diff --git a/include/pybind11/internal/accessor.h b/include/pybind11/internal/accessor.h
index 6d100557..9731e4cf 100644
--- a/include/pybind11/internal/accessor.h
+++ b/include/pybind11/internal/accessor.h
@@ -54,7 +54,7 @@ public:
 
     template <typename Value>
     accessor& operator= (Value&& value) && {
-        policy::set(m_obj, m_key, std::forward<Value>(value));
+        policy::set(m_obj, m_key, pybind11::cast(std::forward<Value>(value)));
         return *this;
     }
 
diff --git a/include/pybind11/internal/builtins.h b/include/pybind11/internal/builtins.h
index 084376cb..494869e0 100644
--- a/include/pybind11/internal/builtins.h
+++ b/include/pybind11/internal/builtins.h
@@ -95,6 +95,10 @@ handle cast(T&& value, return_value_policy policy, handle parent) {
 
     if constexpr(std::is_convertible_v<underlying_type, handle>) {
         return std::forward<T>(value);
+    } else if constexpr(is_unique_ptr_v<underlying_type>) {
+        return impl::type_caster<typename underlying_type::pointer>::cast(value.release(),
+                                                                          return_value_policy::take_ownership,
+                                                                          parent);
     } else {
         static_assert(!is_multiple_pointer_v<underlying_type>, "multiple pointer is not supported.");
         static_assert(!std::is_void_v<std::remove_pointer_t<underlying_type>>,
diff --git a/include/pybind11/internal/object.h b/include/pybind11/internal/object.h
index 007ccf9b..4bbabceb 100644
--- a/include/pybind11/internal/object.h
+++ b/include/pybind11/internal/object.h
@@ -177,7 +177,7 @@ struct type_visitor {
             } else {
                 // some type, like iterable, iterator, they don't have according type in python
                 // but they have a function to check the type, then just call the function
-                return T::type_or_check(obj);
+                return T::type_or_check()(obj);
             }
         } else {
             return vm->isinstance(obj.ptr(), type<T>());
diff --git a/include/pybind11/internal/type_traits.h b/include/pybind11/internal/type_traits.h
index d24374bb..946d5714 100644
--- a/include/pybind11/internal/type_traits.h
+++ b/include/pybind11/internal/type_traits.h
@@ -2,6 +2,7 @@
 #include <tuple>
 #include <string_view>
 #include <type_traits>
+#include <memory>
 
 namespace pybind11 {
 
@@ -195,4 +196,11 @@ constexpr inline overload_cast_t<Args...> overload_cast;
 ///  - regular: static_cast<Return (Class::*)(Arg) const>(&Class::func)
 ///  - sweet:   overload_cast<Arg>(&Class::func, const_)
 constexpr static auto const_ = std::true_type{};
+
+template <typename T>
+constexpr bool is_unique_ptr_v = false;
+
+template <typename T>
+constexpr bool is_unique_ptr_v<std::unique_ptr<T>> = true;
+
 }  // namespace pybind11
diff --git a/include/pybind11/stl.h b/include/pybind11/stl.h
index 92c6667f..8cef42fa 100644
--- a/include/pybind11/stl.h
+++ b/include/pybind11/stl.h
@@ -86,8 +86,14 @@ struct type_caster<T, std::enable_if_t<is_py_list_like_v<T>>> {
     template <typename U>
     static handle cast(U&& src, return_value_policy policy, handle parent) {
         auto list = pybind11::list();
-        for(auto& item: src) {
-            list.append(pybind11::cast(item, policy, parent));
+        if constexpr(std::is_same_v<T, std::vector<bool>>) {
+            for(auto item: src) {
+                list.append(pybind11::cast(bool(item), policy, parent));
+            }
+        } else {
+            for(auto& item: src) {
+                list.append(pybind11::cast(item, policy, parent));
+            }
         }
         return list;
     }