diff --git a/docs/advanced.md b/docs/advanced.md
index 76321dd..9d416e6 100644
--- a/docs/advanced.md
+++ b/docs/advanced.md
@@ -464,6 +464,16 @@ MIME header field.
     It is safe to upload large files this way. File uploads are streaming by default, meaning that only one chunk will be loaded into memory at a time.
  
  Non-file data fields can be included in the multipart form using by passing them to `data=...`.
+ 
+You can also send multiple files in one go with a multiple file field form.
+To do that, pass a list of `(field, <file>)` items instead of a dictionary, allowing you to pass multiple items with the same `field`.
+For instance this request sends 2 files, `foo.png` and `bar.png` in one request on the `images` form field: 
+
+```python
+>>> files = [('images', ('foo.png', open('foo.png', 'rb'), 'image/png')),
+                      ('images', ('bar.png', open('bar.png', 'rb'), 'image/png'))]
+>>> r = httpx.post("https://httpbin.org/post", files=files)
+```
 
 ## Customizing authentication
 
diff --git a/httpx/_content_streams.py b/httpx/_content_streams.py
index 6436be5..402fa95 100644
--- a/httpx/_content_streams.py
+++ b/httpx/_content_streams.py
@@ -328,7 +328,8 @@ class MultipartStream(ContentStream):
             else:
                 yield self.DataField(name=name, value=value)
 
-        for name, value in files.items():
+        file_items = files.items() if isinstance(files, typing.Mapping) else files
+        for name, value in file_items:
             yield self.FileField(name=name, value=value)
 
     def iter_chunks(self) -> typing.Iterator[bytes]:
diff --git a/httpx/_types.py b/httpx/_types.py
index a8925bb..a74020a 100644
--- a/httpx/_types.py
+++ b/httpx/_types.py
@@ -72,4 +72,4 @@ FileTypes = Union[
     # (filename, file (or text), content_type)
     Tuple[Optional[str], FileContent, Optional[str]],
 ]
-RequestFiles = Mapping[str, FileTypes]
+RequestFiles = Union[Mapping[str, FileTypes], List[Tuple[str, FileTypes]]]

Support for multiple files per POST field
```
async def http_upload():
    async with httpx.AsyncClient(verify=False) as client:
        data_path = os.path.join(PARENT_PATH, 'data_file/blob/data')
        index_path = os.path.join(PARENT_PATH, 'data_file/blob/index')
        files = {
            "upload_file": [
                open(data_path, 'rb'),
                open(index_path, 'rb'),
            ]
        }
        # files = [
        #     ("upload_file", open(data_path, 'rb')),
        #     ("upload_file", open(index_path, 'rb'))
        # ]
        params = {
            "requestId": "10001",
            "sdkVersion": "V1.2.3",
            "area": "CH"
        }

        response = await session.post(url, data=params, files=files)
```

```console
self = <httpx.content_streams.MultipartStream.FileField object at 0x7f503c22ea60>

    def render_data(self) -> bytes:
        if isinstance(self.file, str):
            content = self.file
        else:
>           content = self.file.read()
E           AttributeError: 'list' object has no attribute 'read'

or
    def iter_fields(
        self, data: dict, files: dict
    ) -> typing.Iterator[typing.Union["FileField", "DataField"]]:
        for name, value in data.items():
            if isinstance(value, (list, dict)):
                for item in value:
                    yield self.DataField(name=name, value=item)
            else:
                yield self.DataField(name=name, value=value)

>       for name, value in files.items():
E       AttributeError: 'list' object has no attribute 'items'
```

Excuse me, how should I use。
diff --git a/tests/test_content_streams.py b/tests/test_content_streams.py
index c5eb961..2b2adc9 100644
--- a/tests/test_content_streams.py
+++ b/tests/test_content_streams.py
@@ -204,3 +204,50 @@ async def test_empty_request():
 def test_invalid_argument():
     with pytest.raises(TypeError):
         encode(123)
+
+
+@pytest.mark.asyncio
+async def test_multipart_multiple_files_single_input_content():
+    files = [
+        ("file", io.BytesIO(b"<file content 1>")),
+        ("file", io.BytesIO(b"<file content 2>")),
+    ]
+    stream = encode(files=files, boundary=b"+++")
+    sync_content = b"".join([part for part in stream])
+    async_content = b"".join([part async for part in stream])
+
+    assert stream.can_replay()
+    assert stream.get_headers() == {
+        "Content-Length": "271",
+        "Content-Type": "multipart/form-data; boundary=+++",
+    }
+    assert sync_content == b"".join(
+        [
+            b"--+++\r\n",
+            b'Content-Disposition: form-data; name="file"; filename="upload"\r\n',
+            b"Content-Type: application/octet-stream\r\n",
+            b"\r\n",
+            b"<file content 1>\r\n",
+            b"--+++\r\n",
+            b'Content-Disposition: form-data; name="file"; filename="upload"\r\n',
+            b"Content-Type: application/octet-stream\r\n",
+            b"\r\n",
+            b"<file content 2>\r\n",
+            b"--+++--\r\n",
+        ]
+    )
+    assert async_content == b"".join(
+        [
+            b"--+++\r\n",
+            b'Content-Disposition: form-data; name="file"; filename="upload"\r\n',
+            b"Content-Type: application/octet-stream\r\n",
+            b"\r\n",
+            b"<file content 1>\r\n",
+            b"--+++\r\n",
+            b'Content-Disposition: form-data; name="file"; filename="upload"\r\n',
+            b"Content-Type: application/octet-stream\r\n",
+            b"\r\n",
+            b"<file content 2>\r\n",
+            b"--+++--\r\n",
+        ]
+    )

pip install -e .
parse_log_pytest
requirements.txt
pytest
apt-get update apt-get install -y gcc
3.9
requirements.txt
pytest --no-header -rA --tb=line --color=no -p no:cacheprovider -W ignore::DeprecationWarning
aspy.refactor-imports==3.0.2
async-generator==1.10
attrs==25.3.0
autoflake==2.3.1
babel==2.17.0
backports.tarfile==1.2.0
backrefs==5.8
black==25.1.0
brotlipy==0.7.0
certifi==2025.1.31
cffi==1.17.1
chardet==3.0.4
charset-normalizer==3.4.1
click==8.1.8
colorama==0.4.6
coverage==7.8.0
cryptography==44.0.2
docutils==0.21.2
exceptiongroup==1.2.2
flake8==7.2.0
flake8-bugbear==24.12.12
flake8-pie==0.16.0
ghp-import==2.1.0
h11==0.9.0
h2==3.2.0
hpack==3.0.0
hstspreload==2025.1.1
httpcore==0.9.1
-e git+https://github.com/encode/httpx.git@0f7d644b8dba432c5eec08157947a4e551996fa1#egg=httpx
hyperframe==5.2.0
id==1.5.0
idna==2.10
importlib_metadata==8.6.1
iniconfig==2.1.0
isort==6.0.1
jaraco.classes==3.4.0
jaraco.context==6.0.1
jaraco.functools==4.1.0
jeepney==0.9.0
Jinja2==3.1.6
keyring==25.6.0
Markdown==3.7
markdown-it-py==3.0.0
MarkupSafe==3.0.2
mccabe==0.7.0
mdurl==0.1.2
mergedeep==1.3.4
mkautodoc==0.2.0
mkdocs==1.6.1
mkdocs-get-deps==0.2.0
mkdocs-material==9.6.10
mkdocs-material-extensions==1.3.1
more-itertools==10.6.0
mypy==1.15.0
mypy-extensions==1.0.0
nh3==0.2.21
outcome==1.3.0.post0
packaging==24.2
paginate==0.5.7
pathspec==0.12.1
platformdirs==4.3.7
pluggy==1.5.0
pycodestyle==2.13.0
pycparser==2.22
pyflakes==3.3.2
Pygments==2.19.1
pymdown-extensions==10.14.3
pytest==8.3.5
pytest-asyncio==0.26.0
pytest-cov==6.0.0
pytest-trio==0.8.0
python-dateutil==2.9.0.post0
PyYAML==6.0.2
pyyaml_env_tag==0.1
readme_renderer==44.0
requests==2.32.3
requests-toolbelt==1.0.0
rfc3986==1.5.0
rich==14.0.0
SecretStorage==3.3.3
seed-isort-config==2.2.0
six==1.17.0
sniffio==1.3.1
sortedcontainers==2.4.0
tomli==2.2.1
trio==0.29.0
trio-typing==0.10.0
trustme==1.2.1
twine==6.1.0
typing_extensions==4.13.0
urllib3==2.3.0
uvicorn==0.34.0
watchdog==6.0.0
zipp==3.21.0

name: httpx
channels:
  - defaults
  - https://repo.anaconda.com/pkgs/main
  - https://repo.anaconda.com/pkgs/r
  - conda-forge
dependencies:
  - _libgcc_mutex=0.1=main
  - _openmp_mutex=5.1=1_gnu
  - ca-certificates=2025.2.25=h06a4308_0
  - ld_impl_linux-64=2.40=h12ee557_0
  - libffi=3.4.4=h6a678d5_1
  - libgcc-ng=11.2.0=h1234567_1
  - libgomp=11.2.0=h1234567_1
  - libstdcxx-ng=11.2.0=h1234567_1
  - ncurses=6.4=h6a678d5_0
  - openssl=3.0.16=h5eee18b_0
  - pip=25.0=py39h06a4308_0
  - python=3.9.21=he870216_1
  - readline=8.2=h5eee18b_0
  - setuptools=75.8.0=py39h06a4308_0
  - sqlite=3.45.3=h5eee18b_0
  - tk=8.6.14=h39e8969_0
  - tzdata=2025a=h04d1e81_0
  - wheel=0.45.1=py39h06a4308_0
  - xz=5.6.4=h5eee18b_1
  - zlib=1.2.13=h5eee18b_1
  - pip:
      - aspy-refactor-imports==3.0.2
      - async-generator==1.10
      - attrs==25.3.0
      - autoflake==2.3.1
      - babel==2.17.0
      - backports-tarfile==1.2.0
      - backrefs==5.8
      - black==25.1.0
      - brotlipy==0.7.0
      - certifi==2025.1.31
      - cffi==1.17.1
      - chardet==3.0.4
      - charset-normalizer==3.4.1
      - click==8.1.8
      - colorama==0.4.6
      - coverage==7.8.0
      - cryptography==44.0.2
      - docutils==0.21.2
      - exceptiongroup==1.2.2
      - flake8==7.2.0
      - flake8-bugbear==24.12.12
      - flake8-pie==0.16.0
      - ghp-import==2.1.0
      - h11==0.9.0
      - h2==3.2.0
      - hpack==3.0.0
      - hstspreload==2025.1.1
      - httpcore==0.9.1
      - hyperframe==5.2.0
      - id==1.5.0
      - idna==2.10
      - importlib-metadata==8.6.1
      - iniconfig==2.1.0
      - isort==6.0.1
      - jaraco-classes==3.4.0
      - jaraco-context==6.0.1
      - jaraco-functools==4.1.0
      - jeepney==0.9.0
      - jinja2==3.1.6
      - keyring==25.6.0
      - markdown==3.7
      - markdown-it-py==3.0.0
      - markupsafe==3.0.2
      - mccabe==0.7.0
      - mdurl==0.1.2
      - mergedeep==1.3.4
      - mkautodoc==0.2.0
      - mkdocs==1.6.1
      - mkdocs-get-deps==0.2.0
      - mkdocs-material==9.6.10
      - mkdocs-material-extensions==1.3.1
      - more-itertools==10.6.0
      - mypy==1.15.0
      - mypy-extensions==1.0.0
      - nh3==0.2.21
      - outcome==1.3.0.post0
      - packaging==24.2
      - paginate==0.5.7
      - pathspec==0.12.1
      - platformdirs==4.3.7
      - pluggy==1.5.0
      - pycodestyle==2.13.0
      - pycparser==2.22
      - pyflakes==3.3.2
      - pygments==2.19.1
      - pymdown-extensions==10.14.3
      - pytest==8.3.5
      - pytest-asyncio==0.26.0
      - pytest-cov==6.0.0
      - pytest-trio==0.8.0
      - python-dateutil==2.9.0.post0
      - pyyaml==6.0.2
      - pyyaml-env-tag==0.1
      - readme-renderer==44.0
      - requests==2.32.3
      - requests-toolbelt==1.0.0
      - rfc3986==1.5.0
      - rich==14.0.0
      - secretstorage==3.3.3
      - seed-isort-config==2.2.0
      - six==1.17.0
      - sniffio==1.3.1
      - sortedcontainers==2.4.0
      - tomli==2.2.1
      - trio==0.29.0
      - trio-typing==0.10.0
      - trustme==1.2.1
      - twine==6.1.0
      - typing-extensions==4.13.0
      - urllib3==2.3.0
      - uvicorn==0.34.0
      - watchdog==6.0.0
      - zipp==3.21.0
prefix: /opt/conda/envs/httpx

tests/test_content_streams.py::test_multipart_multiple_files_single_input_content
tests/test_content_streams.py::test_base_content tests/test_content_streams.py::test_empty_content tests/test_content_streams.py::test_bytes_content tests/test_content_streams.py::test_iterator_content tests/test_content_streams.py::test_aiterator_content tests/test_content_streams.py::test_json_content tests/test_content_streams.py::test_urlencoded_content tests/test_content_streams.py::test_multipart_files_content tests/test_content_streams.py::test_multipart_data_and_files_content tests/test_content_streams.py::test_empty_request tests/test_content_streams.py::test_invalid_argument
httpx/_content_streams.py docs/advanced.md httpx/_types.py
httpx/_content_streams.py docs/advanced.md httpx/_types.py