects attachments on platforms that can't carry them", async () => {
+    const result = await run(
+      {
+        platform: "phone",
+        conversation_id: "+12025550142",
+        text: "with a file",
+        attachment_paths: ["/tmp/does-not-matter.pdf"],
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-1",
+        assistantId: "ast-alpha",
+        trustClass: "guardian" as const,
+      },
+    );
 
-    test("reports the send's refusal as the tool's error", async () => {
-      sendChannelTextMock.mockImplementationOnce(async () => {
-        throw new Error('Channel "slack" cannot be addressed by person.');
-      });
-      const result = await run(
-        { platform: "slack", conversation_id: "C123", text: "hi" },
-        turn,
-      );
-      expect(result.isError).toBe(true);
-      expect(result.content).toContain("cannot be addressed");
-    });
+    expect(result.isError).toBe(true);
+    expect(result.content).toContain("Gmail and Outlook");
+    expect(sendMessageMock).not.toHaveBeenCalled();
   });
 
-  describe("a provider with a send of its own", () => {
-    test("passes assistantId from tool context to provider send options", async () => {
+  test("reads and forwards attachments onto an Outlook draft", async () => {
+    const dir = mkdtempSync(join(tmpdir(), "msg-send-att-"));
+    const filePath = join(dir, "report.pdf");
+    writeFileSync(filePath, "pdf-bytes");
+    provider = outlookProvider;
+    connection = {
+      id: "outlook-conn-1",
+      provider: "outlook",
+    } as OAuthConnection;
+
+    try {
       const result = await run(
         {
-          platform: "phone",
-          conversation_id: "+12125550100",
-          text: "test message",
+          platform: "outlook",
+          conversation_id: "user@example.com",
+          text: "see attached",
+          subject: "Docs",
+          attachment_paths: [filePath],
         },
         {
           workingDir: "/tmp",
@@ -277,227 +286,411 @@ describe("messaging-send tool", () => {
       );
 
       expect(result.isError).toBe(false);
-      expect(sendChannelTextMock).not.toHaveBeenCalled();
-      expect(sendMessageMock).toHaveBeenCalledWith(
-        undefined,
-        "+12125550100",
-        "test message",
-        {
-          subject: undefined,
-          inReplyTo: undefined,
-          threadId: undefined,
-          attachments: undefined,
-          assistantId: "ast-alpha",
-        },
+      expect(result.content).toContain("Outlook draft created");
+      expect(result.content).toContain("Draft ID: outlook-draft-1");
+      expect(sendMessageMock).not.toHaveBeenCalled();
+      expect(mockOutlookCreateDraft).toHaveBeenCalledTimes(1);
+      expect(mockOutlookCreateDraft).toHaveBeenCalledWith(
+        connection,
+        expect.objectContaining({
+          subject: "Docs",
+          body: { contentType: "text", content: "see attached" },
+          toRecipients: [{ emailAddress: { address: "user@example.com" } }],
+          attachments: [expect.objectContaining({ name: "report.pdf" })],
+        }),
       );
-    });
+    } finally {
+      rmSync(dir, { recursive: true, force: true });
+    }
+  });
 
-    test("passes threadId to provider when replying", async () => {
-      const result = await run(
-        {
-          platform: "phone",
-          conversation_id: "conv-1",
-          text: "reply text",
-          thread_id: "thread-abc",
-        },
-        {
-          workingDir: "/tmp",
-          conversationId: "conv-1",
-          assistantId: "ast-alpha",
-          trustClass: "guardian" as const,
-        },
-      );
+  test("records a threaded channel send in the thread's home, with the delivered thread on the row", async () => {
+    provider = slackProvider;
+    getConversationMock.mockImplementation(() => ({
+      id: "home-topic",
+      createdAt: 1700000000000,
+    }));
+    resolveProactiveHomeConversationMock.mockImplementation(async () => ({
+      conversationId: "home-topic",
+      createdNewConversation: false,
+    }));
+
+    const result = await run(
+      {
+        platform: "slack",
+        conversation_id: "C123",
+        thread_id: "1700000000.000009",
+        text: "hello from A",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+      },
+    );
+
+    expect(result.isError).toBe(false);
+    expect(
+      resolveProactiveHomeConversationMock.mock.calls[0]![0],
+    ).toMatchObject({
+      sourceChannel: "slack",
+      externalChatId: "C123",
+      threadId: "1700000000.000009",
+    });
+    expect(recordDeliveredChannelPostMock.mock.calls[0]![0]).toMatchObject({
+      conversationId: "home-topic",
+      externalChatId: "C123",
+      threadId: "1700000000.000009",
+      providerMessageId: "1700000000.000100",
+    });
+  });
 
-      expect(result.isError).toBe(false);
-      expect(sendMessageMock).toHaveBeenCalledWith(
-        undefined,
-        "conv-1",
-        "reply text",
-        {
-          subject: undefined,
-          inReplyTo: undefined,
-          threadId: "thread-abc",
-          attachments: undefined,
-          assistantId: "ast-alpha",
-        },
-      );
+  test("records a channel send in the chat's home conversation once the provider has it", async () => {
+    provider = telegramProvider;
+    getConversationMock.mockImplementation(() => ({
+      id: "home-1",
+      createdAt: 1700000000000,
+    }));
+
+    const result = await run(
+      {
+        platform: "telegram",
+        conversation_id: "123456789",
+        text: "hello from A",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+      },
+    );
+
+    expect(result.isError).toBe(false);
+    expect(resolveProactiveHomeConversationMock).toHaveBeenCalledTimes(1);
+    expect(
+      resolveProactiveHomeConversationMock.mock.calls[0]![0],
+    ).toMatchObject({
+      sourceChannel: "telegram",
+      externalChatId: "123456789",
+    });
+    expect(recordDeliveredChannelPostMock).toHaveBeenCalledWith({
+      conversationId: "home-1",
+      channel: "telegram",
+      externalChatId: "123456789",
+      text: "hello from A",
+      providerMessageId: "msg-1",
+      crossPostedFrom: "conv-A",
     });
+    expect(syncMessageToDiskMock).toHaveBeenCalledWith(
+      "home-1",
+      "row-1",
+      1700000000000,
+    );
+  });
 
-    test("rejects attachments on platforms that can't carry them", async () => {
-      const result = await run(
-        {
-          platform: "phone",
-          conversation_id: "+12025550142",
-          text: "with a file",
-          attachment_paths: ["/tmp/does-not-matter.pdf"],
-        },
-        {
-          workingDir: "/tmp",
-          conversationId: "conv-1",
-          assistantId: "ast-alpha",
-          trustClass: "guardian" as const,
-        },
-      );
+  test("records nothing when the home conversation is the sender", async () => {
+    provider = telegramProvider;
+    resolveProactiveHomeConversationMock.mockImplementation(async () => ({
+      conversationId: "conv-A",
+      createdNewConversation: false,
+    }));
+
+    await run(
+      {
+        platform: "telegram",
+        conversation_id: "123456789",
+        text: "hello",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+      },
+    );
 
-      expect(result.isError).toBe(true);
-      expect(result.content).toContain("Gmail and Outlook");
-      expect(sendMessageMock).not.toHaveBeenCalled();
-    });
+    expect(recordDeliveredChannelPostMock).not.toHaveBeenCalled();
+  });
 
-    test("a provider with neither a send nor a transport is refused", async () => {
-      provider = { ...makeProvider("fax", "Fax"), sendMessage: undefined };
-      const result = await run(
-        { platform: "fax", conversation_id: "1", text: "hi" },
-        turn,
-      );
-      expect(result.isError).toBe(true);
-      expect(result.content).toContain("Fax cannot send from here");
-      expect(sendChannelTextMock).not.toHaveBeenCalled();
-    });
+  test("records nothing when the post landed in the turn's own thread, even though the home is elsewhere", async () => {
+    // A Slack agent-style DM keys one conversation per thread. Its home
+    // resolves to the chat's notification conversation, so the home test
+    // alone would record this send as a cross-post away from the thread it
+    // was made in. The turn's own snapshot (channel, chat, thread) decides
+    // instead, against the thread the provider says it delivered into.
+    provider = slackProvider;
+
+    await run(
+      {
+        platform: "slack",
+        conversation_id: "D0123456789",
+        thread_id: "1700000000.000001",
+        text: "hello",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+        executionChannel: "slack",
+        requesterChatId: "D0123456789",
+        sourceThreadId: "1700000000.000001",
+      },
+    );
+
+    expect(resolveProactiveHomeConversationMock).not.toHaveBeenCalled();
+    expect(recordDeliveredChannelPostMock).not.toHaveBeenCalled();
   });
 
-  describe("Outlook drafts", () => {
-    test("reads and forwards attachments onto an Outlook draft", async () => {
-      const dir = mkdtempSync(join(tmpdir(), "msg-send-att-"));
-      const filePath = join(dir, "report.pdf");
-      writeFileSync(filePath, "pdf-bytes");
-      provider = outlookProvider;
-      connection = {
-        id: "outlook-conn-1",
-        provider: "outlook",
-      } as OAuthConnection;
+  test("records a send into the turn's chat but a different thread as a cross-post", async () => {
+    provider = slackProvider;
 
-      try {
-        const result = await run(
-          {
-            platform: "outlook",
-            conversation_id: "user@example.com",
-            text: "see attached",
-            subject: "Docs",
-            attachment_paths: [filePath],
-          },
-          {
-            workingDir: "/tmp",
-            conversationId: "conv-1",
-            assistantId: "ast-alpha",
-            trustClass: "guardian" as const,
-          },
-        );
-
-        expect(result.isError).toBe(false);
-        expect(result.content).toContain("Outlook draft created");
-        expect(result.content).toContain("Draft ID: outlook-draft-1");
-        expect(sendMessageMock).not.toHaveBeenCalled();
-        expect(mockOutlookCreateDraft).toHaveBeenCalledTimes(1);
-        expect(mockOutlookCreateDraft).toHaveBeenCalledWith(
-          connection,
-          expect.objectContaining({
-            subject: "Docs",
-            body: { contentType: "text", content: "see attached" },
-            toRecipients: [{ emailAddress: { address: "user@example.com" } }],
-            attachments: [expect.objectContaining({ name: "report.pdf" })],
-          }),
-        );
-      } finally {
-        rmSync(dir, { recursive: true, force: true });
-      }
-    });
+    await run(
+      {
+        platform: "slack",
+        conversation_id: "D0123456789",
+        thread_id: "1700000000.000002",
+        text: "hello",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+        executionChannel: "slack",
+        requesterChatId: "D0123456789",
+        sourceThreadId: "1700000000.000001",
+      },
+    );
+
+    expect(resolveProactiveHomeConversationMock).toHaveBeenCalledTimes(1);
+    expect(recordDeliveredChannelPostMock).toHaveBeenCalledTimes(1);
+  });
 
-    test("creates an Outlook draft without a To address when conversation_id is not an email", async () => {
-      provider = outlookProvider;
-      connection = {
-        id: "outlook-conn-1",
-        provider: "outlook",
-      } as OAuthConnection;
+  test("a thread-less delivery never matches a turn that arrived in a thread", async () => {
+    provider = slackProvider;
 
-      const result = await run(
-        {
-          platform: "outlook",
-          conversation_id: "drafts",
-          text: "Hey team, here is the update.",
-          subject: "Team update",
-        },
-        {
-          workingDir: "/tmp",
-          conversationId: "conv-1",
-          assistantId: "ast-alpha",
-          trustClass: "guardian" as const,
-        },
-      );
+    await run(
+      {
+        platform: "slack",
+        conversation_id: "D0123456789",
+        text: "hello",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+        executionChannel: "slack",
+        requesterChatId: "D0123456789",
+        sourceThreadId: "1700000000.000001",
+      },
+    );
 
-      expect(result.isError).toBe(false);
-      expect(result.content).toContain("Outlook draft created");
-      expect(result.content).toContain("No recipient set");
-      expect(result.content).toContain("Open it:");
-      expect(sendMessageMock).not.toHaveBeenCalled();
-      expect(mockOutlookCreateDraft).toHaveBeenCalledWith(
-        connection,
-        expect.objectContaining({
-          subject: "Team update",
-          body: {
-            contentType: "text",
-            content: "Hey team, here is the update.",
-          },
-        }),
-      );
-      const draftArg = mockOutlookCreateDraft.mock.calls[0][1];
-      expect(draftArg.toRecipients).toBeUndefined();
-    });
+    expect(recordDeliveredChannelPostMock).toHaveBeenCalledTimes(1);
+  });
 
-    test("creates an Outlook reply draft instead of sending when in_reply_to is set", async () => {
-      provider = outlookProvider;
-      connection = {
-        id: "outlook-conn-1",
-        provider: "outlook",
-      } as OAuthConnection;
+  test("decides by where the provider delivered, not by the thread requested", async () => {
+    // Telegram's provider ignores a requested thread and reports none, so a
+    // turn that arrived in a topic and asked for that topic still gets a
+    // post in the thread-less chat; that post is recorded, not suppressed.
+    provider = telegramProvider;
+
+    await run(
+      {
+        platform: "telegram",
+        conversation_id: "123456789",
+        thread_id: "777",
+        text: "hello",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+        executionChannel: "telegram",
+        requesterChatId: "123456789",
+        sourceThreadId: "777",
+      },
+    );
 
-      const result = await run(
-        {
-          platform: "outlook",
-          conversation_id: "user@example.com",
-          text: "Thanks, that works.",
-          in_reply_to: "AAMk-original",
-        },
-        {
-          workingDir: "/tmp",
-          conversationId: "conv-1",
-          assistantId: "ast-alpha",
-          trustClass: "guardian" as const,
-        },
-      );
+    expect(recordDeliveredChannelPostMock).toHaveBeenCalledTimes(1);
+  });
 
-      expect(result.isError).toBe(false);
-      expect(mockOutlookCreateReplyDraft).toHaveBeenCalledWith(
-        connection,
-        "AAMk-original",
-        "Thanks, that works.",
-      );
-      expect(sendMessageMock).not.toHaveBeenCalled();
-      expect(result.content).toContain("outlook-reply-draft-1");
-    });
+  test("a turn that arrived through no channel falls back to the home comparison", async () => {
+    provider = slackProvider;
+    resolveProactiveHomeConversationMock.mockImplementation(async () => ({
+      conversationId: "conv-A",
+      createdNewConversation: false,
+    }));
+
+    await run(
+      {
+        platform: "slack",
+        conversation_id: "D0123456789",
+        text: "hello",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+      },
+    );
 
-    test("errors when Outlook is not connected", async () => {
-      provider = outlookProvider;
-      connection = undefined;
+    expect(resolveProactiveHomeConversationMock).toHaveBeenCalledTimes(1);
+    expect(recordDeliveredChannelPostMock).not.toHaveBeenCalled();
+  });
 
-      const result = await run(
-        {
-          platform: "outlook",
-          conversation_id: "user@example.com",
-          text: "hello",
-        },
-        {
-          workingDir: "/tmp",
-          conversationId: "conv-1",
-          assistantId: "ast-alpha",
-          trustClass: "guardian" as const,
+  test("records nothing for a provider that is not a channel", async () => {
+    provider = outlookProvider;
+    connection = {
+      id: "outlook-conn-1",
+      provider: "outlook",
+    } as OAuthConnection;
+
+    await run(
+      {
+        platform: "outlook",
+        conversation_id: "user@example.com",
+        text: "hello",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+      },
+    );
+
+    expect(resolveProactiveHomeConversationMock).not.toHaveBeenCalled();
+    expect(recordDeliveredChannelPostMock).not.toHaveBeenCalled();
+  });
+
+  test("creates an Outlook draft without a To address when conversation_id is not an email", async () => {
+    provider = outlookProvider;
+    connection = {
+      id: "outlook-conn-1",
+      provider: "outlook",
+    } as OAuthConnection;
+
+    const result = await run(
+      {
+        platform: "outlook",
+        conversation_id: "drafts",
+        text: "Hey team, here is the update.",
+        subject: "Team update",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-1",
+        assistantId: "ast-alpha",
+        trustClass: "guardian" as const,
+      },
+    );
+
+    expect(result.isError).toBe(false);
+    expect(result.content).toContain("Outlook draft created");
+    expect(result.content).toContain("No recipient set");
+    expect(result.content).toContain("Open it:");
+    expect(sendMessageMock).not.toHaveBeenCalled();
+    expect(mockOutlookCreateDraft).toHaveBeenCalledWith(
+      connection,
+      expect.objectContaining({
+        subject: "Team update",
+        body: {
+          contentType: "text",
+          content: "Hey team, here is the update.",
         },
-      );
+      }),
+    );
+    const draftArg = mockOutlookCreateDraft.mock.calls[0][1];
+    expect(draftArg.toRecipients).toBeUndefined();
+  });
 
-      expect(result.isError).toBe(true);
-      expect(result.content).toContain("OAuth connection");
-      expect(mockOutlookCreateDraft).not.toHaveBeenCalled();
+  test("creates an Outlook reply draft instead of sending when in_reply_to is set", async () => {
+    provider = outlookProvider;
+    connection = {
+      id: "outlook-conn-1",
+      provider: "outlook",
+    } as OAuthConnection;
+
+    const result = await run(
+      {
+        platform: "outlook",
+        conversation_id: "user@example.com",
+        text: "Thanks, that works.",
+        in_reply_to: "AAMk-original",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-1",
+        assistantId: "ast-alpha",
+        trustClass: "guardian" as const,
+      },
+    );
+
+    expect(result.isError).toBe(false);
+    expect(mockOutlookCreateReplyDraft).toHaveBeenCalledWith(
+      connection,
+      "AAMk-original",
+      "Thanks, that works.",
+    );
+    expect(sendMessageMock).not.toHaveBeenCalled();
+    expect(result.content).toContain("outlook-reply-draft-1");
+  });
+
+  test("errors when Outlook is not connected", async () => {
+    provider = outlookProvider;
+    connection = undefined;
+
+    const result = await run(
+      {
+        platform: "outlook",
+        conversation_id: "user@example.com",
+        text: "hello",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-1",
+        assistantId: "ast-alpha",
+        trustClass: "guardian" as const,
+      },
+    );
+
+    expect(result.isError).toBe(true);
+    expect(result.content).toContain("OAuth connection");
+    expect(mockOutlookCreateDraft).not.toHaveBeenCalled();
+  });
+
+  test("a record failure does not fail the send", async () => {
+    provider = telegramProvider;
+    getConversationMock.mockImplementation(() => ({
+      id: "home-1",
+      createdAt: 1700000000000,
+    }));
+    recordDeliveredChannelPostMock.mockImplementation(async () => {
+      throw new Error("DB write failed");
     });
+
+    const result = await run(
+      {
+        platform: "telegram",
+        conversation_id: "123456789",
+        text: "hello",
+      },
+      {
+        workingDir: "/tmp",
+        conversationId: "conv-A",
+        assistantId: "ast-1",
+        trustClass: "guardian" as const,
+      },
+    );
+
+    expect(result.isError).toBe(false);
+    expect(result.content).toContain("Message sent");
   });
 
   /**