diff --git a/include/pybind11/detail/holder_caster_foreign_helpers.h b/include/pybind11/detail/holder_caster_foreign_helpers.h
index f636618e9f..cae571b65c 100644
--- a/include/pybind11/detail/holder_caster_foreign_helpers.h
+++ b/include/pybind11/detail/holder_caster_foreign_helpers.h
@@ -31,13 +31,31 @@ struct holder_caster_foreign_helpers {
         PyObject *o;
     };
 
+    // Downcast shared_ptr from the enable_shared_from_this base to the target type.
+    // SFINAE probe: use static_pointer_cast when the static downcast is valid (common case),
+    // fall back to dynamic_pointer_cast when it isn't (virtual inheritance — issue #5989).
+    // We can't use dynamic_pointer_cast unconditionally because it requires polymorphic types;
+    // we can't use is_polymorphic to choose because that's orthogonal to virtual inheritance.
+    // (The implementation uses the "tag dispatch via overload priority" trick.)
+    template <typename type, typename esft_base>
+    static auto esft_downcast(const std::shared_ptr<esft_base> &existing, int /*preferred*/)
+        -> decltype(static_cast<type *>(std::declval<esft_base *>()), std::shared_ptr<type>()) {
+        return std::static_pointer_cast<type>(existing);
+    }
+
+    template <typename type, typename esft_base>
+    static std::shared_ptr<type> esft_downcast(const std::shared_ptr<esft_base> &existing,
+                                               ... /*fallback*/) {
+        return std::dynamic_pointer_cast<type>(existing);
+    }
+
     template <typename type>
     static auto set_via_shared_from_this(type *value, std::shared_ptr<type> *holder_out)
         -> decltype(value->shared_from_this(), bool()) {
         // object derives from enable_shared_from_this;
         // try to reuse an existing shared_ptr if one is known
         if (auto existing = try_get_shared_from_this(value)) {
-            *holder_out = std::static_pointer_cast<type>(existing);
+            *holder_out = esft_downcast<type>(existing, 0);
             return true;
         }
         return false;
diff --git a/tests/test_smart_ptr.cpp b/tests/test_smart_ptr.cpp
index 0ac1a41bd9..f5036eac38 100644
--- a/tests/test_smart_ptr.cpp
+++ b/tests/test_smart_ptr.cpp
@@ -247,6 +247,28 @@ struct SharedFromThisVBase : std::enable_shared_from_this<SharedFromThisVBase> {
 };
 struct SharedFromThisVirt : virtual SharedFromThisVBase {};
 
+// Issue #5989: static_pointer_cast where dynamic_pointer_cast is needed
+// (virtual inheritance with shared_ptr holder)
+struct SftVirtBase : std::enable_shared_from_this<SftVirtBase> {
+    SftVirtBase() = default;
+    virtual ~SftVirtBase() = default;
+    static std::shared_ptr<SftVirtBase> create() { return std::make_shared<SftVirtBase>(); }
+    virtual std::string name() { return "SftVirtBase"; }
+};
+struct SftVirtDerived : SftVirtBase {
+    using SftVirtBase::SftVirtBase;
+    static std::shared_ptr<SftVirtDerived> create() { return std::make_shared<SftVirtDerived>(); }
+    std::string name() override { return "SftVirtDerived"; }
+};
+struct SftVirtDerived2 : virtual SftVirtDerived {
+    using SftVirtDerived::SftVirtDerived;
+    static std::shared_ptr<SftVirtDerived2> create() {
+        return std::make_shared<SftVirtDerived2>();
+    }
+    std::string name() override { return "SftVirtDerived2"; }
+    std::string call_name(const std::shared_ptr<SftVirtDerived2> &d2) { return d2->name(); }
+};
+
 // test_move_only_holder
 struct C {
     C() { print_created(this); }
@@ -522,6 +544,21 @@ TEST_SUBMODULE(smart_ptr, m) {
     py::class_<SharedFromThisVirt, std::shared_ptr<SharedFromThisVirt>>(m, "SharedFromThisVirt")
         .def_static("get", []() { return sft.get(); });
 
+    // Issue #5989: static_pointer_cast where dynamic_pointer_cast is needed
+    py::class_<SftVirtBase, std::shared_ptr<SftVirtBase>>(m, "SftVirtBase")
+        .def(py::init<>(&SftVirtBase::create))
+        .def("name", &SftVirtBase::name);
+    py::class_<SftVirtDerived, SftVirtBase, std::shared_ptr<SftVirtDerived>>(m, "SftVirtDerived")
+        .def(py::init<>(&SftVirtDerived::create));
+    py::class_<SftVirtDerived2, SftVirtDerived, std::shared_ptr<SftVirtDerived2>>(
+        m, "SftVirtDerived2")
+        .def(py::init<>(&SftVirtDerived2::create))
+        // TODO: Remove this once inherited methods work through virtual bases.
+        //       Without it, d2.name() segfaults because pybind11 uses an incorrect
+        //       pointer offset when dispatching through the virtual inheritance chain.
+        .def("name", &SftVirtDerived2::name)
+        .def("call_name", &SftVirtDerived2::call_name, py::arg("d2"));
+
     // test_move_only_holder
     py::class_<C, custom_unique_ptr<C>>(m, "TypeWithMoveOnlyHolder")
         .def_static("make", []() { return custom_unique_ptr<C>(new C); })
diff --git a/tests/test_smart_ptr.py b/tests/test_smart_ptr.py
index 2d48aac78d..76ebd8cf20 100644
--- a/tests/test_smart_ptr.py
+++ b/tests/test_smart_ptr.py
@@ -251,6 +251,19 @@ def test_shared_ptr_from_this_and_references():
     assert y is z
 
 
+def test_shared_from_this_virt_shared_ptr_arg():
+    """Issue #5989: static_pointer_cast fails with virtual inheritance."""
+    b = m.SftVirtBase()
+    assert b.name() == "SftVirtBase"
+
+    d = m.SftVirtDerived()
+    assert d.name() == "SftVirtDerived"
+
+    d2 = m.SftVirtDerived2()
+    assert d2.name() == "SftVirtDerived2"
+    assert d2.call_name(d2) == "SftVirtDerived2"
+
+
 @pytest.mark.skipif("env.GRAALPY", reason="Cannot reliably trigger GC")
 def test_move_only_holder():
     a = m.TypeWithMoveOnlyHolder.make()