what is error message -39?
what is error message -39 i got this message when i tried to sync my iPod classic 160 gb.
iMac (24-inch Early 2009)
If it is a typo and you mean error -69, it mean that the file/s you are tryinhg to sync, is corrupted and is unusable in iPod.
But if it is really error -39, it may means that your Antivirus or firewall software is in conflict with iTunes Sync. (sorry, first time I come across error -39)