I have never had any trouble syncing my iPod Classic (5th Gen) to iTunes until tonight. I updated iTunes first. Now I get error code -39. What is happening and why can't I sync anymore and what is error -39? I have Win 7 (not the XP as listed below. I keep trying to change it and it won't change).
iPod classic, Windows XP
Are you doing photo syncing?
If so, the 39 can indicate a damaged ipod photo cache.
So, just in case, let's try deleting your current iPod photo cache.
For instructions on where to find it, see the following document:
This started with my iPod classic as well back in November, and also an iPod Nano. Nothing to do with photo sync (have that turned off). I now can't sync any music to either iPod (rendering them both useless). All my music is stored on an external NAS, and the problem started after the upgrade to Mavericks (which has caused countless issues with SMB access to lots of NAS's!)
Tried everything and nothing works (new itunes library, deleting and re-adding music). The only way I can sync music onto my ipod now is if it exists on the internal drive - will not work if stored on the NAS.
Oh well, 2 iPod's up for sale now!
error -39 ipod syncing
