diff --git a/src/openai/_files.py b/src/openai/_files.py
index 1a2cc77478..1f271dbf9b 100644
--- a/src/openai/_files.py
+++ b/src/openai/_files.py
@@ -27,16 +27,48 @@ def is_base64_file_input(obj: object) -> TypeGuard[Base64FileInput]:
 
 
 def is_file_content(obj: object) -> TypeGuard[FileContent]:
-    return (
-        isinstance(obj, bytes) or isinstance(obj, tuple) or isinstance(obj, io.IOBase) or isinstance(obj, os.PathLike)
-    )
+    return isinstance(obj, bytes) or isinstance(obj, io.IOBase) or isinstance(obj, os.PathLike)
+
+
+def _is_file_tuple(obj: object) -> bool:
+    if not isinstance(obj, tuple):
+        return False
+
+    obj = cast(tuple[object, ...], obj)
+
+    if len(obj) == 2:
+        filename, file = obj
+        return (filename is None or isinstance(filename, str)) and is_file_content(file)
+
+    if len(obj) == 3:
+        filename, file, content_type = obj
+        return (
+            (filename is None or isinstance(filename, str))
+            and is_file_content(file)
+            and (content_type is None or isinstance(content_type, str))
+        )
+
+    if len(obj) == 4:
+        filename, file, content_type, headers = obj
+        return (
+            (filename is None or isinstance(filename, str))
+            and is_file_content(file)
+            and (content_type is None or isinstance(content_type, str))
+            and is_mapping(headers)
+        )
+
+    return False
+
+
+def _is_file_types(obj: object) -> TypeGuard[FileTypes]:
+    return is_file_content(obj) or _is_file_tuple(obj)
 
 
 def assert_is_file_content(obj: object, *, key: str | None = None) -> None:
-    if not is_file_content(obj):
+    if not _is_file_types(obj):
         prefix = f"Expected entry at `{key}`" if key is not None else f"Expected file input `{obj!r}`"
         raise RuntimeError(
-            f"{prefix} to be bytes, an io.IOBase instance, PathLike or a tuple but received {type(obj)} instead. See https://github.com/openai/openai-python/tree/main#file-uploads"
+            f"{prefix} to be bytes, an io.IOBase instance, PathLike or a supported file tuple but received {type(obj)} instead. See https://github.com/openai/openai-python/tree/main#file-uploads"
         ) from None
 
 
@@ -63,6 +95,9 @@ def to_httpx_files(files: RequestFiles | None) -> HttpxRequestFiles | None:
 
 
 def _transform_file(file: FileTypes) -> HttpxFileTypes:
+    if is_tuple_t(file):
+        return (file[0], read_file_content(file[1]), *file[2:])
+
     if is_file_content(file):
         if isinstance(file, os.PathLike):
             path = pathlib.Path(file)
@@ -70,9 +105,6 @@ def _transform_file(file: FileTypes) -> HttpxFileTypes:
 
         return file
 
-    if is_tuple_t(file):
-        return (file[0], read_file_content(file[1]), *file[2:])
-
     raise TypeError(f"Expected file types input to be a FileContent type or to be a tuple")
 
 
@@ -105,6 +137,9 @@ async def async_to_httpx_files(files: RequestFiles | None) -> HttpxRequestFiles
 
 
 async def _async_transform_file(file: FileTypes) -> HttpxFileTypes:
+    if is_tuple_t(file):
+        return (file[0], await async_read_file_content(file[1]), *file[2:])
+
     if is_file_content(file):
         if isinstance(file, os.PathLike):
             path = anyio.Path(file)
@@ -112,9 +147,6 @@ async def _async_transform_file(file: FileTypes) -> HttpxFileTypes:
 
         return file
 
-    if is_tuple_t(file):
-        return (file[0], await async_read_file_content(file[1]), *file[2:])
-
     raise TypeError(f"Expected file types input to be a FileContent type or to be a tuple")
 
 
diff --git a/tests/test_extract_files.py b/tests/test_extract_files.py
index 54490e133f..6362e85220 100644
--- a/tests/test_extract_files.py
+++ b/tests/test_extract_files.py
@@ -35,6 +35,12 @@ def test_multiple_files() -> None:
     assert query == {"documents": [{}, {}]}
 
 
+def test_invalid_file_tuple_is_rejected() -> None:
+    query = {"file": ("upload.md", "not-a-file")}
+    with pytest.raises(RuntimeError, match="Expected entry at `file`"):
+        extract_files(query, paths=[["file"]])
+
+
 def test_top_level_file_array() -> None:
     query = {"files": [b"file one", b"file two"], "title": "hello"}
     assert extract_files(query, paths=[["files", "<array>"]]) == [("files[]", b"file one"), ("files[]", b"file two")]
diff --git a/tests/test_files.py b/tests/test_files.py
index 56445fb550..f422724e06 100644
--- a/tests/test_files.py
+++ b/tests/test_files.py
@@ -22,6 +22,12 @@ def test_tuple_input() -> None:
     assert result == IsList(IsTuple("file", IsTuple("README.md", IsBytes())))
 
 
+def test_pathlib_inside_file_tuple_content_is_read() -> None:
+    result = to_httpx_files({"file": ("upload.md", readme_path, "text/markdown")})
+    print(result)
+    assert result == IsDict({"file": IsTuple("upload.md", IsBytes(), "text/markdown")})
+
+
 @pytest.mark.asyncio
 async def test_async_pathlib_includes_file_name() -> None:
     result = await async_to_httpx_files({"file": readme_path})
@@ -43,6 +49,13 @@ async def test_async_tuple_input() -> None:
     assert result == IsList(IsTuple("file", IsTuple("README.md", IsBytes())))
 
 
+@pytest.mark.asyncio
+async def test_async_pathlib_inside_file_tuple_content_is_read() -> None:
+    result = await async_to_httpx_files({"file": ("upload.md", readme_path, "text/markdown")})
+    print(result)
+    assert result == IsDict({"file": IsTuple("upload.md", IsBytes(), "text/markdown")})
+
+
 def test_string_not_allowed() -> None:
     with pytest.raises(TypeError, match="Expected file types input to be a FileContent type or to be a tuple"):
         to_httpx_files(