diff --git a/backend/endpoints/roms/__init__.py b/backend/endpoints/roms/__init__.py
index bceb04d62..6d8a536ba 100644
--- a/backend/endpoints/roms/__init__.py
+++ b/backend/endpoints/roms/__init__.py
@@ -1483,13 +1483,18 @@ async def delete_roms(
                         await fs_rom_handler.remove_file(file_path=rom_path)
                         # Clean up empty parent directory if it becomes empty
                         parent = full_path.parent
-                        if (
-                            parent != fs_rom_handler.base_path
-                            and parent.is_dir()
-                            and not any(parent.iterdir())
-                        ):
-                            await fs_rom_handler.remove_directory(
-                                str(parent.relative_to(fs_rom_handler.base_path))
+                        try:
+                            if (
+                                parent != fs_rom_handler.base_path
+                                and parent.is_dir()
+                                and not any(parent.iterdir())
+                            ):
+                                await fs_rom_handler.remove_directory(
+                                    str(parent.relative_to(fs_rom_handler.base_path))
+                                )
+                        except OSError as dir_err:
+                            log.warning(
+                                f"Couldn't clean up empty parent directory for {hl(rom.fs_name)}: {dir_err}"
                             )
                 except FileNotFoundError:
                     error = f"Rom file {hl(rom.fs_name)} not found for platform {hl(rom.platform_display_name, color=BLUE)}[{hl(rom.platform_slug)}]"
diff --git a/backend/tests/endpoints/roms/test_rom.py b/backend/tests/endpoints/roms/test_rom.py
index 15664f70c..50c12a80e 100644
--- a/backend/tests/endpoints/roms/test_rom.py
+++ b/backend/tests/endpoints/roms/test_rom.py
@@ -124,6 +124,10 @@ def test_delete_roms(client: TestClient, access_token: str, rom: Rom):
     assert body["successful_items"] == 1
 
 
+@patch(
+    "endpoints.roms.fs_rom_handler.remove_directory",
+    new_callable=AsyncMock,
+)
 @patch(
     "endpoints.roms.fs_rom_handler.remove_file",
     new_callable=AsyncMock,
@@ -134,6 +138,7 @@ def test_delete_roms(client: TestClient, access_token: str, rom: Rom):
 def test_delete_roms_from_fs_flat(
     mock_validate_path,
     mock_remove_file,
+    mock_remove_directory,
     client: TestClient,
     access_token: str,
     rom: Rom,
@@ -158,6 +163,53 @@ def test_delete_roms_from_fs_flat(
     assert body["successful_items"] == 1
     assert body["failed_items"] == 0
     mock_remove_file.assert_called_once()
+    mock_remove_directory.assert_not_called()
+
+
+@patch(
+    "endpoints.roms.fs_rom_handler.remove_directory",
+    new_callable=AsyncMock,
+)
+@patch(
+    "endpoints.roms.fs_rom_handler.remove_file",
+    new_callable=AsyncMock,
+)
+@patch(
+    "endpoints.roms.fs_rom_handler.validate_path",
+)
+def test_delete_roms_from_fs_flat_cleans_empty_parent(
+    mock_validate_path,
+    mock_remove_file,
+    mock_remove_directory,
+    client: TestClient,
+    access_token: str,
+    rom: Rom,
+):
+    """Test that empty parent directories are cleaned up after flat ROM file deletion."""
+    from pathlib import Path
+    from unittest.mock import MagicMock
+
+    mock_path = MagicMock(spec=Path)
+    mock_path.is_dir.return_value = False
+    # Parent is not the base_path, is a dir, and is empty
+    mock_path.parent.__ne__ = lambda self, other: True
+    mock_path.parent.is_dir.return_value = True
+    mock_path.parent.__iter__ = lambda self: iter([])  # empty directory
+    mock_validate_path.return_value = mock_path
+
+    response = client.post(
+        "/api/roms/delete",
+        headers={"Authorization": f"Bearer {access_token}"},
+        json={"roms": [rom.id], "delete_from_fs": [rom.id]},
+    )
+    assert response.status_code == status.HTTP_200_OK
+
+    body = response.json()
+    assert body["successful_items"] == 1
+    assert body["failed_items"] == 0
+    mock_remove_file.assert_called_once()
+    # remove_directory should be called to clean up the empty parent dir
+    mock_remove_directory.assert_called_once()
 
 
 @patch(