diff --git a/src/anthropic/_files.py b/src/anthropic/_files.py
index f2a6f94e..ee69d8d1 100644
--- a/src/anthropic/_files.py
+++ b/src/anthropic/_files.py
@@ -25,9 +25,7 @@ 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 4b118fe0..42574958 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_pathlike_input_with_content_type() -> None:
+    result = to_httpx_files({"file": ("README.md", readme_path, "text/markdown")})
+    print(result)
+    assert result == IsDict({"file": IsTuple("README.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})
@@ -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_pathlike_input_with_content_type() -> None:
+    result = await async_to_httpx_files({"file": ("README.md", readme_path, "text/markdown")})
+    print(result)
+    assert result == IsDict({"file": IsTuple("README.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(