diff --git a/include/pybind11/cast.h b/include/pybind11/cast.h
index 82ec2b6d0..df18157db 100644
--- a/include/pybind11/cast.h
+++ b/include/pybind11/cast.h
@@ -1366,11 +1366,8 @@ object object_or_cast(T &&o) {
     return pybind11::cast(std::forward<T>(o));
 }
 
-// This is being used to get around the conflict with the deprecated str() function on object_api
-using py_str = str;
-
 // Declared in pytypes.h:
-// Written here so make_caster<T> can be used
+// Implemented here so that make_caster<T> can be used.
 template <typename D>
 template <typename T>
 str_attr_accessor object_api<D>::attr_with_type_hint(const char *key) const {
@@ -1390,19 +1387,8 @@ str_attr_accessor object_api<D>::attr_with_type_hint(const char *key) const {
 template <typename D>
 template <typename T>
 obj_attr_accessor object_api<D>::attr_with_type_hint(handle key) const {
-#if !defined(__cpp_inline_variables)
-    static_assert(!std::is_same<T, T>::value,
-                  "C++17 feature __cpp_inline_variables not available: "
-                  "https://en.cppreference.com/w/cpp/language/static#Static_data_members");
-#endif
-    object ann = annotations();
-    auto reinterpreted_key = reinterpret_borrow<object>(key);
-    if (ann.contains(reinterpreted_key)) {
-        throw std::runtime_error("__annotations__[\"" + std::string(py_str(reinterpreted_key))
-                                 + "\"] was set already.");
-    }
-    ann[key] = make_caster<T>::name.text;
-    return {derived(), reinterpreted_key};
+    (void) attr_with_type_hint<T>(key.cast<std::string>().c_str());
+    return {derived(), reinterpret_borrow<object>(key)};
 }
 
 // Placeholder type for the unneeded (and dead code) static variable in the
diff --git a/include/pybind11/pytypes.h b/include/pybind11/pytypes.h
index d8d158b95..def7a122f 100644
--- a/include/pybind11/pytypes.h
+++ b/include/pybind11/pytypes.h
@@ -116,7 +116,6 @@ public:
     // attr_with_type_hint is implemented in cast.h:
     template <typename T>
     obj_attr_accessor attr_with_type_hint(handle key) const;
-
     template <typename T>
     str_attr_accessor attr_with_type_hint(const char *key) const;
 
diff --git a/tests/test_pytypes.cpp b/tests/test_pytypes.cpp
index 311aa50b5..b4fa99192 100644
--- a/tests/test_pytypes.cpp
+++ b/tests/test_pytypes.cpp
@@ -1039,8 +1039,10 @@ TEST_SUBMODULE(pytypes, m) {
 #endif
 
 #if defined(__cpp_inline_variables)
+    // Exercises const char* overload:
     m.attr_with_type_hint<py::typing::List<int>>("list_int") = py::list();
-    m.attr_with_type_hint<py::typing::Set<py::str>>("set_str") = py::set();
+    // Exercises py::handle overload:
+    m.attr_with_type_hint<py::typing::Set<py::str>>(py::str("set_str")) = py::set();
 
     struct Empty {};
     py::class_<Empty>(m, "EmptyAnnotationClass");