diff --git a/docs/advanced.md b/docs/advanced.md
index 76321dd1b2..9d416e6f01 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 6436be563a..402fa959c8 100644
--- a/httpx/_content_streams.py
+++ b/httpx/_content_streams.py
@@ -328,7 +328,8 @@ def _iter_fields(
             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 a8925bbe76..a74020a4ae 100644
--- a/httpx/_types.py
+++ b/httpx/_types.py
@@ -72,4 +72,4 @@
     # (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]]]
diff --git a/tests/test_content_streams.py b/tests/test_content_streams.py
index c5eb961ddc..2b2adc92ae 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",
+        ]
+    )