diff --git a/extensions/bluebubbles/src/channel.ts b/extensions/bluebubbles/src/channel.ts
index b78f41659..da594e763 100644
--- a/extensions/bluebubbles/src/channel.ts
+++ b/extensions/bluebubbles/src/channel.ts
@@ -20,6 +20,7 @@ import {
   resolveDefaultBlueBubblesAccountId,
 } from "./accounts.js";
 import { BlueBubblesConfigSchema } from "./config-schema.js";
+import { resolveBlueBubblesMessageId } from "./monitor.js";
 import { probeBlueBubbles, type BlueBubblesProbe } from "./probe.js";
 import { sendMessageBlueBubbles } from "./send.js";
 import {
@@ -237,7 +238,9 @@ export const bluebubblesPlugin: ChannelPlugin<ResolvedBlueBubblesAccount> = {
       return { ok: true, to: trimmed };
     },
     sendText: async ({ cfg, to, text, accountId, replyToId }) => {
-      const replyToMessageGuid = typeof replyToId === "string" ? replyToId.trim() : "";
+      const rawReplyToId = typeof replyToId === "string" ? replyToId.trim() : "";
+      // Resolve short ID (e.g., "5") to full UUID
+      const replyToMessageGuid = rawReplyToId ? resolveBlueBubblesMessageId(rawReplyToId) : "";
       const result = await sendMessageBlueBubbles(to, text, {
         cfg: cfg as ClawdbotConfig,
         accountId: accountId ?? undefined,
diff --git a/extensions/bluebubbles/src/media-send.ts b/extensions/bluebubbles/src/media-send.ts
index 254cecafd..5fc9895e3 100644
--- a/extensions/bluebubbles/src/media-send.ts
+++ b/extensions/bluebubbles/src/media-send.ts
@@ -4,8 +4,9 @@ import { fileURLToPath } from "node:url";
 import { resolveChannelMediaMaxBytes, type ClawdbotConfig } from "clawdbot/plugin-sdk";
 
 import { sendBlueBubblesAttachment } from "./attachments.js";
-import { sendMessageBlueBubbles } from "./send.js";
+import { resolveBlueBubblesMessageId } from "./monitor.js";
 import { getBlueBubblesRuntime } from "./runtime.js";
+import { sendMessageBlueBubbles } from "./send.js";
 
 const HTTP_URL_RE = /^https?:\/\//i;
 const MB = 1024 * 1024;
@@ -134,12 +135,17 @@ export async function sendBlueBubblesMedia(params: {
     }
   }
 
+  // Resolve short ID (e.g., "5") to full UUID
+  const replyToMessageGuid = replyToId?.trim()
+    ? resolveBlueBubblesMessageId(replyToId.trim())
+    : undefined;
+
   const attachmentResult = await sendBlueBubblesAttachment({
     to,
     buffer,
     filename: resolvedFilename ?? "attachment",
     contentType: resolvedContentType ?? undefined,
-    replyToMessageGuid: replyToId?.trim() || undefined,
+    replyToMessageGuid,
     opts: {
       cfg,
       accountId,
@@ -151,7 +157,7 @@ export async function sendBlueBubblesMedia(params: {
     await sendMessageBlueBubbles(to, trimmedCaption, {
       cfg,
       accountId,
-      replyToMessageGuid: replyToId?.trim() || undefined,
+      replyToMessageGuid,
     });
   }
 
diff --git a/extensions/bluebubbles/src/monitor.test.ts b/extensions/bluebubbles/src/monitor.test.ts
index 14c896427..f3be7d6ed 100644
--- a/extensions/bluebubbles/src/monitor.test.ts
+++ b/extensions/bluebubbles/src/monitor.test.ts
@@ -1175,8 +1175,8 @@ describe("BlueBubbles webhook monitor", () => {
       expect(callArgs.ctx.ReplyToId).toBe("msg-0");
       expect(callArgs.ctx.ReplyToBody).toBe("original message");
       expect(callArgs.ctx.ReplyToSender).toBe("+15550000000");
-      // Body still uses the full UUID since it wasn't cached
-      expect(callArgs.ctx.Body).toContain("[Replying to +15550000000 id:msg-0]");
+      // Body uses just the ID (no sender) for token savings
+      expect(callArgs.ctx.Body).toContain("[Replying to id:msg-0]");
       expect(callArgs.ctx.Body).toContain("original message");
     });
 
@@ -1245,8 +1245,8 @@ describe("BlueBubbles webhook monitor", () => {
       expect(callArgs.ctx.ReplyToId).toBe("1");
       expect(callArgs.ctx.ReplyToBody).toBe("original message (cached)");
       expect(callArgs.ctx.ReplyToSender).toBe("+15550000000");
-      // Body uses short ID for token savings
-      expect(callArgs.ctx.Body).toContain("[Replying to +15550000000 id:1]");
+      // Body uses just the short ID (no sender) for token savings
+      expect(callArgs.ctx.Body).toContain("[Replying to id:1]");
       expect(callArgs.ctx.Body).toContain("original message (cached)");
     });
 
diff --git a/extensions/bluebubbles/src/monitor.ts b/extensions/bluebubbles/src/monitor.ts
index 4c2b4a225..c7a4188c0 100644
--- a/extensions/bluebubbles/src/monitor.ts
+++ b/extensions/bluebubbles/src/monitor.ts
@@ -376,6 +376,8 @@ function buildMessagePlaceholder(message: NormalizedWebhookMessage): string {
   return "";
 }
 
+const REPLY_BODY_TRUNCATE_LENGTH = 60;
+
 function formatReplyContext(message: {
   replyToId?: string;
   replyToShortId?: string;
@@ -383,15 +385,20 @@ function formatReplyContext(message: {
   replyToSender?: string;
 }): string | null {
   if (!message.replyToId && !message.replyToBody && !message.replyToSender) return null;
-  const sender = message.replyToSender?.trim() || "unknown sender";
   // Prefer short ID for token savings
   const displayId = message.replyToShortId || message.replyToId;
-  const idPart = displayId ? ` id:${displayId}` : "";
-  const body = message.replyToBody?.trim();
-  if (!body) {
-    return `[Replying to ${sender}${idPart}]\n[/Replying]`;
+  // Only include sender if we don't have an ID (fallback)
+  const label = displayId ? `id:${displayId}` : (message.replyToSender?.trim() || "unknown");
+  const rawBody = message.replyToBody?.trim();
+  if (!rawBody) {
+    return `[Replying to ${label}]\n[/Replying]`;
   }
-  return `[Replying to ${sender}${idPart}]\n${body}\n[/Replying]`;
+  // Truncate long reply bodies for token savings
+  const body =
+    rawBody.length > REPLY_BODY_TRUNCATE_LENGTH
+      ? `${rawBody.slice(0, REPLY_BODY_TRUNCATE_LENGTH)}…`
+      : rawBody;
+  return `[Replying to ${label}]\n${body}\n[/Replying]`;
 }
 
 function readNumberLike(record: Record<string, unknown> | null, key: string): number | undefined {
@@ -1661,8 +1668,12 @@ async function processMessage(
           if (!chunks.length && payload.text) chunks.push(payload.text);
           if (!chunks.length) return;
           for (const chunk of chunks) {
-            const replyToMessageGuid =
+            const rawReplyToId =
               typeof payload.replyToId === "string" ? payload.replyToId.trim() : "";
+            // Resolve short ID (e.g., "5") to full UUID
+            const replyToMessageGuid = rawReplyToId
+              ? resolveBlueBubblesMessageId(rawReplyToId)
+              : "";
             const result = await sendMessageBlueBubbles(outboundTarget, chunk, {
               cfg: config,
               accountId: account.accountId,