I've seen similar issues mentioned here, but maybe not this exact one. I had bought a new Mac last year and the only hiccup is that it won't play my older iTunes-bought songs. When it shuffles to one of them in my library, I'm asked to authorize it. I enter the password, it notifies me that the song is now authorized on two of five computers. But then trying to play the song will bring up another request for a password to authorize it. No matter how many times I do it for the same song, it still contacts the Music Store and says I'm authorized on 2 of 5 computers. Despite that assurance, it doesn't stick. Since it's not authorizing on the new Mac, it's not transferring to my iPod either. It's like iTunes is ignoring its own actions. iTunes works normally in every other way except for this. Any thoughts as to why this might be?