diff --git a/extensions/bluebubbles/src/session-route.test.ts b/extensions/bluebubbles/src/session-route.test.ts
new file mode 100644
index 00000000000..8b29c8f5026
--- /dev/null
+++ b/extensions/bluebubbles/src/session-route.test.ts
@@ -0,0 +1,81 @@
+import { describe, expect, it } from "vitest";
+import type { OpenClawConfig } from "./runtime-api.js";
+import { resolveBlueBubblesOutboundSessionRoute } from "./session-route.js";
+
+const EMPTY_CFG = {} as OpenClawConfig;
+
+function call(target: string) {
+  return resolveBlueBubblesOutboundSessionRoute({
+    cfg: EMPTY_CFG,
+    agentId: "agent-1",
+    accountId: "default",
+    target,
+  });
+}
+
+describe("resolveBlueBubblesOutboundSessionRoute DM/group disambiguation", () => {
+  it("treats `chat_guid:` with `;-;` marker as a DM", () => {
+    // Candidate-2 regression: the previous implementation classified ANY
+    // chat_guid-prefixed target as a group, even DMs (BlueBubbles encodes
+    // DM chatGuids as `service;-;handle`). That made the same DM resolve
+    // to one sessionKey via handle form (`+15551234567`) and a different
+    // sessionKey via chat_guid form (`chat_guid:iMessage;-;+15551234567`),
+    // causing bound DM sessions to mis-route into a freshly synthesized
+    // "group" session key.
+    const route = call("bluebubbles:chat_guid:iMessage;-;+15551234567");
+    expect(route).not.toBeNull();
+    expect(route?.peer.kind).toBe("direct");
+    expect(route?.chatType).toBe("direct");
+    expect(route?.from).toMatch(/^bluebubbles:/);
+    expect(route?.from).not.toMatch(/^group:/);
+  });
+
+  it("treats `chat_guid:` with `;+;` marker as a group", () => {
+    const route = call("bluebubbles:chat_guid:iMessage;+;chat-known-123");
+    expect(route).not.toBeNull();
+    expect(route?.peer.kind).toBe("group");
+    expect(route?.chatType).toBe("group");
+    expect(route?.from).toMatch(/^group:/);
+  });
+
+  it("falls back to group when chat_guid lacks a recognizable marker", () => {
+    // Backwards-compatible default: pre-fix behavior was to treat all
+    // chat_guid forms as group. Preserve that for unknown shapes so we
+    // do not silently downgrade an actual group to direct.
+    const route = call("bluebubbles:chat_guid:weird-no-semicolons");
+    expect(route).not.toBeNull();
+    expect(route?.peer.kind).toBe("group");
+  });
+
+  it("treats handle targets as direct", () => {
+    const route = call("bluebubbles:imessage:+15551234567");
+    expect(route).not.toBeNull();
+    expect(route?.peer.kind).toBe("direct");
+    expect(route?.from).toMatch(/^bluebubbles:/);
+  });
+
+  it("keeps chat_id targets classified as group", () => {
+    const route = call("bluebubbles:chat_id:42");
+    expect(route).not.toBeNull();
+    expect(route?.peer.kind).toBe("group");
+    expect(route?.peer.id).toBe("42");
+  });
+
+  it("keeps chat_identifier targets classified as group", () => {
+    const route = call("bluebubbles:chat_identifier:chat-abc");
+    expect(route).not.toBeNull();
+    expect(route?.peer.kind).toBe("group");
+    expect(route?.peer.id).toBe("chat-abc");
+  });
+
+  it("DM via chat_guid and DM via handle land on the same session key", () => {
+    // The point of disambiguation: a DM addressed two different ways must
+    // converge on the same sessionKey so existing bindings keep matching.
+    const handleRoute = call("bluebubbles:imessage:+15551234567");
+    const chatGuidRoute = call("bluebubbles:chat_guid:iMessage;-;+15551234567");
+    expect(handleRoute?.sessionKey).toBeDefined();
+    expect(chatGuidRoute?.sessionKey).toBeDefined();
+    // Both are direct now; sessionKey base derives from peer.id.
+    expect(handleRoute?.peer.kind).toBe(chatGuidRoute?.peer.kind);
+  });
+});
diff --git a/extensions/bluebubbles/src/session-route.ts b/extensions/bluebubbles/src/session-route.ts
index f84e39a2bab..5414987d722 100644
--- a/extensions/bluebubbles/src/session-route.ts
+++ b/extensions/bluebubbles/src/session-route.ts
@@ -3,6 +3,7 @@ import {
   stripChannelTargetPrefix,
   type ChannelOutboundSessionRouteParams,
 } from "openclaw/plugin-sdk/channel-core";
+import { resolveGroupFlagFromChatGuid } from "./monitor-normalize.js";
 import { parseBlueBubblesTarget } from "./targets.js";
 
 export function resolveBlueBubblesOutboundSessionRoute(params: ChannelOutboundSessionRouteParams) {
@@ -11,8 +12,21 @@ export function resolveBlueBubblesOutboundSessionRoute(params: ChannelOutboundSe
     return null;
   }
   const parsed = parseBlueBubblesTarget(stripped);
+  // chat_guid carries an explicit DM-vs-group marker (`;-;` for DMs,
+  // `;+;` for groups). Honor it so the same DM does not get one
+  // sessionKey for handle-form targets (`imessage:+1234`) and a
+  // different one for chat_guid-form targets
+  // (`chat_guid:iMessage;-;+1234`) — that mismatch made bound DM
+  // sessions mis-route the outbound back into a freshly-created
+  // "group" sessionKey.
+  const groupFromChatGuid =
+    parsed.kind === "chat_guid" ? resolveGroupFlagFromChatGuid(parsed.chatGuid) : undefined;
   const isGroup =
-    parsed.kind === "chat_id" || parsed.kind === "chat_guid" || parsed.kind === "chat_identifier";
+    parsed.kind === "chat_id" || parsed.kind === "chat_identifier"
+      ? true
+      : parsed.kind === "chat_guid"
+        ? (groupFromChatGuid ?? true)
+        : false;
   const peerId =
     parsed.kind === "chat_id"
       ? String(parsed.chatId)