From 81ece77f8c012d7131e4b5cbd9a236f7a33c55cf Mon Sep 17 00:00:00 2001
From: Ayaan Zaidi <hi@obviy.us>
Date: Sun, 3 May 2026 20:07:24 +0530
Subject: [PATCH] test(telegram): cover polling after webhook cleanup timeout

---
 extensions/telegram/src/monitor.test.ts       | 37 ++++++-------------
 .../telegram/src/polling-session.test.ts      | 24 ++++++++++++
 2 files changed, 35 insertions(+), 26 deletions(-)

diff --git a/extensions/telegram/src/monitor.test.ts b/extensions/telegram/src/monitor.test.ts
index 757540a833d..a44f856468d 100644
--- a/extensions/telegram/src/monitor.test.ts
+++ b/extensions/telegram/src/monitor.test.ts
@@ -495,50 +495,35 @@ describe("monitorTelegramProvider (grammY)", () => {
     expect(order).toEqual(["deleteWebhook", "run"]);
   });
 
-  it("retries recoverable deleteWebhook failures before polling", async () => {
+  it("starts polling after recoverable deleteWebhook failures", async () => {
     const abort = new AbortController();
     const cleanupError = makeRecoverableFetchError();
     api.deleteWebhook.mockReset();
-    api.getWebhookInfo.mockReset().mockResolvedValueOnce({ url: "https://example.test/hook" });
-    api.deleteWebhook.mockRejectedValueOnce(cleanupError).mockResolvedValueOnce(true);
-    mockRunOnceAndAbort(abort);
-
-    await monitorTelegramProvider({ token: "tok", abortSignal: abort.signal });
-
-    expect(api.deleteWebhook).toHaveBeenCalledTimes(2);
-    expect(api.getWebhookInfo).toHaveBeenCalledTimes(1);
-    expectRecoverableRetryState(1);
-  });
-
-  it("continues polling when deleteWebhook transiently fails but webhook is already absent", async () => {
-    const abort = new AbortController();
-    const cleanupError = makeRecoverableFetchError();
-    api.deleteWebhook.mockReset();
-    api.getWebhookInfo.mockReset().mockResolvedValueOnce({ url: "" });
+    api.getWebhookInfo.mockReset();
     api.deleteWebhook.mockRejectedValueOnce(cleanupError);
     mockRunOnceAndAbort(abort);
 
     await monitorTelegramProvider({ token: "tok", abortSignal: abort.signal });
 
     expect(api.deleteWebhook).toHaveBeenCalledTimes(1);
-    expect(api.getWebhookInfo).toHaveBeenCalledTimes(1);
-    expect(runSpy).toHaveBeenCalledTimes(1);
-    expect(sleepWithAbort).not.toHaveBeenCalled();
+    expect(api.getWebhookInfo).not.toHaveBeenCalled();
+    expectRecoverableRetryState(1);
   });
 
-  it("retries cleanup when deleteWebhook and webhook confirmation both transiently fail", async () => {
+  it("does not run webhook confirmation when deleteWebhook transiently fails", async () => {
     const abort = new AbortController();
     const cleanupError = makeRecoverableFetchError();
     api.deleteWebhook.mockReset();
-    api.getWebhookInfo.mockReset().mockRejectedValueOnce(makeRecoverableFetchError());
-    api.deleteWebhook.mockRejectedValueOnce(cleanupError).mockResolvedValueOnce(true);
+    api.getWebhookInfo.mockReset();
+    api.deleteWebhook.mockRejectedValueOnce(cleanupError);
     mockRunOnceAndAbort(abort);
 
     await monitorTelegramProvider({ token: "tok", abortSignal: abort.signal });
 
-    expect(api.deleteWebhook).toHaveBeenCalledTimes(2);
-    expect(api.getWebhookInfo).toHaveBeenCalledTimes(1);
-    expectRecoverableRetryState(1);
+    expect(api.deleteWebhook).toHaveBeenCalledTimes(1);
+    expect(api.getWebhookInfo).not.toHaveBeenCalled();
+    expect(runSpy).toHaveBeenCalledTimes(1);
+    expect(sleepWithAbort).not.toHaveBeenCalled();
   });
 
   it("retries setup-time recoverable errors before starting polling", async () => {
diff --git a/extensions/telegram/src/polling-session.test.ts b/extensions/telegram/src/polling-session.test.ts
index e86923c5ac2..553fb750080 100644
--- a/extensions/telegram/src/polling-session.test.ts
+++ b/extensions/telegram/src/polling-session.test.ts
@@ -572,6 +572,30 @@ describe("TelegramPollingSession", () => {
     expect(createTelegramTransport).toHaveBeenCalledTimes(1);
   });
 
+  it("starts polling when webhook cleanup times out during startup", async () => {
+    const abort = new AbortController();
+    const cleanupError = new Error("Telegram deleteWebhook timed out after 15000ms");
+    const bot = makeBot();
+    bot.api.deleteWebhook.mockRejectedValueOnce(cleanupError);
+    createTelegramBotMock.mockReturnValueOnce(bot);
+    runMock.mockReturnValueOnce({
+      task: async () => {
+        abort.abort();
+      },
+      stop: vi.fn(async () => undefined),
+      isRunning: () => false,
+    });
+
+    const session = createPollingSession({
+      abortSignal: abort.signal,
+    });
+
+    await session.runUntilAbort();
+
+    expect(bot.api.deleteWebhook).toHaveBeenCalledTimes(1);
+    expect(runMock).toHaveBeenCalledTimes(1);
+  });
+
   it("does not trigger stall restart shortly after a getUpdates error", async () => {
     const abort = new AbortController();
     const botStop = vi.fn(async () => undefined);