Is this on MMA, or on MMW? If the latter, which Build (Help > About)?

I can reproduce, added as: https://www.ventismedia.com/mantis/view.php?id=20949

You can use the skip 5 seconds backward hotkey as a solution.

I'd try MediaMonkey 2024 where Shuffle has been completely reworked.

I use several external drives and none of them have issues ripping with MediaMonkey. Can you please detail what issues you're actually having. You've mentioned something with an error message initially, but without the full error message I'm unsure what it is. You've also mentioned tag changes made ...

This is not possible. Imported Playlists will always end up in the Imported Playlists node.

It's best to use MediaMonkey to manage the Playlists and the content on it, and export if needed.

I'm unable to reproduce. What Build (Help > About) of MediaMonkey are you seeing this with?

Yes, the license is tied to the store you purchased from and store account you used for the purchase.

Right click > Remove still works as work-around.

I can reproduce, added as: https://www.ventismedia.com/mantis/view.php?id=20935

Either the Amazon App store or the Google Play store.

Please capture this in a debug log (step 4b) and attach the log to a Support Ticket: https://www.mediamonkey.com/forum/viewtopic.php?t=86643

If upgrades are the primary cause, start DebugView before you do a first run of the next available update.

Repeat is off by default, so somewhere you must have accidentally enabled it.

So the issue is with MMA? Are you asking about how multiple discs are displayed in MMA or actual file organization on the device?

Which Build (Help > About) of MediaMonkey are you seeing this on?

What is loaded in the Playing? That is what will actually be played. no matter what's on the Playlist.

Also make sure no Repeat is enabled.