diff --git a/extensions/bluebubbles/src/attachments.ts b/extensions/bluebubbles/src/attachments.ts
index 83124b61b84..deea76094ba 100644
--- a/extensions/bluebubbles/src/attachments.ts
+++ b/extensions/bluebubbles/src/attachments.ts
@@ -95,6 +95,79 @@ function readMediaFetchErrorCode(error: unknown): MediaFetchErrorCode | undefine
     : undefined;
 }
 
+/**
+ * Fetch attachment metadata for a message from the BlueBubbles API.
+ *
+ * BlueBubbles sometimes fires the `new-message` webhook before attachment
+ * indexing is complete, so `attachments` arrives as `[]`. This function
+ * GETs the message by GUID and returns whatever attachments the server
+ * has indexed by now. (#65430, #67437)
+ */
+export async function fetchBlueBubblesMessageAttachments(
+  messageGuid: string,
+  opts: {
+    baseUrl: string;
+    password: string;
+    timeoutMs?: number;
+    allowPrivateNetwork?: boolean;
+  },
+): Promise<BlueBubblesAttachment[]> {
+  const url = buildBlueBubblesApiUrl({
+    baseUrl: opts.baseUrl,
+    path: `/api/v1/message/${encodeURIComponent(messageGuid)}`,
+    password: opts.password,
+  });
+  const policy = opts.allowPrivateNetwork ? { allowPrivateNetwork: true } : {};
+  const response = await blueBubblesFetchWithTimeout(
+    url,
+    { method: "GET" },
+    opts.timeoutMs,
+    policy,
+  );
+  if (!response.ok) {
+    return [];
+  }
+  const json = (await response.json()) as Record<string, unknown>;
+  const data = json.data as Record<string, unknown> | undefined;
+  const rawAttachments = data?.attachments;
+  if (!Array.isArray(rawAttachments)) {
+    return [];
+  }
+  const out: BlueBubblesAttachment[] = [];
+  for (const entry of rawAttachments) {
+    if (!entry || typeof entry !== "object") {
+      continue;
+    }
+    const record = entry as Record<string, unknown>;
+    const guid = typeof record.guid === "string" ? record.guid.trim() : undefined;
+    if (!guid) {
+      continue;
+    }
+    out.push({
+      guid,
+      mimeType:
+        typeof record.mimeType === "string"
+          ? record.mimeType
+          : typeof record.mime_type === "string"
+            ? record.mime_type
+            : undefined,
+      transferName:
+        typeof record.transferName === "string"
+          ? record.transferName
+          : typeof record.transfer_name === "string"
+            ? record.transfer_name
+            : undefined,
+      totalBytes:
+        typeof record.totalBytes === "number"
+          ? record.totalBytes
+          : typeof record.total_bytes === "number"
+            ? record.total_bytes
+            : undefined,
+    });
+  }
+  return out;
+}
+
 export async function downloadBlueBubblesAttachment(
   attachment: BlueBubblesAttachment,
   opts: BlueBubblesAttachmentOpts & { maxBytes?: number } = {},
diff --git a/extensions/bluebubbles/src/inbound-dedupe.test.ts b/extensions/bluebubbles/src/inbound-dedupe.test.ts
index cd78be834bc..46034ef8f20 100644
--- a/extensions/bluebubbles/src/inbound-dedupe.test.ts
+++ b/extensions/bluebubbles/src/inbound-dedupe.test.ts
@@ -2,6 +2,7 @@ import { beforeEach, describe, expect, it } from "vitest";
 import {
   _resetBlueBubblesInboundDedupForTest,
   claimBlueBubblesInboundMessage,
+  resolveBlueBubblesInboundDedupeKey,
 } from "./inbound-dedupe.js";
 
 async function claimAndFinalize(guid: string | undefined, accountId: string): Promise<string> {
@@ -56,3 +57,38 @@ describe("claimBlueBubblesInboundMessage", () => {
     expect(await claimAndFinalize("g1", "acc")).toBe("claimed");
   });
 });
+
+describe("resolveBlueBubblesInboundDedupeKey", () => {
+  it("returns messageId for new-message events", () => {
+    expect(resolveBlueBubblesInboundDedupeKey({ messageId: "msg-1" })).toBe("msg-1");
+  });
+
+  it("returns associatedMessageGuid for balloon events", () => {
+    expect(
+      resolveBlueBubblesInboundDedupeKey({
+        messageId: "balloon-1",
+        balloonBundleId: "com.apple.messages.URLBalloonProvider",
+        associatedMessageGuid: "msg-1",
+      }),
+    ).toBe("msg-1");
+  });
+
+  it("suffixes key with :updated for updated-message events", () => {
+    expect(
+      resolveBlueBubblesInboundDedupeKey({ messageId: "msg-1", eventType: "updated-message" }),
+    ).toBe("msg-1:updated");
+  });
+
+  it("updated-message and new-message for same GUID produce distinct keys", () => {
+    const newKey = resolveBlueBubblesInboundDedupeKey({ messageId: "msg-1" });
+    const updatedKey = resolveBlueBubblesInboundDedupeKey({
+      messageId: "msg-1",
+      eventType: "updated-message",
+    });
+    expect(newKey).not.toBe(updatedKey);
+  });
+
+  it("returns undefined when messageId is missing", () => {
+    expect(resolveBlueBubblesInboundDedupeKey({})).toBeUndefined();
+  });
+});
diff --git a/extensions/bluebubbles/src/inbound-dedupe.ts b/extensions/bluebubbles/src/inbound-dedupe.ts
index deffa49685f..1be0dadedb9 100644
--- a/extensions/bluebubbles/src/inbound-dedupe.ts
+++ b/extensions/bluebubbles/src/inbound-dedupe.ts
@@ -136,15 +136,27 @@ function sanitizeGuid(guid: string | undefined | null): string | null {
 export function resolveBlueBubblesInboundDedupeKey(
   message: Pick<
     NormalizedWebhookMessage,
-    "messageId" | "balloonBundleId" | "associatedMessageGuid"
+    "messageId" | "balloonBundleId" | "associatedMessageGuid" | "eventType"
   >,
 ): string | undefined {
   const balloonBundleId = message.balloonBundleId?.trim();
   const associatedMessageGuid = message.associatedMessageGuid?.trim();
+  let base: string | undefined;
   if (balloonBundleId && associatedMessageGuid) {
-    return associatedMessageGuid;
+    base = associatedMessageGuid;
+  } else {
+    base = message.messageId?.trim() || undefined;
   }
-  return message.messageId?.trim() || undefined;
+  if (!base) {
+    return undefined;
+  }
+  // `updated-message` events get a distinct key so they are not rejected as
+  // duplicates of the already-committed `new-message` for the same GUID.
+  // This lets attachment-carrying follow-up webhooks through. (#65430, #52277)
+  if (message.eventType === "updated-message") {
+    return `${base}:updated`;
+  }
+  return base;
 }
 
 export type InboundDedupeClaim =
diff --git a/extensions/bluebubbles/src/monitor-normalize.ts b/extensions/bluebubbles/src/monitor-normalize.ts
index 463e1939b1b..4cd1bc6d194 100644
--- a/extensions/bluebubbles/src/monitor-normalize.ts
+++ b/extensions/bluebubbles/src/monitor-normalize.ts
@@ -477,6 +477,8 @@ export type NormalizedWebhookMessage = {
   replyToId?: string;
   replyToBody?: string;
   replyToSender?: string;
+  /** Webhook event type preserved for dedup key differentiation. */
+  eventType?: string;
 };
 
 export type NormalizedWebhookReaction = {
@@ -687,6 +689,7 @@ function extractMessagePayload(payload: Record<string, unknown>): Record<string,
 
 export function normalizeWebhookMessage(
   payload: Record<string, unknown>,
+  options?: { eventType?: string },
 ): NormalizedWebhookMessage | null {
   const message = extractMessagePayload(payload);
   if (!message) {
@@ -774,6 +777,7 @@ export function normalizeWebhookMessage(
     replyToId: replyMetadata.replyToId,
     replyToBody: replyMetadata.replyToBody,
     replyToSender: replyMetadata.replyToSender,
+    eventType: options?.eventType,
   };
 }
 
diff --git a/extensions/bluebubbles/src/monitor-processing.ts b/extensions/bluebubbles/src/monitor-processing.ts
index e2ef93c070f..dd01a37cfed 100644
--- a/extensions/bluebubbles/src/monitor-processing.ts
+++ b/extensions/bluebubbles/src/monitor-processing.ts
@@ -9,7 +9,10 @@ import {
   normalizeOptionalLowercaseString,
   normalizeOptionalString,
 } from "openclaw/plugin-sdk/text-runtime";
-import { downloadBlueBubblesAttachment } from "./attachments.js";
+import {
+  downloadBlueBubblesAttachment,
+  fetchBlueBubblesMessageAttachments,
+} from "./attachments.js";
 import { markBlueBubblesChatRead, sendBlueBubblesTyping } from "./chat.js";
 import { resolveBlueBubblesConversationRoute } from "./conversation-route.js";
 import { fetchBlueBubblesHistory } from "./history.js";
@@ -1065,14 +1068,52 @@ async function processMessageAfterDedupe(
       ? account.config.mediaMaxMb * 1024 * 1024
       : 8 * 1024 * 1024;
 
+  // BlueBubbles may fire the webhook before attachment indexing is complete,
+  // so the initial `attachments` array can be empty for messages that actually
+  // have media. When the message text is empty (image-only) or this is an
+  // `updated-message` event, wait briefly and re-fetch from the BB API as a
+  // fallback for cases where BB doesn't send a follow-up webhook. (#65430, #67437)
+  let resolvedAttachments = attachments;
+  const shouldRetryAttachments =
+    resolvedAttachments.length === 0 &&
+    message.messageId &&
+    baseUrl &&
+    password &&
+    (text.length === 0 || message.eventType === "updated-message");
+  if (shouldRetryAttachments) {
+    try {
+      await new Promise<void>((resolve) => setTimeout(resolve, 2_000));
+      const fetched = await fetchBlueBubblesMessageAttachments(message.messageId!, {
+        baseUrl,
+        password,
+        timeoutMs: 10_000,
+        allowPrivateNetwork: isPrivateNetworkOptInEnabled(account.config),
+      });
+      if (fetched.length > 0) {
+        logVerbose(
+          core,
+          runtime,
+          `attachment retry found ${fetched.length} attachment(s) for msgId=${message.messageId}`,
+        );
+        resolvedAttachments = fetched;
+      }
+    } catch (err) {
+      logVerbose(
+        core,
+        runtime,
+        `attachment retry failed for msgId=${message.messageId}: ${String(err)}`,
+      );
+    }
+  }
+
   let mediaUrls: string[] = [];
   let mediaPaths: string[] = [];
   let mediaTypes: string[] = [];
-  if (attachments.length > 0) {
+  if (resolvedAttachments.length > 0) {
     if (!baseUrl || !password) {
       logVerbose(core, runtime, "attachment download skipped (missing serverUrl/password)");
     } else {
-      for (const attachment of attachments) {
+      for (const attachment of resolvedAttachments) {
         if (!attachment.guid) {
           continue;
         }
diff --git a/extensions/bluebubbles/src/monitor.ts b/extensions/bluebubbles/src/monitor.ts
index f34f725dddb..2c7d0c908cf 100644
--- a/extensions/bluebubbles/src/monitor.ts
+++ b/extensions/bluebubbles/src/monitor.ts
@@ -249,11 +249,21 @@ export async function handleBlueBubblesWebhookRequest(
         return true;
       }
       const reaction = normalizeWebhookReaction(payload);
+      // BlueBubbles fires `updated-message` when attachments are indexed after the
+      // initial `new-message` (which may arrive with attachments: []). Let those
+      // through so the agent can ingest the image. (#65430)
+      const dataRecord = asRecord(asRecord(payload)?.data);
+      const dataAttachments = dataRecord?.attachments;
+      const isAttachmentUpdate =
+        eventType === "updated-message" &&
+        Array.isArray(dataAttachments) &&
+        dataAttachments.length > 0;
       if (
         (eventType === "updated-message" ||
           eventType === "message-reaction" ||
           eventType === "reaction") &&
-        !reaction
+        !reaction &&
+        !isAttachmentUpdate
       ) {
         res.statusCode = 200;
         res.end("ok");
@@ -266,7 +276,7 @@ export async function handleBlueBubblesWebhookRequest(
         }
         return true;
       }
-      const message = reaction ? null : normalizeWebhookMessage(payload);
+      const message = reaction ? null : normalizeWebhookMessage(payload, { eventType });
       if (!message && !reaction) {
         res.statusCode = 400;
         res.end("invalid payload");
diff --git a/extensions/bluebubbles/src/types.ts b/extensions/bluebubbles/src/types.ts
index 90a4dbafc0a..d5c777fc935 100644
--- a/extensions/bluebubbles/src/types.ts
+++ b/extensions/bluebubbles/src/types.ts
@@ -175,10 +175,16 @@ export async function blueBubblesFetchWithTimeout(
       await release();
     }
   }
+  // Strip `dispatcher` from init — the SSRF guard may have attached a bundled-undici
+  // dispatcher that is incompatible with Node 22+'s built-in undici backing globalThis.fetch().
+  // Passing it through causes a silent TypeError (invalid onRequestStart method). (#64105)
+  const { dispatcher: _dispatcher, ...safeInit } = (init ?? {}) as RequestInit & {
+    dispatcher?: unknown;
+  };
   const controller = new AbortController();
   const timer = setTimeout(() => controller.abort(), timeoutMs);
   try {
-    return await fetch(url, { ...init, signal: controller.signal });
+    return await fetch(url, { ...safeInit, signal: controller.signal });
   } finally {
     clearTimeout(timer);
   }