diff --git a/src/openai/_files.py b/src/openai/_files.py
index 7b23ca084a..f4796050e8 100644
--- a/src/openai/_files.py
+++ b/src/openai/_files.py
@@ -61,6 +61,9 @@ 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)
@@ -68,9 +71,6 @@ 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")
 
 
@@ -103,6 +103,9 @@ 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)
@@ -110,9 +113,6 @@ 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_files.py b/tests/test_files.py
index 15d5c6a811..ce9ac7e21f 100644
--- a/tests/test_files.py
+++ b/tests/test_files.py
@@ -21,6 +21,12 @@ def test_tuple_input() -> None:
     assert result == IsList(IsTuple("file", IsTuple("README.md", IsBytes())))
 
 
+def test_tuple_content_supports_pathlike() -> None:
+    result = to_httpx_files({"file": ("custom.txt", readme_path)})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom.txt", IsBytes())})
+
+
 @pytest.mark.asyncio
 async def test_async_pathlib_includes_file_name() -> None:
     result = await async_to_httpx_files({"file": readme_path})
@@ -42,6 +48,13 @@ async def test_async_tuple_input() -> None:
     assert result == IsList(IsTuple("file", IsTuple("README.md", IsBytes())))
 
 
+@pytest.mark.asyncio
+async def test_async_tuple_content_supports_pathlike() -> None:
+    result = await async_to_httpx_files({"file": ("custom.txt", readme_path)})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom.txt", IsBytes())})
+
+
 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(