fix(cloudflare): Use original waitUntil to not create a deadlock

packages/cloudflare/src/flush.ts

@@ -9,6 +9,7 @@ type FlushLock = {
 
 type FlushLockRegistry = {
   readonly locks: Set<FlushLockInternal>;
+  readonly originalWaitUntil: ExecutionContext['waitUntil'];
 };
 
 type FlushLockInternal = FlushLock & {
@@ -18,6 +19,27 @@ type FlushLockInternal = FlushLock & {
 
 const flushLockRegistries = new WeakMap<ExecutionContext['waitUntil'], FlushLockRegistry>();
 
+/**
+ * Returns the original (un-instrumented) waitUntil function for a context.
+ * This should be used when calling waitUntil with flushAndDispose to avoid deadlock.
+ *
+ * The flush lock mechanism wraps context.waitUntil to track pending tasks.
+ * If we call waitUntil(flushAndDispose(client)) through the instrumented version,
+ * it creates a deadlock because:
+ * 1. The instrumented waitUntil acquires the flush lock
+ * 2. flushAndDispose calls client.flush() which waits for the lock to be released
+ * 3. The lock won't be released until the waitUntil promise completes
+ * 4. The waitUntil promise won't complete until flush() returns
+ *
+ * By using the original waitUntil for flush operations, we bypass this issue.
+ */
+export function getOriginalWaitUntil(context: ExecutionContext): ExecutionContext['waitUntil'] | undefined {
+  // eslint-disable-next-line @typescript-eslint/unbound-method
+  const currentWaitUntil = context.waitUntil;
+  const original = flushLockRegistries.get(currentWaitUntil)?.originalWaitUntil;
+  return original ?? currentWaitUntil;
+}
+
 /**
  * Enhances the given execution context by wrapping its `waitUntil` method with a proxy
  * to monitor pending tasks, and provides a flusher function to ensure all tasks
@@ -67,8 +89,8 @@ function getOrCreateFlushLockRegistry(context: ExecutionContext): FlushLockRegis
     return existingRegistry;
   }
 
-  const registry: FlushLockRegistry = { locks: new Set() };
   const originalWaitUntil = context.waitUntil.bind(context) as typeof context.waitUntil;
+  const registry: FlushLockRegistry = { locks: new Set(), originalWaitUntil };
   const instrumentedWaitUntil: typeof context.waitUntil = promise => {
     // Snapshot active locks so locks created after this call do not wait for earlier waitUntil work.
     const locks = [...registry.locks];

packages/cloudflare/src/request.ts

@@ -14,7 +14,7 @@ import {
 } from '@sentry/core';
 import { captureIncomingRequestBody } from './integrations/httpServer';
 import type { CloudflareOptions } from './client';
-import { flushAndDispose } from './flush';
+import { flushAndDispose, getOriginalWaitUntil } from './flush';
 import { addCloudResourceContext, addCultureContext, addRequest } from './scope-utils';
 import { init } from './sdk';
 import { classifyResponseStreaming } from './utils/streaming';
@@ -47,7 +47,12 @@ export function wrapRequestHandler(
     const { options, request, captureErrors = true } = wrapperOptions;
     const context = wrapperOptions.context;
 
-    const waitUntil = context?.waitUntil?.bind?.(context);
+    // Use getOriginalWaitUntil to get the un-instrumented waitUntil function.
+    // This is crucial to avoid deadlock: the flush lock mechanism wraps waitUntil
+    // to track pending tasks. If we use the instrumented version for flushAndDispose,
+    // it acquires the lock, then flushAndDispose tries to wait for the same lock,
+    // creating a deadlock.
+    const waitUntil = context ? getOriginalWaitUntil(context)?.bind(context) : undefined;
 
     const client = init({ ...options, ctx: context });
     isolationScope.setClient(client);

packages/cloudflare/test/flush.test.ts

@@ -2,7 +2,7 @@ import { type ExecutionContext } from '@cloudflare/workers-types';
 import * as sentryCore from '@sentry/core';
 import { type Client } from '@sentry/core';
 import { describe, expect, it, onTestFinished, vi } from 'vitest';
-import { flushAndDispose, makeFlushLock } from '../src/flush';
+import { flushAndDispose, getOriginalWaitUntil, makeFlushLock } from '../src/flush';
 
 describe('Flush buffer test', () => {
   const waitUntilPromises: Promise<void>[] = [];
@@ -109,3 +109,78 @@ describe('flushAndDispose', () => {
     flushSpy.mockRestore();
   });
 });
+
+describe('getOriginalWaitUntil', () => {
+  it('returns the original waitUntil before instrumentation', () => {
+    const originalWaitUntil = vi.fn();
+    const context: ExecutionContext = {
+      waitUntil: originalWaitUntil,
+      passThroughOnException: vi.fn(),
+    };
+
+    const result = getOriginalWaitUntil(context);
+    expect(result).toBe(originalWaitUntil);
+  });
+
+  it('returns the original waitUntil after instrumentation', () => {
+    const originalWaitUntil = vi.fn();
+    const context: ExecutionContext = {
+      waitUntil: originalWaitUntil,
+      passThroughOnException: vi.fn(),
+    };
+
+    makeFlushLock(context);
+
+    const result = getOriginalWaitUntil(context);
+
+    expect(result).not.toBe(context.waitUntil);
+    expect(result).toBeDefined();
+    result!(Promise.resolve());
+    expect(originalWaitUntil).toHaveBeenCalled();
+  });
+
+  it('returns the original waitUntil after multiple instrumentations', () => {
+    const originalWaitUntil = vi.fn();
+    const context: ExecutionContext = {
+      waitUntil: originalWaitUntil,
+      passThroughOnException: vi.fn(),
+    };
+
+    makeFlushLock(context);
+    makeFlushLock(context);
+    makeFlushLock(context);
+
+    const result = getOriginalWaitUntil(context);
+
+    expect(result).not.toBe(context.waitUntil);
+    result!(Promise.resolve());
+    expect(originalWaitUntil).toHaveBeenCalled();
+  });
+
+  it('allows flushAndDispose to complete when called via original waitUntil', async () => {
+    const waitUntilPromises: Promise<void>[] = [];
+    const context: ExecutionContext = {
+      waitUntil: vi.fn(promise => {
+        waitUntilPromises.push(promise);
+      }),
+      passThroughOnException: vi.fn(),
+    };
+
+    const lock = makeFlushLock(context);
+
+    const mockClient = {
+      flush: vi.fn(async () => {
+        await lock.finalize();
+        return true;
+      }),
+      dispose: vi.fn(),
+    } as unknown as Client;
+
+    const originalWaitUntil = getOriginalWaitUntil(context);
+    originalWaitUntil!.call(context, flushAndDispose(mockClient));
+
+    await vi.waitFor(() => Promise.all(waitUntilPromises));
+    expect(mockClient.flush).toHaveBeenCalled();
+    expect(mockClient.dispose).toHaveBeenCalled();
+  });
+});