diff --git a/legendary/lfs/tests/test_wine_helpers.py b/legendary/lfs/tests/test_wine_helpers.py
new file mode 100644
index 0000000..45aa8e8
--- /dev/null
+++ b/legendary/lfs/tests/test_wine_helpers.py
@@ -0,0 +1,14 @@
+import unittest
+import os
+from unittest.mock import patch
+from legendary.lfs.wine_helpers import case_insensitive_file_search
+
+class TestWineHelpers(unittest.TestCase):
+    @patch('os.path.exists')
+    def test_case_insensitive_file_search_nonexistent_dir(self, mock_exists):
+        mock_exists.return_value = False
+        result = case_insensitive_file_search('/nonexistent/path/to/file.txt')
+        self.assertIsNone(result)
+
+if __name__ == '__main__':
+    unittest.main()
diff --git a/legendary/lfs/wine_helpers.py b/legendary/lfs/wine_helpers.py
index e884a90..1a55a1c 100644
--- a/legendary/lfs/wine_helpers.py
+++ b/legendary/lfs/wine_helpers.py
@@ -25,6 +25,9 @@ def case_insensitive_file_search(path: str) -> str:
     Similar to case_insensitive_path_search: Finds a file case-insensitively
     Note that this *does* work on Windows, although it's rather pointless
     """
+    if not os.path.exists(os.path.dirname(path)):
+        return None
+
     path_parts = os.path.normpath(path).split(os.sep)
     # If path_parts[0] is empty, we're on Unix and thus start searching at /
     if not path_parts[0]: