We had to intall a new hard drive and upgraded to Windows 8.1.  We can see all our music on I-tunes but when we try to sync the gen 5 nano our new music (since upgrade to 8.1) does not end up on the i-pod.  Any ideas.

We recently installed Window 8.1 and now our new music does not sync to our i-pod nano.  Any ideas?
We have tried both a generation 5 Nano and new Nano.

Hey Terrible Teddy,
Thanks for the question. I understand you are experiencing issues with the iTunes library on your PC. To begin, I see that you recently installed a new hard drive. Did you happen to copy over files from the previous hard drive? If not, I suspect that the iTunes library is no longer locally stored, and what you are seeing is your iTunes in the Cloud purchases.
Do the tracks have a download icon that looks like this?:
If so, you’ll want to download these purchases as they are not locally stored on your computer:
Downloading past purchases from the iTunes Store, App Store, and iBooks Store
http://support.apple.com/kb/HT2519
After doing so, go ahead and attempt to sync your iPod once more.
Additional Information:
iTunes 11 for Windows: Symbols used in iTunes
http://support.apple.com/kb/PH12306
iTunes 11 for Windows: Download previous purchases from the iTunes Store
http://support.apple.com/kb/PH12491
Thanks,
Matt M.

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