diff --git a/extensions/telegram/src/webhook.test.ts b/extensions/telegram/src/webhook.test.ts
index 9b9ca471d330..397f1241dbaf 100644
--- a/extensions/telegram/src/webhook.test.ts
+++ b/extensions/telegram/src/webhook.test.ts
@@ -920,6 +920,28 @@ describe("startTelegramWebhook", () => {
     }
   });
 
+  it("continues webhook shutdown after bot stop fails", async () => {
+    const runtimeError = vi.fn();
+    const setStatus = vi.fn();
+    stopSpy.mockRejectedValueOnce(new Error("bot stop failed"));
+
+    const started = await startTelegramWebhook({
+      token: TELEGRAM_TOKEN,
+      port: 0,
+      secret: TELEGRAM_SECRET,
+      path: TELEGRAM_WEBHOOK_PATH,
+      spoolDir: requireWebhookSpoolDir(),
+      setStatus,
+      runtime: { log: vi.fn(), error: runtimeError, exit: vi.fn() },
+    });
+
+    await expect(started.stop()).resolves.toBeUndefined();
+
+    expect(transportCloseSpies[0]).toHaveBeenCalledOnce();
+    expect(setStatus).toHaveBeenLastCalledWith({ mode: "webhook", connected: false });
+    expectMockMessageContains(runtimeError, "telegram webhook bot stop failed");
+  });
+
   it("marks delivery accepted only after the durable enqueue commits", async () => {
     let releaseEnqueue: (() => void) | undefined;
     let markEnqueueStarted: (() => void) | undefined;
diff --git a/extensions/telegram/src/webhook.ts b/extensions/telegram/src/webhook.ts
index 3224a2df1650..7bb9dd417c47 100644
--- a/extensions/telegram/src/webhook.ts
+++ b/extensions/telegram/src/webhook.ts
@@ -529,24 +529,41 @@ export async function startTelegramWebhook(opts: {
   });
 
   let webhookAdvertised = false;
+  const runShutdownPhase = async (
+    label: string,
+    run: () => void | Promise<void>,
+  ): Promise<void> => {
+    try {
+      await run();
+    } catch (err) {
+      runtime.error?.(`telegram webhook ${label} failed: ${formatErrorMessage(err)}`);
+    }
+  };
   const shutdown = async () => {
     if (shutDown) {
       return;
     }
-    botAbortController.abort();
     shutDown = true;
+    botAbortController.abort();
     shutdownAbortController.abort();
-    const ingressStopTask = webhookIngressMonitor?.stop();
+    // Every fallible phase is isolated so one failed release cannot skip the
+    // remaining resources or reject the fire-and-forget abort hook.
+    const ingressMonitor = webhookIngressMonitor;
     webhookIngressMonitor = undefined;
-    server.close();
-    await bot.stop();
+    const ingressStopTask = ingressMonitor
+      ? runShutdownPhase("ingress stop", () => ingressMonitor.stop())
+      : undefined;
+    await runShutdownPhase("server close", () => {
+      server.close();
+    });
+    await runShutdownPhase("bot stop", () => bot.stop());
     // The webhook owns this transport because it resolved and injected it into
     // createTelegramBot; close once so abort/startup-failure paths cannot leak sockets.
-    await closeTransportOnce();
-    await waitForWebhookIngressStop(ingressStopTask);
-    status.noteWebhookStop();
+    await runShutdownPhase("transport close", closeTransportOnce);
+    await runShutdownPhase("ingress drain", () => waitForWebhookIngressStop(ingressStopTask));
+    await runShutdownPhase("status update", () => status.noteWebhookStop());
     if (diagnosticsEnabled) {
-      stopDiagnosticHeartbeat();
+      await runShutdownPhase("diagnostics stop", () => stopDiagnosticHeartbeat());
     }
   };
   if (opts.abortSignal?.aborted) {