diff --git a/include/pybind11/stl.h b/include/pybind11/stl.h
index 2c017b4fef..5c0592f80d 100644
--- a/include/pybind11/stl.h
+++ b/include/pybind11/stl.h
@@ -252,8 +252,8 @@ template<typename T> struct optional_caster {
     static handle cast(T_ &&src, return_value_policy policy, handle parent) {
         if (!src)
             return none().inc_ref();
-        if (!std::is_lvalue_reference<T>::value) {
-            policy = return_value_policy_override<T>::policy(policy);
+        if (!std::is_lvalue_reference<T_>::value) {
+            policy = return_value_policy_override<typename T::value_type>::policy(policy);
         }
         return value_conv::cast(*std::forward<T_>(src), policy, parent);
     }
diff --git a/tests/test_stl.cpp b/tests/test_stl.cpp
index 7e3363c5ea..186d758b84 100644
--- a/tests/test_stl.cpp
+++ b/tests/test_stl.cpp
@@ -20,9 +20,18 @@
 #include <string>
 
 // Test with `std::variant` in C++17 mode, or with `boost::variant` in C++11/14
-#if defined(PYBIND11_HAS_VARIANT)
+#if defined(PYBIND11_HAS_OPTIONAL) && defined(PYBIND11_HAS_VARIANT)
+using std::nullopt;
+using std::nullopt_t;
+using std::optional;
 using std::variant;
 #elif defined(PYBIND11_TEST_BOOST) && (!defined(_MSC_VER) || _MSC_VER >= 1910)
+#  include <boost/none.hpp>
+#  include <boost/optional.hpp>
+#  define PYBIND11_HAS_OPTIONAL 1
+template <typename T> using optional = boost::optional<T>;
+using nullopt_t = boost::none_t;
+const nullopt_t nullopt = boost::none;
 #  include <boost/variant.hpp>
 #  define PYBIND11_HAS_VARIANT 1
 using boost::variant;
@@ -38,6 +47,11 @@ struct visit_helper<boost::variant> {
         return boost::apply_visitor(args...);
     }
 };
+
+template <typename T>
+struct type_caster<boost::optional<T>> : optional_caster<boost::optional<T>> {};
+
+template<> struct type_caster<nullopt_t> : public void_caster<nullopt_t> {};
 }} // namespace pybind11::detail
 #endif
 
@@ -192,27 +206,46 @@ TEST_SUBMODULE(stl, m) {
     // test_optional
     m.attr("has_optional") = true;
 
-    using opt_int = std::optional<int>;
-    using opt_no_assign = std::optional<NoAssign>;
+    using opt_int = optional<int>;
+    using opt_no_assign = optional<NoAssign>;
     m.def("double_or_zero", [](const opt_int& x) -> int {
         return x.value_or(0) * 2;
     });
     m.def("half_or_none", [](int x) -> opt_int { return x != 0 ? opt_int(x / 2) : opt_int(); });
     m.def("test_nullopt", [](opt_int x) {
         return x.value_or(42);
-    }, py::arg_v("x", std::nullopt, "None"));
+    }, py::arg_v("x", nullopt, "None"));
     m.def("test_no_assign", [](const opt_no_assign &x) {
         return x ? x->value : 42;
-    }, py::arg_v("x", std::nullopt, "None"));
+    }, py::arg_v("x", nullopt, "None"));
 
-    m.def("nodefer_none_optional", [](std::optional<int>) { return true; });
+    m.def("nodefer_none_optional", [](optional<int>) { return true; });
     m.def("nodefer_none_optional", [](const py::none &) { return false; });
 
-    using opt_holder = OptionalHolder<std::optional, MoveOutDetector>;
+    using opt_holder = OptionalHolder<optional, MoveOutDetector>;
     py::class_<opt_holder>(m, "OptionalHolder", "Class with optional member")
         .def(py::init<>())
         .def_readonly("member", &opt_holder::member)
         .def("member_initialized", &opt_holder::member_initialized);
+
+    // issue_3330
+    enum class IssueKEnum {
+        k0 = 0,
+        k1 = 1,
+    };
+
+    struct BoostOptionalIssue {
+        optional<IssueKEnum> value = IssueKEnum::k1;
+    };
+
+    py::enum_<IssueKEnum>(m, "IssueKEnum").value("k0", IssueKEnum::k0).value("k1", IssueKEnum::k1);
+
+    py::class_<BoostOptionalIssue>(m, "BoostOptionalIssue")
+        .def(py::init<>())
+        .def_property_readonly(
+            "by_ref", [](BoostOptionalIssue &a) -> optional<IssueKEnum> & { return a.value; })
+        .def_property_readonly(
+            "by_copy", [](BoostOptionalIssue &a) -> optional<IssueKEnum> { return a.value; });
 #endif
 
 #ifdef PYBIND11_HAS_EXP_OPTIONAL
@@ -279,7 +312,7 @@ TEST_SUBMODULE(stl, m) {
     m.def("tpl_ctor_map", [](std::unordered_map<TplCtorClass, TplCtorClass> &) {});
     m.def("tpl_ctor_set", [](std::unordered_set<TplCtorClass> &) {});
 #if defined(PYBIND11_HAS_OPTIONAL)
-    m.def("tpl_constr_optional", [](std::optional<TplCtorClass> &) {});
+    m.def("tpl_constr_optional", [](optional<TplCtorClass> &) {});
 #elif defined(PYBIND11_HAS_EXP_OPTIONAL)
     m.def("tpl_constr_optional", [](std::experimental::optional<TplCtorClass> &) {});
 #endif
diff --git a/tests/test_stl.py b/tests/test_stl.py
index 3f63d6c3a4..059742d77f 100644
--- a/tests/test_stl.py
+++ b/tests/test_stl.py
@@ -131,6 +131,10 @@ def test_optional():
     mvalue = holder.member
     assert mvalue.initialized
     assert holder.member_initialized()
+    a = m.BoostOptionalIssue().by_ref
+    assert a is not None
+    b = m.BoostOptionalIssue().by_copy
+    assert b is not None
 
 
 @pytest.mark.skipif(