iTunes won't upload album to iPod
So a little while ago, I decided to update some album artwork in my iTunes library. I got the artwork to an album that I uploaded from a CD that was already on my iPod. When I tried to update the artwork onto my iPod, it wouldn’t update straight to it from iTunes (it worked for other albums). I figured that I could try deleting the album and re-downloading onto my iPod to see if that would work. So that’s what I tried but after deleting the album, iTunes wouldn’t sync the album onto my iPod. Every time I try adding the album, iTunes says “Preparing to update” on the top bar and shows a loading bar that quickly fills but then nothing happens. I’m not quite sure how to troubleshoot or what to do if the troubleshooting doesn’t work. Anyone know things that I could try?
Note: My iPod is a 3rd generation Touch with 13.0 GB available that runs on iOS 5.1.1. (Pretty old, I know) I also run iTunes on Windows.
-Thanks!