diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5151bdff365..ae4be395195 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -285,6 +285,7 @@ Docs: https://docs.openclaw.ai
 - Gateway/systemd service restart hardening: clear stale gateway listeners by explicit run-port before service bind, add restart stale-pid port-override support, tune systemd start/stop/exit handling, and disable detached child mode only in service-managed runtime so cgroup stop semantics clean up descendants reliably. (#38463) Thanks @spirittechie.
 - Discord/plugin native command aliases: let plugins declare provider-specific slash names so native Discord registration can avoid built-in command collisions; the bundled Talk voice plugin now uses `/talkvoice` natively on Discord while keeping text `/voice`.
 - Daemon/Windows schtasks status normalization: derive runtime state from locale-neutral numeric `Last Run Result` codes only (without language string matching) and surface unknown when numeric result data is unavailable, preventing locale-specific misclassification drift. (#39153) Thanks @scoootscooob.
+- Telegram/polling conflict recovery: reset the polling `webhookCleared` latch on `getUpdates` 409 conflicts so webhook cleanup re-runs on restart cycles and polling avoids infinite conflict loops. (#39205) Thanks @amittell.
 
 ## 2026.3.2
 
diff --git a/src/telegram/monitor.test.ts b/src/telegram/monitor.test.ts
index b5f072ebfd1..d5dc43c5335 100644
--- a/src/telegram/monitor.test.ts
+++ b/src/telegram/monitor.test.ts
@@ -591,6 +591,44 @@ describe("monitorTelegramProvider (grammY)", () => {
     expect(api.getUpdates).not.toHaveBeenCalled();
   });
 
+  it("resets webhookCleared latch on 409 conflict so deleteWebhook re-runs", async () => {
+    const abort = new AbortController();
+    api.deleteWebhook.mockReset();
+    api.deleteWebhook.mockResolvedValue(true);
+
+    const conflictError = Object.assign(
+      new Error("Conflict: terminated by other getUpdates request"),
+      {
+        error_code: 409,
+        method: "getUpdates",
+      },
+    );
+
+    let pollingCycle = 0;
+    runSpy
+      // First cycle: throw 409 conflict
+      .mockImplementationOnce(() =>
+        makeRunnerStub({
+          task: () => {
+            pollingCycle++;
+            return Promise.reject(conflictError);
+          },
+        }),
+      )
+      // Second cycle: succeed then abort
+      .mockImplementationOnce(() => {
+        pollingCycle++;
+        return makeAbortRunner(abort);
+      });
+
+    await monitorTelegramProvider({ token: "tok", abortSignal: abort.signal });
+
+    // deleteWebhook should be called twice: once on initial cleanup, once after 409 reset
+    expect(api.deleteWebhook).toHaveBeenCalledTimes(2);
+    expect(pollingCycle).toBe(2);
+    expect(runSpy).toHaveBeenCalledTimes(2);
+  });
+
   it("falls back to configured webhookSecret when not passed explicitly", async () => {
     await monitorTelegramProvider({
       token: "tok",
diff --git a/src/telegram/monitor.ts b/src/telegram/monitor.ts
index 16c2db551b4..c4e12959953 100644
--- a/src/telegram/monitor.ts
+++ b/src/telegram/monitor.ts
@@ -373,6 +373,9 @@ export async function monitorTelegramProvider(opts: MonitorTelegramOpts = {}) {
           throw err;
         }
         const isConflict = isGetUpdatesConflict(err);
+        if (isConflict) {
+          webhookCleared = false;
+        }
         const isRecoverable = isRecoverableTelegramNetworkError(err, { context: "polling" });
         if (!isConflict && !isRecoverable) {
           throw err;