diff --git a/Lib/test/test_asyncgen.py b/Lib/test/test_asyncgen.py
index b5e0891feb794e..e05dcd6203bd3a 100644
--- a/Lib/test/test_asyncgen.py
+++ b/Lib/test/test_asyncgen.py
@@ -905,6 +905,47 @@ def test_aiter_callable_exhausted(self):
         with self.assertRaises(StopAsyncIteration):
             self.loop.run_until_complete(anext(it))
 
+    def test_aiter_callable_reentrant_sentinel_compare(self):
+        stop = False
+        destroyed = []
+        compared = []
+
+        async def produce():
+            return Result()
+
+        def fetch():
+            nonlocal stop
+            if stop:
+                raise StopAsyncIteration
+            return produce()
+
+        class Sentinel:
+            def __del__(self):
+                destroyed.append(True)
+
+            def __eq__(self, other):
+                nonlocal stop
+                stop = True
+                aw = ait.__anext__()
+                try:
+                    aw.__await__().send(None)
+                except StopAsyncIteration:
+                    pass
+                return NotImplemented
+
+        class Result:
+            def __eq__(self, other):
+                compared.append(isinstance(other, Sentinel) and not destroyed)
+                return NotImplemented
+
+        ait = aiter(fetch, Sentinel())
+        with self.assertRaises(StopIteration) as cm:
+            ait.__anext__().__await__().send(None)
+        self.assertIsInstance(cm.exception.value, Result)
+        self.assertEqual(compared, [True])
+        with self.assertRaises(StopAsyncIteration):
+            ait.__anext__().__await__().send(None)
+
     def test_aiter_callable_lazy(self):
         # The callable is only called when the awaitable is awaited
         calls = []
diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2026-09-23-21-41-01.gh-issue-158033.mK8rLt.rst b/Misc/NEWS.d/next/Core_and_Builtins/2026-09-23-21-41-01.gh-issue-158033.mK8rLt.rst
new file mode 100644
index 00000000000000..3dd5aac5625d87
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2026-09-23-21-41-01.gh-issue-158033.mK8rLt.rst
@@ -0,0 +1,3 @@
+Fix a use-after-free in the two-argument form of :func:`aiter` when comparing
+the sentinel. A reentrant equality comparison could exhaust the iterator and
+free the sentinel while the comparison was still using it.
diff --git a/Objects/iterobject.c b/Objects/iterobject.c
index 2d5e3709a27dfb..a8278d81713146 100644
--- a/Objects/iterobject.c
+++ b/Objects/iterobject.c
@@ -641,7 +641,9 @@ acallawaitable_handle_error(acallawaitableobject *aw)
         }
         int ok = 0;
         if (it->it_sentinel != NULL) {
-            ok = PyObject_RichCompareBool(it->it_sentinel, value, Py_EQ);
+            PyObject *sentinel = Py_NewRef(it->it_sentinel);
+            ok = PyObject_RichCompareBool(sentinel, value, Py_EQ);
+            Py_DECREF(sentinel);
         }
         if (ok == 0) {
             (void)_PyGen_SetStopIterationValue(value);