diff --git a/extensions/bluebubbles/src/attachments.ts b/extensions/bluebubbles/src/attachments.ts
index 106a53111..1729f27fe 100644
--- a/extensions/bluebubbles/src/attachments.ts
+++ b/extensions/bluebubbles/src/attachments.ts
@@ -170,6 +170,8 @@ export async function sendBlueBubblesAttachment(params: {
   // Add optional caption
   if (caption) {
     addField("message", caption);
+    addField("text", caption);
+    addField("caption", caption);
   }
 
   // Close the multipart body
diff --git a/extensions/bluebubbles/src/channel.ts b/extensions/bluebubbles/src/channel.ts
index 5b09793cd..fce596465 100644
--- a/extensions/bluebubbles/src/channel.ts
+++ b/extensions/bluebubbles/src/channel.ts
@@ -229,7 +229,7 @@ export const bluebubblesPlugin: ChannelPlugin<ResolvedBlueBubblesAccount> = {
       return { channel: "bluebubbles", ...result };
     },
     sendMedia: async (ctx) => {
-      const { cfg, to, text, mediaUrl, accountId } = ctx;
+      const { cfg, to, text, mediaUrl, accountId, replyToId } = ctx;
       const { mediaPath, mediaBuffer, contentType, filename, caption } = ctx as {
         mediaPath?: string;
         mediaBuffer?: Uint8Array;
@@ -247,6 +247,7 @@ export const bluebubblesPlugin: ChannelPlugin<ResolvedBlueBubblesAccount> = {
         contentType,
         filename,
         caption: resolvedCaption ?? undefined,
+        replyToId: replyToId ?? null,
         accountId: accountId ?? undefined,
       });
 
diff --git a/extensions/bluebubbles/src/media-send.ts b/extensions/bluebubbles/src/media-send.ts
index 025590237..c86ab21c7 100644
--- a/extensions/bluebubbles/src/media-send.ts
+++ b/extensions/bluebubbles/src/media-send.ts
@@ -4,6 +4,7 @@ import { fileURLToPath } from "node:url";
 import type { ClawdbotConfig } from "clawdbot/plugin-sdk";
 
 import { sendBlueBubblesAttachment } from "./attachments.js";
+import { sendMessageBlueBubbles } from "./send.js";
 import { getBlueBubblesRuntime } from "./runtime.js";
 
 const HTTP_URL_RE = /^https?:\/\//i;
@@ -46,6 +47,7 @@ export async function sendBlueBubblesMedia(params: {
   contentType?: string;
   filename?: string;
   caption?: string;
+  replyToId?: string | null;
   accountId?: string;
 }) {
   const {
@@ -57,6 +59,7 @@ export async function sendBlueBubblesMedia(params: {
     contentType,
     filename,
     caption,
+    replyToId,
     accountId,
   } = params;
   const core = getBlueBubblesRuntime();
@@ -106,15 +109,25 @@ export async function sendBlueBubblesMedia(params: {
     }
   }
 
-  return sendBlueBubblesAttachment({
+  const attachmentResult = await sendBlueBubblesAttachment({
     to,
     buffer,
     filename: resolvedFilename ?? "attachment",
     contentType: resolvedContentType ?? undefined,
-    caption: caption ?? undefined,
     opts: {
       cfg,
       accountId,
     },
   });
+
+  const trimmedCaption = caption?.trim();
+  if (trimmedCaption) {
+    await sendMessageBlueBubbles(to, trimmedCaption, {
+      cfg,
+      accountId,
+      replyToMessageGuid: replyToId?.trim() || undefined,
+    });
+  }
+
+  return attachmentResult;
 }
diff --git a/extensions/bluebubbles/src/monitor.test.ts b/extensions/bluebubbles/src/monitor.test.ts
index f8a8b1eae..e91e88611 100644
--- a/extensions/bluebubbles/src/monitor.test.ts
+++ b/extensions/bluebubbles/src/monitor.test.ts
@@ -1396,6 +1396,55 @@ describe("BlueBubbles webhook monitor", () => {
     });
   });
 
+  describe("outbound message ids", () => {
+    it("enqueues system event for outbound message id", async () => {
+      mockEnqueueSystemEvent.mockClear();
+
+      mockDispatchReplyWithBufferedBlockDispatcher.mockImplementationOnce(async (params) => {
+        await params.dispatcherOptions.deliver({ text: "replying now" }, { kind: "final" });
+      });
+
+      const account = createMockAccount();
+      const config: ClawdbotConfig = {};
+      const core = createMockRuntime();
+      setBlueBubblesRuntime(core);
+
+      unregister = registerBlueBubblesWebhookTarget({
+        account,
+        config,
+        runtime: { log: vi.fn(), error: vi.fn() },
+        core,
+        path: "/bluebubbles-webhook",
+      });
+
+      const payload = {
+        type: "new-message",
+        data: {
+          text: "hello",
+          handle: { address: "+15551234567" },
+          isGroup: false,
+          isFromMe: false,
+          guid: "msg-1",
+          chatGuid: "iMessage;-;+15551234567",
+          date: Date.now(),
+        },
+      };
+
+      const req = createMockRequest("POST", "/bluebubbles-webhook", payload);
+      const res = createMockResponse();
+
+      await handleBlueBubblesWebhookRequest(req, res);
+      await new Promise((resolve) => setTimeout(resolve, 50));
+
+      expect(mockEnqueueSystemEvent).toHaveBeenCalledWith(
+        "BlueBubbles sent message id: msg-123",
+        expect.objectContaining({
+          sessionKey: "agent:main:bluebubbles:dm:+15551234567",
+        }),
+      );
+    });
+  });
+
   describe("reaction events", () => {
     it("enqueues system event for reaction added", async () => {
       mockEnqueueSystemEvent.mockClear();
diff --git a/extensions/bluebubbles/src/monitor.ts b/extensions/bluebubbles/src/monitor.ts
index b13781c47..7133107cc 100644
--- a/extensions/bluebubbles/src/monitor.ts
+++ b/extensions/bluebubbles/src/monitor.ts
@@ -1316,6 +1316,15 @@ async function processMessage(
       ? formatBlueBubblesChatTarget({ chatGuid: chatGuidForActions })
       : message.senderId;
 
+  const maybeEnqueueOutboundMessageId = (messageId?: string) => {
+    const trimmed = messageId?.trim();
+    if (!trimmed || trimmed === "ok" || trimmed === "unknown") return;
+    core.system.enqueueSystemEvent(`BlueBubbles sent message id: ${trimmed}`, {
+      sessionKey: route.sessionKey,
+      contextKey: `bluebubbles:outbound:${outboundTarget}:${trimmed}`,
+    });
+  };
+
   const ctxPayload = {
     Body: body,
     BodyForAgent: body,
@@ -1368,13 +1377,15 @@ async function processMessage(
             for (const mediaUrl of mediaList) {
               const caption = first ? payload.text : undefined;
               first = false;
-              await sendBlueBubblesMedia({
+              const result = await sendBlueBubblesMedia({
                 cfg: config,
                 to: outboundTarget,
                 mediaUrl,
                 caption: caption ?? undefined,
+                replyToId: payload.replyToId ?? null,
                 accountId: account.accountId,
               });
+              maybeEnqueueOutboundMessageId(result.messageId);
               sentMessage = true;
               statusSink?.({ lastOutboundAt: Date.now() });
             }
@@ -1391,11 +1402,12 @@ async function processMessage(
           for (const chunk of chunks) {
             const replyToMessageGuid =
               typeof payload.replyToId === "string" ? payload.replyToId.trim() : "";
-            await sendMessageBlueBubbles(outboundTarget, chunk, {
+            const result = await sendMessageBlueBubbles(outboundTarget, chunk, {
               cfg: config,
               accountId: account.accountId,
               replyToMessageGuid: replyToMessageGuid || undefined,
             });
+            maybeEnqueueOutboundMessageId(result.messageId);
             sentMessage = true;
             statusSink?.({ lastOutboundAt: Date.now() });
           }
diff --git a/src/auto-reply/reply.queue.test.ts b/src/auto-reply/reply.queue.test.ts
index 331fe6795..717303322 100644
--- a/src/auto-reply/reply.queue.test.ts
+++ b/src/auto-reply/reply.queue.test.ts
@@ -82,7 +82,7 @@ describe("queue followups", () => {
       });
 
       const first = await getReplyFromConfig(
-        { Body: "first", From: "+1001", To: "+2000" },
+        { Body: "first", From: "+1001", To: "+2000", MessageSid: "m-1" },
         {},
         cfg,
       );
@@ -105,7 +105,11 @@ describe("queue followups", () => {
       await Promise.resolve();
 
       expect(runEmbeddedPiAgent).toHaveBeenCalledTimes(2);
-      expect(prompts.some((p) => p.includes("[Queued messages while agent was busy]"))).toBe(true);
+      const queuedPrompt = prompts.find((p) =>
+        p.includes("[Queued messages while agent was busy]"),
+      );
+      expect(queuedPrompt).toBeTruthy();
+      expect(queuedPrompt).toContain("[message_id: m-1]");
     });
   });
 
diff --git a/src/auto-reply/reply/get-reply-run.ts b/src/auto-reply/reply/get-reply-run.ts
index fab496081..42c68110b 100644
--- a/src/auto-reply/reply/get-reply-run.ts
+++ b/src/auto-reply/reply/get-reply-run.ts
@@ -377,9 +377,14 @@ export async function runPreparedReply(
   const sessionIdFinal = sessionId ?? crypto.randomUUID();
   const sessionFile = resolveSessionFilePath(sessionIdFinal, sessionEntry);
   const queueBodyBase = [threadStarterNote, baseBodyFinal].filter(Boolean).join("\n\n");
-  const queuedBody = mediaNote
-    ? [mediaNote, mediaReplyHint, queueBodyBase].filter(Boolean).join("\n").trim()
+  const queueMessageId = sessionCtx.MessageSid?.trim();
+  const queueMessageIdHint = queueMessageId ? `[message_id: ${queueMessageId}]` : "";
+  const queueBodyWithId = queueMessageIdHint
+    ? `${queueBodyBase}\n${queueMessageIdHint}`
     : queueBodyBase;
+  const queuedBody = mediaNote
+    ? [mediaNote, mediaReplyHint, queueBodyWithId].filter(Boolean).join("\n").trim()
+    : queueBodyWithId;
   const resolvedQueue = resolveQueueSettings({
     cfg,
     channel: sessionCtx.Provider,
diff --git a/src/config/zod-schema.providers-core.ts b/src/config/zod-schema.providers-core.ts
index 7147c4fee..906ef5433 100644
--- a/src/config/zod-schema.providers-core.ts
+++ b/src/config/zod-schema.providers-core.ts
@@ -492,6 +492,7 @@ const BlueBubblesActionSchema = z
     reply: z.boolean().optional(),
     sendWithEffect: z.boolean().optional(),
     renameGroup: z.boolean().optional(),
+    setGroupIcon: z.boolean().optional(),
     addParticipant: z.boolean().optional(),
     removeParticipant: z.boolean().optional(),
     leaveGroup: z.boolean().optional(),