diff --git a/tests/test_smart_ptr.cpp b/tests/test_smart_ptr.cpp
index 2a51de9304..a301ef2975 100644
--- a/tests/test_smart_ptr.cpp
+++ b/tests/test_smart_ptr.cpp
@@ -404,4 +404,26 @@ TEST_SUBMODULE(smart_ptr, m) {
     py::class_<UniquePtrDerived, UniquePtrHeld>(m, "UniquePtrDerived")
         .def(py::init<int, std::string>())
         .def("name", &UniquePtrDerived::name);
+
+    class FirstT {};
+    py::class_<FirstT>(m, "FirstT")
+        .def(py::init());
+    class SecondT {};
+    py::class_<SecondT>(m, "SecondT")
+        .def(py::init());
+
+    m.def("unique_ptr_overload",
+        [](std::unique_ptr<UniquePtrHeld> obj, FirstT) {
+            py::dict out;
+            out["obj"] = py::cast(std::move(obj));
+            out["overload"] = 1;
+            return out;
+        });
+    m.def("unique_ptr_overload",
+        [](std::unique_ptr<UniquePtrHeld> obj, SecondT) {
+            py::dict out;
+            out["obj"] = py::cast(std::move(obj));
+            out["overload"] = 2;
+            return out;
+        });
 }
diff --git a/tests/test_smart_ptr.py b/tests/test_smart_ptr.py
index 9e7f618cf3..a27810f326 100644
--- a/tests/test_smart_ptr.py
+++ b/tests/test_smart_ptr.py
@@ -328,3 +328,14 @@ def test_unique_ptr_derived():
     assert obj.value() == 1
     assert obj.name() == "a"
     del obj
+
+
+def test_unique_ptr_overload_fail():
+    obj = m.UniquePtrHeld(1)
+    # These overloads pass ownership back to Python.
+    out = m.unique_ptr_overload(obj, m.FirstT())
+    assert out["obj"] is obj
+    assert out["overload"] == 1
+    out = m.unique_ptr_overload(obj, m.SecondT())
+    assert out["obj"] is obj
+    assert out["overload"] == 2