diff --git a/src/openai/_files.py b/src/openai/_files.py
index 1a2cc77478..22b9f02e95 100644
--- a/src/openai/_files.py
+++ b/src/openai/_files.py
@@ -63,6 +63,9 @@ 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 +73,6 @@ 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 +105,9 @@ 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 +115,6 @@ 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 56445fb550..8ee736edf9 100644
--- a/tests/test_files.py
+++ b/tests/test_files.py
@@ -22,6 +22,30 @@ def test_tuple_input() -> None:
     assert result == IsList(IsTuple("file", IsTuple("README.md", IsBytes())))
 
 
+def test_tuple_pathlike_content() -> None:
+    result = to_httpx_files({"file": ("custom.txt", readme_path)})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom.txt", IsBytes())})
+
+
+def test_sequence_tuple_pathlike_content() -> None:
+    result = to_httpx_files([("file", ("custom.txt", readme_path))])
+    print(result)
+    assert result == IsList(IsTuple("file", IsTuple("custom.txt", IsBytes())))
+
+
+def test_tuple_pathlike_content_with_content_type() -> None:
+    result = to_httpx_files({"file": ("custom.txt", readme_path, "text/markdown")})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom.txt", IsBytes(), "text/markdown")})
+
+
+def test_tuple_pathlike_content_with_headers() -> None:
+    result = to_httpx_files({"file": ("custom.txt", readme_path, "text/markdown", {"X-Test": "1"})})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom.txt", IsBytes(), "text/markdown", {"X-Test": "1"})})
+
+
 @pytest.mark.asyncio
 async def test_async_pathlib_includes_file_name() -> None:
     result = await async_to_httpx_files({"file": readme_path})
@@ -43,6 +67,36 @@ async def test_async_tuple_input() -> None:
     assert result == IsList(IsTuple("file", IsTuple("README.md", IsBytes())))
 
 
+@pytest.mark.asyncio
+async def test_async_tuple_pathlike_content() -> None:
+    result = await async_to_httpx_files({"file": ("custom.txt", anyio.Path(readme_path))})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom.txt", IsBytes())})
+
+
+@pytest.mark.asyncio
+async def test_async_sequence_tuple_pathlike_content() -> None:
+    result = await async_to_httpx_files([("file", ("custom.txt", anyio.Path(readme_path)))])
+    print(result)
+    assert result == IsList(IsTuple("file", IsTuple("custom.txt", IsBytes())))
+
+
+@pytest.mark.asyncio
+async def test_async_tuple_pathlike_content_with_content_type() -> None:
+    result = await async_to_httpx_files({"file": ("custom.txt", anyio.Path(readme_path), "text/markdown")})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom.txt", IsBytes(), "text/markdown")})
+
+
+@pytest.mark.asyncio
+async def test_async_tuple_pathlike_content_with_headers() -> None:
+    result = await async_to_httpx_files(
+        {"file": ("custom.txt", anyio.Path(readme_path), "text/markdown", {"X-Test": "1"})}
+    )
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom.txt", IsBytes(), "text/markdown", {"X-Test": "1"})})
+
+
 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(