From 3c800d5ae6af956f94c5aae90767511a96c5d42b Mon Sep 17 00:00:00 2001
From: Pranjal Bhatia <233476158+pranjalbhatia710@users.noreply.github.com>
Date: Wed, 8 Jul 2026 08:30:23 +0400
Subject: [PATCH 1/2] fix(files): normalize PathLike upload tuples

---
 src/openai/_files.py |  4 +---
 tests/test_files.py  | 26 ++++++++++++++++++++++++++
 2 files changed, 27 insertions(+), 3 deletions(-)

diff --git a/src/openai/_files.py b/src/openai/_files.py
index 1a2cc77478..cb8fcbebf8 100644
--- a/src/openai/_files.py
+++ b/src/openai/_files.py
@@ -27,9 +27,7 @@ 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 assert_is_file_content(obj: object, *, key: str | None = None) -> None:
diff --git a/tests/test_files.py b/tests/test_files.py
index 56445fb550..60ad480783 100644
--- a/tests/test_files.py
+++ b/tests/test_files.py
@@ -22,6 +22,18 @@ def test_tuple_input() -> None:
     assert result == IsList(IsTuple("file", IsTuple("README.md", IsBytes())))
 
 
+def test_file_tuple_with_pathlike_content() -> None:
+    result = to_httpx_files({"file": ("custom-name.md", readme_path)})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom-name.md", IsBytes())})
+
+
+def test_file_tuple_with_pathlike_content_and_metadata() -> None:
+    result = to_httpx_files({"file": ("custom-name.md", readme_path, "text/markdown")})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom-name.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 +55,20 @@ async def test_async_tuple_input() -> None:
     assert result == IsList(IsTuple("file", IsTuple("README.md", IsBytes())))
 
 
+@pytest.mark.asyncio
+async def test_async_file_tuple_with_pathlike_content() -> None:
+    result = await async_to_httpx_files({"file": ("custom-name.md", readme_path)})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom-name.md", IsBytes())})
+
+
+@pytest.mark.asyncio
+async def test_async_file_tuple_with_pathlike_content_and_metadata() -> None:
+    result = await async_to_httpx_files({"file": ("custom-name.md", readme_path, "text/markdown")})
+    print(result)
+    assert result == IsDict({"file": IsTuple("custom-name.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(

From 2f0860ff319e8b8119d0e32566831f24a4a25cfc Mon Sep 17 00:00:00 2001
From: Pranjal Bhatia <pranjalbhatia710@users.noreply.github.com>
Date: Wed, 8 Jul 2026 10:03:49 +0400
Subject: [PATCH 2/2] fix(files): preserve tuple uploads during extraction

---
 src/openai/_files.py |  2 +-
 tests/test_files.py  | 11 +++++++++++
 2 files changed, 12 insertions(+), 1 deletion(-)

diff --git a/src/openai/_files.py b/src/openai/_files.py
index cb8fcbebf8..76f71238ff 100644
--- a/src/openai/_files.py
+++ b/src/openai/_files.py
@@ -31,7 +31,7 @@ def is_file_content(obj: object) -> TypeGuard[FileContent]:
 
 
 def assert_is_file_content(obj: object, *, key: str | None = None) -> None:
-    if not is_file_content(obj):
+    if not is_file_content(obj) and not is_tuple_t(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"
diff --git a/tests/test_files.py b/tests/test_files.py
index 60ad480783..180643e312 100644
--- a/tests/test_files.py
+++ b/tests/test_files.py
@@ -143,6 +143,17 @@ def test_extract_files_does_not_mutate_original_top_level(self) -> None:
         assert original == {"file": file_bytes, "other": "value"}
         assert copied == {"other": "value"}
 
+    def test_extract_files_accepts_file_tuple(self) -> None:
+        file_tuple = ("custom-name.jsonl", b"contents", "application/jsonl")
+        original = {"file": file_tuple, "purpose": "batch"}
+
+        copied = deepcopy_with_paths(original, [["file"]])
+        extracted = extract_files(copied, paths=[["file"]])
+
+        assert extracted == [("file", file_tuple)]
+        assert original == {"file": file_tuple, "purpose": "batch"}
+        assert copied == {"purpose": "batch"}
+
     def test_extract_files_does_not_mutate_original_nested_array_path(self) -> None:
         file1 = b"f1"
         file2 = b"f2"