diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1afd7f318a7..8b9daf4e4b8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -243,6 +243,7 @@ Docs: https://docs.openclaw.ai
 - Auth/Codex CLI reuse: sync reused Codex CLI credentials into the supported `openai-codex:default` OAuth profile instead of reviving the deprecated `openai-codex:codex-cli` slot, so doctor cleanup no longer loops. (#45353) thanks @Gugu-sugar.
 - Deps/audit: bump the pinned `fast-xml-parser` override to the first patched release so `pnpm audit --prod --audit-level=high` no longer fails on the AWS Bedrock XML builder path. Thanks @vincentkoc.
 - Hooks/after_compaction: forward `sessionFile` for direct/manual compaction events and add `sessionFile` plus `sessionKey` to wired auto-compaction hook context so plugins receive the session metadata already declared in the hook types. (#40781) Thanks @jarimustonen.
+- Sessions/BlueBubbles/cron: persist outbound session routing and transcript mirroring for new targets, auto-create BlueBubbles chats before attachment sends, and only suppress isolated cron deliveries when the run started hours late instead of merely finishing late. (#50092)
 
 ### Breaking
 
diff --git a/extensions/bluebubbles/src/attachments.test.ts b/extensions/bluebubbles/src/attachments.test.ts
index 704b907eb8b..cb40ca810e3 100644
--- a/extensions/bluebubbles/src/attachments.test.ts
+++ b/extensions/bluebubbles/src/attachments.test.ts
@@ -484,4 +484,94 @@ describe("sendBlueBubblesAttachment", () => {
     expect(bodyText).not.toContain('name="selectedMessageGuid"');
     expect(bodyText).not.toContain('name="partIndex"');
   });
+
+  it("auto-creates a new chat when sending to a phone number with no existing chat", async () => {
+    // First call: resolveChatGuidForTarget queries chats, returns empty (no match)
+    mockFetch.mockResolvedValueOnce({
+      ok: true,
+      json: () => Promise.resolve({ data: [] }),
+    });
+    // Second call: createChatForHandle creates new chat
+    mockFetch.mockResolvedValueOnce({
+      ok: true,
+      text: () =>
+        Promise.resolve(
+          JSON.stringify({
+            data: { chatGuid: "iMessage;-;+15559876543", guid: "iMessage;-;+15559876543" },
+          }),
+        ),
+    });
+    // Third call: actual attachment send
+    mockFetch.mockResolvedValueOnce({
+      ok: true,
+      text: () => Promise.resolve(JSON.stringify({ data: { guid: "attach-msg-1" } })),
+    });
+
+    const result = await sendBlueBubblesAttachment({
+      to: "+15559876543",
+      buffer: new Uint8Array([1, 2, 3]),
+      filename: "photo.jpg",
+      contentType: "image/jpeg",
+      opts: { serverUrl: "http://localhost:1234", password: "test" },
+    });
+
+    expect(result.messageId).toBe("attach-msg-1");
+    // Verify chat creation was called
+    const createCallBody = JSON.parse(mockFetch.mock.calls[1][1].body);
+    expect(createCallBody.addresses).toEqual(["+15559876543"]);
+    // Verify attachment was sent to the newly created chat
+    const attachBody = mockFetch.mock.calls[2][1]?.body as Uint8Array;
+    const attachText = decodeBody(attachBody);
+    expect(attachText).toContain("iMessage;-;+15559876543");
+  });
+
+  it("retries chatGuid resolution after creating a chat with no returned guid", async () => {
+    mockFetch.mockResolvedValueOnce({
+      ok: true,
+      json: () => Promise.resolve({ data: [] }),
+    });
+    mockFetch.mockResolvedValueOnce({
+      ok: true,
+      text: () => Promise.resolve(JSON.stringify({ data: {} })),
+    });
+    mockFetch.mockResolvedValueOnce({
+      ok: true,
+      json: () => Promise.resolve({ data: [{ guid: "iMessage;-;+15557654321" }] }),
+    });
+    mockFetch.mockResolvedValueOnce({
+      ok: true,
+      text: () => Promise.resolve(JSON.stringify({ data: { guid: "attach-msg-2" } })),
+    });
+
+    const result = await sendBlueBubblesAttachment({
+      to: "+15557654321",
+      buffer: new Uint8Array([4, 5, 6]),
+      filename: "photo.jpg",
+      contentType: "image/jpeg",
+      opts: { serverUrl: "http://localhost:1234", password: "test" },
+    });
+
+    expect(result.messageId).toBe("attach-msg-2");
+    const createCallBody = JSON.parse(mockFetch.mock.calls[1][1].body);
+    expect(createCallBody.addresses).toEqual(["+15557654321"]);
+    const attachBody = mockFetch.mock.calls[3][1]?.body as Uint8Array;
+    const attachText = decodeBody(attachBody);
+    expect(attachText).toContain("iMessage;-;+15557654321");
+  });
+
+  it("still throws for non-handle targets when chatGuid is not found", async () => {
+    mockFetch.mockResolvedValueOnce({
+      ok: true,
+      json: () => Promise.resolve({ data: [] }),
+    });
+
+    await expect(
+      sendBlueBubblesAttachment({
+        to: "chat_id:999",
+        buffer: new Uint8Array([1, 2, 3]),
+        filename: "photo.jpg",
+        opts: { serverUrl: "http://localhost:1234", password: "test" },
+      }),
+    ).rejects.toThrow("chatGuid not found");
+  });
 });
diff --git a/extensions/bluebubbles/src/attachments.ts b/extensions/bluebubbles/src/attachments.ts
index 5aab9fd3b68..4c6fd09d6d5 100644
--- a/extensions/bluebubbles/src/attachments.ts
+++ b/extensions/bluebubbles/src/attachments.ts
@@ -10,7 +10,7 @@ import { resolveRequestUrl } from "./request-url.js";
 import type { OpenClawConfig } from "./runtime-api.js";
 import { getBlueBubblesRuntime, warnBlueBubbles } from "./runtime.js";
 import { extractBlueBubblesMessageId, resolveBlueBubblesSendTarget } from "./send-helpers.js";
-import { resolveChatGuidForTarget } from "./send.js";
+import { resolveChatGuidForTarget, createChatForHandle } from "./send.js";
 import {
   blueBubblesFetchWithTimeout,
   buildBlueBubblesApiUrl,
@@ -180,16 +180,37 @@ export async function sendBlueBubblesAttachment(params: {
   }
 
   const target = resolveBlueBubblesSendTarget(to);
-  const chatGuid = await resolveChatGuidForTarget({
+  let chatGuid = await resolveChatGuidForTarget({
     baseUrl,
     password,
     timeoutMs: opts.timeoutMs,
     target,
   });
   if (!chatGuid) {
-    throw new Error(
-      "BlueBubbles attachment send failed: chatGuid not found for target. Use a chat_guid target or ensure the chat exists.",
-    );
+    // For handle targets (phone numbers/emails), auto-create a new DM chat
+    if (target.kind === "handle") {
+      const created = await createChatForHandle({
+        baseUrl,
+        password,
+        address: target.address,
+        timeoutMs: opts.timeoutMs,
+      });
+      chatGuid = created.chatGuid;
+      // If we still don't have a chatGuid, try resolving again (chat was created server-side)
+      if (!chatGuid) {
+        chatGuid = await resolveChatGuidForTarget({
+          baseUrl,
+          password,
+          timeoutMs: opts.timeoutMs,
+          target,
+        });
+      }
+    }
+    if (!chatGuid) {
+      throw new Error(
+        "BlueBubbles attachment send failed: chatGuid not found for target. Use a chat_guid target or ensure the chat exists.",
+      );
+    }
   }
 
   const url = buildBlueBubblesApiUrl({
diff --git a/extensions/bluebubbles/src/send.test.ts b/extensions/bluebubbles/src/send.test.ts
index f820ebd9b8b..ecb8b1f68e0 100644
--- a/extensions/bluebubbles/src/send.test.ts
+++ b/extensions/bluebubbles/src/send.test.ts
@@ -3,7 +3,7 @@ import { beforeEach, describe, expect, it, vi } from "vitest";
 import "./test-mocks.js";
 import { getCachedBlueBubblesPrivateApiStatus } from "./probe.js";
 import { clearBlueBubblesRuntime, setBlueBubblesRuntime } from "./runtime.js";
-import { sendMessageBlueBubbles, resolveChatGuidForTarget } from "./send.js";
+import { sendMessageBlueBubbles, resolveChatGuidForTarget, createChatForHandle } from "./send.js";
 import {
   BLUE_BUBBLES_PRIVATE_API_STATUS,
   installBlueBubblesFetchTestHooks,
@@ -781,4 +781,109 @@ describe("send", () => {
       expect(body.tempGuid.length).toBeGreaterThan(0);
     });
   });
+
+  describe("createChatForHandle", () => {
+    it("creates a new chat and returns chatGuid from response", async () => {
+      mockFetch.mockResolvedValueOnce({
+        ok: true,
+        text: () =>
+          Promise.resolve(
+            JSON.stringify({
+              data: { guid: "iMessage;-;+15559876543", chatGuid: "iMessage;-;+15559876543" },
+            }),
+          ),
+      });
+
+      const result = await createChatForHandle({
+        baseUrl: "http://localhost:1234",
+        password: "test",
+        address: "+15559876543",
+        message: "Hello!",
+      });
+
+      expect(result.chatGuid).toBe("iMessage;-;+15559876543");
+      expect(result.messageId).toBeDefined();
+      const body = JSON.parse(mockFetch.mock.calls[0][1].body);
+      expect(body.addresses).toEqual(["+15559876543"]);
+      expect(body.message).toBe("Hello!");
+    });
+
+    it("creates a new chat without a message when message is omitted", async () => {
+      mockFetch.mockResolvedValueOnce({
+        ok: true,
+        text: () =>
+          Promise.resolve(
+            JSON.stringify({
+              data: { guid: "iMessage;-;+15559876543" },
+            }),
+          ),
+      });
+
+      const result = await createChatForHandle({
+        baseUrl: "http://localhost:1234",
+        password: "test",
+        address: "+15559876543",
+      });
+
+      expect(result.chatGuid).toBe("iMessage;-;+15559876543");
+      const body = JSON.parse(mockFetch.mock.calls[0][1].body);
+      expect(body.message).toBe("");
+    });
+
+    it.each([
+      ["data.chatGuid", { data: { chatGuid: "shape-chat-guid" } }, "shape-chat-guid"],
+      ["data.guid", { data: { guid: "shape-guid" } }, "shape-guid"],
+      [
+        "data.chats[0].guid",
+        { data: { chats: [{ guid: "shape-array-guid" }] } },
+        "shape-array-guid",
+      ],
+      ["data.chat.guid", { data: { chat: { guid: "shape-object-guid" } } }, "shape-object-guid"],
+    ])("extracts chatGuid from %s", async (_label, responseBody, expectedChatGuid) => {
+      mockFetch.mockResolvedValueOnce({
+        ok: true,
+        text: () => Promise.resolve(JSON.stringify(responseBody)),
+      });
+
+      const result = await createChatForHandle({
+        baseUrl: "http://localhost:1234",
+        password: "test",
+        address: "+15559876543",
+      });
+
+      expect(result.chatGuid).toBe(expectedChatGuid);
+    });
+
+    it("throws when Private API is not enabled", async () => {
+      mockFetch.mockResolvedValueOnce({
+        ok: false,
+        status: 403,
+        text: () => Promise.resolve("Private API not enabled"),
+      });
+
+      await expect(
+        createChatForHandle({
+          baseUrl: "http://localhost:1234",
+          password: "test",
+          address: "+15559876543",
+        }),
+      ).rejects.toThrow("Private API must be enabled");
+    });
+
+    it("returns null chatGuid when response has no chat data", async () => {
+      mockFetch.mockResolvedValueOnce({
+        ok: true,
+        text: () => Promise.resolve(JSON.stringify({ data: {} })),
+      });
+
+      const result = await createChatForHandle({
+        baseUrl: "http://localhost:1234",
+        password: "test",
+        address: "+15559876543",
+        message: "Hello",
+      });
+
+      expect(result.chatGuid).toBeNull();
+    });
+  });
 });
diff --git a/extensions/bluebubbles/src/send.ts b/extensions/bluebubbles/src/send.ts
index 8fe622d13ff..a59bf993a55 100644
--- a/extensions/bluebubbles/src/send.ts
+++ b/extensions/bluebubbles/src/send.ts
@@ -312,16 +312,20 @@ export async function resolveChatGuidForTarget(params: {
 }
 
 /**
- * Creates a new chat (DM) and optionally sends an initial message.
+ * Creates a new DM chat for the given address and returns the chat GUID.
  * Requires Private API to be enabled in BlueBubbles.
+ *
+ * If a `message` is provided it is sent as the initial message in the new chat;
+ * otherwise an empty-string message body is used (BlueBubbles still creates the
+ * chat but will not deliver a visible bubble).
  */
-async function createNewChatWithMessage(params: {
+export async function createChatForHandle(params: {
   baseUrl: string;
   password: string;
   address: string;
-  message: string;
+  message?: string;
   timeoutMs?: number;
-}): Promise<BlueBubblesSendResult> {
+}): Promise<{ chatGuid: string | null; messageId: string }> {
   const url = buildBlueBubblesApiUrl({
     baseUrl: params.baseUrl,
     path: "/api/v1/chat/new",
@@ -329,7 +333,7 @@ async function createNewChatWithMessage(params: {
   });
   const payload = {
     addresses: [params.address],
-    message: params.message,
+    message: params.message ?? "",
     tempGuid: `temp-${crypto.randomUUID()}`,
   };
   const res = await blueBubblesFetchWithTimeout(
@@ -343,7 +347,6 @@ async function createNewChatWithMessage(params: {
   );
   if (!res.ok) {
     const errorText = await res.text();
-    // Check for Private API not enabled error
     if (
       res.status === 400 ||
       res.status === 403 ||
@@ -355,7 +358,64 @@ async function createNewChatWithMessage(params: {
     }
     throw new Error(`BlueBubbles create chat failed (${res.status}): ${errorText || "unknown"}`);
   }
-  return parseBlueBubblesMessageResponse(res);
+  const body = await res.text();
+  let messageId = "ok";
+  let chatGuid: string | null = null;
+  if (body) {
+    try {
+      const parsed = JSON.parse(body) as Record<string, unknown>;
+      messageId = extractBlueBubblesMessageId(parsed);
+      // Extract chatGuid from the response data
+      const data = parsed.data as Record<string, unknown> | undefined;
+      if (data) {
+        chatGuid =
+          (typeof data.chatGuid === "string" && data.chatGuid) ||
+          (typeof data.guid === "string" && data.guid) ||
+          null;
+        // Also try nested chats array (some BB versions nest it)
+        if (!chatGuid) {
+          const chats = data.chats ?? data.chat;
+          if (Array.isArray(chats) && chats.length > 0) {
+            const first = chats[0] as Record<string, unknown> | undefined;
+            chatGuid =
+              (typeof first?.guid === "string" && first.guid) ||
+              (typeof first?.chatGuid === "string" && first.chatGuid) ||
+              null;
+          } else if (chats && typeof chats === "object" && !Array.isArray(chats)) {
+            const chatObj = chats as Record<string, unknown>;
+            chatGuid =
+              (typeof chatObj.guid === "string" && chatObj.guid) ||
+              (typeof chatObj.chatGuid === "string" && chatObj.chatGuid) ||
+              null;
+          }
+        }
+      }
+    } catch {
+      // ignore parse errors
+    }
+  }
+  return { chatGuid, messageId };
+}
+
+/**
+ * Creates a new chat (DM) and sends an initial message.
+ * Requires Private API to be enabled in BlueBubbles.
+ */
+async function createNewChatWithMessage(params: {
+  baseUrl: string;
+  password: string;
+  address: string;
+  message: string;
+  timeoutMs?: number;
+}): Promise<BlueBubblesSendResult> {
+  const result = await createChatForHandle({
+    baseUrl: params.baseUrl,
+    password: params.password,
+    address: params.address,
+    message: params.message,
+    timeoutMs: params.timeoutMs,
+  });
+  return { messageId: result.messageId };
 }
 
 export async function sendMessageBlueBubbles(
diff --git a/extensions/slack/src/channel.test.ts b/extensions/slack/src/channel.test.ts
index 73acfe3aeb7..691b6126557 100644
--- a/extensions/slack/src/channel.test.ts
+++ b/extensions/slack/src/channel.test.ts
@@ -308,6 +308,84 @@ describe("slackPlugin agentPrompt", () => {
   });
 });
 
+describe("slackPlugin outbound new targets", () => {
+  const cfg = {
+    channels: {
+      slack: {
+        botToken: "xoxb-test",
+        appToken: "xapp-test",
+      },
+    },
+  };
+
+  it("sends to a new user target via DM without erroring", async () => {
+    const sendSlack = vi.fn().mockResolvedValue({ messageId: "m-new-user", channelId: "D999" });
+    const sendText = slackPlugin.outbound?.sendText;
+    expect(sendText).toBeDefined();
+
+    const result = await sendText!({
+      cfg,
+      to: "user:U99NEW",
+      text: "hello new user",
+      accountId: "default",
+      deps: { sendSlack },
+    });
+
+    expect(sendSlack).toHaveBeenCalledWith(
+      "user:U99NEW",
+      "hello new user",
+      expect.objectContaining({ cfg }),
+    );
+    expect(result).toEqual({ channel: "slack", messageId: "m-new-user", channelId: "D999" });
+  });
+
+  it("sends to a new channel target without erroring", async () => {
+    const sendSlack = vi.fn().mockResolvedValue({ messageId: "m-new-chan", channelId: "C555" });
+    const sendText = slackPlugin.outbound?.sendText;
+    expect(sendText).toBeDefined();
+
+    const result = await sendText!({
+      cfg,
+      to: "channel:C555NEW",
+      text: "hello channel",
+      accountId: "default",
+      deps: { sendSlack },
+    });
+
+    expect(sendSlack).toHaveBeenCalledWith(
+      "channel:C555NEW",
+      "hello channel",
+      expect.objectContaining({ cfg }),
+    );
+    expect(result).toEqual({ channel: "slack", messageId: "m-new-chan", channelId: "C555" });
+  });
+
+  it("sends media to a new user target without erroring", async () => {
+    const sendSlack = vi.fn().mockResolvedValue({ messageId: "m-new-media", channelId: "D888" });
+    const sendMedia = slackPlugin.outbound?.sendMedia;
+    expect(sendMedia).toBeDefined();
+
+    const result = await sendMedia!({
+      cfg,
+      to: "user:U88NEW",
+      text: "here is a file",
+      mediaUrl: "https://example.com/file.png",
+      accountId: "default",
+      deps: { sendSlack },
+    });
+
+    expect(sendSlack).toHaveBeenCalledWith(
+      "user:U88NEW",
+      "here is a file",
+      expect.objectContaining({
+        cfg,
+        mediaUrl: "https://example.com/file.png",
+      }),
+    );
+    expect(result).toEqual({ channel: "slack", messageId: "m-new-media", channelId: "D888" });
+  });
+});
+
 describe("slackPlugin config", () => {
   it("treats HTTP mode accounts with bot token + signing secret as configured", async () => {
     const cfg: OpenClawConfig = {
diff --git a/src/config/sessions/sessions.test.ts b/src/config/sessions/sessions.test.ts
index eedf63913eb..c0afc4aad8e 100644
--- a/src/config/sessions/sessions.test.ts
+++ b/src/config/sessions/sessions.test.ts
@@ -425,6 +425,52 @@ describe("appendAssistantMessageToSessionTranscript", () => {
     expect(messageLine.message.content[0].text).toBe("Hello from delivery mirror!");
   });
 
+  it("finds session entry using normalized (lowercased) key", async () => {
+    const sessionId = "test-session-normalized";
+    // Store key is lowercase (as written by updateSessionStore/normalizeStoreSessionKey)
+    const storeKey = "agent:main:bluebubbles:direct:+15551234567";
+    const store = {
+      [storeKey]: {
+        sessionId,
+        chatType: "direct",
+        channel: "bluebubbles",
+      },
+    };
+    fs.writeFileSync(fixture.storePath(), JSON.stringify(store), "utf-8");
+
+    // Pass a mixed-case key — append should still find the entry via normalization
+    const result = await appendAssistantMessageToSessionTranscript({
+      sessionKey: "agent:main:BlueBubbles:direct:+15551234567",
+      text: "Hello normalized!",
+      storePath: fixture.storePath(),
+    });
+
+    expect(result.ok).toBe(true);
+  });
+
+  it("finds Slack session entry using normalized (lowercased) key", async () => {
+    const sessionId = "test-slack-session";
+    // Slack session keys include channel type and target ID; store key is lowercase
+    const storeKey = "agent:main:slack:direct:u12345abc";
+    const store = {
+      [storeKey]: {
+        sessionId,
+        chatType: "direct",
+        channel: "slack",
+      },
+    };
+    fs.writeFileSync(fixture.storePath(), JSON.stringify(store), "utf-8");
+
+    // Pass a mixed-case key (as resolveSlackSession might produce) — normalization should match
+    const result = await appendAssistantMessageToSessionTranscript({
+      sessionKey: "agent:main:slack:direct:U12345ABC",
+      text: "Hello Slack user!",
+      storePath: fixture.storePath(),
+    });
+
+    expect(result.ok).toBe(true);
+  });
+
   it("ignores malformed transcript lines when checking mirror idempotency", async () => {
     writeTranscriptStore();
 
diff --git a/src/config/sessions/transcript.ts b/src/config/sessions/transcript.ts
index aa1890de953..78bf1eb0cb9 100644
--- a/src/config/sessions/transcript.ts
+++ b/src/config/sessions/transcript.ts
@@ -10,7 +10,7 @@ import {
   resolveSessionTranscriptPath,
 } from "./paths.js";
 import { resolveAndPersistSessionFile } from "./session-file.js";
-import { loadSessionStore } from "./store.js";
+import { loadSessionStore, normalizeStoreSessionKey } from "./store.js";
 import type { SessionEntry } from "./types.js";
 
 function stripQuery(value: string): string {
@@ -154,7 +154,8 @@ export async function appendAssistantMessageToSessionTranscript(params: {
 
   const storePath = params.storePath ?? resolveDefaultSessionStorePath(params.agentId);
   const store = loadSessionStore(storePath, { skipCache: true });
-  const entry = store[sessionKey] as SessionEntry | undefined;
+  const normalizedKey = normalizeStoreSessionKey(sessionKey);
+  const entry = (store[normalizedKey] ?? store[sessionKey]) as SessionEntry | undefined;
   if (!entry?.sessionId) {
     return { ok: false, reason: `unknown sessionKey: ${sessionKey}` };
   }
diff --git a/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts b/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
index b245b4b9c94..4ed41f7de3a 100644
--- a/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
+++ b/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
@@ -143,6 +143,7 @@ describe("dispatchCronDelivery — double-announce guard", () => {
   });
 
   afterEach(() => {
+    vi.useRealTimers();
     vi.unstubAllEnvs();
   });
 
@@ -255,6 +256,59 @@ describe("dispatchCronDelivery — double-announce guard", () => {
     ).toBe(false);
   });
 
+  it("skips stale cron deliveries while still suppressing fallback main summary", async () => {
+    vi.useFakeTimers();
+    vi.setSystemTime(new Date("2026-03-18T17:00:00.000Z"));
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+
+    const params = makeBaseParams({ synthesizedText: "Yesterday's morning briefing." });
+    (params.job as { state?: { nextRunAtMs?: number } }).state = {
+      nextRunAtMs: Date.now() - (3 * 60 * 60_000 + 1),
+    };
+
+    const state = await dispatchCronDelivery(params);
+
+    expect(state.result).toEqual(
+      expect.objectContaining({
+        status: "ok",
+        delivered: false,
+        deliveryAttempted: true,
+      }),
+    );
+    expect(deliverOutboundPayloads).not.toHaveBeenCalled();
+    expect(
+      shouldEnqueueCronMainSummary({
+        summaryText: "Yesterday's morning briefing.",
+        deliveryRequested: true,
+        delivered: state.result?.delivered,
+        deliveryAttempted: state.result?.deliveryAttempted,
+        suppressMainSummary: false,
+        isCronSystemEvent: () => true,
+      }),
+    ).toBe(false);
+  });
+
+  it("still delivers when the run started on time but finished more than three hours later", async () => {
+    vi.useFakeTimers();
+    vi.setSystemTime(new Date("2026-03-18T17:00:00.000Z"));
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+    vi.mocked(deliverOutboundPayloads).mockResolvedValue([{ ok: true } as never]);
+
+    const params = makeBaseParams({ synthesizedText: "Long running report finished." });
+    params.runStartedAt = Date.now() - (3 * 60 * 60_000 + 1);
+    (params.job as { state?: { nextRunAtMs?: number } }).state = {
+      nextRunAtMs: params.runStartedAt,
+    };
+
+    const state = await dispatchCronDelivery(params);
+
+    expect(deliverOutboundPayloads).toHaveBeenCalledTimes(1);
+    expect(state.delivered).toBe(true);
+    expect(state.deliveryAttempted).toBe(true);
+  });
+
   it("text delivery fires exactly once (no double-deliver)", async () => {
     vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
     vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
diff --git a/src/cron/isolated-agent/delivery-dispatch.ts b/src/cron/isolated-agent/delivery-dispatch.ts
index 6ddddf20669..eda32740e4a 100644
--- a/src/cron/isolated-agent/delivery-dispatch.ts
+++ b/src/cron/isolated-agent/delivery-dispatch.ts
@@ -134,6 +134,8 @@ const PERMANENT_DIRECT_CRON_DELIVERY_ERROR_PATTERNS: readonly RegExp[] = [
   /outbound not configured for channel/i,
 ];
 
+const STALE_CRON_DELIVERY_MAX_START_DELAY_MS = 3 * 60 * 60_000;
+
 type CompletedDirectCronDelivery = {
   ts: number;
   results: OutboundDeliveryResult[];
@@ -174,6 +176,21 @@ function pruneCompletedDirectCronDeliveries(now: number) {
   }
 }
 
+function resolveCronDeliveryScheduledAtMs(params: { job: CronJob; runStartedAt: number }): number {
+  const scheduledAt = params.job.state?.nextRunAtMs;
+  return typeof scheduledAt === "number" && Number.isFinite(scheduledAt)
+    ? scheduledAt
+    : params.runStartedAt;
+}
+
+function resolveCronDeliveryStartDelayMs(params: { job: CronJob; runStartedAt: number }): number {
+  return params.runStartedAt - resolveCronDeliveryScheduledAtMs(params);
+}
+
+function isStaleCronDelivery(params: { job: CronJob; runStartedAt: number }): boolean {
+  return resolveCronDeliveryStartDelayMs(params) > STALE_CRON_DELIVERY_MAX_START_DELAY_MS;
+}
+
 function rememberCompletedDirectCronDelivery(
   idempotencyKey: string,
   results: readonly OutboundDeliveryResult[],
@@ -331,6 +348,35 @@ export async function dispatchCronDelivery(
           ...params.telemetry,
         });
       }
+      if (
+        params.deliveryRequested &&
+        isStaleCronDelivery({
+          job: params.job,
+          runStartedAt: params.runStartedAt,
+        })
+      ) {
+        deliveryAttempted = true;
+        const nowMs = Date.now();
+        const scheduledAtMs = resolveCronDeliveryScheduledAtMs({
+          job: params.job,
+          runStartedAt: params.runStartedAt,
+        });
+        const startDelayMs = resolveCronDeliveryStartDelayMs({
+          job: params.job,
+          runStartedAt: params.runStartedAt,
+        });
+        logWarn(
+          `[cron:${params.job.id}] skipping stale delivery scheduled at ${new Date(scheduledAtMs).toISOString()}, started ${Math.round(startDelayMs / 60_000)}m late, current age ${Math.round((nowMs - scheduledAtMs) / 60_000)}m`,
+        );
+        return params.withRunSession({
+          status: "ok",
+          summary,
+          outputText,
+          deliveryAttempted,
+          delivered: false,
+          ...params.telemetry,
+        });
+      }
       deliveryAttempted = true;
       const cachedResults = getCompletedDirectCronDelivery(deliveryIdempotencyKey);
       if (cachedResults) {
diff --git a/src/infra/outbound/outbound-session.ts b/src/infra/outbound/outbound-session.ts
index 6d990c8b0e6..8eefc3e5504 100644
--- a/src/infra/outbound/outbound-session.ts
+++ b/src/infra/outbound/outbound-session.ts
@@ -1,11 +1,31 @@
+import { parseDiscordTarget } from "../../../extensions/discord/src/targets.js";
+import {
+  parseIMessageTarget,
+  normalizeIMessageHandle,
+} from "../../../extensions/imessage/src/targets.js";
+import {
+  looksLikeUuid,
+  resolveSignalPeerId,
+  resolveSignalRecipient,
+  resolveSignalSender,
+} from "../../../extensions/signal/src/identity.js";
+import { resolveSlackAccount } from "../../../extensions/slack/src/accounts.js";
+import { createSlackWebClient } from "../../../extensions/slack/src/client.js";
+import { normalizeAllowListLower } from "../../../extensions/slack/src/monitor/allow-list.js";
+import { parseSlackTarget } from "../../../extensions/slack/src/targets.js";
+import { buildTelegramGroupPeerId } from "../../../extensions/telegram/src/bot/helpers.js";
+import { resolveTelegramTargetChatType } from "../../../extensions/telegram/src/inline-buttons.js";
+import { parseTelegramThreadId } from "../../../extensions/telegram/src/outbound-params.js";
+import { parseTelegramTarget } from "../../../extensions/telegram/src/targets.js";
 import type { MsgContext } from "../../auto-reply/templating.js";
 import type { ChatType } from "../../channels/chat-type.js";
 import { getChannelPlugin } from "../../channels/plugins/index.js";
 import type { ChannelId } from "../../channels/plugins/types.js";
 import type { OpenClawConfig } from "../../config/config.js";
 import { recordSessionMetaFromInbound, resolveStorePath } from "../../config/sessions.js";
-import type { RoutePeer } from "../../routing/resolve-route.js";
-import { buildOutboundBaseSessionKey } from "./base-session-key.js";
+import { buildAgentSessionKey, type RoutePeer } from "../../routing/resolve-route.js";
+import { resolveThreadSessionKeys } from "../../routing/session-key.js";
+import { isWhatsAppGroupJid, normalizeWhatsAppTarget } from "../../whatsapp/normalize.js";
 import type { ResolvedMessagingTarget } from "./target-resolver.js";
 
 export type OutboundSessionRoute = {
@@ -29,6 +49,23 @@ export type ResolveOutboundSessionRouteParams = {
   threadId?: string | number | null;
 };
 
+// Cache Slack channel type lookups to avoid repeated API calls.
+const SLACK_CHANNEL_TYPE_CACHE = new Map<string, "channel" | "group" | "dm" | "unknown">();
+
+function normalizeThreadId(value?: string | number | null): string | undefined {
+  if (value == null) {
+    return undefined;
+  }
+  if (typeof value === "number") {
+    if (!Number.isFinite(value)) {
+      return undefined;
+    }
+    return String(Math.trunc(value));
+  }
+  const trimmed = value.trim();
+  return trimmed ? trimmed : undefined;
+}
+
 function stripProviderPrefix(raw: string, channel: string): string {
   const trimmed = raw.trim();
   const lower = trimmed.toLowerCase();
@@ -74,7 +111,779 @@ function buildBaseSessionKey(params: {
   accountId?: string | null;
   peer: RoutePeer;
 }): string {
-  return buildOutboundBaseSessionKey(params);
+  return buildAgentSessionKey({
+    agentId: params.agentId,
+    channel: params.channel,
+    accountId: params.accountId,
+    peer: params.peer,
+    dmScope: params.cfg.session?.dmScope ?? "main",
+    identityLinks: params.cfg.session?.identityLinks,
+  });
+}
+
+// Best-effort mpim detection: allowlist/config, then Slack API (if token available).
+async function resolveSlackChannelType(params: {
+  cfg: OpenClawConfig;
+  accountId?: string | null;
+  channelId: string;
+}): Promise<"channel" | "group" | "dm" | "unknown"> {
+  const channelId = params.channelId.trim();
+  if (!channelId) {
+    return "unknown";
+  }
+  const cached = SLACK_CHANNEL_TYPE_CACHE.get(`${params.accountId ?? "default"}:${channelId}`);
+  if (cached) {
+    return cached;
+  }
+
+  const account = resolveSlackAccount({ cfg: params.cfg, accountId: params.accountId });
+  const groupChannels = normalizeAllowListLower(account.dm?.groupChannels);
+  const channelIdLower = channelId.toLowerCase();
+  if (
+    groupChannels.includes(channelIdLower) ||
+    groupChannels.includes(`slack:${channelIdLower}`) ||
+    groupChannels.includes(`channel:${channelIdLower}`) ||
+    groupChannels.includes(`group:${channelIdLower}`) ||
+    groupChannels.includes(`mpim:${channelIdLower}`)
+  ) {
+    SLACK_CHANNEL_TYPE_CACHE.set(`${account.accountId}:${channelId}`, "group");
+    return "group";
+  }
+
+  const channelKeys = Object.keys(account.channels ?? {});
+  if (
+    channelKeys.some((key) => {
+      const normalized = key.trim().toLowerCase();
+      return (
+        normalized === channelIdLower ||
+        normalized === `channel:${channelIdLower}` ||
+        normalized.replace(/^#/, "") === channelIdLower
+      );
+    })
+  ) {
+    SLACK_CHANNEL_TYPE_CACHE.set(`${account.accountId}:${channelId}`, "channel");
+    return "channel";
+  }
+
+  const token = account.botToken?.trim() || account.userToken || "";
+  if (!token) {
+    SLACK_CHANNEL_TYPE_CACHE.set(`${account.accountId}:${channelId}`, "unknown");
+    return "unknown";
+  }
+
+  try {
+    const client = createSlackWebClient(token);
+    const info = await client.conversations.info({ channel: channelId });
+    const channel = info.channel as { is_im?: boolean; is_mpim?: boolean } | undefined;
+    const type = channel?.is_im ? "dm" : channel?.is_mpim ? "group" : "channel";
+    SLACK_CHANNEL_TYPE_CACHE.set(`${account.accountId}:${channelId}`, type);
+    return type;
+  } catch {
+    SLACK_CHANNEL_TYPE_CACHE.set(`${account.accountId}:${channelId}`, "unknown");
+    return "unknown";
+  }
+}
+
+async function resolveSlackSession(
+  params: ResolveOutboundSessionRouteParams,
+): Promise<OutboundSessionRoute | null> {
+  const parsed = parseSlackTarget(params.target, { defaultKind: "channel" });
+  if (!parsed) {
+    return null;
+  }
+  const isDm = parsed.kind === "user";
+  let peerKind: ChatType = isDm ? "direct" : "channel";
+  if (!isDm && /^G/i.test(parsed.id)) {
+    // Slack mpim/group DMs share the G-prefix; detect to align session keys with inbound.
+    const channelType = await resolveSlackChannelType({
+      cfg: params.cfg,
+      accountId: params.accountId,
+      channelId: parsed.id,
+    });
+    if (channelType === "group") {
+      peerKind = "group";
+    }
+    if (channelType === "dm") {
+      peerKind = "direct";
+    }
+  }
+  const peer: RoutePeer = {
+    kind: peerKind,
+    id: parsed.id,
+  };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "slack",
+    accountId: params.accountId,
+    peer,
+  });
+  const threadId = normalizeThreadId(params.threadId ?? params.replyToId);
+  const threadKeys = resolveThreadSessionKeys({
+    baseSessionKey,
+    threadId,
+  });
+  return {
+    sessionKey: threadKeys.sessionKey,
+    baseSessionKey,
+    peer,
+    chatType: peerKind === "direct" ? "direct" : "channel",
+    from:
+      peerKind === "direct"
+        ? `slack:${parsed.id}`
+        : peerKind === "group"
+          ? `slack:group:${parsed.id}`
+          : `slack:channel:${parsed.id}`,
+    to: peerKind === "direct" ? `user:${parsed.id}` : `channel:${parsed.id}`,
+    threadId,
+  };
+}
+
+function resolveDiscordSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  const parsed = parseDiscordTarget(params.target, {
+    defaultKind: resolveDiscordOutboundTargetKindHint(params),
+  });
+  if (!parsed) {
+    return null;
+  }
+  const isDm = parsed.kind === "user";
+  const peer: RoutePeer = {
+    kind: isDm ? "direct" : "channel",
+    id: parsed.id,
+  };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "discord",
+    accountId: params.accountId,
+    peer,
+  });
+  const explicitThreadId = normalizeThreadId(params.threadId);
+  const threadCandidate = explicitThreadId ?? normalizeThreadId(params.replyToId);
+  // Discord threads use their own channel id; avoid adding a :thread suffix.
+  const threadKeys = resolveThreadSessionKeys({
+    baseSessionKey,
+    threadId: threadCandidate,
+    useSuffix: false,
+  });
+  return {
+    sessionKey: threadKeys.sessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isDm ? "direct" : "channel",
+    from: isDm ? `discord:${parsed.id}` : `discord:channel:${parsed.id}`,
+    to: isDm ? `user:${parsed.id}` : `channel:${parsed.id}`,
+    threadId: explicitThreadId ?? undefined,
+  };
+}
+
+function resolveDiscordOutboundTargetKindHint(
+  params: ResolveOutboundSessionRouteParams,
+): "user" | "channel" | undefined {
+  const resolvedKind = params.resolvedTarget?.kind;
+  if (resolvedKind === "user") {
+    return "user";
+  }
+  if (resolvedKind === "group" || resolvedKind === "channel") {
+    return "channel";
+  }
+
+  const target = params.target.trim();
+  if (/^channel:/i.test(target)) {
+    return "channel";
+  }
+  if (/^(user:|discord:|@|<@!?)/i.test(target)) {
+    return "user";
+  }
+  return undefined;
+}
+
+function resolveTelegramSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  const parsed = parseTelegramTarget(params.target);
+  const chatId = parsed.chatId.trim();
+  if (!chatId) {
+    return null;
+  }
+  const parsedThreadId = parsed.messageThreadId;
+  const fallbackThreadId = normalizeThreadId(params.threadId);
+  const resolvedThreadId = parsedThreadId ?? parseTelegramThreadId(fallbackThreadId);
+  // Telegram topics are encoded in the peer id (chatId:topic:<id>).
+  const chatType = resolveTelegramTargetChatType(params.target);
+  // If the target is a username and we lack a resolvedTarget, default to DM to avoid group keys.
+  const isGroup =
+    chatType === "group" ||
+    (chatType === "unknown" &&
+      params.resolvedTarget?.kind &&
+      params.resolvedTarget.kind !== "user");
+  // For groups: include thread ID in peerId. For DMs: use simple chatId (thread handled via suffix).
+  const peerId =
+    isGroup && resolvedThreadId ? buildTelegramGroupPeerId(chatId, resolvedThreadId) : chatId;
+  const peer: RoutePeer = {
+    kind: isGroup ? "group" : "direct",
+    id: peerId,
+  };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "telegram",
+    accountId: params.accountId,
+    peer,
+  });
+  // Use thread suffix for DM topics to match inbound session key format
+  const threadKeys =
+    resolvedThreadId && !isGroup
+      ? { sessionKey: `${baseSessionKey}:thread:${resolvedThreadId}` }
+      : null;
+  return {
+    sessionKey: threadKeys?.sessionKey ?? baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isGroup ? "group" : "direct",
+    from: isGroup
+      ? `telegram:group:${peerId}`
+      : resolvedThreadId
+        ? `telegram:${chatId}:topic:${resolvedThreadId}`
+        : `telegram:${chatId}`,
+    to: `telegram:${chatId}`,
+    threadId: resolvedThreadId,
+  };
+}
+
+function resolveWhatsAppSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  const normalized = normalizeWhatsAppTarget(params.target);
+  if (!normalized) {
+    return null;
+  }
+  const isGroup = isWhatsAppGroupJid(normalized);
+  const peer: RoutePeer = {
+    kind: isGroup ? "group" : "direct",
+    id: normalized,
+  };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "whatsapp",
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isGroup ? "group" : "direct",
+    from: normalized,
+    to: normalized,
+  };
+}
+
+function resolveSignalSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  const stripped = stripProviderPrefix(params.target, "signal");
+  const lowered = stripped.toLowerCase();
+  if (lowered.startsWith("group:")) {
+    const groupId = stripped.slice("group:".length).trim();
+    if (!groupId) {
+      return null;
+    }
+    const peer: RoutePeer = { kind: "group", id: groupId };
+    const baseSessionKey = buildBaseSessionKey({
+      cfg: params.cfg,
+      agentId: params.agentId,
+      channel: "signal",
+      accountId: params.accountId,
+      peer,
+    });
+    return {
+      sessionKey: baseSessionKey,
+      baseSessionKey,
+      peer,
+      chatType: "group",
+      from: `group:${groupId}`,
+      to: `group:${groupId}`,
+    };
+  }
+
+  let recipient = stripped.trim();
+  if (lowered.startsWith("username:")) {
+    recipient = stripped.slice("username:".length).trim();
+  } else if (lowered.startsWith("u:")) {
+    recipient = stripped.slice("u:".length).trim();
+  }
+  if (!recipient) {
+    return null;
+  }
+
+  const uuidCandidate = recipient.toLowerCase().startsWith("uuid:")
+    ? recipient.slice("uuid:".length)
+    : recipient;
+  const sender = resolveSignalSender({
+    sourceUuid: looksLikeUuid(uuidCandidate) ? uuidCandidate : null,
+    sourceNumber: looksLikeUuid(uuidCandidate) ? null : recipient,
+  });
+  const peerId = sender ? resolveSignalPeerId(sender) : recipient;
+  const displayRecipient = sender ? resolveSignalRecipient(sender) : recipient;
+  const peer: RoutePeer = { kind: "direct", id: peerId };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "signal",
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: "direct",
+    from: `signal:${displayRecipient}`,
+    to: `signal:${displayRecipient}`,
+  };
+}
+
+function resolveIMessageSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  const parsed = parseIMessageTarget(params.target);
+  if (parsed.kind === "handle") {
+    const handle = normalizeIMessageHandle(parsed.to);
+    if (!handle) {
+      return null;
+    }
+    const peer: RoutePeer = { kind: "direct", id: handle };
+    const baseSessionKey = buildBaseSessionKey({
+      cfg: params.cfg,
+      agentId: params.agentId,
+      channel: "imessage",
+      accountId: params.accountId,
+      peer,
+    });
+    return {
+      sessionKey: baseSessionKey,
+      baseSessionKey,
+      peer,
+      chatType: "direct",
+      from: `imessage:${handle}`,
+      to: `imessage:${handle}`,
+    };
+  }
+
+  const peerId =
+    parsed.kind === "chat_id"
+      ? String(parsed.chatId)
+      : parsed.kind === "chat_guid"
+        ? parsed.chatGuid
+        : parsed.chatIdentifier;
+  if (!peerId) {
+    return null;
+  }
+  const peer: RoutePeer = { kind: "group", id: peerId };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "imessage",
+    accountId: params.accountId,
+    peer,
+  });
+  const toPrefix =
+    parsed.kind === "chat_id"
+      ? "chat_id"
+      : parsed.kind === "chat_guid"
+        ? "chat_guid"
+        : "chat_identifier";
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: "group",
+    from: `imessage:group:${peerId}`,
+    to: `${toPrefix}:${peerId}`,
+  };
+}
+
+function resolveMatrixSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  const stripped = stripProviderPrefix(params.target, "matrix");
+  const isUser =
+    params.resolvedTarget?.kind === "user" || stripped.startsWith("@") || /^user:/i.test(stripped);
+  const rawId = stripKindPrefix(stripped);
+  if (!rawId) {
+    return null;
+  }
+  const peer: RoutePeer = { kind: isUser ? "direct" : "channel", id: rawId };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "matrix",
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isUser ? "direct" : "channel",
+    from: isUser ? `matrix:${rawId}` : `matrix:channel:${rawId}`,
+    to: `room:${rawId}`,
+  };
+}
+
+function resolveMSTeamsSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  let trimmed = params.target.trim();
+  if (!trimmed) {
+    return null;
+  }
+  trimmed = trimmed.replace(/^(msteams|teams):/i, "").trim();
+
+  const lower = trimmed.toLowerCase();
+  const isUser = lower.startsWith("user:");
+  const rawId = stripKindPrefix(trimmed);
+  if (!rawId) {
+    return null;
+  }
+  const conversationId = rawId.split(";")[0] ?? rawId;
+  const isChannel = !isUser && /@thread\.tacv2/i.test(conversationId);
+  const peer: RoutePeer = {
+    kind: isUser ? "direct" : isChannel ? "channel" : "group",
+    id: conversationId,
+  };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "msteams",
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isUser ? "direct" : isChannel ? "channel" : "group",
+    from: isUser
+      ? `msteams:${conversationId}`
+      : isChannel
+        ? `msteams:channel:${conversationId}`
+        : `msteams:group:${conversationId}`,
+    to: isUser ? `user:${conversationId}` : `conversation:${conversationId}`,
+  };
+}
+
+function resolveMattermostSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  let trimmed = params.target.trim();
+  if (!trimmed) {
+    return null;
+  }
+  trimmed = trimmed.replace(/^mattermost:/i, "").trim();
+  const lower = trimmed.toLowerCase();
+  const resolvedKind = params.resolvedTarget?.kind;
+  const isUser =
+    resolvedKind === "user" ||
+    (resolvedKind !== "channel" &&
+      resolvedKind !== "group" &&
+      (lower.startsWith("user:") || trimmed.startsWith("@")));
+  if (trimmed.startsWith("@")) {
+    trimmed = trimmed.slice(1).trim();
+  }
+  const rawId = stripKindPrefix(trimmed);
+  if (!rawId) {
+    return null;
+  }
+  const peer: RoutePeer = { kind: isUser ? "direct" : "channel", id: rawId };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "mattermost",
+    accountId: params.accountId,
+    peer,
+  });
+  const threadId = normalizeThreadId(params.replyToId ?? params.threadId);
+  const threadKeys = resolveThreadSessionKeys({
+    baseSessionKey,
+    threadId,
+  });
+  return {
+    sessionKey: threadKeys.sessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isUser ? "direct" : "channel",
+    from: isUser ? `mattermost:${rawId}` : `mattermost:channel:${rawId}`,
+    to: isUser ? `user:${rawId}` : `channel:${rawId}`,
+    threadId,
+  };
+}
+
+function resolveBlueBubblesSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  const stripped = stripProviderPrefix(params.target, "bluebubbles");
+  const lower = stripped.toLowerCase();
+  const isGroup =
+    lower.startsWith("chat_id:") ||
+    lower.startsWith("chat_guid:") ||
+    lower.startsWith("chat_identifier:") ||
+    lower.startsWith("group:");
+  const rawPeerId = isGroup
+    ? stripKindPrefix(stripped)
+    : stripped.replace(/^(imessage|sms|auto):/i, "");
+  // BlueBubbles inbound group ids omit chat_* prefixes; strip them to align sessions.
+  const peerId = isGroup
+    ? rawPeerId.replace(/^(chat_id|chat_guid|chat_identifier):/i, "")
+    : rawPeerId;
+  if (!peerId) {
+    return null;
+  }
+  const peer: RoutePeer = {
+    kind: isGroup ? "group" : "direct",
+    id: peerId,
+  };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "bluebubbles",
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isGroup ? "group" : "direct",
+    from: isGroup ? `group:${peerId}` : `bluebubbles:${peerId}`,
+    to: `bluebubbles:${stripped}`,
+  };
+}
+
+function resolveNextcloudTalkSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  let trimmed = params.target.trim();
+  if (!trimmed) {
+    return null;
+  }
+  trimmed = trimmed.replace(/^(nextcloud-talk|nc-talk|nc):/i, "").trim();
+  trimmed = trimmed.replace(/^room:/i, "").trim();
+  if (!trimmed) {
+    return null;
+  }
+  const peer: RoutePeer = { kind: "group", id: trimmed };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "nextcloud-talk",
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: "group",
+    from: `nextcloud-talk:room:${trimmed}`,
+    to: `nextcloud-talk:${trimmed}`,
+  };
+}
+
+function resolveZaloSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  return resolveZaloLikeSession(params, "zalo", /^(zl):/i);
+}
+
+function resolveZaloLikeSession(
+  params: ResolveOutboundSessionRouteParams,
+  channel: "zalo" | "zalouser",
+  aliasPrefix: RegExp,
+): OutboundSessionRoute | null {
+  const trimmed = stripProviderPrefix(params.target, channel).replace(aliasPrefix, "").trim();
+  if (!trimmed) {
+    return null;
+  }
+  const isGroup = trimmed.toLowerCase().startsWith("group:");
+  const peerId = stripKindPrefix(trimmed);
+  const peer: RoutePeer = { kind: isGroup ? "group" : "direct", id: peerId };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel,
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isGroup ? "group" : "direct",
+    from: isGroup ? `${channel}:group:${peerId}` : `${channel}:${peerId}`,
+    to: `${channel}:${peerId}`,
+  };
+}
+
+function resolveZalouserSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  // Keep DM vs group aligned with inbound sessions for Zalo Personal.
+  return resolveZaloLikeSession(params, "zalouser", /^(zlu):/i);
+}
+
+function resolveNostrSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  const trimmed = stripProviderPrefix(params.target, "nostr").trim();
+  if (!trimmed) {
+    return null;
+  }
+  const peer: RoutePeer = { kind: "direct", id: trimmed };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "nostr",
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: "direct",
+    from: `nostr:${trimmed}`,
+    to: `nostr:${trimmed}`,
+  };
+}
+
+function normalizeTlonShip(raw: string): string {
+  const trimmed = raw.trim();
+  if (!trimmed) {
+    return trimmed;
+  }
+  return trimmed.startsWith("~") ? trimmed : `~${trimmed}`;
+}
+
+function resolveTlonSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  let trimmed = stripProviderPrefix(params.target, "tlon");
+  trimmed = trimmed.trim();
+  if (!trimmed) {
+    return null;
+  }
+  const lower = trimmed.toLowerCase();
+  let isGroup =
+    lower.startsWith("group:") || lower.startsWith("room:") || lower.startsWith("chat/");
+  let peerId = trimmed;
+  if (lower.startsWith("group:") || lower.startsWith("room:")) {
+    peerId = trimmed.replace(/^(group|room):/i, "").trim();
+    if (!peerId.startsWith("chat/")) {
+      const parts = peerId.split("/").filter(Boolean);
+      if (parts.length === 2) {
+        peerId = `chat/${normalizeTlonShip(parts[0])}/${parts[1]}`;
+      }
+    }
+    isGroup = true;
+  } else if (lower.startsWith("dm:")) {
+    peerId = normalizeTlonShip(trimmed.slice("dm:".length));
+    isGroup = false;
+  } else if (lower.startsWith("chat/")) {
+    peerId = trimmed;
+    isGroup = true;
+  } else if (trimmed.includes("/")) {
+    const parts = trimmed.split("/").filter(Boolean);
+    if (parts.length === 2) {
+      peerId = `chat/${normalizeTlonShip(parts[0])}/${parts[1]}`;
+      isGroup = true;
+    }
+  } else {
+    peerId = normalizeTlonShip(trimmed);
+  }
+
+  const peer: RoutePeer = { kind: isGroup ? "group" : "direct", id: peerId };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "tlon",
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isGroup ? "group" : "direct",
+    from: isGroup ? `tlon:group:${peerId}` : `tlon:${peerId}`,
+    to: `tlon:${peerId}`,
+  };
+}
+
+/**
+ * Feishu ID formats:
+ * - oc_xxx: chat_id (can be group or DM, use chat_mode to distinguish or explicit dm:/group: prefix)
+ * - ou_xxx: user open_id (DM)
+ * - on_xxx: user union_id (DM)
+ * - cli_xxx: app_id (not a valid send target)
+ */
+function resolveFeishuSession(
+  params: ResolveOutboundSessionRouteParams,
+): OutboundSessionRoute | null {
+  let trimmed = stripProviderPrefix(params.target, "feishu");
+  trimmed = stripProviderPrefix(trimmed, "lark").trim();
+  if (!trimmed) {
+    return null;
+  }
+
+  const lower = trimmed.toLowerCase();
+  let isGroup = false;
+  let typeExplicit = false;
+
+  if (lower.startsWith("group:") || lower.startsWith("chat:")) {
+    trimmed = trimmed.replace(/^(group|chat):/i, "").trim();
+    isGroup = true;
+    typeExplicit = true;
+  } else if (lower.startsWith("user:") || lower.startsWith("dm:")) {
+    trimmed = trimmed.replace(/^(user|dm):/i, "").trim();
+    isGroup = false;
+    typeExplicit = true;
+  }
+
+  const idLower = trimmed.toLowerCase();
+  // Only infer type from ID prefix if not explicitly specified
+  // Note: oc_ is a chat_id and can be either group or DM (must check chat_mode from API)
+  // Only ou_/on_ can be reliably identified as user IDs (always DM)
+  if (!typeExplicit) {
+    if (idLower.startsWith("ou_") || idLower.startsWith("on_")) {
+      isGroup = false;
+    }
+    // oc_ requires explicit prefix: dm:oc_xxx or group:oc_xxx
+  }
+
+  const peer: RoutePeer = {
+    kind: isGroup ? "group" : "direct",
+    id: trimmed,
+  };
+  const baseSessionKey = buildBaseSessionKey({
+    cfg: params.cfg,
+    agentId: params.agentId,
+    channel: "feishu",
+    accountId: params.accountId,
+    peer,
+  });
+  return {
+    sessionKey: baseSessionKey,
+    baseSessionKey,
+    peer,
+    chatType: isGroup ? "group" : "direct",
+    from: isGroup ? `feishu:group:${trimmed}` : `feishu:${trimmed}`,
+    to: trimmed,
+  };
 }
 
 function resolveFallbackSession(
@@ -115,6 +924,29 @@ function resolveFallbackSession(
   };
 }
 
+type OutboundSessionResolver = (
+  params: ResolveOutboundSessionRouteParams,
+) => OutboundSessionRoute | null | Promise<OutboundSessionRoute | null>;
+
+const OUTBOUND_SESSION_RESOLVERS: Partial<Record<ChannelId, OutboundSessionResolver>> = {
+  slack: resolveSlackSession,
+  discord: resolveDiscordSession,
+  telegram: resolveTelegramSession,
+  whatsapp: resolveWhatsAppSession,
+  signal: resolveSignalSession,
+  imessage: resolveIMessageSession,
+  matrix: resolveMatrixSession,
+  msteams: resolveMSTeamsSession,
+  mattermost: resolveMattermostSession,
+  bluebubbles: resolveBlueBubblesSession,
+  "nextcloud-talk": resolveNextcloudTalkSession,
+  zalo: resolveZaloSession,
+  zalouser: resolveZalouserSession,
+  nostr: resolveNostrSession,
+  tlon: resolveTlonSession,
+  feishu: resolveFeishuSession,
+};
+
 export async function resolveOutboundSessionRoute(
   params: ResolveOutboundSessionRouteParams,
 ): Promise<OutboundSessionRoute | null> {
@@ -123,21 +955,11 @@ export async function resolveOutboundSessionRoute(
     return null;
   }
   const nextParams = { ...params, target };
-  const pluginRoute = await getChannelPlugin(
-    params.channel,
-  )?.messaging?.resolveOutboundSessionRoute?.({
-    cfg: nextParams.cfg,
-    agentId: nextParams.agentId,
-    accountId: nextParams.accountId,
-    target,
-    resolvedTarget: nextParams.resolvedTarget,
-    replyToId: nextParams.replyToId,
-    threadId: nextParams.threadId,
-  });
-  if (pluginRoute) {
-    return pluginRoute;
+  const resolver = OUTBOUND_SESSION_RESOLVERS[params.channel];
+  if (!resolver) {
+    return resolveFallbackSession(nextParams);
   }
-  return resolveFallbackSession(nextParams);
+  return await resolver(nextParams);
 }
 
 export async function ensureOutboundSessionEntry(params: {
diff --git a/src/infra/outbound/outbound.test.ts b/src/infra/outbound/outbound.test.ts
index 7dcdab184ed..f90fc7f221e 100644
--- a/src/infra/outbound/outbound.test.ts
+++ b/src/infra/outbound/outbound.test.ts
@@ -1196,6 +1196,30 @@ describe("resolveOutboundSessionRoute", () => {
           chatType: "direct",
         },
       },
+      {
+        name: "Slack user DM target",
+        cfg: perChannelPeerCfg,
+        channel: "slack",
+        target: "user:U12345ABC",
+        expected: {
+          sessionKey: "agent:main:slack:direct:u12345abc",
+          from: "slack:U12345ABC",
+          to: "user:U12345ABC",
+          chatType: "direct",
+        },
+      },
+      {
+        name: "Slack channel target without thread",
+        cfg: baseConfig,
+        channel: "slack",
+        target: "channel:C999XYZ",
+        expected: {
+          sessionKey: "agent:main:slack:channel:c999xyz",
+          from: "slack:channel:C999XYZ",
+          to: "channel:C999XYZ",
+          chatType: "channel",
+        },
+      },
     ];
 
     for (const testCase of cases) {