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

So this is new... see image.
Appeared after clicking APPLY after I added one more playlost selection to increase the number of files that would be ynced.
[img]https://www.dropbox.com/scl/fi/8evdvabg2wacn8zz7cjsk/Screenshot-2023-11-12-101343.png?rlkey=9u8utr4xcg3moq4aih4qkyc4n&dl=0[/img]
I've restarted... But let's see if the sync works

Build 5.0.4.2693
Yes. 2 other 160Gb identical ipods, both 'restored to factory' in same itunes on same laptop. I rotate these as my in CAR music source. And I was hoping to have the third one also in the process and as a more portable option.
Running a sync again now. reduced the list. You appreciate it takes time. This time I'm trying to see if it removes the 'OTHER' assuming it completes the sync. I have the setting to delete ALL other media.
I may reduce it to just a small set of files to debug. Will let you know

[img]https://www.dropbox.com/scl/fi/h5sp6seh1sggy1euq1g13/Screenshot-2023-11-09-183333.png?rlkey=fa7al7n1hi6ikerpx06wz0x7u&dl=0[/img]

******UPDATE ******
After a 4 hour sync process failed again... I did a "Quick Format", then an "iTunes restore", and a small sync of 162 mp3 files was successful. I am now running a further 1000 or files (ie. Syncing playlists, a few at a time). Will leave overnight and update on status tomorrow.

Which Build (Help > About) of MediaMonkey?

To be clear, the exact same sync list works with a different iPod?

I've been unable to complete a sync, It gives various errors towards end of a sync saying "Problem while copying file" and a list of files, But the list seems to change. Its a red herring. The files are fine. . Another ipod 160gb classic syncs no probs.
SO... I have formatted and restored the ipod - no joy. Same error.
I've run CHKDSK /F and it says the ipod is fine. But a FULL windows format never completes. It gets 90% + and then fails.
Chkdsk will still show a healthy disk.
So I restart the sync... it eventually fails. I'm working on only 70gig of a poss 160.

Now its also ignoring the 'no to all' option where it recognises file exists.
After the sync fails, a view of what is on the ipod from MM shows lots of files. But when disconnected it says NO MUSIC and the space is allocated as 'other'

Suggestions ? Ideas ?
Is there a way to fully format an ipod when chkdsk says the disk is ok. A iTunes restore works OK. but a full MM Sync consistently fails ?
W11 latest. Latest MM release.~

The image shows how 'other' is visible on the ipod. THis is after a prev sunc has failed.

[img]https://www.dropbox.com/scl/fi/tqettyb65a8qowabe6i6x/Screenshot-2023-11-09-182434.png?rlkey=ozszgspdmmcd9oih6oodioiol&dl=0[/img]