diff --git a/msgspec/_core.c b/msgspec/_core.c
index 4b964d38..221d9a57 100644
--- a/msgspec/_core.c
+++ b/msgspec/_core.c
@@ -10174,6 +10174,7 @@ enum mpack_code {
 };
 
 static int mpack_encode_inline(EncoderState *self, PyObject *obj);
+static int mpack_encode_dict_key_inline(EncoderState *self, PyObject *obj);
 static int mpack_encode(EncoderState *self, PyObject *obj);
 
 static int
@@ -10532,7 +10533,7 @@ mpack_encode_dict(EncoderState *self, PyObject *obj)
     if (len == 0) return 0;
     if (Py_EnterRecursiveCall(" while serializing an object")) return -1;
     while (PyDict_Next(obj, &pos, &key, &val)) {
-        if (mpack_encode_inline(self, key) < 0) goto error;
+        if (mpack_encode_dict_key_inline(self, key) < 0) goto error;
         if (mpack_encode_inline(self, val) < 0) goto error;
     }
     status = 0;
@@ -11023,6 +11024,31 @@ mpack_encode_inline(EncoderState *self, PyObject *obj)
     }
 }
 
+static MS_INLINE int
+mpack_encode_dict_key_inline(EncoderState *self, PyObject *obj)
+{
+    PyTypeObject *type = Py_TYPE(obj);
+
+    if (PyUnicode_Check(obj)) {
+        return mpack_encode_str(self, obj);
+    }
+    else if (type == &PyLong_Type) {
+        return mpack_encode_long(self, obj);
+    }
+    else if (type == &PyFloat_Type) {
+        return mpack_encode_float(self, obj);
+    }
+    else if (PyList_Check(obj)) {
+        return mpack_encode_list(self, obj);
+    }
+    else if (PyDict_Check(obj)) {
+        return mpack_encode_dict(self, obj);
+    }
+    else {
+        return mpack_encode_uncommon(self, type, obj);
+    }
+}
+
 static int
 mpack_encode(EncoderState *self, PyObject *obj) {
     return mpack_encode_inline(self, obj);
@@ -11555,7 +11581,7 @@ json_encode_dict(EncoderState *self, PyObject *obj)
     if (ms_write(self, "{", 1) < 0) return -1;
     if (Py_EnterRecursiveCall(" while serializing an object")) return -1;
     while (PyDict_Next(obj, &pos, &key, &val)) {
-        if (MS_LIKELY(PyUnicode_CheckExact(key))) {
+        if (MS_LIKELY(PyUnicode_Check(key))) {
             if (json_encode_str(self, key) < 0) goto cleanup;
         }
         else {
@@ -17460,6 +17486,9 @@ to_builtins(ToBuiltinsState *self, PyObject *obj, bool is_key) {
     else if (Py_TYPE(type) == self->mod->EnumMetaType) {
         return to_builtins_enum(self, obj);
     }
+    else if (is_key & PyUnicode_Check(obj)) {
+        return PyObject_Str(obj);
+    }
     else if (PyType_IsSubtype(type, (PyTypeObject *)(self->mod->UUIDType))) {
         if (self->builtin_types & MS_BUILTIN_UUID) goto builtin;
         return to_builtins_uuid(self, obj);
diff --git a/tests/test_json.py b/tests/test_json.py
index b6344495..a81a3f9b 100644
--- a/tests/test_json.py
+++ b/tests/test_json.py
@@ -1840,6 +1840,13 @@ def test_decode_dict_int_literal_key(self):
         with pytest.raises(msgspec.ValidationError, match="Invalid enum value 3"):
             dec.decode(b'{"-1": 10, "3": 20}')
 
+    def test_encode_dict_str_subclass_key(self):
+        class mystr(str):
+            pass
+
+        msg = msgspec.json.encode({mystr("test"): 1})
+        assert msg == b'{"test":1}'
+
     @pytest.mark.parametrize(
         "s, error",
         [
diff --git a/tests/test_msgpack.py b/tests/test_msgpack.py
index 6727a961..5e6e5c01 100644
--- a/tests/test_msgpack.py
+++ b/tests/test_msgpack.py
@@ -1026,6 +1026,14 @@ def test_dict_any_key(self):
         ):
             dec.decode(enc.encode({1: 2}))
 
+    def test_dict_str_subclass_key(self):
+        class mystr(str):
+            pass
+
+        msg1 = msgspec.msgpack.encode({mystr("test"): 1})
+        msg2 = msgspec.msgpack.encode({"test": 1})
+        assert msg1 == msg2
+
     def test_dict_typed(self):
         enc = msgspec.msgpack.Encoder()
         dec = msgspec.msgpack.Decoder(Dict[str, int])
diff --git a/tests/test_to_builtins.py b/tests/test_to_builtins.py
index 004ef0d7..ae4769d4 100644
--- a/tests/test_to_builtins.py
+++ b/tests/test_to_builtins.py
@@ -262,6 +262,14 @@ class in_type(dict):
         res = to_builtins(in_type())
         assert res == {}
 
+    def test_dict_str_subclass_key(self):
+        class mystr(str):
+            pass
+
+        msg = to_builtins({mystr("test"): 1})
+        assert msg == {"test": 1}
+        assert type(list(msg.keys())[0]) is str
+
     def test_dict_unsupported_key(self):
         msg = {Bad(): 1}
         with pytest.raises(TypeError, match="Encoding objects of type Bad"):