diff --git a/src/web/auto-reply.test.ts b/src/web/auto-reply.test.ts
index fc48794bb..0a503cb99 100644
--- a/src/web/auto-reply.test.ts
+++ b/src/web/auto-reply.test.ts
@@ -202,6 +202,58 @@ describe("partial reply gating", () => {
     expect(reply).toHaveBeenCalledWith("final reply");
   });
 
+  it("updates last-route for direct chats without senderE164", async () => {
+    const now = Date.now();
+    const store = await makeSessionStore({
+      main: { sessionId: "sid", updatedAt: now - 1 },
+    });
+
+    const replyResolver = vi.fn().mockResolvedValue(undefined);
+
+    const mockConfig: ClawdisConfig = {
+      inbound: {
+        allowFrom: ["*"],
+        reply: {
+          mode: "command",
+          session: { store: store.storePath, mainKey: "main" },
+        },
+      },
+    };
+
+    setLoadConfigMock(mockConfig);
+
+    await monitorWebProvider(
+      false,
+      async ({ onMessage }) => {
+        await onMessage({
+          id: "m1",
+          from: "+1000",
+          conversationId: "+1000",
+          to: "+2000",
+          body: "hello",
+          timestamp: now,
+          chatType: "direct",
+          chatId: "direct:+1000",
+          sendComposing: vi.fn().mockResolvedValue(undefined),
+          reply: vi.fn().mockResolvedValue(undefined),
+          sendMedia: vi.fn().mockResolvedValue(undefined),
+        });
+        return { close: vi.fn().mockResolvedValue(undefined) };
+      },
+      false,
+      replyResolver,
+    );
+
+    const stored = JSON.parse(await fs.readFile(store.storePath, "utf8")) as {
+      main?: { lastChannel?: string; lastTo?: string };
+    };
+    expect(stored.main?.lastChannel).toBe("whatsapp");
+    expect(stored.main?.lastTo).toBe("+1000");
+
+    resetLoadConfigMock();
+    await store.cleanup();
+  });
+
   it("defaults to self-only when no config is present", async () => {
     const cfg: ClawdisConfig = {
       inbound: {
@@ -661,6 +713,10 @@ describe("web auto-reply", () => {
     const originalMax = process.getMaxListeners();
     process.setMaxListeners?.(1); // force low to confirm bump
 
+    const store = await makeSessionStore({
+      main: { sessionId: "sid", updatedAt: Date.now() },
+    });
+
     const sendMedia = vi.fn();
     const reply = vi.fn().mockResolvedValue(undefined);
     const sendComposing = vi.fn();
@@ -684,7 +740,12 @@ describe("web auto-reply", () => {
       .spyOn(commandQueue, "getQueueSize")
       .mockImplementation(() => (queueBusy ? 1 : 0));
 
-    setLoadConfigMock(() => ({ inbound: { timestampPrefix: "UTC" } }));
+    setLoadConfigMock(() => ({
+      inbound: {
+        timestampPrefix: "UTC",
+        reply: { mode: "command", session: { store: store.storePath } },
+      },
+    }));
 
     await monitorWebProvider(false, listenerFactory, false, resolver);
     expect(capturedOnMessage).toBeDefined();
@@ -713,7 +774,7 @@ describe("web auto-reply", () => {
 
     // Let the queued batch flush once the queue is free
     queueBusy = false;
-    vi.advanceTimersByTime(200);
+    await vi.advanceTimersByTimeAsync(200);
 
     expect(resolver).toHaveBeenCalledTimes(1);
     const args = resolver.mock.calls[0][0];
@@ -730,6 +791,7 @@ describe("web auto-reply", () => {
     queueSpy.mockRestore();
     process.setMaxListeners?.(originalMax);
     vi.useRealTimers();
+    await store.cleanup();
   });
 
   it("falls back to text when media send fails", async () => {
diff --git a/src/web/auto-reply.ts b/src/web/auto-reply.ts
index aa84f1071..e762f4b52 100644
--- a/src/web/auto-reply.ts
+++ b/src/web/auto-reply.ts
@@ -783,7 +783,7 @@ export async function monitorWebProvider(
       const batch = pendingBatches.get(conversationId);
       if (!batch || batch.messages.length === 0) return;
       if (getQueueSize() > 0) {
-        batch.timer = setTimeout(() => void processBatch(conversationId), 150);
+        batch.timer = setTimeout(() => processBatch(conversationId), 150);
         return;
       }
       pendingBatches.delete(conversationId);
@@ -854,15 +854,25 @@ export async function monitorWebProvider(
         const sessionCfg = cfg.inbound?.reply?.session;
         const mainKey = (sessionCfg?.mainKey ?? "main").trim() || "main";
         const storePath = resolveStorePath(sessionCfg?.store);
-        const to = latest.senderE164
-          ? normalizeE164(latest.senderE164)
-          : jidToE164(latest.from);
+        const to = (() => {
+          if (latest.senderE164) return normalizeE164(latest.senderE164);
+          // In direct chats, `latest.from` is already the canonical conversation id,
+          // which is an E.164 string (e.g. "+1555"). Only fall back to JID parsing
+          // when we were handed a JID-like string.
+          if (latest.from.includes("@")) return jidToE164(latest.from);
+          return normalizeE164(latest.from);
+        })();
         if (to) {
-          await updateLastRoute({
+          void updateLastRoute({
             storePath,
             sessionKey: mainKey,
             channel: "whatsapp",
             to,
+          }).catch((err) => {
+            replyLogger.warn(
+              { error: String(err), storePath, sessionKey: mainKey, to },
+              "failed updating last route",
+            );
           });
         }
       }
@@ -969,8 +979,7 @@ export async function monitorWebProvider(
       if (getQueueSize() === 0) {
         await processBatch(key);
       } else {
-        bucket.timer =
-          bucket.timer ?? setTimeout(() => void processBatch(key), 150);
+        bucket.timer = bucket.timer ?? setTimeout(() => processBatch(key), 150);
       }
     };
 
@@ -1401,6 +1410,12 @@ export async function monitorWebProvider(
         },
         "web reconnect: max attempts reached; continuing in degraded mode",
       );
+      runtime.error(
+        danger(
+          `WhatsApp Web reconnect: max attempts reached (${reconnectAttempts}/${reconnectPolicy.maxAttempts}). Stopping web monitoring.`,
+        ),
+      );
+      await closeListener();
       break;
     }