I had some albums in Apple Lossless on my desktop which I converted into AAC for use on my laptop. On the desktop, they downloaded cover art fine from iTunes: however, on the laptop they won't download art. I've checked the following: iTunes store has the albums & art ID3 tags appear identical for both sets of files (and to the versions on the iTunes store) Both machines are signed in to the iTunes store with the same iTunes account Both versions of iTunes are the same (latest build) Other albums on the laptop download art fine as well, so it obviously can connect to iTunes to get the data. What the hell is going on? Why would the art download on one machine, but not the other? More importantly, any way I can fix this? I know I can add the art manually, but as it's there on iTunes I'd rather get it that way than embed it in all the files and make them larger.