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castlema

macrumors regular
Original poster
Nov 21, 2003
127
84
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

macrumors 65816
Mar 24, 2010
1,318
1,708
Have you tried a restore since this started happening?
 

crobcary

macrumors newbie
May 13, 2019
21
15
Atlanta, GA
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

macrumors regular
Original poster
Nov 21, 2003
127
84
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.
 
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