This tends to indicate that the Paths on the Playlist files don't point to where the files are actually located. You can use any text editor (like Notepad) to review and fix Paths on Playlists prior to import.

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

If MediaMonkey Synced the files to the phone, yes. If not, maybe, as it depends on Sync matching the files between the 2 devices.

Use Sync and select the Playlists to be synced.

The Media Tree is missing a horizontal scroll: https://www.ventismedia.com/mantis/view.php?id=15757

MediaMonkey for Android only supports what is supported natively by your phone. If your phone doesn't support you'll need to convert to a format (like FLAC) that it does support.

I recommend using the latest MediaMonkey 2024 beta instead. If you still get new duplicates with that version, please let us know.

What exact error do you get when manual tagging?

What Addon do you use for Auto-Tag from Web?

Which Build (Help > About) of MediaMonkey did you use this time and was it again a wi-fi Sync?

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?