diff --git a/CHANGELOG.md b/CHANGELOG.md
index 85916a30d9e..b0f6c76c617 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,12 @@
 
 Docs: https://docs.openclaw.ai
 
+## Unreleased
+
+### Fixes
+
+- WhatsApp: drain pending outbound deliveries on a 30s periodic timer in addition to the reconnect handler, so messages enqueued while the provider is already connected no longer wait for the next reconnect to send. (#79083) Thanks @Oviemudiaga.
+
 ## 2026.5.19
 
 ### Changes
diff --git a/extensions/whatsapp/src/auto-reply.web-auto-reply.connection-and-logging.e2e.test.ts b/extensions/whatsapp/src/auto-reply.web-auto-reply.connection-and-logging.e2e.test.ts
index 0e9f54dd66d..76a54a20d01 100644
--- a/extensions/whatsapp/src/auto-reply.web-auto-reply.connection-and-logging.e2e.test.ts
+++ b/extensions/whatsapp/src/auto-reply.web-auto-reply.connection-and-logging.e2e.test.ts
@@ -27,6 +27,25 @@ import {
   startWebAutoReplyMonitor,
 } from "./auto-reply.test-harness.js";
 
+type DrainSelectionEntry = {
+  channel: string;
+  accountId?: string | null;
+  lastError?: string;
+};
+type DrainPendingDeliveriesCall = {
+  drainKey: string;
+  logLabel: string;
+  selectEntry: (entry: DrainSelectionEntry) => { match: boolean; bypassBackoff: boolean };
+};
+
+const deliveryQueueMocks = vi.hoisted(() => ({
+  drainPendingDeliveries: vi.fn(async (_opts: unknown) => undefined),
+}));
+
+vi.mock("openclaw/plugin-sdk/delivery-queue-runtime", () => ({
+  drainPendingDeliveries: deliveryQueueMocks.drainPendingDeliveries,
+}));
+
 installWebAutoReplyTestHomeHooks();
 
 function requireOnMessage(
@@ -247,6 +266,78 @@ describe("web auto-reply connection", () => {
     expect(sleep).toHaveBeenCalled();
   });
 
+  it("drains pending deliveries while connected and stops after close", async () => {
+    vi.useFakeTimers();
+    try {
+      const sleep = vi.fn(async () => {});
+      const scripted = createScriptedWebListenerFactory();
+      const { controller, run } = startWebAutoReplyMonitor({
+        monitorWebChannelFn: monitorWebChannel as never,
+        listenerFactory: scripted.listenerFactory,
+        sleep,
+        accountId: "work",
+      });
+
+      await vi.waitFor(
+        () => {
+          expect(scripted.getListenerCount()).toBe(1);
+        },
+        { timeout: 250, interval: 2 },
+      );
+      expect(deliveryQueueMocks.drainPendingDeliveries).toHaveBeenCalledWith(
+        expect.objectContaining({
+          drainKey: "whatsapp:work",
+          logLabel: "WhatsApp reconnect drain",
+        }),
+      );
+
+      deliveryQueueMocks.drainPendingDeliveries.mockClear();
+      await vi.advanceTimersByTimeAsync(30_000);
+      await vi.waitFor(() => {
+        expect(deliveryQueueMocks.drainPendingDeliveries).toHaveBeenCalledTimes(1);
+      });
+
+      const periodicCall = deliveryQueueMocks.drainPendingDeliveries.mock.calls.at(-1)?.[0] as
+        | DrainPendingDeliveriesCall
+        | undefined;
+      expect(periodicCall).toBeDefined();
+      if (!periodicCall) {
+        throw new Error("Expected WhatsApp periodic drain call");
+      }
+      expect(periodicCall.drainKey).toBe("whatsapp:work");
+      expect(periodicCall.logLabel).toBe("WhatsApp periodic drain");
+      expect(
+        periodicCall.selectEntry({
+          channel: "whatsapp",
+          accountId: "work",
+        }),
+      ).toEqual({ match: true, bypassBackoff: false });
+      expect(
+        periodicCall.selectEntry({
+          channel: "whatsapp",
+          accountId: "default",
+        }),
+      ).toEqual({ match: false, bypassBackoff: false });
+      expect(
+        periodicCall.selectEntry({
+          channel: "telegram",
+          accountId: "work",
+        }),
+      ).toEqual({ match: false, bypassBackoff: false });
+
+      controller.abort();
+      scripted.resolveClose(0, { status: 499, isLoggedOut: false, error: "aborted" });
+      await Promise.resolve();
+      await run;
+
+      deliveryQueueMocks.drainPendingDeliveries.mockClear();
+      await vi.advanceTimersByTimeAsync(30_000);
+      expect(deliveryQueueMocks.drainPendingDeliveries).not.toHaveBeenCalled();
+    } finally {
+      vi.useRealTimers();
+    }
+  });
+
   it("treats status 440 as non-retryable and stops without retrying", async () => {
     const sleep = vi.fn(async () => {});
     const scripted = createScriptedWebListenerFactory();
diff --git a/extensions/whatsapp/src/auto-reply/monitor.ts b/extensions/whatsapp/src/auto-reply/monitor.ts
index 1990fd89bf1..795112c65bb 100644
--- a/extensions/whatsapp/src/auto-reply/monitor.ts
+++ b/extensions/whatsapp/src/auto-reply/monitor.ts
@@ -541,17 +541,40 @@ export async function monitorWebChannel(
         );
       });
 
+      const periodicDrainInterval = setInterval(() => {
+        void drainPendingDeliveries({
+          drainKey: `whatsapp:${normalizedAccountId}`,
+          logLabel: "WhatsApp periodic drain",
+          cfg,
+          log: reconnectLogger,
+          selectEntry: (entry) => ({
+            match:
+              entry.channel === "whatsapp" &&
+              normalizeReconnectAccountId(entry.accountId) === normalizedAccountId,
+            bypassBackoff: false,
+          }),
+        }).catch((err) => {
+          reconnectLogger.warn(
+            { connectionId: connection.connectionId, error: String(err) },
+            "periodic drain failed",
+          );
+        });
+      }, 30_000);
+
       whatsappLog.info("Listening for personal WhatsApp inbound messages.");
       if (process.stdout.isTTY || process.stderr.isTTY) {
         whatsappLog.raw("Ctrl+C to stop.");
       }
 
       if (!keepAlive) {
+        clearInterval(periodicDrainInterval);
         await controller.shutdown();
         return;
       }
 
-      const reason = await controller.waitForClose();
+      const reason = await controller
+        .waitForClose()
+        .finally(() => clearInterval(periodicDrainInterval));
       if (stopRequested() || sigintStop || reason === "aborted") {
         await controller.shutdown();
         break;