diff --git a/tests/sync/test_sync_service.py b/tests/sync/test_sync_service.py
index 2993b08c..a2e332e9 100644
--- a/tests/sync/test_sync_service.py
+++ b/tests/sync/test_sync_service.py
@@ -778,14 +778,28 @@ test content
 
     # Check permalinks
     file_two_content, _ = await file_service.read_file(two_file)
-    assert "permalink: one-1" in file_two_content
+    assert "permalink: two" in file_two_content
+
+    # new content with duplicate permalink
+    new_content = """
+---
+title: new.md
+type: note
+permalink: one
+tags: []
+---
+
+test content
+"""
+    new_file = project_dir / "new.md"
+    await create_test_file(new_file)
 
     # Run another time 
     await sync_service.sync(test_config.home)
 
     # Should still have same permalink
-    file_one_content, _ = await file_service.read_file(two_file)
-    assert "permalink: one-1" in file_one_content
+    new_file_content, _ = await file_service.read_file(new_file)
+    assert "permalink: new" in new_file_content