diff --git a/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/src/env.d.ts b/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/src/env.d.ts
index aaf72be7640b..15557b010a50 100644
--- a/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/src/env.d.ts
+++ b/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/src/env.d.ts
@@ -1,4 +1,5 @@
 interface Env {
   E2E_TEST_DSN: string;
   SLEEP_WORKFLOW: Workflow;
+  AI: Ai;
 }
diff --git a/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/src/index.ts b/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/src/index.ts
index 93f1c24f124e..324c9161cf69 100644
--- a/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/src/index.ts
+++ b/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/src/index.ts
@@ -27,6 +27,10 @@ export default {
       }
       case '/test-unhandled-error':
         throw new Error('E2E test unhandled error');
+      case '/test-workers-ai': {
+        await env.AI.run('@cf/meta/llama-3.2-1b-instruct', { prompt: 'Say hi', max_tokens: 5 });
+        return Response.json({ traceId: spanContext?.traceId });
+      }
       case '/test-span':
         return Response.json({ spanId: spanContext?.spanId, traceId: spanContext?.traceId });
       case '/test-workflow-sleep': {
diff --git a/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/tests/send-to-sentry.test.ts b/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/tests/send-to-sentry.test.ts
index 8578ecb7bee7..044883dea3b0 100644
--- a/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/tests/send-to-sentry.test.ts
+++ b/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/tests/send-to-sentry.test.ts
@@ -2,6 +2,7 @@ import { randomBytes } from 'node:crypto';
 import { expect, test } from '@playwright/test';
 import {
   EVENT_POLLING_OPTIONS,
+  fetchSpanAttributes,
   fetchTrace,
   findErrorInTrace,
   findSpanInTrace,
@@ -73,3 +74,22 @@ test('Sends the spans of Workflow steps before the Workflow goes to sleep', asyn
   );
   expect(['running', 'waiting']).toContain(status);
 });
+
+test('Sends a Workers AI gen_ai span to Sentry', async () => {
+  const { traceId }: { traceId: string } = JSON.parse(await fetchFromWorker(`${workerUrl}/test-workers-ai`, 200));
+
+  console.log(`Polling for gen_ai.chat span: sentry trace view ${traceTarget(traceId)}`);
+
+  let spanId: string | undefined;
+  await expect
+    .poll(() => (spanId = findSpanInTrace(traceId, 'gen_ai.chat')?.event_id), EVENT_POLLING_OPTIONS)
+    .toBeDefined();
+
+  // Sentry stores `gen_ai.response.text` as `gen_ai.output.messages`.
+  await expect
+    .poll(() => fetchSpanAttributes(traceId, spanId!), EVENT_POLLING_OPTIONS)
+    .toMatchObject({
+      'gen_ai.input.messages': expect.stringContaining('Say hi'),
+      'gen_ai.output.messages': expect.stringContaining('"role":"assistant"'),
+    });
+});
diff --git a/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/wrangler.jsonc b/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/wrangler.jsonc
index d6b15b1dbf5e..f1c0857ea5dd 100644
--- a/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/wrangler.jsonc
+++ b/dev-packages/e2e-tests/test-applications/cloudflare-workers-send-to-sentry/wrangler.jsonc
@@ -6,6 +6,7 @@
   "compatibility_date": "2026-05-20",
   "compatibility_flags": ["nodejs_compat"],
   "workers_dev": true,
+  "ai": { "binding": "AI" },
   // Workers Logs keep the invocations of the last 7 days, so a failed CI run can still be inspected.
   "observability": { "enabled": true },
   // Workflow names are unique per account, so deployWorker() renames it to the worker name.