Back in November I did a post called An iTunes Mystery - The Case Of The Disappearing Cover Art . I think I can finally say that the case is closed, mystery solved.
I was having problems with artwork disappearing from iTunes, and consequently from my iPod the next time I synced.
I won't bore you again with all the details, but you can read them in the link to the original post above if your not one of my three dedicated readers. The bottom line is that once I unchecked “Automatically download missing album artwork” on the General Tab under Preferences, it stopped happening. Although it was an intermittent problem, it's now been 5 months since I changed it and I haven't lost any artwork.
Now remember, this worked for me on a specific platform (XP Pro/Windows Media Center 2005), and in a specific situation (the disappearing artwork was all added by hand to ripped music when iTunes couldn't find it). This solution also has one obvious drawback. While iTunes purchased music is still downloaded with cover art, once you uncheck the "automatically download missing album artwork" box, music you rip and then import into iTunes won't have cover art. I think this is the lesser of the two evils. I'd rather add cover art once when I import a song, then constantly have to re add random batches of artwork. It was an insidious problem because usually by the time I noticed it I had synced repeatedly and then I'd have to go back through the entire library looking for the newly naked tunes.
I finally decided enough time had passed to give you an update on this one plus I noticed recently that the search keywords that bring the most traffic to my site are variations on "Missing iTunes Artwork". I guess there are quite a few others out there who have shared my misery.
You know, I'm almost afraid to upload this, 'cause I know that as soon as I do...
Nah. Never happen.