Go to Tracks instead of Albums and hit Shuffle Play to get the desired result. Does that work?

No, but you can use nested Playlists to create some form of organization under Playlists too.

Collections are available to create separate Libraries within the same MediaMonkey Library.

That's not possible, there is no report per Playlist. An AutoPlaylist could be used, but it's global and track play based, not Playlist track plays based.

Last Played is a field that can be displayed as a Column. When it's displayed as a column you can sort on that column.

The AutoPlaylist method is another option.

You can sort on Last Played in any view or have an AutoPlaylist limit to x files Selected by Played (most recent).

Did you try https:// website. com/?

Where are you copying it to? It should a local drive with enough space to fit all the files you're copying from the iPod.

Please see: https://www.mediamonkey.com/wiki/WebHel ... 0#Location

This is a tagging operation, it will save the MediaMonkey database values (what you see) to the files tags.

iTunes is needed for iOS based iPod's, but not for non-iOS based iPod's. I presume you're not on an iOS device as you've been able to access it already in MediaMonkey.

You'll need to copy the files to the PC and then tag them on the PC, and resync them again.

Do you have a regular or Portable Install of MediaMonkey 2024?

This is how Apple stores files on the iPod.

Are you having an issue with tags (like Artist, Album, Title) or with the filenames?

Try this in File Explorer address bar: %APPDATA%\MediaMonkey5\MetadataCache\