I have a 2nd gen shuffle, I was able to load music on it. Now I want to change the music and am having trouble. I have iTunes 11.0.1. I see the ipod in the iTunes left hand pane and in the top window pane it says iPod sync is complete. Under settings I have the 'sync only checked song' checked. I want it to sync with a music file in my playlist. Under on this ipod, I have autofill from with the playlist selected. Under this in autofill settings, i have replace all items when autofilling. I select the autofill button and get a waiting for ipod. I've selected only 4 files and want the original files on the ipod replaced with the new ones. It does not appear to work. It says updating files, finishing snyc. After running for a long time, sometimes it says it's too full, sometimes it says can't find ipod. It always ends up failed. I don't have anything else connected. I've changed ipods, chargers and USB ports with the same result. Any ideas?
I happened upon a fix - at least this one time. I had to powerdown the laptop, plug in the usb charger to the laptop and have the ipod shuffle in the charger. I powered up the laptop and all went well. If I made any changes, I had to powerdown and start again.