diff --git a/modules/openapi-generator/src/main/java/org/openapitools/codegen/languages/AbstractPythonCodegen.java b/modules/openapi-generator/src/main/java/org/openapitools/codegen/languages/AbstractPythonCodegen.java
index 3c76c7dd170..12dad3e640c 100644
--- a/modules/openapi-generator/src/main/java/org/openapitools/codegen/languages/AbstractPythonCodegen.java
+++ b/modules/openapi-generator/src/main/java/org/openapitools/codegen/languages/AbstractPythonCodegen.java
@@ -1747,6 +1747,7 @@ public abstract class AbstractPythonCodegen extends DefaultCodegen implements Co
     @Override
     public OperationsMap postProcessOperationsWithModels(OperationsMap objs, List<ModelMap> allModels) {
         hasModelsToImport = false;
+        boolean importAnnotated = false;
         TreeSet<String> typingImports = new TreeSet<>();
         TreeSet<String> pydanticImports = new TreeSet<>();
         TreeSet<String> datetimeImports = new TreeSet<>();
@@ -1807,6 +1808,7 @@ public abstract class AbstractPythonCodegen extends DefaultCodegen implements Co
                     param.vendorExtensions.put("x-py-typing", typing);
                 } else {
                     param.vendorExtensions.put("x-py-typing", String.format(Locale.ROOT, "Annotated[%s, %s]", typing, fieldCustomization));
+                    importAnnotated = true;
                 }
             }
 
@@ -1838,6 +1840,12 @@ public abstract class AbstractPythonCodegen extends DefaultCodegen implements Co
 
         List<Map<String, String>> newImports = new ArrayList<>();
 
+        if (importAnnotated) {
+            Map<String, String> item = new HashMap<>();
+            item.put("import", String.format(Locale.ROOT, String.format(Locale.ROOT, "from typing_extensions import Annotated")));
+            newImports.add(item);
+        }
+
         // need datetime import
         if (!datetimeImports.isEmpty()) {
             Map<String, String> item = new HashMap<>();
diff --git a/modules/openapi-generator/src/main/resources/python/api.mustache b/modules/openapi-generator/src/main/resources/python/api.mustache
index 70f316a2e7f..740f2b2f20d 100644
--- a/modules/openapi-generator/src/main/resources/python/api.mustache
+++ b/modules/openapi-generator/src/main/resources/python/api.mustache
@@ -7,8 +7,9 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated{{#asyncio}}
-from typing import overload, Optional, Union, Awaitable{{/asyncio}}
+{{#asyncio}}
+from typing import overload, Optional, Union, Awaitable
+{{/asyncio}}
 
 {{#imports}}
 {{import}}
diff --git a/samples/client/echo_api/python/openapi_client/api/auth_api.py b/samples/client/echo_api/python/openapi_client/api/auth_api.py
index 07cdda86f58..16ee7463aad 100644
--- a/samples/client/echo_api/python/openapi_client/api/auth_api.py
+++ b/samples/client/echo_api/python/openapi_client/api/auth_api.py
@@ -18,7 +18,6 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
 
 from openapi_client.api_client import ApiClient
diff --git a/samples/client/echo_api/python/openapi_client/api/body_api.py b/samples/client/echo_api/python/openapi_client/api/body_api.py
index 196e2a6389f..553feae23a3 100644
--- a/samples/client/echo_api/python/openapi_client/api/body_api.py
+++ b/samples/client/echo_api/python/openapi_client/api/body_api.py
@@ -18,8 +18,8 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
+from typing_extensions import Annotated
 from pydantic import Field, StrictBytes, StrictStr, conlist
 
 from typing import Any, Dict, Optional, Union
diff --git a/samples/client/echo_api/python/openapi_client/api/form_api.py b/samples/client/echo_api/python/openapi_client/api/form_api.py
index 808dd48ffa2..0071725761d 100644
--- a/samples/client/echo_api/python/openapi_client/api/form_api.py
+++ b/samples/client/echo_api/python/openapi_client/api/form_api.py
@@ -18,7 +18,6 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
 from pydantic import StrictBool, StrictInt, StrictStr
 
diff --git a/samples/client/echo_api/python/openapi_client/api/header_api.py b/samples/client/echo_api/python/openapi_client/api/header_api.py
index a67fc13b277..7f9dc25354f 100644
--- a/samples/client/echo_api/python/openapi_client/api/header_api.py
+++ b/samples/client/echo_api/python/openapi_client/api/header_api.py
@@ -18,7 +18,6 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
 from pydantic import StrictBool, StrictInt, StrictStr
 
diff --git a/samples/client/echo_api/python/openapi_client/api/path_api.py b/samples/client/echo_api/python/openapi_client/api/path_api.py
index 13203624883..35d0c6a11b0 100644
--- a/samples/client/echo_api/python/openapi_client/api/path_api.py
+++ b/samples/client/echo_api/python/openapi_client/api/path_api.py
@@ -18,7 +18,6 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
 from pydantic import StrictInt, StrictStr
 
diff --git a/samples/client/echo_api/python/openapi_client/api/query_api.py b/samples/client/echo_api/python/openapi_client/api/query_api.py
index 59465cdc0cc..09d55efd2f5 100644
--- a/samples/client/echo_api/python/openapi_client/api/query_api.py
+++ b/samples/client/echo_api/python/openapi_client/api/query_api.py
@@ -18,7 +18,6 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
 from datetime import date, datetime
 
diff --git a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/another_fake_api.py b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/another_fake_api.py
index 3ba5d212b86..140dcf43460 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/another_fake_api.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/another_fake_api.py
@@ -17,9 +17,9 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 from typing import overload, Optional, Union, Awaitable
 
+from typing_extensions import Annotated
 from pydantic import Field
 
 from petstore_api.models.client import Client
diff --git a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/default_api.py b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/default_api.py
index 69cfa5ebedf..be02dd6b8a7 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/default_api.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/default_api.py
@@ -17,7 +17,6 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 from typing import overload, Optional, Union, Awaitable
 
 from petstore_api.models.foo_get_default_response import FooGetDefaultResponse
diff --git a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_api.py b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_api.py
index 201644a2177..3c0ef29b788 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_api.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_api.py
@@ -17,9 +17,9 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 from typing import overload, Optional, Union, Awaitable
 
+from typing_extensions import Annotated
 from datetime import date, datetime
 
 from pydantic import Field, StrictBool, StrictBytes, StrictInt, StrictStr, conbytes, confloat, conint, conlist, constr, validator
diff --git a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_classname_tags123_api.py b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_classname_tags123_api.py
index 1553c2d10b8..6b9c88c1212 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_classname_tags123_api.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_classname_tags123_api.py
@@ -17,9 +17,9 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 from typing import overload, Optional, Union, Awaitable
 
+from typing_extensions import Annotated
 from pydantic import Field
 
 from petstore_api.models.client import Client
diff --git a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/pet_api.py b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/pet_api.py
index 21954fd08a9..72e29e7d042 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/pet_api.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/pet_api.py
@@ -17,9 +17,9 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 from typing import overload, Optional, Union, Awaitable
 
+from typing_extensions import Annotated
 from pydantic import Field, StrictBytes, StrictInt, StrictStr, conlist, validator
 
 from typing import List, Optional, Union
diff --git a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/store_api.py b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/store_api.py
index f1e80d7e27b..e52b31ee5e1 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/store_api.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/store_api.py
@@ -17,9 +17,9 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 from typing import overload, Optional, Union, Awaitable
 
+from typing_extensions import Annotated
 from pydantic import Field, StrictStr, conint
 
 from typing import Dict
diff --git a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/user_api.py b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/user_api.py
index b17529a75a9..3c059d73339 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/user_api.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/user_api.py
@@ -17,9 +17,9 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 from typing import overload, Optional, Union, Awaitable
 
+from typing_extensions import Annotated
 from pydantic import Field, StrictStr, conlist
 
 from petstore_api.models.user import User
diff --git a/samples/openapi3/client/petstore/python/petstore_api/api/another_fake_api.py b/samples/openapi3/client/petstore/python/petstore_api/api/another_fake_api.py
index 13a77052ca0..c8ae8d0af13 100755
--- a/samples/openapi3/client/petstore/python/petstore_api/api/another_fake_api.py
+++ b/samples/openapi3/client/petstore/python/petstore_api/api/another_fake_api.py
@@ -17,8 +17,8 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
+from typing_extensions import Annotated
 from pydantic import Field
 
 from petstore_api.models.client import Client
diff --git a/samples/openapi3/client/petstore/python/petstore_api/api/default_api.py b/samples/openapi3/client/petstore/python/petstore_api/api/default_api.py
index 3b615de2250..b5269287737 100755
--- a/samples/openapi3/client/petstore/python/petstore_api/api/default_api.py
+++ b/samples/openapi3/client/petstore/python/petstore_api/api/default_api.py
@@ -17,7 +17,6 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
 from petstore_api.models.foo_get_default_response import FooGetDefaultResponse
 
diff --git a/samples/openapi3/client/petstore/python/petstore_api/api/fake_api.py b/samples/openapi3/client/petstore/python/petstore_api/api/fake_api.py
index df112200f14..1bdbf4e06a9 100755
--- a/samples/openapi3/client/petstore/python/petstore_api/api/fake_api.py
+++ b/samples/openapi3/client/petstore/python/petstore_api/api/fake_api.py
@@ -17,8 +17,8 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
+from typing_extensions import Annotated
 from datetime import date, datetime
 
 from pydantic import Field, StrictBool, StrictBytes, StrictFloat, StrictInt, StrictStr, conbytes, confloat, conint, conlist, constr, validator
diff --git a/samples/openapi3/client/petstore/python/petstore_api/api/fake_classname_tags123_api.py b/samples/openapi3/client/petstore/python/petstore_api/api/fake_classname_tags123_api.py
index 56620e1baa2..acfe8c01a94 100644
--- a/samples/openapi3/client/petstore/python/petstore_api/api/fake_classname_tags123_api.py
+++ b/samples/openapi3/client/petstore/python/petstore_api/api/fake_classname_tags123_api.py
@@ -17,8 +17,8 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
+from typing_extensions import Annotated
 from pydantic import Field
 
 from petstore_api.models.client import Client
diff --git a/samples/openapi3/client/petstore/python/petstore_api/api/pet_api.py b/samples/openapi3/client/petstore/python/petstore_api/api/pet_api.py
index 0325f335357..f0eefd7ec89 100755
--- a/samples/openapi3/client/petstore/python/petstore_api/api/pet_api.py
+++ b/samples/openapi3/client/petstore/python/petstore_api/api/pet_api.py
@@ -17,8 +17,8 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
+from typing_extensions import Annotated
 from pydantic import Field, StrictBytes, StrictInt, StrictStr, conlist, validator
 
 from typing import List, Optional, Union
diff --git a/samples/openapi3/client/petstore/python/petstore_api/api/store_api.py b/samples/openapi3/client/petstore/python/petstore_api/api/store_api.py
index 9ccbc98603d..b5b845531fe 100755
--- a/samples/openapi3/client/petstore/python/petstore_api/api/store_api.py
+++ b/samples/openapi3/client/petstore/python/petstore_api/api/store_api.py
@@ -17,8 +17,8 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
+from typing_extensions import Annotated
 from pydantic import Field, StrictStr, conint
 
 from typing import Dict
diff --git a/samples/openapi3/client/petstore/python/petstore_api/api/user_api.py b/samples/openapi3/client/petstore/python/petstore_api/api/user_api.py
index 3bb8e99417d..240a692ebca 100755
--- a/samples/openapi3/client/petstore/python/petstore_api/api/user_api.py
+++ b/samples/openapi3/client/petstore/python/petstore_api/api/user_api.py
@@ -17,8 +17,8 @@ import io
 import warnings
 
 from pydantic import validate_arguments, ValidationError
-from typing_extensions import Annotated
 
+from typing_extensions import Annotated
 from pydantic import Field, StrictStr, conlist
 
 from petstore_api.models.user import User