iTunes suddenly skipping over songs on my Apple Music account has been a source of major frustration for me recently. It appears that one of the latest updates caused issues with authorized devices on Apple ID accounts. Here is the quick fix to stop the song skipping in Apple Music/iTunes:
- Open iTunes
- Select ACCOUNT in the menu bar.
- Hover over AUTHORIZATIONS menu item.
- Click AUTHORIZE THIS COMPUTER.
- Enter in APPLE ID challenge information.
That’s it. That will get back up and running. Please note that I can verify this works on macOS High Sierra. I’m not sure if it will work on other versions of macOS (I would be surprised if it did not work) or on Windows (who ever knows with Windows).