My 160MB iPod Classic won't sync from iTunes.  This is a recent problem.  The error message is "The iPod cannot be synched.  An unknown error occurred (-39)." The end result is that music will sync but photos will not.  Current software on Mac and iPod.

My iPod classic won't synch from iTunes.  This is a recent problem.  The error message reads "The iPod cannot be synched.  An unknown error occurred (-39)." The end result is that the music will sync but photos will not sync.  I am running current versions of software on the iPod and the iMac / iTunes.  HELP! J

First try to resolve #2 by:
See
iOS: Device not recognized in iTunes for Windows
- I would start with
Removing and Reinstalling iTunes, QuickTime, and other software components for Windows XP
or               
Removing and reinstalling iTunes and other software components for Windows Vista, Windows 7, or Windows 8
However, after your remove the Apple software components also remove the iCloud Control Panel via Windows Programs and Featurs appin the Window Control Panel. Then reinstall all the Apple software components
- New cable and different USB port
- Run this and see if the results help with determine the cause
iTunes for Windows: Device Sync Tests
- Try on another computer to help determine if computer or iPod problem
If you can resolve #1 and still get same message for #1 then you have to restore the iPod like the message says.

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