diff --git a/include/pybind11/pybind11.h b/include/pybind11/pybind11.h
index 4c5c830a9..ac33ab285 100644
--- a/include/pybind11/pybind11.h
+++ b/include/pybind11/pybind11.h
@@ -1205,12 +1205,30 @@ public:
         def("__int__", [](Type value) { return (UnderlyingType) value; });
         def("__eq__", [](const Type &value, Type *value2) { return value2 && value == *value2; });
         def("__ne__", [](const Type &value, Type *value2) { return !value2 || value != *value2; });
+        def("__lt__", [](const Type &value, Type *value2) { return value2 && value < *value2; });
+        def("__gt__", [](const Type &value, Type *value2) { return value2 && value > *value2; });
+        def("__le__", [](const Type &value, Type *value2) { return value2 && value <= *value2; });
+        def("__ge__", [](const Type &value, Type *value2) { return value2 && value >= *value2; });
         if (std::is_convertible<Type, UnderlyingType>::value) {
             // Don't provide comparison with the underlying type if the enum isn't convertible,
             // i.e. if Type is a scoped enum, mirroring the C++ behaviour.  (NB: we explicitly
             // convert Type to UnderlyingType below anyway because this needs to compile).
             def("__eq__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value == value2; });
             def("__ne__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value != value2; });
+            def("__lt__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value < value2; });
+            def("__gt__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value > value2; });
+            def("__le__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value <= value2; });
+            def("__ge__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value >= value2; });
+            def("__invert__", [](const Type &value) { return ~((UnderlyingType) value); });
+            def("__and__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value & value2; });
+            def("__or__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value | value2; });
+            def("__xor__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value ^ value2; });
+            def("__rand__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value & value2; });
+            def("__ror__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value | value2; });
+            def("__rxor__", [](const Type &value, UnderlyingType value2) { return (UnderlyingType) value ^ value2; });
+            def("__and__", [](const Type &value, const Type &value2) { return (UnderlyingType) value & (UnderlyingType) value2; });
+            def("__or__", [](const Type &value, const Type &value2) { return (UnderlyingType) value | (UnderlyingType) value2; });
+            def("__xor__", [](const Type &value, const Type &value2) { return (UnderlyingType) value ^ (UnderlyingType) value2; });
         }
         def("__hash__", [](const Type &value) { return (UnderlyingType) value; });
         // Pickling and unpickling -- needed for use with the 'multiprocessing' module
diff --git a/tests/test_enum.cpp b/tests/test_enum.cpp
index 87cb7d0d4..70a694a09 100644
--- a/tests/test_enum.cpp
+++ b/tests/test_enum.cpp
@@ -19,6 +19,12 @@ enum class ScopedEnum {
     Three
 };
 
+enum Flags {
+    Read = 4,
+    Write = 2,
+    Execute = 1
+};
+
 class ClassWithUnscopedEnum {
 public:
     enum EMode {
@@ -48,6 +54,13 @@ test_initializer enums([](py::module &m) {
         .value("Three", ScopedEnum::Three)
         ;
 
+    py::enum_<Flags>(m, "Flags")
+        .value("Read", Flags::Read)
+        .value("Write", Flags::Write)
+        .value("Execute", Flags::Execute)
+        .export_values();
+        ;
+
     py::class_<ClassWithUnscopedEnum> exenum_class(m, "ClassWithUnscopedEnum");
     exenum_class.def_static("test_function", &ClassWithUnscopedEnum::test_function);
     py::enum_<ClassWithUnscopedEnum::EMode>(exenum_class, "EMode")
diff --git a/tests/test_enum.py b/tests/test_enum.py
index efabae7f7..5dfdbbeb4 100644
--- a/tests/test_enum.py
+++ b/tests/test_enum.py
@@ -16,6 +16,24 @@ def test_unscoped_enum():
     assert int(UnscopedEnum.ETwo) == 2
     assert str(UnscopedEnum(2)) == "UnscopedEnum.ETwo"
 
+    # order
+    assert UnscopedEnum.EOne < UnscopedEnum.ETwo
+    assert UnscopedEnum.EOne < 2
+    assert UnscopedEnum.ETwo > UnscopedEnum.EOne
+    assert UnscopedEnum.ETwo > 1
+    assert UnscopedEnum.ETwo <= 2
+    assert UnscopedEnum.ETwo >= 2
+    assert UnscopedEnum.EOne <= UnscopedEnum.ETwo
+    assert UnscopedEnum.EOne <= 2
+    assert UnscopedEnum.ETwo >= UnscopedEnum.EOne
+    assert UnscopedEnum.ETwo >= 1
+    assert not (UnscopedEnum.ETwo < UnscopedEnum.EOne)
+    assert not (2 < UnscopedEnum.EOne)
+
+def test_scoped_enum():
+    from pybind11_tests import ScopedEnum, test_scoped_enum
+
+    assert test_scoped_enum(ScopedEnum.Three) == "ScopedEnum::Three"
 
 def test_scoped_enum():
     from pybind11_tests import ScopedEnum, test_scoped_enum
@@ -30,6 +48,13 @@ def test_scoped_enum():
     with pytest.raises(TypeError):
         assert z != 3
 
+    # order
+    assert ScopedEnum.Two < ScopedEnum.Three
+    assert ScopedEnum.Three > ScopedEnum.Two
+    assert ScopedEnum.Two <= ScopedEnum.Three
+    assert ScopedEnum.Two <= ScopedEnum.Two
+    assert ScopedEnum.Two >= ScopedEnum.Two
+    assert ScopedEnum.Three >= ScopedEnum.Two
 
 def test_implicit_conversion():
     from pybind11_tests import ClassWithUnscopedEnum
@@ -61,3 +86,26 @@ def test_implicit_conversion():
     x[f(second)] = 4
     # Hashing test
     assert str(x) == "{EMode.EFirstMode: 3, EMode.ESecondMode: 4}"
+
+def test_binary_operators():
+    from pybind11_tests import Flags
+
+    assert int(Flags.Read) == 4
+    assert int(Flags.Write) == 2
+    assert int(Flags.Execute) == 1
+    assert int(Flags.Read | Flags.Write | Flags.Execute) == 7
+    assert int(Flags.Read | Flags.Write) == 6
+    assert int(Flags.Read | Flags.Execute) == 5
+    assert int(Flags.Write | Flags.Execute) == 3
+    assert int(Flags.Write | 1) == 3
+
+    state = Flags.Read | Flags.Write
+    assert (state & Flags.Read) != 0
+    assert (state & Flags.Write) != 0
+    assert (state & Flags.Execute) == 0
+    assert (state & 1) == 0
+
+    state2 = ~state
+    assert state2 == -7
+    assert int(state ^ state2) == -1
+