[Zubersoft]

If you set the duplicate behavior to create new songs, then yes, it's going to generate duplicate songs in the library using the same files as the existing songs in the library. If you import a file named "Test.pdf" then import another file called "Test.pdf" with different contents, you should see the conflict dialog without having to restart the application or anything of that sort. I just ran this test and it worked fine regardless of what selection is made for the duplicate dropdown.

Thanks,
Mike