Originally Posted by puma1552
Ideas? I feel like I play this artwork song and dance every damn time I do a clean install. I know for a fact that every single time I do a clean install I have to MANUALLY add the artwork back for literally close to 1000 albums...
I played that game for a while. It turned out that between version 8 and 9
(or some such, it's been a while), iTunes changed the structure of the folders in which it kept media files and artwork. If you updated over the old structure, the library KEPT the old structure, which wasn't entirely compatible with the new, expected, structure. This caused things like disappearing artwork.
Tossing the old iTunes folder onto a backup drive, and starting over with the new, properly structured
folder that iTunes will create for you under those circumstances, and reimporting all my music, and a bunch of lost artwork, fixed the problem. I can now update without losing any artwork.
Doing the above was a major pain, but substantially reduced my annoyance down the road. Same may
work for you.