diff --git a/end_to_end_tests/custom-templates-golden-record/my_test_api_client/api/tests/__init__.py b/end_to_end_tests/custom-templates-golden-record/my_test_api_client/api/tests/__init__.py
index dcb864fe9..28a4f10c1 100644
--- a/end_to_end_tests/custom-templates-golden-record/my_test_api_client/api/tests/__init__.py
+++ b/end_to_end_tests/custom-templates-golden-record/my_test_api_client/api/tests/__init__.py
@@ -19,6 +19,7 @@
     token_with_cookie_auth_token_with_cookie_get,
     unsupported_content_tests_unsupported_content_get,
     upload_file_tests_upload_post,
+    upload_multiple_files_tests_upload_post,
 )
 
 
@@ -72,6 +73,13 @@ def upload_file_tests_upload_post(cls) -> types.ModuleType:
         """
         return upload_file_tests_upload_post
 
+    @classmethod
+    def upload_multiple_files_tests_upload_post(cls) -> types.ModuleType:
+        """
+        Upload several files in the same request
+        """
+        return upload_multiple_files_tests_upload_post
+
     @classmethod
     def json_body_tests_json_body_post(cls) -> types.ModuleType:
         """
diff --git a/end_to_end_tests/golden-record/my_test_api_client/api/tests/upload_multiple_files_tests_upload_post.py b/end_to_end_tests/golden-record/my_test_api_client/api/tests/upload_multiple_files_tests_upload_post.py
new file mode 100644
index 000000000..e5e42d546
--- /dev/null
+++ b/end_to_end_tests/golden-record/my_test_api_client/api/tests/upload_multiple_files_tests_upload_post.py
@@ -0,0 +1,126 @@
+from typing import Any, Dict, List, Optional, Union
+
+import httpx
+
+from ...client import Client
+from ...models.http_validation_error import HTTPValidationError
+from ...types import UNSET, File, Response, Unset
+
+
+def _get_kwargs(
+    *,
+    client: Client,
+    multipart_data: List[File],
+    keep_alive: Union[Unset, bool] = UNSET,
+) -> Dict[str, Any]:
+    url = "{}/tests/upload/multiple".format(client.base_url)
+
+    headers: Dict[str, Any] = client.get_headers()
+    cookies: Dict[str, Any] = client.get_cookies()
+
+    if keep_alive is not UNSET:
+        headers["keep-alive"] = keep_alive
+
+    multipart_multipart_data = []
+    for multipart_data_item_data in multipart_data:
+        multipart_data_item = multipart_data_item_data.to_tuple()
+
+        multipart_multipart_data.append(multipart_data_item)
+
+    return {
+        "url": url,
+        "headers": headers,
+        "cookies": cookies,
+        "timeout": client.get_timeout(),
+        "files": multipart_multipart_data,
+    }
+
+
+def _parse_response(*, response: httpx.Response) -> Optional[Union[Any, HTTPValidationError]]:
+    if response.status_code == 200:
+        response_200 = response.json()
+
+        return response_200
+    if response.status_code == 422:
+        response_422 = HTTPValidationError.from_dict(response.json())
+
+        return response_422
+    return None
+
+
+def _build_response(*, response: httpx.Response) -> Response[Union[Any, HTTPValidationError]]:
+    return Response(
+        status_code=response.status_code,
+        content=response.content,
+        headers=response.headers,
+        parsed=_parse_response(response=response),
+    )
+
+
+def sync_detailed(
+    *,
+    client: Client,
+    multipart_data: List[File],
+    keep_alive: Union[Unset, bool] = UNSET,
+) -> Response[Union[Any, HTTPValidationError]]:
+    kwargs = _get_kwargs(
+        client=client,
+        multipart_data=multipart_data,
+        keep_alive=keep_alive,
+    )
+
+    response = httpx.post(
+        **kwargs,
+    )
+
+    return _build_response(response=response)
+
+
+def sync(
+    *,
+    client: Client,
+    multipart_data: List[File],
+    keep_alive: Union[Unset, bool] = UNSET,
+) -> Optional[Union[Any, HTTPValidationError]]:
+    """Upload several files in the same request"""
+
+    return sync_detailed(
+        client=client,
+        multipart_data=multipart_data,
+        keep_alive=keep_alive,
+    ).parsed
+
+
+async def asyncio_detailed(
+    *,
+    client: Client,
+    multipart_data: List[File],
+    keep_alive: Union[Unset, bool] = UNSET,
+) -> Response[Union[Any, HTTPValidationError]]:
+    kwargs = _get_kwargs(
+        client=client,
+        multipart_data=multipart_data,
+        keep_alive=keep_alive,
+    )
+
+    async with httpx.AsyncClient() as _client:
+        response = await _client.post(**kwargs)
+
+    return _build_response(response=response)
+
+
+async def asyncio(
+    *,
+    client: Client,
+    multipart_data: List[File],
+    keep_alive: Union[Unset, bool] = UNSET,
+) -> Optional[Union[Any, HTTPValidationError]]:
+    """Upload several files in the same request"""
+
+    return (
+        await asyncio_detailed(
+            client=client,
+            multipart_data=multipart_data,
+            keep_alive=keep_alive,
+        )
+    ).parsed
diff --git a/end_to_end_tests/openapi.json b/end_to_end_tests/openapi.json
index 3724f428c..5e8c2cbe8 100644
--- a/end_to_end_tests/openapi.json
+++ b/end_to_end_tests/openapi.json
@@ -269,6 +269,61 @@
         }
       }
     },
+    "/tests/upload/multiple": {
+      "post": {
+        "tags": [
+          "tests"
+        ],
+        "summary": "Upload multiple files",
+        "description": "Upload several files in the same request",
+        "operationId": "upload_multiple_files_tests_upload_post",
+        "parameters": [
+          {
+            "required": false,
+            "schema": {
+              "title": "Keep-Alive",
+              "type": "boolean"
+            },
+            "name": "keep-alive",
+            "in": "header"
+          }
+        ],
+        "requestBody": {
+          "content": {
+            "multipart/form-data": {
+              "schema": {
+                "type": "array",
+                "items": {
+                  "type": "string",
+                  "format": "binary"
+                }
+              }
+            }
+          },
+          "required": true
+        },
+        "responses": {
+          "200": {
+            "description": "Successful Response",
+            "content": {
+              "application/json": {
+                "schema": {}
+              }
+            }
+          },
+          "422": {
+            "description": "Validation Error",
+            "content": {
+              "application/json": {
+                "schema": {
+                  "$ref": "#/components/schemas/HTTPValidationError"
+                }
+              }
+            }
+          }
+        }
+      }
+    },
     "/tests/json_body": {
       "post": {
         "tags": [
diff --git a/openapi_python_client/templates/property_templates/list_property.py.jinja b/openapi_python_client/templates/property_templates/list_property.py.jinja
index b955ad40a..44dac097e 100644
--- a/openapi_python_client/templates/property_templates/list_property.py.jinja
+++ b/openapi_python_client/templates/property_templates/list_property.py.jinja
@@ -17,7 +17,7 @@ for {{ inner_source }} in (_{{ property.python_name }} or []):
 {% endif %}
 {% endmacro %}
 
-{% macro _transform(property, source, destination, stringify) %}
+{% macro _transform(property, source, destination, stringify, transform_method) %}
 {% set inner_property = property.inner_property %}
 {% if stringify %}
 {% set stringified_destination = destination %}
@@ -28,7 +28,7 @@ for {{ inner_source }} in (_{{ property.python_name }} or []):
 {{ destination }} = []
 for {{ inner_source }} in {{ source }}:
     {% from "property_templates/" + inner_property.template import transform %}
-    {{ transform(inner_property, inner_source, inner_property.python_name) | indent(4) }}
+    {{ transform(inner_property, inner_source, inner_property.python_name, transform_method) | indent(4) }}
     {{ destination }}.append({{ inner_property.python_name }})
 {% else %}
 {{ destination }} = {{ source }}
@@ -40,7 +40,7 @@ for {{ inner_source }} in {{ source }}:
 
 {% macro check_type_for_construct(property, source) %}isinstance({{ source }}, list){% endmacro %}
 
-{% macro transform(property, source, destination, declare_type=True, stringify=False) %}
+{% macro transform(property, source, destination, declare_type=True, stringify=False, transform_method="to_dict") %}
 {% set inner_property = property.inner_property %}
 {% if stringify %}
     {% set type_string = "Union[Unset, Tuple[None, str, str]]" %}
@@ -52,9 +52,9 @@ for {{ inner_source }} in {{ source }}:
 if {{ source }} is None:
     {{ destination }} = None
 else:
-    {{ _transform(property, source, destination, stringify) | indent(4) }}
+    {{ _transform(property, source, destination, stringify, transform_method) | indent(4) }}
 {% else %}
-{{ _transform(property, source, destination, stringify) }}
+{{ _transform(property, source, destination, stringify, transform_method) }}
 {% endif %}
 {% else %}
 {{ destination }}{% if declare_type %}: {{ type_string }}{% endif %} = UNSET
@@ -63,11 +63,15 @@ if not isinstance({{ source }}, Unset):
     if {{ source }} is None:
         {{ destination }} = None
     else:
-        {{ _transform(property, source, destination, stringify) | indent(8)}}
+        {{ _transform(property, source, destination, stringify, transform_method) | indent(8)}}
 {% else %}
-    {{ _transform(property, source, destination, stringify) | indent(4)}}
+    {{ _transform(property, source, destination, stringify, transform_method) | indent(4)}}
 {% endif %}
 {% endif %}
 
 
 {% endmacro %}
+
+{% macro transform_multipart(property, source, destination) %}
+{{ transform(property, source, destination, transform_method="to_multipart") }}
+{% endmacro %}