diff --git a/pylint/testutils/configuration_test.py b/pylint/testutils/configuration_test.py
index 14944471a73..12f4a32635d 100644
--- a/pylint/testutils/configuration_test.py
+++ b/pylint/testutils/configuration_test.py
@@ -12,7 +12,7 @@
 
 from pylint.lint import Run
 
-USER_SPECIFIC_PATH = str(Path(__file__).parent.parent.parent)
+USER_SPECIFIC_PATH = Path(__file__).parent.parent.parent
 # We use Any in this typing because the configuration contains real objects and constants
 # that could be a lot of things.
 ConfigurationValue = Any
@@ -71,10 +71,10 @@ def get_expected_configuration(
     return result
 
 
-def get_relative_path(path: str, user_specific_path: str = USER_SPECIFIC_PATH) -> str:
+def get_relative_path(path: str, user_specific_path: Path = USER_SPECIFIC_PATH) -> str:
     """Get the relative path we want without the user specific path"""
     # [1:] is to remove the opening '/'
-    return path.split(user_specific_path)[1][1:]
+    return str(Path(path).relative_to(user_specific_path))
 
 
 def get_expected_output(configuration_path: str) -> Tuple[int, str]:
@@ -91,7 +91,7 @@ def get_expected_output(configuration_path: str) -> Tuple[int, str]:
     else:
         logging.info(".out file does not exists, so the expected exit code is 0")
         exit_code = 0
-    relpath = get_relative_path(configuration_path, USER_SPECIFIC_PATH)
+    relpath = get_relative_path(configuration_path)
     return exit_code, output.format(abspath=configuration_path, relpath=relpath)