iPod iPod nano sync issue

[castlema]

I have a very odd issue. For various reasons I and still using a 3rd gen iPod nano because I have to have one that uses a 30-pin connector. I have strange sync issues for the past few months which I have finally traced down to the "Sync music onto [name]" button coming randomly unchecked. As an example this morning I synced the iPod to Music and everything went fine. When I got home and connected the iPod to the computer that box was now unchecked.

Has anyone else ever had this issue? If you have what did you do about it? I like to keep my play count and last played current and with this issue I can't do that.

 

[Slix]

Have you tried a restore since this started happening?

 

[castlema]

Several times. It made no difference.

 

[crobcary]

I have the exact same issue, but with my 7th-generation Classic syncing with Monterey. ”Sync [Music, Movies, and TV shows]” randomly get unchecked—I then have to re-enable the checkbox and it erases/full-syncs as though I am syncing with a new library. Did you uncover any fixes?

 

[castlema]

I have the exact same issue, but with my 7th-generation Classic syncing with Monterey. ”Sync [Music, Movies, and TV shows]” randomly get unchecked—I then have to re-enable the checkbox and it erases/full-syncs as though I am syncing with a new library. Did you uncover any fixes?

I have never found a permanent solution. It seems that disabling Disk Mode seems to help but does not eliminate the problem.

 

[crobcary]

I have never found a permanent solution. It seems that disabling Disk Mode seems to help but does not eliminate the problem.

I’ve actually never had Disk Mode enabled. How annoying! Thanks for replying!