diff --git a/include/pybind11/pybind11.h b/include/pybind11/pybind11.h
index 1806583e6..d71068bae 100644
--- a/include/pybind11/pybind11.h
+++ b/include/pybind11/pybind11.h
@@ -101,6 +101,31 @@ inline std::string replace_newlines_and_squash(const char *text) {
 #    define PYBIND11_COMPAT_STRDUP strdup
 #endif
 
+/// Type trait checker for `descr`.
+template<typename>
+struct is_descr : std::false_type {};
+
+template<size_t N, typename... Ts>
+struct is_descr<descr<N, Ts...>> : std::true_type {};
+
+template<size_t N, typename... Ts>
+struct is_descr<const descr<N, Ts...>> : std::true_type {};
+
+/// Checks for `return_name` in `type_caster` to replace `name` for return type hints.
+/// this is useful for having a different python type hint for args vs return value,
+/// e.g., `std::filesystem::path` -> Arg: `Union[os.PathLike, str, bytes]`, return: `Path`.
+template<typename T, typename Enable = void>
+struct as_return_type
+{
+    static constexpr auto name = T::name;
+};
+
+template <typename T>
+struct as_return_type<T, typename std::enable_if_t<is_descr<decltype(T::return_name)>::value>>
+{
+    static constexpr auto name = T::return_name;
+};
+
 PYBIND11_NAMESPACE_END(detail)
 
 /// Wraps an arbitrary C++ function/method/lambda function/.. into a callable Python object
@@ -320,7 +345,8 @@ protected:
         /* Generate a readable signature describing the function's arguments and return
            value types */
         static constexpr auto signature
-            = const_name("(") + cast_in::arg_names + const_name(") -> ") + cast_out::name;
+            = const_name("(") + cast_in::arg_names + const_name(") -> ")
+            + as_return_type<cast_out>::name;
         PYBIND11_DESCR_CONSTEXPR auto types = decltype(signature)::types();
 
         /* Register the function with Python from generic (non-templated) code */