diff --git a/tests/test_request_params/test_file/test_nullable_and_defaults.py b/tests/test_request_params/test_file/test_nullable_and_defaults.py
new file mode 100644
index 0000000000..5602aa6e53
--- /dev/null
+++ b/tests/test_request_params/test_file/test_nullable_and_defaults.py
@@ -0,0 +1,480 @@
+from typing import Annotated, Any, Union
+from unittest.mock import Mock, patch
+
+import pytest
+from dirty_equals import IsOneOf
+from fastapi import FastAPI, File, UploadFile
+from fastapi.testclient import TestClient
+from pydantic import BeforeValidator
+from starlette.datastructures import UploadFile as StarletteUploadFile
+
+from .utils import get_body_model_name
+
+app = FastAPI()
+
+
+def convert(v: Any) -> Any:
+    return v
+
+
+# =====================================================================================
+# Nullable required
+
+
+@app.post("/nullable-required-bytes")
+async def read_nullable_required_bytes(
+    file: Annotated[
+        Union[bytes, None],
+        File(),
+        BeforeValidator(lambda v: convert(v)),
+    ],
+    files: Annotated[
+        Union[list[bytes], None],
+        File(),
+        BeforeValidator(lambda v: convert(v)),
+    ],
+):
+    return {
+        "file": len(file) if file is not None else None,
+        "files": [len(f) for f in files] if files is not None else None,
+    }
+
+
+@app.post("/nullable-required-uploadfile")
+async def read_nullable_required_uploadfile(
+    file: Annotated[
+        Union[UploadFile, None],
+        File(),
+        BeforeValidator(lambda v: convert(v)),
+    ],
+    files: Annotated[
+        Union[list[UploadFile], None],
+        File(),
+        BeforeValidator(lambda v: convert(v)),
+    ],
+):
+    return {
+        "file": file.size if file is not None else None,
+        "files": [f.size for f in files] if files is not None else None,
+    }
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-required-bytes",
+        "/nullable-required-uploadfile",
+    ],
+)
+def test_nullable_required_schema(path: str):
+    openapi = app.openapi()
+    body_model_name = get_body_model_name(openapi, path)
+
+    assert app.openapi()["components"]["schemas"][body_model_name] == {
+        "properties": {
+            "file": {
+                "title": "File",
+                "anyOf": [{"type": "string", "format": "binary"}, {"type": "null"}],
+            },
+            "files": {
+                "title": "Files",
+                "anyOf": [
+                    {"type": "array", "items": {"type": "string", "format": "binary"}},
+                    {"type": "null"},
+                ],
+            },
+        },
+        "required": ["file", "files"],
+        "title": body_model_name,
+        "type": "object",
+    }
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-required-bytes",
+        "/nullable-required-uploadfile",
+    ],
+)
+def test_nullable_required_missing(path: str):
+    client = TestClient(app)
+
+    with patch(f"{__name__}.convert", Mock(wraps=convert)) as mock_convert:
+        response = client.post(path)
+
+    assert mock_convert.call_count == 0, (
+        "Validator should not be called if the value is missing"
+    )
+    assert response.status_code == 422
+    assert response.json() == {
+        "detail": [
+            {
+                "type": "missing",
+                "loc": ["body", "file"],
+                "msg": "Field required",
+                "input": IsOneOf(None, {}),
+            },
+            {
+                "type": "missing",
+                "loc": ["body", "files"],
+                "msg": "Field required",
+                "input": IsOneOf(None, {}),
+            },
+        ]
+    }
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-required-bytes",
+        "/nullable-required-uploadfile",
+    ],
+)
+def test_nullable_required_pass_empty_file(path: str):
+    client = TestClient(app)
+
+    with patch(f"{__name__}.convert", Mock(wraps=convert)) as mock_convert:
+        response = client.post(
+            path,
+            files=[("file", b""), ("files", b""), ("files", b"")],
+        )
+
+    assert mock_convert.call_count == 2, "Validator should be called for each field"
+    call_args = [call_args_item.args for call_args_item in mock_convert.call_args_list]
+    file_call_arg_1 = call_args[0][0]
+    files_call_arg_1 = call_args[1][0]
+
+    assert (
+        (file_call_arg_1 == b"")  # file as bytes
+        or isinstance(file_call_arg_1, StarletteUploadFile)  # file as UploadFile
+    )
+    assert (
+        (files_call_arg_1 == [b"", b""])  # files as bytes
+        or all(  # files as UploadFile
+            isinstance(f, StarletteUploadFile) for f in files_call_arg_1
+        )
+    )
+
+    assert response.status_code == 200, response.text
+    assert response.json() == {
+        "file": 0,
+        "files": [0, 0],
+    }
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-required-bytes",
+        "/nullable-required-uploadfile",
+    ],
+)
+def test_nullable_required_pass_file(path: str):
+    client = TestClient(app)
+
+    with patch(f"{__name__}.convert", Mock(wraps=convert)) as mock_convert:
+        response = client.post(
+            path,
+            files=[
+                ("file", b"test 1"),
+                ("files", b"test 2"),
+                ("files", b"test 3"),
+            ],
+        )
+
+    assert mock_convert.call_count == 2, "Validator should be called for each field"
+    assert response.status_code == 200, response.text
+    assert response.json() == {"file": 6, "files": [6, 6]}
+
+
+# =====================================================================================
+# Nullable with default=None
+
+
+@app.post("/nullable-non-required-bytes")
+async def read_nullable_non_required_bytes(
+    file: Annotated[
+        Union[bytes, None],
+        File(),
+        BeforeValidator(lambda v: convert(v)),
+    ] = None,
+    files: Annotated[
+        Union[list[bytes], None],
+        File(),
+        BeforeValidator(lambda v: convert(v)),
+    ] = None,
+):
+    return {
+        "file": len(file) if file is not None else None,
+        "files": [len(f) for f in files] if files is not None else None,
+    }
+
+
+@app.post("/nullable-non-required-uploadfile")
+async def read_nullable_non_required_uploadfile(
+    file: Annotated[
+        Union[UploadFile, None],
+        File(),
+        BeforeValidator(lambda v: convert(v)),
+    ] = None,
+    files: Annotated[
+        Union[list[UploadFile], None],
+        File(),
+        BeforeValidator(lambda v: convert(v)),
+    ] = None,
+):
+    return {
+        "file": file.size if file is not None else None,
+        "files": [f.size for f in files] if files is not None else None,
+    }
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-non-required-bytes",
+        "/nullable-non-required-uploadfile",
+    ],
+)
+def test_nullable_non_required_schema(path: str):
+    openapi = app.openapi()
+    body_model_name = get_body_model_name(openapi, path)
+
+    assert app.openapi()["components"]["schemas"][body_model_name] == {
+        "properties": {
+            "file": {
+                "title": "File",
+                "anyOf": [{"type": "string", "format": "binary"}, {"type": "null"}],
+                # "default": None, # `None` values are omitted in OpenAPI schema
+            },
+            "files": {
+                "title": "Files",
+                "anyOf": [
+                    {"type": "array", "items": {"type": "string", "format": "binary"}},
+                    {"type": "null"},
+                ],
+                # "default": None, # `None` values are omitted in OpenAPI schema
+            },
+        },
+        "title": body_model_name,
+        "type": "object",
+    }
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-non-required-bytes",
+        "/nullable-non-required-uploadfile",
+    ],
+)
+def test_nullable_non_required_missing(path: str):
+    client = TestClient(app)
+
+    with patch(f"{__name__}.convert", Mock(wraps=convert)) as mock_convert:
+        response = client.post(path)
+
+    assert mock_convert.call_count == 0, (
+        "Validator should not be called if the value is missing"
+    )
+    assert response.status_code == 200
+    assert response.json() == {
+        "file": None,
+        "files": None,
+    }
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-non-required-bytes",
+        "/nullable-non-required-uploadfile",
+    ],
+)
+def test_nullable_non_required_pass_empty_file(path: str):
+    client = TestClient(app)
+
+    with patch(f"{__name__}.convert", Mock(wraps=convert)) as mock_convert:
+        response = client.post(
+            path,
+            files=[("file", b""), ("files", b""), ("files", b"")],
+        )
+
+    assert mock_convert.call_count == 2, "Validator should be called for each field"
+    call_args = [call_args_item.args for call_args_item in mock_convert.call_args_list]
+    file_call_arg_1 = call_args[0][0]
+    files_call_arg_1 = call_args[1][0]
+
+    assert (
+        (file_call_arg_1 == b"")  # file as bytes
+        or isinstance(file_call_arg_1, StarletteUploadFile)  # file as UploadFile
+    )
+    assert (
+        (files_call_arg_1 == [b"", b""])  # files as bytes
+        or all(  # files as UploadFile
+            isinstance(f, StarletteUploadFile) for f in files_call_arg_1
+        )
+    )
+
+    assert response.status_code == 200, response.text
+    assert response.json() == {"file": 0, "files": [0, 0]}
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-non-required-bytes",
+        "/nullable-non-required-uploadfile",
+    ],
+)
+def test_nullable_non_required_pass_file(path: str):
+    client = TestClient(app)
+
+    with patch(f"{__name__}.convert", Mock(wraps=convert)) as mock_convert:
+        response = client.post(
+            path,
+            files=[("file", b"test 1"), ("files", b"test 2"), ("files", b"test 3")],
+        )
+
+    assert mock_convert.call_count == 2, "Validator should be called for each field"
+    assert response.status_code == 200, response.text
+    assert response.json() == {"file": 6, "files": [6, 6]}
+
+
+# =====================================================================================
+# Nullable with not-None default
+
+
+@app.post("/nullable-with-non-null-default-bytes")
+async def read_nullable_with_non_null_default_bytes(
+    *,
+    file: Annotated[
+        Union[bytes, None],
+        File(),
+        BeforeValidator(lambda v: convert(v)),
+    ] = b"default",
+    files: Annotated[
+        Union[list[bytes], None],
+        File(default_factory=lambda: [b"default"]),
+        BeforeValidator(lambda v: convert(v)),
+    ],
+):
+    return {
+        "file": len(file) if file is not None else None,
+        "files": [len(f) for f in files] if files is not None else None,
+    }
+
+
+# Note: It seems to be not possible to create endpoint with UploadFile and non-None default
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-with-non-null-default-bytes",
+    ],
+)
+def test_nullable_with_non_null_default_schema(path: str):
+    openapi = app.openapi()
+    body_model_name = get_body_model_name(openapi, path)
+
+    assert app.openapi()["components"]["schemas"][body_model_name] == {
+        "properties": {
+            "file": {
+                "title": "File",
+                "anyOf": [{"type": "string", "format": "binary"}, {"type": "null"}],
+                "default": "default",  # <= Default value for file looks strange to me
+            },
+            "files": {
+                "title": "Files",
+                "anyOf": [
+                    {"type": "array", "items": {"type": "string", "format": "binary"}},
+                    {"type": "null"},
+                ],
+                # "default": None,  # default_factory is not reflected in OpenAPI schema
+            },
+        },
+        "title": body_model_name,
+        "type": "object",
+    }
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        pytest.param(
+            "/nullable-with-non-null-default-bytes",
+            marks=pytest.mark.xfail(
+                reason="AttributeError: 'bytes' object has no attribute 'read'",
+            ),
+        ),
+    ],
+)
+def test_nullable_with_non_null_default_missing(path: str):
+    client = TestClient(app)
+
+    with patch(f"{__name__}.convert", Mock(wraps=convert)) as mock_convert:
+        response = client.post(path)
+
+    assert mock_convert.call_count == 0, (
+        "Validator should not be called if the value is missing"
+    )
+    assert response.status_code == 200
+    assert response.json() == {"file": None, "files": None}
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-with-non-null-default-bytes",
+    ],
+)
+def test_nullable_with_non_null_default_pass_empty_file(path: str):
+    client = TestClient(app)
+
+    with patch(f"{__name__}.convert", Mock(wraps=convert)) as mock_convert:
+        response = client.post(
+            path,
+            files=[("file", b""), ("files", b""), ("files", b"")],
+        )
+
+    assert mock_convert.call_count == 2, "Validator should be called for each field"
+    call_args = [call_args_item.args for call_args_item in mock_convert.call_args_list]
+    file_call_arg_1 = call_args[0][0]
+    files_call_arg_1 = call_args[1][0]
+
+    assert (
+        (file_call_arg_1 == b"")  # file as bytes
+        or isinstance(file_call_arg_1, StarletteUploadFile)  # file as UploadFile
+    )
+    assert (
+        (files_call_arg_1 == [b"", b""])  # files as bytes
+        or all(  # files as UploadFile
+            isinstance(f, StarletteUploadFile) for f in files_call_arg_1
+        )
+    )
+
+    assert response.status_code == 200, response.text
+    assert response.json() == {"file": 0, "files": [0, 0]}
+
+
+@pytest.mark.parametrize(
+    "path",
+    [
+        "/nullable-with-non-null-default-bytes",
+    ],
+)
+def test_nullable_with_non_null_default_pass_file(path: str):
+    client = TestClient(app)
+
+    with patch(f"{__name__}.convert", Mock(wraps=convert)) as mock_convert:
+        response = client.post(
+            path,
+            files=[("file", b"test 1"), ("files", b"test 2"), ("files", b"test 3")],
+        )
+
+    assert mock_convert.call_count == 2, "Validator should be called for each field"
+    assert response.status_code == 200, response.text
+    assert response.json() == {"file": 6, "files": [6, 6]}