--- /dev/null
+"""
+Regression test: preserve order when using list[bytes] + File()
+See https://github.com/fastapi/fastapi/discussions/14811
+Related: PR #3372
+"""
+
+from typing import Annotated
+
+import anyio
+import pytest
+from fastapi import FastAPI, File
+from fastapi.testclient import TestClient
+from starlette.datastructures import UploadFile as StarletteUploadFile
+
+
+def test_list_bytes_file_preserves_order(
+ monkeypatch: pytest.MonkeyPatch,
+) -> None:
+ app = FastAPI()
+
+ @app.post("/upload")
+ async def upload(files: Annotated[list[bytes], File()]):
+ # return something that makes order obvious
+ return [b[0] for b in files]
+
+ original_read = StarletteUploadFile.read
+
+ async def patched_read(self: StarletteUploadFile, size: int = -1) -> bytes:
+ # Make the FIRST file slower *deterministically*
+ if self.filename == "slow.txt":
+ await anyio.sleep(0.05)
+ return await original_read(self, size)
+
+ monkeypatch.setattr(StarletteUploadFile, "read", patched_read)
+
+ client = TestClient(app)
+
+ files = [
+ ("files", ("slow.txt", b"A" * 10, "text/plain")),
+ ("files", ("fast.txt", b"B" * 10, "text/plain")),
+ ]
+ r = client.post("/upload", files=files)
+ assert r.status_code == 200, r.text
+
+ # Must preserve request order: slow first, fast second
+ assert r.json() == [ord("A"), ord("B")]