diff --git a/jupyter_core/tests/test_paths.py b/jupyter_core/tests/test_paths.py
index 07c8225a..534e82cd 100644
--- a/jupyter_core/tests/test_paths.py
+++ b/jupyter_core/tests/test_paths.py
@@ -198,11 +198,15 @@ def test_jupyter_path():
 def test_jupyter_path_user_site():
     with no_config_env, patch.object(site, 'ENABLE_USER_SITE', True):
         path = jupyter_path()
-    sitedir = os.path.join(site.getuserbase(), 'share', 'jupyter')
-    assert path.pop(0) == jupyter_data_dir()
-    if jupyter_data_dir() != sitedir:
-        assert path.pop(0) == sitedir
-    assert path.pop(0) == paths.ENV_JUPYTER_PATH[0]
+
+    # deduplicated expected values
+    values = list(dict.fromkeys([
+        jupyter_data_dir(),
+        os.path.join(site.getuserbase(), 'share', 'jupyter'),
+        paths.ENV_JUPYTER_PATH[0]
+    ]))
+    for p,v in zip(path, values):
+        assert p == v
 
 def test_jupyter_path_no_user_site():
     with no_config_env, patch.object(site, 'ENABLE_USER_SITE', False):
@@ -241,11 +245,14 @@ def test_jupyter_path_subdir():
 def test_jupyter_config_path():
     with patch.object(site, 'ENABLE_USER_SITE', True):
         path = jupyter_config_path()
-    sitedir = os.path.join(site.USER_BASE, 'etc', 'jupyter')
-    assert path.pop(0) == jupyter_config_dir()
-    if jupyter_config_dir() != sitedir:
-        assert path.pop(0) == sitedir
-    assert path.pop(0) == paths.ENV_CONFIG_PATH[0]
+    # deduplicated expected values
+    values = list(dict.fromkeys([
+        jupyter_config_dir(),
+        os.path.join(site.USER_BASE, 'etc', 'jupyter'),
+        paths.ENV_CONFIG_PATH[0]
+    ]))
+    for p,v in zip(path, values):
+        assert p == v
 
 def test_jupyter_config_path_no_user_site():
     with patch.object(site, 'ENABLE_USER_SITE', False):