diff --git a/include/pybind11/pytypes.h b/include/pybind11/pytypes.h
index d7482927b..feb18ac63 100644
--- a/include/pybind11/pytypes.h
+++ b/include/pybind11/pytypes.h
@@ -2571,11 +2571,10 @@ template <typename D>
 object object_api<D>::annotations() const {
 // Python 3.8, 3.9
 #if PY_MAJOR_VERSION == 3 && PY_MINOR_VERSION <= 9
-    if (hasattr(derived(), "__dict__")) {
-        return getattr(getattr(derived(), "__dict__"), "__annotations__", dict());
-    } else {
-        return getattr(derived(), "__annotations__", dict());
+    if (!hasattr(derived(), "__annotations__")) {
+        setattr(derived(), "__annotations__", dict());
     }
+    return attr("__annotations__");
 // Python 3.10+
 #else
     return getattr(derived(), "__annotations__", dict());
diff --git a/tests/test_pytypes.py b/tests/test_pytypes.py
index 332f2125e..44f161a14 100644
--- a/tests/test_pytypes.py
+++ b/tests/test_pytypes.py
@@ -1125,7 +1125,6 @@ def test_class_attribute_types() -> None:
     assert empty_annotations == {}
     assert annotations["x"] == "float"
     assert annotations["dict_str_int"] == "dict[str, int]"
-    assert False
 
 
 def test_final_annotation() -> None: