This is generally sufficient in most cases and is more efficient this way. This will be reviewed for a future version of MMA.

How did you transfer the file?

Please see the following on greyed out files: https://www.mediamonkey.com/support/kno ... s-to-play/

It generally occurs when files were moved/renamed outside of MediaMonkey and thus can't be found.

Which Build (Help > About) of MediaMonkey are you using?

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

Which Build (Help > About) of MediaMonkey are you using and do those files play in MediaMonkey?

Generally the first thing to try is to Sync from iTunes to the device, especially as it's an older device, the hardware may be failing.

Do you have problems with wi-fi or USB Sync? Which Build (Help > About) of MediaMonkey for Windows are you using and which version of Android are you running MMA on?

Which Build (Help > About) of MediaMonkey is crashing and what are you doing at the time?

The Mask you show in Auto-Organize will work from the folder the file is already in. So you're adding the Artist and Album folder from there. Presumably you want to start at a higher level, so you may want to include full Path in your Mask, something like: E:\MP3\<Album Artist>\<Album>\<Title>

Auto-Tag probably used that site in the Artwork lookup it does. Artwork lookup source isn't controlled by MediaMonkey, it's whatever is found on the web.

Have you tried removing the Playlists (the once not working) from MediaMonkey and then rescan them again?

If that fails, then presumably there are still Path issues on the Playlists.

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

This will help a developer analyze why this happens on your setup.

Paths on the Playlists are relative, thus where the Playlists are stored matters. Based on the information the Playlists should be in the root M drive for scanning.

Which Build (Help > About) is this happening on?

It often turns out to be other files like Classical Music (which may show in Music in MMW, but is separate in MMA), or things like Audiobooks, Podcasts, videos, ect. not selected to be Synced.