diff --git a/backend/brain-config.ts b/backend/brain-config.ts
index 94feaa4d..5d7ada57 100644
--- a/backend/brain-config.ts
+++ b/backend/brain-config.ts
@@ -33,6 +33,7 @@ export interface BrainConfig {
   maxThinkContextNodes: number;          // base budget for think context node selection
   selfCritiqueEnabled: boolean;          // enable pre-send quality gate for proactive messages
   selfCritiqueThreshold: number;         // minimum score (1-10) to allow sending; default 6
+  staleMsgThresholdMs: number;           // max age (ms) for queued outgoing WhatsApp messages; older are discarded on reconnect
   /** Per-action model selection. Claude: "sonnet", "haiku", "opus". Grok: "grok", "grok-mini". */
   models: {
     think: string;          // brain think ticks
@@ -203,6 +204,7 @@ function envDefaults(): BrainConfig {
     maxThinkContextNodes: 35,
     selfCritiqueEnabled: process.env.SELF_CRITIQUE_ENABLED !== "false",
     selfCritiqueThreshold: Number(process.env.SELF_CRITIQUE_THRESHOLD ?? 6),
+    staleMsgThresholdMs: Number(process.env.STALE_MSG_THRESHOLD_MS ?? 5 * 60 * 1000),
     models: {
       think: "sonnet",
       consolidate: "haiku",
diff --git a/backend/integrations/whatsapp.ts b/backend/integrations/whatsapp.ts
index 875beb82..e37b9b55 100644
--- a/backend/integrations/whatsapp.ts
+++ b/backend/integrations/whatsapp.ts
@@ -18,6 +18,7 @@ import { EventEmitter } from "events";
 import { createLogger } from "../logger.js";
 import { transcribeAudio } from "../utils/transcribe.js";
 import { describeImage, isVisionRefusal } from "../utils/vision.js";
+import { getBrainConfig } from "../brain-config.js";
 
 // Emits 'logout' when WhatsApp session is logged out.
 // Listeners can perform cleanup before the process exits.
@@ -79,6 +80,48 @@ setInterval(() => {
   sweepDedupCache(sentMessages, MESSAGE_DEDUP_TTL, MAX_DEDUP_CACHE_SIZE);
 }, DEDUP_SWEEP_INTERVAL).unref();
 
+// Outgoing send queue — populated when sendMessage is called while disconnected.
+// Drained on connection 'open' with a stale-age filter so that messages enqueued
+// before a long offline period are not sent with obsolete context (see offlinemsgbug).
+interface PendingSend {
+  jid: string;
+  text: string;
+  queuedAt: number;
+  scheduled: boolean; // bypass stale check when true
+  resolve: () => void;
+  reject: (err: Error) => void;
+}
+const pendingSendQueue: PendingSend[] = [];
+
+async function flushPendingSendQueue(): Promise<void> {
+  if (pendingSendQueue.length === 0) return;
+  const threshold = getBrainConfig().staleMsgThresholdMs;
+  const now = Date.now();
+  const drained = pendingSendQueue.splice(0, pendingSendQueue.length);
+
+  const fresh: PendingSend[] = [];
+  for (const item of drained) {
+    const age = now - item.queuedAt;
+    if (!item.scheduled && age > threshold) {
+      log.warn(
+        `Discarding stale queued message to ${item.jid} (age=${Math.round(age / 1000)}s, threshold=${Math.round(threshold / 1000)}s): "${item.text.slice(0, 80)}"`,
+      );
+      item.reject(new Error(`Stale outgoing message discarded after reconnect (age ${Math.round(age / 1000)}s > ${Math.round(threshold / 1000)}s)`));
+    } else {
+      fresh.push(item);
+    }
+  }
+
+  for (const item of fresh) {
+    try {
+      await sock.sendMessage(item.jid, { text: item.text });
+      item.resolve();
+    } catch (err) {
+      item.reject(err instanceof Error ? err : new Error(String(err)));
+    }
+  }
+}
+
 // Group name cache with TTL to prevent unbounded memory growth
 const GROUP_CACHE_TTL = 60 * 60 * 1000; // 1 hour
 const MAX_GROUP_CACHE_SIZE = 500;
@@ -264,6 +307,11 @@ export async function startWhatsApp(
       isConnected = true;
       reconnectAttempt = 0; // Reset backoff on successful connection
       log.info("Connected!");
+      // Drain any messages enqueued while disconnected, discarding ones older
+      // than staleMsgThresholdMs to avoid sending out-of-context messages.
+      flushPendingSendQueue().catch((err) =>
+        log.error(`Pending send queue flush error: ${err}`),
+      );
     }
   });
 
@@ -465,12 +513,11 @@ export async function syncContacts(): Promise<void> {
   log.info("Contact sync triggered, waiting for events...");
 }
 
-export async function sendMessage(jid: string, text: string): Promise<void> {
-  if (!isConnected) {
-    log.warn("Cannot send message — not connected");
-    throw new Error("WhatsApp not connected");
-  }
-
+export async function sendMessage(
+  jid: string,
+  text: string,
+  options?: { scheduled?: boolean },
+): Promise<void> {
   // Outgoing dedup: prevent duplicate sends within 5 minutes (mirrors incoming dedup pattern)
   const hash = createHash("sha256").update(text).digest("hex").slice(0, 16);
   const dedupKey = `${jid}|${hash}`;
@@ -480,6 +527,21 @@ export async function sendMessage(jid: string, text: string): Promise<void> {
   }
   sentMessages.set(dedupKey, Date.now());
 
+  if (!isConnected) {
+    // Queue for delivery on reconnect; flush will discard if too old.
+    log.warn(`sendMessage queued (not connected): ${jid} "${text.slice(0, 60)}"`);
+    return new Promise<void>((resolve, reject) => {
+      pendingSendQueue.push({
+        jid,
+        text,
+        queuedAt: Date.now(),
+        scheduled: options?.scheduled === true,
+        resolve,
+        reject,
+      });
+    });
+  }
+
   await sock.sendMessage(jid, { text });
 }