diff --git a/samples/controlled_generation.py b/samples/controlled_generation.py
index 4942481f6..5c9c362a5 100644
--- a/samples/controlled_generation.py
+++ b/samples/controlled_generation.py
@@ -73,6 +73,36 @@ class Choice(enum.Enum):
         print(result)  # "Keyboard"
         # [END json_enum]
 
+    def test_enum_in_json(self):
+        # [START enum_in_json]
+        import enum
+        from typing_extensions import TypedDict
+
+        class Grade(enum.Enum):
+            A_PLUS = "a+"
+            A = "a"
+            B = "b"
+            C = "c"
+            D = "d"
+            F = "f"
+
+        class Recipe(TypedDict):
+            recipe_name: str
+            grade: Grade
+
+
+        model = genai.GenerativeModel("gemini-1.5-pro-latest")
+
+        result = model.generate_content(
+            "List about 10 cookie recipes, grade them based on popularity",
+            generation_config=genai.GenerationConfig(
+                response_mime_type="application/json",
+                response_schema=list[Recipe]
+            ),
+        )
+        print(result)  # [{"grade": "a+", "recipe_name": "Chocolate Chip Cookies"}, ...]
+        # [END enum_in_json]
+
     def test_json_enum_raw(self):
         # [START json_enum_raw]
         model = genai.GenerativeModel("gemini-1.5-pro-latest")
@@ -92,5 +122,46 @@ def test_json_enum_raw(self):
         # [END json_enum_raw]
 
 
+    def test_x_enum(self):
+        # [START x_enum]
+        import enum
+
+        class Choice(enum.Enum):
+            PERCUSSION = "Percussion"
+            STRING = "String"
+            WOODWIND = "Woodwind"
+            BRASS = "Brass"
+            KEYBOARD = "Keyboard"
+
+        model = genai.GenerativeModel("gemini-1.5-pro-latest")
+
+        organ = genai.upload_file(media / "organ.jpg")
+        result = model.generate_content(
+            ["What kind of instrument is this:", organ],
+            generation_config=genai.GenerationConfig(
+                response_mime_type="text/x.enum", response_schema=Choice
+            ),
+        )
+        print(result)  # "Keyboard"
+        # [END x_enum]
+
+    def test_x_enum_raw(self):
+        # [START x_enum_raw]
+        model = genai.GenerativeModel("gemini-1.5-pro-latest")
+
+        organ = genai.upload_file(media / "organ.jpg")
+        result = model.generate_content(
+            ["What kind of instrument is this:", organ],
+            generation_config=genai.GenerationConfig(
+                response_mime_type="text/x.enum",
+                response_schema={
+                    "type": "STRING",
+                    "enum": ["Percussion", "String", "Woodwind", "Brass", "Keyboard"],
+                },
+            ),
+        )
+        print(result)  # "Keyboard"
+        # [END x_enum_raw]
+
 if __name__ == "__main__":
     absltest.main()