Q: I downloaded the new iTunes and clicked on the “Get Artwork” feature you described last week. Most of my “artless” music selections were succesfully updated and now have the album artwork in iTunes, which is great. The problem, however, is that this artwork does not show up on my iPod, unlike artwork I’ve collected myself. Any ideas on how to get the artwork that iTunes assigned to my previously “artless” selections to show up on my iPod?
A: In our experimenting, we’ve noticed the exact same thing, and we definitely suspect it to be another one of the many bugs expected to be fixed by an update to iTunes 7 that Apple is undoubtedly working feverishly on.
In the meantime, this particular bug appears easy to fix: users on our iLounge Discussion Forums are reporting that the album artwork downloaded from iTunes’ new feature can in fact be transferred to the iPod, but that the bug seems to be that simply downloading the artwork doesn’t “flag” the tracks to be updated on the iPod.
Thus, the problem is fixed if you choose to restore your iPod (forcing all tracks to be ‘flagged’ for transfer), or if you otherwise trick iTunes into thinking the songs need to be updated on the iPod (for example, if you make an edit to the songs’ Comments fields). In either case, after they’ve been instructed to transfer to the iPod, they’ll do so along with their associated artwork.
Again, we expect a bug this simple to be squashed very soon, but in the meantime, use this workaround.