diff --git a/extensions/bluebubbles/src/monitor.test.ts b/extensions/bluebubbles/src/monitor.test.ts
index d4f03f07cc..1e652ade28 100644
--- a/extensions/bluebubbles/src/monitor.test.ts
+++ b/extensions/bluebubbles/src/monitor.test.ts
@@ -1150,6 +1150,136 @@ describe("BlueBubbles webhook monitor", () => {
     });
   });
 
+  describe("inbound debouncing", () => {
+    it("coalesces text-only then attachment webhook events by messageId", async () => {
+      vi.useFakeTimers();
+      try {
+        const account = createMockAccount({ dmPolicy: "open" });
+        const config: OpenClawConfig = {};
+        const core = createMockRuntime();
+
+        // Use a timing-aware debouncer test double that respects debounceMs/buildKey/shouldDebounce.
+        core.channel.debounce.createInboundDebouncer = vi.fn((params: any) => {
+          type Item = any;
+          const buckets = new Map<string, { items: Item[]; timer: ReturnType<typeof setTimeout> | null }>();
+
+          const flush = async (key: string) => {
+            const bucket = buckets.get(key);
+            if (!bucket) return;
+            if (bucket.timer) {
+              clearTimeout(bucket.timer);
+              bucket.timer = null;
+            }
+            const items = bucket.items;
+            bucket.items = [];
+            if (items.length > 0) {
+              try {
+                await params.onFlush(items);
+              } catch (err) {
+                params.onError?.(err);
+                throw err;
+              }
+            }
+          };
+
+          return {
+            enqueue: async (item: Item) => {
+              if (params.shouldDebounce && !params.shouldDebounce(item)) {
+                await params.onFlush([item]);
+                return;
+              }
+
+              const key = params.buildKey(item);
+              const existing = buckets.get(key);
+              const bucket = existing ?? { items: [], timer: null };
+              bucket.items.push(item);
+              if (bucket.timer) clearTimeout(bucket.timer);
+              bucket.timer = setTimeout(async () => {
+                await flush(key);
+              }, params.debounceMs);
+              buckets.set(key, bucket);
+            },
+            flushKey: vi.fn(async (key: string) => {
+              await flush(key);
+            }),
+          };
+        }) as unknown as PluginRuntime["channel"]["debounce"]["createInboundDebouncer"];
+
+        setBlueBubblesRuntime(core);
+
+        unregister = registerBlueBubblesWebhookTarget({
+          account,
+          config,
+          runtime: { log: vi.fn(), error: vi.fn() },
+          core,
+          path: "/bluebubbles-webhook",
+        });
+
+        const messageId = "race-msg-1";
+        const chatGuid = "iMessage;-;+15551234567";
+
+        const payloadA = {
+          type: "new-message",
+          data: {
+            text: "hello",
+            handle: { address: "+15551234567" },
+            isGroup: false,
+            isFromMe: false,
+            guid: messageId,
+            chatGuid,
+            date: Date.now(),
+          },
+        };
+
+        const payloadB = {
+          type: "new-message",
+          data: {
+            text: "hello",
+            handle: { address: "+15551234567" },
+            isGroup: false,
+            isFromMe: false,
+            guid: messageId,
+            chatGuid,
+            attachments: [
+              {
+                guid: "att-1",
+                mimeType: "image/jpeg",
+                totalBytes: 1024,
+              },
+            ],
+            date: Date.now(),
+          },
+        };
+
+        await handleBlueBubblesWebhookRequest(
+          createMockRequest("POST", "/bluebubbles-webhook", payloadA),
+          createMockResponse(),
+        );
+
+        // Simulate the real-world delay where the attachment-bearing webhook arrives shortly after.
+        await vi.advanceTimersByTimeAsync(300);
+
+        await handleBlueBubblesWebhookRequest(
+          createMockRequest("POST", "/bluebubbles-webhook", payloadB),
+          createMockResponse(),
+        );
+
+        // Not flushed yet; still within the debounce window.
+        expect(mockDispatchReplyWithBufferedBlockDispatcher).not.toHaveBeenCalled();
+
+        // After the debounce window, the combined message should be processed exactly once.
+        await vi.advanceTimersByTimeAsync(600);
+
+        expect(mockDispatchReplyWithBufferedBlockDispatcher).toHaveBeenCalledTimes(1);
+        const callArgs = mockDispatchReplyWithBufferedBlockDispatcher.mock.calls[0][0];
+        expect(callArgs.ctx.MediaPaths).toEqual(["/tmp/test-media.jpg"]);
+        expect(callArgs.ctx.Body).toContain("hello");
+      } finally {
+        vi.useRealTimers();
+      }
+    });
+  });
+
   describe("reply metadata", () => {
     it("surfaces reply fields in ctx when provided", async () => {
       const account = createMockAccount({ dmPolicy: "open" });
diff --git a/extensions/bluebubbles/src/monitor.ts b/extensions/bluebubbles/src/monitor.ts
index cd5ff998b9..67a5947ab9 100644
--- a/extensions/bluebubbles/src/monitor.ts
+++ b/extensions/bluebubbles/src/monitor.ts
@@ -264,7 +264,7 @@ type BlueBubblesDebounceEntry = {
  * This helps combine URL text + link preview balloon messages that BlueBubbles
  * sends as separate webhook events when no explicit inbound debounce config exists.
  */
-const DEFAULT_INBOUND_DEBOUNCE_MS = 350;
+const DEFAULT_INBOUND_DEBOUNCE_MS = 500;
 
 /**
  * Combines multiple debounced messages into a single message for processing.
@@ -363,7 +363,23 @@ function getOrCreateDebouncer(target: WebhookTarget) {
     debounceMs: resolveBlueBubblesDebounceMs(config, core),
     buildKey: (entry) => {
       const msg = entry.message;
-      // Build key from account + chat + sender to coalesce messages from same source
+      // Prefer stable, shared identifiers to coalesce rapid-fire webhook events for the
+      // same message (e.g., text-only then text+attachment).
+      //
+      // For balloons (URL previews, stickers, etc), BlueBubbles often uses a different
+      // messageId than the originating text. When present, key by associatedMessageGuid
+      // to keep text + balloon coalescing working.
+      const balloonBundleId = msg.balloonBundleId?.trim();
+      const associatedMessageGuid = msg.associatedMessageGuid?.trim();
+      if (balloonBundleId && associatedMessageGuid) {
+        return `bluebubbles:${account.accountId}:balloon:${associatedMessageGuid}`;
+      }
+
+      const messageId = msg.messageId?.trim();
+      if (messageId) {
+        return `bluebubbles:${account.accountId}:msg:${messageId}`;
+      }
+
       const chatKey =
         msg.chatGuid?.trim() ??
         msg.chatIdentifier?.trim() ??
@@ -372,13 +388,12 @@ function getOrCreateDebouncer(target: WebhookTarget) {
     },
     shouldDebounce: (entry) => {
       const msg = entry.message;
-      // Skip debouncing for messages with attachments - process immediately
-      if (msg.attachments && msg.attachments.length > 0) return false;
       // Skip debouncing for from-me messages (they're just cached, not processed)
       if (msg.fromMe) return false;
       // Skip debouncing for control commands - process immediately
       if (core.channel.text.hasControlCommand(msg.text, config)) return false;
-      // Debounce normal text messages and URL balloon messages
+      // Debounce all other messages to coalesce rapid-fire webhook events
+      // (e.g., text+image arriving as separate webhooks for the same messageId)
       return true;
     },
     onFlush: async (entries) => {