feat(python): handle multiple file parameters (#19329)

* test: fix broken python test

* fix: handle multiple file parameters

Previously an array of files was not handled correctly, despite the type
annotation implying it was.

* feat: handle filename,filedata tuples in file param

This allows for users to pass filenames with their data in file params,
which is useful for multipart formdata requests. Without this, the list
of files added in the previous commit would have the same filename for
all files (the parameter name).

modules/openapi-generator/src/main/java/org/openapitools/codegen/languages/AbstractPythonCodegen.java

@@ -1951,9 +1951,22 @@ public abstract class AbstractPythonCodegen extends DefaultCodegen implements Co
                 }
 
                 moduleImports.add("typing", "Union");
+
                 PythonType pt = new PythonType("Union");
                 pt.addTypeParam(bytest);
                 pt.addTypeParam(strt);
+
+                if (cp.getIsBinary()) {
+                    moduleImports.add("typing", "Tuple");
+
+                    PythonType tt = new PythonType("Tuple");
+                    // this string is a filename, not a validated value
+                    tt.addTypeParam(new PythonType("str"));
+                    tt.addTypeParam(bytest);
+
+                    pt.addTypeParam(tt);
+                }
+
                 return pt;
             } else {
                 // same as above which has validation
@@ -1964,6 +1977,17 @@ public abstract class AbstractPythonCodegen extends DefaultCodegen implements Co
                 PythonType pt = new PythonType("Union");
                 pt.addTypeParam(new PythonType("StrictBytes"));
                 pt.addTypeParam(new PythonType("StrictStr"));
+
+                if (cp.getIsBinary()) {
+                    moduleImports.add("typing", "Tuple");
+
+                    PythonType tt = new PythonType("Tuple");
+                    tt.addTypeParam(new PythonType("StrictStr"));
+                    tt.addTypeParam(new PythonType("StrictBytes"));
+
+                    pt.addTypeParam(tt);
+                }
+
                 return pt;
             }
         }

modules/openapi-generator/src/main/resources/python/api.mustache

@@ -101,7 +101,9 @@ class {{classname}}:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -165,6 +167,9 @@ class {{classname}}:
             if isinstance({{paramName}}, str):
                 with open({{paramName}}, "rb") as _fp:
                     _body_params = _fp.read()
+            elif isinstance({{paramName}}, tuple):
+                # drop the filename from the tuple
+                _body_params = {{paramName}}[1]
             else:
                 _body_params = {{paramName}}
             {{/isBinary}}

modules/openapi-generator/src/main/resources/python/api_client.mustache

@@ -543,7 +543,10 @@ class ApiClient:
 
         return "&".join(["=".join(map(str, item)) for item in new_params])
 
-    def files_parameters(self, files: Dict[str, Union[str, bytes]]):
+    def files_parameters(
+        self,
+        files: Dict[str, Union[str, bytes, List[str], List[bytes], Tuple[str, bytes]]],
+    ):
         """Builds form parameters.
 
         :param files: File parameters.
@@ -558,6 +561,12 @@ class ApiClient:
             elif isinstance(v, bytes):
                 filename = k
                 filedata = v
+            elif isinstance(v, tuple):
+                filename, filedata = v
+            elif isinstance(v, list):
+                for file_param in v:
+                    params.extend(self.files_parameters({k: file_param}))
+                continue
             else:
                 raise ValueError("Unsupported file value")
             mimetype = (

samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api/auth_api.py

@@ -239,7 +239,9 @@ class AuthApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -483,7 +485,9 @@ class AuthApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api/body_api.py

@@ -18,7 +18,7 @@ from typing import Any, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 
 from pydantic import Field, StrictBytes, StrictStr
-from typing import Any, Dict, List, Optional, Union
+from typing import Any, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 from openapi_client.models.pet import Pet
 from openapi_client.models.string_enum_ref import StringEnumRef
@@ -244,7 +244,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -288,7 +290,7 @@ class BodyApi:
     @validate_call
     def test_body_application_octetstream_binary(
         self,
-        body: Optional[Union[StrictBytes, StrictStr]] = None,
+        body: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -355,7 +357,7 @@ class BodyApi:
     @validate_call
     def test_body_application_octetstream_binary_with_http_info(
         self,
-        body: Optional[Union[StrictBytes, StrictStr]] = None,
+        body: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -422,7 +424,7 @@ class BodyApi:
     @validate_call
     def test_body_application_octetstream_binary_without_preload_content(
         self,
-        body: Optional[Union[StrictBytes, StrictStr]] = None,
+        body: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -500,7 +502,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -513,6 +517,9 @@ class BodyApi:
             if isinstance(body, str):
                 with open(body, "rb") as _fp:
                     _body_params = _fp.read()
+            elif isinstance(body, tuple):
+                # drop the filename from the tuple
+                _body_params = body[1]
             else:
                 _body_params = body
 
@@ -564,7 +571,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_array_of_binary(
         self,
-        files: List[Union[StrictBytes, StrictStr]],
+        files: List[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -631,7 +638,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_array_of_binary_with_http_info(
         self,
-        files: List[Union[StrictBytes, StrictStr]],
+        files: List[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -698,7 +705,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_array_of_binary_without_preload_content(
         self,
-        files: List[Union[StrictBytes, StrictStr]],
+        files: List[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -777,7 +784,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -836,7 +845,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_single_binary(
         self,
-        my_file: Optional[Union[StrictBytes, StrictStr]] = None,
+        my_file: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -903,7 +912,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_single_binary_with_http_info(
         self,
-        my_file: Optional[Union[StrictBytes, StrictStr]] = None,
+        my_file: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -970,7 +979,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_single_binary_without_preload_content(
         self,
-        my_file: Optional[Union[StrictBytes, StrictStr]] = None,
+        my_file: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -1048,7 +1057,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1319,7 +1330,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1590,7 +1603,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1861,7 +1876,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2132,7 +2149,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2403,7 +2422,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2674,7 +2695,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api/form_api.py

@@ -280,7 +280,9 @@ class FormApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -555,7 +557,9 @@ class FormApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -891,7 +895,9 @@ class FormApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api/header_api.py

@@ -306,7 +306,9 @@ class HeaderApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api/path_api.py

@@ -292,7 +292,9 @@ class PathApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api/query_api.py

@@ -270,7 +270,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -560,7 +562,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -872,7 +876,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1140,7 +1146,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1400,7 +1408,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1661,7 +1671,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1922,7 +1934,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2182,7 +2196,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2442,7 +2458,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2702,7 +2720,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api_client.py

@@ -536,7 +536,10 @@ class ApiClient:
 
         return "&".join(["=".join(map(str, item)) for item in new_params])
 
-    def files_parameters(self, files: Dict[str, Union[str, bytes]]):
+    def files_parameters(
+        self,
+        files: Dict[str, Union[str, bytes, List[str], List[bytes], Tuple[str, bytes]]],
+    ):
         """Builds form parameters.
 
         :param files: File parameters.
@@ -551,6 +554,12 @@ class ApiClient:
             elif isinstance(v, bytes):
                 filename = k
                 filedata = v
+            elif isinstance(v, tuple):
+                filename, filedata = v
+            elif isinstance(v, list):
+                for file_param in v:
+                    params.extend(self.files_parameters({k: file_param}))
+                continue
             else:
                 raise ValueError("Unsupported file value")
             mimetype = (

samples/client/echo_api/python/openapi_client/api/auth_api.py

@@ -239,7 +239,9 @@ class AuthApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -483,7 +485,9 @@ class AuthApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python/openapi_client/api/body_api.py

@@ -18,7 +18,7 @@ from typing import Any, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 
 from pydantic import Field, StrictBytes, StrictStr
-from typing import Any, Dict, List, Optional, Union
+from typing import Any, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 from openapi_client.models.pet import Pet
 from openapi_client.models.string_enum_ref import StringEnumRef
@@ -244,7 +244,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -288,7 +290,7 @@ class BodyApi:
     @validate_call
     def test_body_application_octetstream_binary(
         self,
-        body: Optional[Union[StrictBytes, StrictStr]] = None,
+        body: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -355,7 +357,7 @@ class BodyApi:
     @validate_call
     def test_body_application_octetstream_binary_with_http_info(
         self,
-        body: Optional[Union[StrictBytes, StrictStr]] = None,
+        body: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -422,7 +424,7 @@ class BodyApi:
     @validate_call
     def test_body_application_octetstream_binary_without_preload_content(
         self,
-        body: Optional[Union[StrictBytes, StrictStr]] = None,
+        body: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -500,7 +502,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -513,6 +517,9 @@ class BodyApi:
             if isinstance(body, str):
                 with open(body, "rb") as _fp:
                     _body_params = _fp.read()
+            elif isinstance(body, tuple):
+                # drop the filename from the tuple
+                _body_params = body[1]
             else:
                 _body_params = body
 
@@ -564,7 +571,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_array_of_binary(
         self,
-        files: List[Union[StrictBytes, StrictStr]],
+        files: List[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -631,7 +638,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_array_of_binary_with_http_info(
         self,
-        files: List[Union[StrictBytes, StrictStr]],
+        files: List[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -698,7 +705,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_array_of_binary_without_preload_content(
         self,
-        files: List[Union[StrictBytes, StrictStr]],
+        files: List[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -777,7 +784,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -836,7 +845,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_single_binary(
         self,
-        my_file: Optional[Union[StrictBytes, StrictStr]] = None,
+        my_file: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -903,7 +912,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_single_binary_with_http_info(
         self,
-        my_file: Optional[Union[StrictBytes, StrictStr]] = None,
+        my_file: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -970,7 +979,7 @@ class BodyApi:
     @validate_call
     def test_body_multipart_formdata_single_binary_without_preload_content(
         self,
-        my_file: Optional[Union[StrictBytes, StrictStr]] = None,
+        my_file: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -1048,7 +1057,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1319,7 +1330,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1590,7 +1603,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1861,7 +1876,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2132,7 +2149,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2403,7 +2422,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2674,7 +2695,9 @@ class BodyApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python/openapi_client/api/form_api.py

@@ -280,7 +280,9 @@ class FormApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -555,7 +557,9 @@ class FormApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -891,7 +895,9 @@ class FormApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python/openapi_client/api/header_api.py

@@ -306,7 +306,9 @@ class HeaderApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python/openapi_client/api/path_api.py

@@ -292,7 +292,9 @@ class PathApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python/openapi_client/api/query_api.py

@@ -270,7 +270,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -560,7 +562,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -872,7 +876,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1140,7 +1146,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1400,7 +1408,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1661,7 +1671,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1922,7 +1934,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2182,7 +2196,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2442,7 +2458,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2702,7 +2720,9 @@ class QueryApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/client/echo_api/python/openapi_client/api_client.py

@@ -536,7 +536,10 @@ class ApiClient:
 
         return "&".join(["=".join(map(str, item)) for item in new_params])
 
-    def files_parameters(self, files: Dict[str, Union[str, bytes]]):
+    def files_parameters(
+        self,
+        files: Dict[str, Union[str, bytes, List[str], List[bytes], Tuple[str, bytes]]],
+    ):
         """Builds form parameters.
 
         :param files: File parameters.
@@ -551,6 +554,12 @@ class ApiClient:
             elif isinstance(v, bytes):
                 filename = k
                 filedata = v
+            elif isinstance(v, tuple):
+                filename, filedata = v
+            elif isinstance(v, list):
+                for file_param in v:
+                    params.extend(self.files_parameters({k: file_param}))
+                continue
             else:
                 raise ValueError("Unsupported file value")
             mimetype = (

samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/another_fake_api.py

@@ -253,7 +253,9 @@ class AnotherFakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/default_api.py

@@ -232,7 +232,9 @@ class DefaultApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_api.py

@@ -18,7 +18,7 @@ from typing_extensions import Annotated
 
 from datetime import date, datetime
 from pydantic import Field, StrictBool, StrictBytes, StrictInt, StrictStr, field_validator
-from typing import Any, Dict, List, Optional, Union
+from typing import Any, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 from petstore_api.models.client import Client
 from petstore_api.models.enum_class import EnumClass
@@ -263,7 +263,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -524,7 +526,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -761,7 +765,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1040,7 +1046,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1312,7 +1320,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1583,7 +1593,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1854,7 +1866,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2125,7 +2139,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2410,7 +2426,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2669,7 +2687,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2909,7 +2929,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -3149,7 +3171,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -3389,7 +3413,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -3629,7 +3655,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -3869,7 +3897,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -4109,7 +4139,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -4349,7 +4381,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -4589,7 +4623,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -4829,7 +4865,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -5082,7 +5120,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -5335,7 +5375,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -5387,7 +5429,7 @@ class FakeApi:
     @validate_call
     async def test_body_with_binary(
         self,
-        body: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="image to upload")],
+        body: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="image to upload")],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -5454,7 +5496,7 @@ class FakeApi:
     @validate_call
     async def test_body_with_binary_with_http_info(
         self,
-        body: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="image to upload")],
+        body: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="image to upload")],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -5521,7 +5563,7 @@ class FakeApi:
     @validate_call
     async def test_body_with_binary_without_preload_content(
         self,
-        body: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="image to upload")],
+        body: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="image to upload")],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -5599,7 +5641,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -5612,6 +5656,9 @@ class FakeApi:
             if isinstance(body, str):
                 with open(body, "rb") as _fp:
                     _body_params = _fp.read()
+            elif isinstance(body, tuple):
+                # drop the filename from the tuple
+                _body_params = body[1]
             else:
                 _body_params = body
 
@@ -5868,7 +5915,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -6142,7 +6191,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -6410,7 +6461,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -6691,7 +6744,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -6947,7 +7002,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -7000,7 +7057,7 @@ class FakeApi:
         int64: Annotated[Optional[StrictInt], Field(description="None")] = None,
         var_float: Annotated[Optional[Annotated[float, Field(le=987.6)]], Field(description="None")] = None,
         string: Annotated[Optional[Annotated[str, Field(strict=True)]], Field(description="None")] = None,
-        binary: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="None")] = None,
+        binary: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="None")] = None,
         byte_with_max_length: Annotated[Optional[Union[Annotated[bytes, Field(strict=True, max_length=64)], Annotated[str, Field(strict=True, max_length=64)]]], Field(description="None")] = None,
         var_date: Annotated[Optional[date], Field(description="None")] = None,
         date_time: Annotated[Optional[datetime], Field(description="None")] = None,
@@ -7124,7 +7181,7 @@ class FakeApi:
         int64: Annotated[Optional[StrictInt], Field(description="None")] = None,
         var_float: Annotated[Optional[Annotated[float, Field(le=987.6)]], Field(description="None")] = None,
         string: Annotated[Optional[Annotated[str, Field(strict=True)]], Field(description="None")] = None,
-        binary: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="None")] = None,
+        binary: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="None")] = None,
         byte_with_max_length: Annotated[Optional[Union[Annotated[bytes, Field(strict=True, max_length=64)], Annotated[str, Field(strict=True, max_length=64)]]], Field(description="None")] = None,
         var_date: Annotated[Optional[date], Field(description="None")] = None,
         date_time: Annotated[Optional[datetime], Field(description="None")] = None,
@@ -7248,7 +7305,7 @@ class FakeApi:
         int64: Annotated[Optional[StrictInt], Field(description="None")] = None,
         var_float: Annotated[Optional[Annotated[float, Field(le=987.6)]], Field(description="None")] = None,
         string: Annotated[Optional[Annotated[str, Field(strict=True)]], Field(description="None")] = None,
-        binary: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="None")] = None,
+        binary: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="None")] = None,
         byte_with_max_length: Annotated[Optional[Union[Annotated[bytes, Field(strict=True, max_length=64)], Annotated[str, Field(strict=True, max_length=64)]]], Field(description="None")] = None,
         var_date: Annotated[Optional[date], Field(description="None")] = None,
         date_time: Annotated[Optional[datetime], Field(description="None")] = None,
@@ -7388,7 +7445,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -7671,7 +7730,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -7992,7 +8053,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -8262,7 +8325,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -8526,7 +8591,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -8803,7 +8870,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -9066,7 +9135,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -9413,7 +9484,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -9690,7 +9763,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/fake_classname_tags123_api.py

@@ -253,7 +253,9 @@ class FakeClassnameTags123Api:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/import_test_datetime_api.py

@@ -235,7 +235,9 @@ class ImportTestDatetimeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/pet_api.py

@@ -17,7 +17,7 @@ from typing import Any, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 
 from pydantic import Field, StrictBytes, StrictInt, StrictStr, field_validator
-from typing import List, Optional, Union
+from typing import List, Optional, Tuple, Union
 from typing_extensions import Annotated
 from petstore_api.models.model_api_response import ModelApiResponse
 from petstore_api.models.pet import Pet
@@ -258,7 +258,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -541,7 +543,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -799,7 +803,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1069,7 +1075,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1338,7 +1346,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1607,7 +1617,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1903,7 +1915,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1962,7 +1976,7 @@ class PetApi:
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
-        file: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="file to upload")] = None,
+        file: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="file to upload")] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -2037,7 +2051,7 @@ class PetApi:
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
-        file: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="file to upload")] = None,
+        file: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="file to upload")] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -2112,7 +2126,7 @@ class PetApi:
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
-        file: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="file to upload")] = None,
+        file: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="file to upload")] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -2198,7 +2212,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2263,7 +2279,7 @@ class PetApi:
     async def upload_file_with_required_file(
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
-        required_file: Annotated[Union[StrictBytes, StrictStr], Field(description="file to upload")],
+        required_file: Annotated[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]], Field(description="file to upload")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
         _request_timeout: Union[
             None,
@@ -2338,7 +2354,7 @@ class PetApi:
     async def upload_file_with_required_file_with_http_info(
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
-        required_file: Annotated[Union[StrictBytes, StrictStr], Field(description="file to upload")],
+        required_file: Annotated[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]], Field(description="file to upload")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
         _request_timeout: Union[
             None,
@@ -2413,7 +2429,7 @@ class PetApi:
     async def upload_file_with_required_file_without_preload_content(
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
-        required_file: Annotated[Union[StrictBytes, StrictStr], Field(description="file to upload")],
+        required_file: Annotated[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]], Field(description="file to upload")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
         _request_timeout: Union[
             None,
@@ -2500,7 +2516,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/store_api.py

@@ -257,7 +257,9 @@ class StoreApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -495,7 +497,9 @@ class StoreApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -758,7 +762,9 @@ class StoreApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1020,7 +1026,9 @@ class StoreApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python-aiohttp/petstore_api/api/user_api.py

@@ -256,7 +256,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -518,7 +520,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -780,7 +784,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1047,7 +1053,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1304,7 +1312,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1579,7 +1589,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1828,7 +1840,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2093,7 +2107,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python-aiohttp/petstore_api/api_client.py

@@ -538,7 +538,10 @@ class ApiClient:
 
         return "&".join(["=".join(map(str, item)) for item in new_params])
 
-    def files_parameters(self, files: Dict[str, Union[str, bytes]]):
+    def files_parameters(
+        self,
+        files: Dict[str, Union[str, bytes, List[str], List[bytes], Tuple[str, bytes]]],
+    ):
         """Builds form parameters.
 
         :param files: File parameters.
@@ -553,6 +556,12 @@ class ApiClient:
             elif isinstance(v, bytes):
                 filename = k
                 filedata = v
+            elif isinstance(v, tuple):
+                filename, filedata = v
+            elif isinstance(v, list):
+                for file_param in v:
+                    params.extend(self.files_parameters({k: file_param}))
+                continue
             else:
                 raise ValueError("Unsupported file value")
             mimetype = (

samples/openapi3/client/petstore/python-aiohttp/petstore_api/models/format_test.py

@@ -20,7 +20,7 @@ import json
 from datetime import date, datetime
 from decimal import Decimal
 from pydantic import BaseModel, ConfigDict, Field, StrictBytes, StrictInt, StrictStr, field_validator
-from typing import Any, ClassVar, Dict, List, Optional, Union
+from typing import Any, ClassVar, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 from typing import Optional, Set
 from typing_extensions import Self
@@ -39,7 +39,7 @@ class FormatTest(BaseModel):
     string: Optional[Annotated[str, Field(strict=True)]] = None
     string_with_double_quote_pattern: Optional[Annotated[str, Field(strict=True)]] = None
     byte: Optional[Union[StrictBytes, StrictStr]] = None
-    binary: Optional[Union[StrictBytes, StrictStr]] = None
+    binary: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None
     var_date: date = Field(alias="date")
     date_time: Optional[datetime] = Field(default=None, alias="dateTime")
     uuid: Optional[StrictStr] = None

samples/openapi3/client/petstore/python/petstore_api/api/another_fake_api.py

@@ -253,7 +253,9 @@ class AnotherFakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python/petstore_api/api/default_api.py

@@ -232,7 +232,9 @@ class DefaultApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python/petstore_api/api/fake_api.py

@@ -18,7 +18,7 @@ from typing_extensions import Annotated
 
 from datetime import date, datetime
 from pydantic import Field, StrictBool, StrictBytes, StrictFloat, StrictInt, StrictStr, field_validator
-from typing import Any, Dict, List, Optional, Union
+from typing import Any, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 from petstore_api.models.client import Client
 from petstore_api.models.enum_class import EnumClass
@@ -263,7 +263,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -524,7 +526,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -761,7 +765,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1040,7 +1046,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1312,7 +1320,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1583,7 +1593,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1854,7 +1866,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2125,7 +2139,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2410,7 +2426,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2669,7 +2687,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2909,7 +2929,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -3149,7 +3171,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -3389,7 +3413,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -3629,7 +3655,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -3869,7 +3897,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -4109,7 +4139,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -4349,7 +4381,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -4589,7 +4623,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -4829,7 +4865,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -5082,7 +5120,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -5335,7 +5375,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -5387,7 +5429,7 @@ class FakeApi:
     @validate_call
     def test_body_with_binary(
         self,
-        body: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="image to upload")],
+        body: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="image to upload")],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -5454,7 +5496,7 @@ class FakeApi:
     @validate_call
     def test_body_with_binary_with_http_info(
         self,
-        body: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="image to upload")],
+        body: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="image to upload")],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -5521,7 +5563,7 @@ class FakeApi:
     @validate_call
     def test_body_with_binary_without_preload_content(
         self,
-        body: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="image to upload")],
+        body: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="image to upload")],
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -5599,7 +5641,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -5612,6 +5656,9 @@ class FakeApi:
             if isinstance(body, str):
                 with open(body, "rb") as _fp:
                     _body_params = _fp.read()
+            elif isinstance(body, tuple):
+                # drop the filename from the tuple
+                _body_params = body[1]
             else:
                 _body_params = body
 
@@ -5868,7 +5915,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -6142,7 +6191,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -6410,7 +6461,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -6691,7 +6744,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -6947,7 +7002,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -7000,7 +7057,7 @@ class FakeApi:
         int64: Annotated[Optional[StrictInt], Field(description="None")] = None,
         var_float: Annotated[Optional[Annotated[float, Field(le=987.6, strict=True)]], Field(description="None")] = None,
         string: Annotated[Optional[Annotated[str, Field(strict=True)]], Field(description="None")] = None,
-        binary: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="None")] = None,
+        binary: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="None")] = None,
         byte_with_max_length: Annotated[Optional[Union[Annotated[bytes, Field(strict=True, max_length=64)], Annotated[str, Field(strict=True, max_length=64)]]], Field(description="None")] = None,
         var_date: Annotated[Optional[date], Field(description="None")] = None,
         date_time: Annotated[Optional[datetime], Field(description="None")] = None,
@@ -7124,7 +7181,7 @@ class FakeApi:
         int64: Annotated[Optional[StrictInt], Field(description="None")] = None,
         var_float: Annotated[Optional[Annotated[float, Field(le=987.6, strict=True)]], Field(description="None")] = None,
         string: Annotated[Optional[Annotated[str, Field(strict=True)]], Field(description="None")] = None,
-        binary: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="None")] = None,
+        binary: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="None")] = None,
         byte_with_max_length: Annotated[Optional[Union[Annotated[bytes, Field(strict=True, max_length=64)], Annotated[str, Field(strict=True, max_length=64)]]], Field(description="None")] = None,
         var_date: Annotated[Optional[date], Field(description="None")] = None,
         date_time: Annotated[Optional[datetime], Field(description="None")] = None,
@@ -7248,7 +7305,7 @@ class FakeApi:
         int64: Annotated[Optional[StrictInt], Field(description="None")] = None,
         var_float: Annotated[Optional[Annotated[float, Field(le=987.6, strict=True)]], Field(description="None")] = None,
         string: Annotated[Optional[Annotated[str, Field(strict=True)]], Field(description="None")] = None,
-        binary: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="None")] = None,
+        binary: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="None")] = None,
         byte_with_max_length: Annotated[Optional[Union[Annotated[bytes, Field(strict=True, max_length=64)], Annotated[str, Field(strict=True, max_length=64)]]], Field(description="None")] = None,
         var_date: Annotated[Optional[date], Field(description="None")] = None,
         date_time: Annotated[Optional[datetime], Field(description="None")] = None,
@@ -7388,7 +7445,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -7671,7 +7730,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -7992,7 +8053,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -8262,7 +8325,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -8526,7 +8591,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -8803,7 +8870,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -9066,7 +9135,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -9413,7 +9484,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -9690,7 +9763,9 @@ class FakeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python/petstore_api/api/fake_classname_tags123_api.py

@@ -253,7 +253,9 @@ class FakeClassnameTags123Api:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python/petstore_api/api/import_test_datetime_api.py

@@ -235,7 +235,9 @@ class ImportTestDatetimeApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python/petstore_api/api/pet_api.py

@@ -17,7 +17,7 @@ from typing import Any, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 
 from pydantic import Field, StrictBytes, StrictInt, StrictStr, field_validator
-from typing import List, Optional, Union
+from typing import List, Optional, Tuple, Union
 from typing_extensions import Annotated
 from petstore_api.models.model_api_response import ModelApiResponse
 from petstore_api.models.pet import Pet
@@ -258,7 +258,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -541,7 +543,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -799,7 +803,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1069,7 +1075,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1338,7 +1346,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1607,7 +1617,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1903,7 +1915,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1962,7 +1976,7 @@ class PetApi:
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
-        file: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="file to upload")] = None,
+        file: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="file to upload")] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -2037,7 +2051,7 @@ class PetApi:
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
-        file: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="file to upload")] = None,
+        file: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="file to upload")] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -2112,7 +2126,7 @@ class PetApi:
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
-        file: Annotated[Optional[Union[StrictBytes, StrictStr]], Field(description="file to upload")] = None,
+        file: Annotated[Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]], Field(description="file to upload")] = None,
         _request_timeout: Union[
             None,
             Annotated[StrictFloat, Field(gt=0)],
@@ -2198,7 +2212,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2263,7 +2279,7 @@ class PetApi:
     def upload_file_with_required_file(
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
-        required_file: Annotated[Union[StrictBytes, StrictStr], Field(description="file to upload")],
+        required_file: Annotated[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]], Field(description="file to upload")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
         _request_timeout: Union[
             None,
@@ -2338,7 +2354,7 @@ class PetApi:
     def upload_file_with_required_file_with_http_info(
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
-        required_file: Annotated[Union[StrictBytes, StrictStr], Field(description="file to upload")],
+        required_file: Annotated[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]], Field(description="file to upload")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
         _request_timeout: Union[
             None,
@@ -2413,7 +2429,7 @@ class PetApi:
     def upload_file_with_required_file_without_preload_content(
         self,
         pet_id: Annotated[StrictInt, Field(description="ID of pet to update")],
-        required_file: Annotated[Union[StrictBytes, StrictStr], Field(description="file to upload")],
+        required_file: Annotated[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]], Field(description="file to upload")],
         additional_metadata: Annotated[Optional[StrictStr], Field(description="Additional data to pass to server")] = None,
         _request_timeout: Union[
             None,
@@ -2500,7 +2516,9 @@ class PetApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python/petstore_api/api/store_api.py

@@ -257,7 +257,9 @@ class StoreApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -495,7 +497,9 @@ class StoreApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -758,7 +762,9 @@ class StoreApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1020,7 +1026,9 @@ class StoreApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python/petstore_api/api/user_api.py

@@ -256,7 +256,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -518,7 +520,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -780,7 +784,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1047,7 +1053,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1304,7 +1312,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1579,7 +1589,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -1828,7 +1840,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters
@@ -2093,7 +2107,9 @@ class UserApi:
         _query_params: List[Tuple[str, str]] = []
         _header_params: Dict[str, Optional[str]] = _headers or {}
         _form_params: List[Tuple[str, str]] = []
-        _files: Dict[str, Union[str, bytes]] = {}
+        _files: Dict[
+            str, Union[str, bytes, List[str], List[bytes], List[Tuple[str, bytes]]]
+        ] = {}
         _body_params: Optional[bytes] = None
 
         # process the path parameters

samples/openapi3/client/petstore/python/petstore_api/api_client.py

@@ -535,7 +535,10 @@ class ApiClient:
 
         return "&".join(["=".join(map(str, item)) for item in new_params])
 
-    def files_parameters(self, files: Dict[str, Union[str, bytes]]):
+    def files_parameters(
+        self,
+        files: Dict[str, Union[str, bytes, List[str], List[bytes], Tuple[str, bytes]]],
+    ):
         """Builds form parameters.
 
         :param files: File parameters.
@@ -550,6 +553,12 @@ class ApiClient:
             elif isinstance(v, bytes):
                 filename = k
                 filedata = v
+            elif isinstance(v, tuple):
+                filename, filedata = v
+            elif isinstance(v, list):
+                for file_param in v:
+                    params.extend(self.files_parameters({k: file_param}))
+                continue
             else:
                 raise ValueError("Unsupported file value")
             mimetype = (

samples/openapi3/client/petstore/python/petstore_api/models/format_test.py

@@ -20,7 +20,7 @@ import json
 from datetime import date, datetime
 from decimal import Decimal
 from pydantic import BaseModel, ConfigDict, Field, StrictBytes, StrictInt, StrictStr, field_validator
-from typing import Any, ClassVar, Dict, List, Optional, Union
+from typing import Any, ClassVar, Dict, List, Optional, Tuple, Union
 from typing_extensions import Annotated
 from typing import Optional, Set
 from typing_extensions import Self
@@ -39,7 +39,7 @@ class FormatTest(BaseModel):
     string: Optional[Annotated[str, Field(strict=True)]] = None
     string_with_double_quote_pattern: Optional[Annotated[str, Field(strict=True)]] = None
     byte: Optional[Union[StrictBytes, StrictStr]] = None
-    binary: Optional[Union[StrictBytes, StrictStr]] = None
+    binary: Optional[Union[StrictBytes, StrictStr, Tuple[StrictStr, StrictBytes]]] = None
     var_date: date = Field(alias="date")
     date_time: Optional[datetime] = Field(default=None, alias="dateTime")
     uuid: Optional[StrictStr] = None

samples/openapi3/client/petstore/python/tests/test_api_client.py

@@ -184,7 +184,7 @@ class ApiClientTests(unittest.TestCase):
     def test_sanitize_for_serialization_decimal(self):
         data = Decimal("1.0")
         result = self.api_client.sanitize_for_serialization(data)
-        self.assertEquals(result, "1.0")
+        self.assertEqual(result, "1.0")
 
     def test_sanitize_for_serialization_list_enum(self):
         class EnumSerialization(int, Enum):