diff --git a/modules/openapi-generator/src/main/resources/python/api_client.mustache b/modules/openapi-generator/src/main/resources/python/api_client.mustache
index eef8edc60de5..874d9cd3efef 100644
--- a/modules/openapi-generator/src/main/resources/python/api_client.mustache
+++ b/modules/openapi-generator/src/main/resources/python/api_client.mustache
@@ -591,6 +591,12 @@ https://github.com/OpenAPITools/openapi-generator/blob/c84b949df1a9ec04ba75989cb
             return None
 
         if isinstance(klass, str):
+            if klass.startswith('Optional['):
+                m = re.match(r'Optional\[(.*)]', klass)
+                assert m is not None, "Malformed Optional type definition"
+                # data is not None here, so the optionality is already resolved
+                return self.__deserialize(data, m.group(1))
+
             if klass.startswith('List['):
                 m = re.match(r'List\[(.*)]', klass)
                 assert m is not None, "Malformed List type definition"
diff --git a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api_client.py b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api_client.py
index cf6c5499750e..17c439964cee 100644
--- a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api_client.py
+++ b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api_client.py
@@ -440,6 +440,12 @@ def __deserialize(self, data, klass):
             return None
 
         if isinstance(klass, str):
+            if klass.startswith('Optional['):
+                m = re.match(r'Optional\[(.*)]', klass)
+                assert m is not None, "Malformed Optional type definition"
+                # data is not None here, so the optionality is already resolved
+                return self.__deserialize(data, m.group(1))
+
             if klass.startswith('List['):
                 m = re.match(r'List\[(.*)]', klass)
                 assert m is not None, "Malformed List type definition"
diff --git a/samples/client/echo_api/python/openapi_client/api_client.py b/samples/client/echo_api/python/openapi_client/api_client.py
index cf6c5499750e..17c439964cee 100644
--- a/samples/client/echo_api/python/openapi_client/api_client.py
+++ b/samples/client/echo_api/python/openapi_client/api_client.py
@@ -440,6 +440,12 @@ def __deserialize(self, data, klass):
             return None
 
         if isinstance(klass, str):
+            if klass.startswith('Optional['):
+                m = re.match(r'Optional\[(.*)]', klass)
+                assert m is not None, "Malformed Optional type definition"
+                # data is not None here, so the optionality is already resolved
+                return self.__deserialize(data, m.group(1))
+
             if klass.startswith('List['):
                 m = re.match(r'List\[(.*)]', klass)
                 assert m is not None, "Malformed List type definition"
diff --git a/samples/client/others/python-legacy-model-dictionaries/legacy_model_dict_client/api_client.py b/samples/client/others/python-legacy-model-dictionaries/legacy_model_dict_client/api_client.py
index d9538b2c5e36..baab728d4dd5 100644
--- a/samples/client/others/python-legacy-model-dictionaries/legacy_model_dict_client/api_client.py
+++ b/samples/client/others/python-legacy-model-dictionaries/legacy_model_dict_client/api_client.py
@@ -548,6 +548,12 @@ def __deserialize(self, data, klass):
             return None
 
         if isinstance(klass, str):
+            if klass.startswith('Optional['):
+                m = re.match(r'Optional\[(.*)]', klass)
+                assert m is not None, "Malformed Optional type definition"
+                # data is not None here, so the optionality is already resolved
+                return self.__deserialize(data, m.group(1))
+
             if klass.startswith('List['):
                 m = re.match(r'List\[(.*)]', klass)
                 assert m is not None, "Malformed List type definition"
diff --git a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api_client.py b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api_client.py
index 51dedc06d75c..49b32fc8edd6 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api_client.py
@@ -439,6 +439,12 @@ def __deserialize(self, data, klass):
             return None
 
         if isinstance(klass, str):
+            if klass.startswith('Optional['):
+                m = re.match(r'Optional\[(.*)]', klass)
+                assert m is not None, "Malformed Optional type definition"
+                # data is not None here, so the optionality is already resolved
+                return self.__deserialize(data, m.group(1))
+
             if klass.startswith('List['):
                 m = re.match(r'List\[(.*)]', klass)
                 assert m is not None, "Malformed List type definition"
diff --git a/samples/openapi3/client/petstore/python-httpx-sync/petstore_api/api_client.py b/samples/openapi3/client/petstore/python-httpx-sync/petstore_api/api_client.py
index 439f7b281e22..b7eb3a9170cb 100644
--- a/samples/openapi3/client/petstore/python-httpx-sync/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python-httpx-sync/petstore_api/api_client.py
@@ -442,6 +442,12 @@ def __deserialize(self, data, klass):
             return None
 
         if isinstance(klass, str):
+            if klass.startswith('Optional['):
+                m = re.match(r'Optional\[(.*)]', klass)
+                assert m is not None, "Malformed Optional type definition"
+                # data is not None here, so the optionality is already resolved
+                return self.__deserialize(data, m.group(1))
+
             if klass.startswith('List['):
                 m = re.match(r'List\[(.*)]', klass)
                 assert m is not None, "Malformed List type definition"
diff --git a/samples/openapi3/client/petstore/python-httpx/petstore_api/api_client.py b/samples/openapi3/client/petstore/python-httpx/petstore_api/api_client.py
index 439f7b281e22..b7eb3a9170cb 100644
--- a/samples/openapi3/client/petstore/python-httpx/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python-httpx/petstore_api/api_client.py
@@ -442,6 +442,12 @@ def __deserialize(self, data, klass):
             return None
 
         if isinstance(klass, str):
+            if klass.startswith('Optional['):
+                m = re.match(r'Optional\[(.*)]', klass)
+                assert m is not None, "Malformed Optional type definition"
+                # data is not None here, so the optionality is already resolved
+                return self.__deserialize(data, m.group(1))
+
             if klass.startswith('List['):
                 m = re.match(r'List\[(.*)]', klass)
                 assert m is not None, "Malformed List type definition"
diff --git a/samples/openapi3/client/petstore/python-lazyImports/petstore_api/api_client.py b/samples/openapi3/client/petstore/python-lazyImports/petstore_api/api_client.py
index 2712a55fb468..8dcae18708cf 100644
--- a/samples/openapi3/client/petstore/python-lazyImports/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python-lazyImports/petstore_api/api_client.py
@@ -439,6 +439,12 @@ def __deserialize(self, data, klass):
             return None
 
         if isinstance(klass, str):
+            if klass.startswith('Optional['):
+                m = re.match(r'Optional\[(.*)]', klass)
+                assert m is not None, "Malformed Optional type definition"
+                # data is not None here, so the optionality is already resolved
+                return self.__deserialize(data, m.group(1))
+
             if klass.startswith('List['):
                 m = re.match(r'List\[(.*)]', klass)
                 assert m is not None, "Malformed List type definition"
diff --git a/samples/openapi3/client/petstore/python/petstore_api/api_client.py b/samples/openapi3/client/petstore/python/petstore_api/api_client.py
index e790556da632..899983e443d6 100755
--- a/samples/openapi3/client/petstore/python/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python/petstore_api/api_client.py
@@ -439,6 +439,12 @@ def __deserialize(self, data, klass):
             return None
 
         if isinstance(klass, str):
+            if klass.startswith('Optional['):
+                m = re.match(r'Optional\[(.*)]', klass)
+                assert m is not None, "Malformed Optional type definition"
+                # data is not None here, so the optionality is already resolved
+                return self.__deserialize(data, m.group(1))
+
             if klass.startswith('List['):
                 m = re.match(r'List\[(.*)]', klass)
                 assert m is not None, "Malformed List type definition"
diff --git a/samples/openapi3/client/petstore/python/tests/test_deserialization.py b/samples/openapi3/client/petstore/python/tests/test_deserialization.py
index b3626e5cc9cb..ba9d9521599b 100644
--- a/samples/openapi3/client/petstore/python/tests/test_deserialization.py
+++ b/samples/openapi3/client/petstore/python/tests/test_deserialization.py
@@ -251,6 +251,59 @@ def test_deserialize_none(self):
         deserialized = self.deserialize(response, "datetime", 'application/json')
         self.assertIsNone(deserialized)
 
+    def test_deserialize_optional_dict_str_object(self):
+        """ deserialize Dict[str, Optional[object]] """
+        data = {
+            "foo": 1,
+            "bar": None
+        }
+        response = json.dumps(data)
+
+        deserialized = self.deserialize(response, "Dict[str, Optional[object]]", 'application/json')
+        self.assertEqual(deserialized, {"foo": 1, "bar": None})
+
+    def test_deserialize_optional_pet(self):
+        """ deserialize Optional[Pet] """
+        data = {
+            "id": 0,
+            "category": {
+                "id": 0,
+                "name": "string"
+            },
+            "name": "doggie",
+            "photoUrls": [
+                "string"
+            ],
+            "tags": [
+                {
+                    "id": 0,
+                    "name": "string"
+                }
+            ],
+            "status": "available"
+        }
+        response = json.dumps(data)
+
+        deserialized = self.deserialize(response, "Optional[Pet]", 'application/json')
+        self.assertTrue(isinstance(deserialized, petstore_api.Pet))
+        self.assertEqual(deserialized.id, 0)
+        self.assertEqual(deserialized.name, "doggie")
+
+    def test_deserialize_optional_list_of_str(self):
+        """ deserialize Optional[List[str]] """
+        data = ["foo", "bar"]
+        response = json.dumps(data)
+
+        deserialized = self.deserialize(response, "Optional[List[str]]", 'application/json')
+        self.assertEqual(deserialized, ["foo", "bar"])
+
+    def test_deserialize_optional_none(self):
+        """ deserialize Optional[Pet] when the body is null """
+        response = json.dumps(None)
+
+        deserialized = self.deserialize(response, "Optional[Pet]", 'application/json')
+        self.assertIsNone(deserialized)
+
     def test_deserialize_pig(self):
         """ deserialize pig (oneOf) """
         wire_name = """class'"\\Name"""