diff --git a/include/pybind11/pytypes.h b/include/pybind11/pytypes.h
index 6606b7c03..ee8cc82bf 100644
--- a/include/pybind11/pytypes.h
+++ b/include/pybind11/pytypes.h
@@ -2567,7 +2567,13 @@ str_attr_accessor object_api<D>::doc() const {
 
 template <typename D>
 str_attr_accessor object_api<D>::annotations() const {
-    str_attr_accessor annotations_dict = attr("__annotations__");
+    // Create dict automatically
+
+    #if !defined(PYPY_VERSION) && PY_MAJOR_VERSION == 3 && PY_MINOR_VERSION <= 9
+        str_attr_accessor annotations_dict = attr("__dict__").attr("__annotations__");
+    #else
+        str_attr_accessor annotations_dict = attr("__annotations__");
+    #endif
     // Create dict automatically
     if (!isinstance<dict>(annotations_dict)) {
         annotations_dict = dict();