@@ -1713,6 +1713,37 @@ def annotate(format, /):
             with self.assertRaises(DemoException):
                 annotationlib.call_annotate_function(annotate, format=fmt)
 
+    def test_generated_annotate_non_bool_compare_result(self):
+        class NonBool(int):
+            def __gt__(self, other):
+                return None
+
+        # Function __annotate__
+        def func(x: int):
+            pass
+
+        self.assertEqual(
+            func.__annotate__(NonBool(1)),
+            {"x": int},
+        )
+
+        # Class __annotate__
+        class C:
+            y: int
+
+        self.assertEqual(
+            C.__annotate__(NonBool(1)),
+            {"y": int},
+        )
+
+        # Module __annotate__
+        ns = {}
+        exec("z: int", ns)
+
+        self.assertEqual(
+            ns["__annotate__"](NonBool(1)),
+            {"z": int},
+        )
 
 class MetaclassTests(unittest.TestCase):
     def test_annotated_meta(self):

diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2026-07-09-13-28-27.gh-issue-153354.It4Jj_.rst b/Misc/NEWS.d/next/Core_and_Builtins/2026-07-09-13-28-27.gh-issue-153354.It4Jj_.rst
@@ -0,0 +1,2 @@
+Fix a crash in compiler-generated ``__annotate__`` functions when the
+annotation format comparison returned a non-boolean result.
@@ -724,6 +724,7 @@ codegen_setup_annotations_scope(compiler *c, location loc,
     ADDOP_I(c, loc, LOAD_FAST, 0);
     ADDOP_LOAD_CONST_NEW(c, loc, value_with_fake_globals);
     ADDOP_I(c, loc, COMPARE_OP, (Py_GT << 5) | compare_masks[Py_GT]);
+    ADDOP(c, loc, TO_BOOL);
     NEW_JUMP_TARGET_LABEL(c, body);
     ADDOP_JUMP(c, loc, POP_JUMP_IF_FALSE, body);
     ADDOP_I(c, loc, LOAD_COMMON_CONSTANT, CONSTANT_NOTIMPLEMENTEDERROR);
Original file line number	Diff line number	Diff line change
		@@ -0,0 +1,2 @@
		Fix a crash in compiler-generated ``__annotate__`` functions when the
		annotation format comparison returned a non-boolean result.