First of all, this is not my iPod so I may be slow at additional testing. I tried to add songs to a second generation Nano, a new window opened and next to all tracks was the message Copy failed. I tried dragging from Now playing to the ipod library view (not allowed) and to ipods music icon on the left column (same thing). The same ipod later synced fine with foobar + iPod manager component (just added files to a playlist and selected Send files to iPod).