Hi
For some reason after a new install of Apprentice on the Mac I'm stuck in a Licensing Administrator endless loop.

After being prompted what do i want to do next? I select Run and then instead of Apprentice launching I get the License Administrator again…and again.

That is a known bug that has been there for years. You need to be the admin of the computer before you launch for the first time. So after install, set your user name to admin of machine. After the first launch you can change the user permission back. You may have to do that every time the license finally expire.