diff --git a/include/pybind11/detail/class.h b/include/pybind11/detail/class.h
index cd7e87f845..64e371db4c 100644
--- a/include/pybind11/detail/class.h
+++ b/include/pybind11/detail/class.h
@@ -334,6 +334,7 @@ inline void enable_try_inc_ref(PyObject *obj) {
 #endif
 
 inline bool register_instance_impl(void *ptr, instance *self) {
+    assert(ptr);
 #ifdef Py_GIL_DISABLED
     enable_try_inc_ref(reinterpret_cast<PyObject *>(self));
 #endif
@@ -341,6 +342,7 @@ inline bool register_instance_impl(void *ptr, instance *self) {
     return true; // unused, but gives the same signature as the deregister func
 }
 inline bool deregister_instance_impl(void *ptr, instance *self) {
+    assert(ptr);
     return with_instance_map(ptr, [&](instance_map &instances) {
         auto range = instances.equal_range(ptr);
         for (auto it = range.first; it != range.second; ++it) {
diff --git a/include/pybind11/detail/type_caster_base.h b/include/pybind11/detail/type_caster_base.h
index 23d9407350..a95cb1ab64 100644
--- a/include/pybind11/detail/type_caster_base.h
+++ b/include/pybind11/detail/type_caster_base.h
@@ -657,9 +657,8 @@ handle smart_holder_from_shared_ptr(const std::shared_ptr<T> &src,
         return none().release();
     }
 
-    auto src_raw_ptr = src.get();
+    void *src_raw_void_ptr = const_cast<void *>(st.first);
     assert(st.second != nullptr);
-    void *src_raw_void_ptr = static_cast<void *>(src_raw_ptr);
     const detail::type_info *tinfo = st.second;
     if (handle existing_inst = find_registered_python_instance(src_raw_void_ptr, tinfo)) {
         // PYBIND11:REMINDER: MISSING: Enforcement of consistency with existing smart_holder.
@@ -673,8 +672,7 @@ handle smart_holder_from_shared_ptr(const std::shared_ptr<T> &src,
     void *&valueptr = values_and_holders(inst_raw_ptr).begin()->value_ptr();
     valueptr = src_raw_void_ptr;
 
-    auto smhldr
-        = smart_holder::from_shared_ptr(std::shared_ptr<void>(src, const_cast<void *>(st.first)));
+    auto smhldr = smart_holder::from_shared_ptr(std::shared_ptr<void>(src, src_raw_void_ptr));
     tinfo->init_instance(inst_raw_ptr, static_cast<const void *>(&smhldr));
 
     if (policy == return_value_policy::reference_internal) {
diff --git a/tests/CMakeLists.txt b/tests/CMakeLists.txt
index 34b22a57ae..6ec7de51cd 100644
--- a/tests/CMakeLists.txt
+++ b/tests/CMakeLists.txt
@@ -171,6 +171,7 @@ set(PYBIND11_TEST_FILES
     test_scoped_critical_section
     test_sequences_and_iterators
     test_smart_ptr
+    test_animal_cat_tiger
     test_stl
     test_stl_binders
     test_tagbased_polymorphic
diff --git a/tests/test_animal_cat_tiger.cpp b/tests/test_animal_cat_tiger.cpp
new file mode 100644
index 0000000000..be3a4d003b
--- /dev/null
+++ b/tests/test_animal_cat_tiger.cpp
@@ -0,0 +1,71 @@
+#include "pybind11_tests.h"
+
+#include <memory>
+
+namespace pybind11_tests {
+namespace class_animal {
+
+template <int> // Using int as a trick to easily generate a series of types.
+struct Multi {
+
+    class Animal {
+    public:
+        Animal() = default;
+        Animal(const Animal &) = default;
+        Animal &operator=(const Animal &) = default;
+        virtual std::shared_ptr<Animal> clone() const = 0;
+        virtual ~Animal() = default;
+    };
+
+    class Cat : virtual public Animal {
+    public:
+        Cat() = default;
+        Cat(const Cat &) = default;
+        Cat &operator=(const Cat &) = default;
+        ~Cat() override = default;
+    };
+
+    class Tiger : virtual public Cat {
+    public:
+        Tiger() = default;
+        Tiger(const Tiger &) = default;
+        Tiger &operator=(const Tiger &) = default;
+        ~Tiger() override = default;
+        std::shared_ptr<Animal> clone() const override { return std::make_shared<Tiger>(*this); }
+    };
+};
+
+namespace py = pybind11;
+
+void bind_using_shared_ptr(py::module_ &m) {
+    using M = Multi<0>;
+
+    py::class_<M::Animal, std::shared_ptr<M::Animal>>(m, "AnimalSP");
+
+    py::class_<M::Cat, M::Animal, std::shared_ptr<M::Cat>>(m, "CatSP");
+
+    py::class_<M::Tiger, M::Cat, std::shared_ptr<M::Tiger>>(
+        m, "TigerSP", py::multiple_inheritance())
+        .def(py::init<>())
+        .def("clone", &M::Tiger::clone);
+}
+
+void bind_using_smart_holder(py::module_ &m) {
+    using M = Multi<1>;
+
+    py::class_<M::Animal, py::smart_holder>(m, "AnimalSH");
+
+    py::class_<M::Cat, M::Animal, py::smart_holder>(m, "CatSH");
+
+    py::class_<M::Tiger, M::Cat, py::smart_holder>(m, "TigerSH", py::multiple_inheritance())
+        .def(py::init<>())
+        .def("clone", &M::Tiger::clone);
+}
+
+TEST_SUBMODULE(class_animal, m) {
+    bind_using_shared_ptr(m);
+    bind_using_smart_holder(m);
+}
+
+} // namespace class_animal
+} // namespace pybind11_tests
diff --git a/tests/test_animal_cat_tiger.py b/tests/test_animal_cat_tiger.py
new file mode 100644
index 0000000000..a377025676
--- /dev/null
+++ b/tests/test_animal_cat_tiger.py
@@ -0,0 +1,12 @@
+from __future__ import annotations
+
+import pytest
+
+from pybind11_tests import class_animal as m
+
+
+@pytest.mark.parametrize("tiger_type", [m.TigerSP, m.TigerSH])
+def test_clone(tiger_type):
+    tiger = tiger_type()
+    cloned = tiger.clone()
+    assert isinstance(cloned, tiger_type)