Q: I’m having trouble moving purchased songs from my library onto my iPod… I can drag it from Purchased Music into my library, but then when I try to drag it onto my iPod, it won’t “take.” Can you tell me how to fix this?
A: There are two possibilities. The first is that your iPod is set to synchronize automatically. If this is the case, you don’t need to drag the song onto the iPod icon; when you connect your iPod, iTunes automatically copies everything. You can check this in the iPod preferences (iTunes > Preferences > iPod) in iTunes.
If, however, you are manually updating your iPod (in which case you should be dragging songs onto it) you probably have a problem with the authorization for your iPod, or for your copy of iTunes. This happens occasionally, and you can fix it by trying two things.
First, in iTunes, select Advanced > Deauthorize this computer, then select Advanced > Authorize this computer. This will ask you to re-enter your user name and password.
As for the iPod, you should first make sure you have the latest iPod software. Go to the Apple web site and download the iPod Software Updater. Then, after you follow the updater’s instructions, try connecting your iPod. If your music still doesn’t transfer to the iPod, use the software updater to “restore your iPod to factory settings”. This will erase everything on the iPod, so make sure you have your music backed up. After this update, reconnect your iPod. Set it to sync your music automatically, and everything should work.