I believe I figured it out.

I noticed that a lot of the Album Art was not listed as Cover (Front). So I did the following:

1. Selected all the songs from the album that wasn't displaying album art
2. Went to Properties
3. Went to Album Art
4. Ensured the listing read Cover (Front).
5. ***Checked the Apply to all selected files checkbox***
6. Clicked OK

What I'm guessing happened is that iTunes was only tagging the first song with the Album Art; doing step 5. above has enabled all album art to display. So it's just a matter of keeping track of which albums need album art "re-added" and I'm good to go.

I also tried using the Album Art scripts (recommended in various topics); they didn't find any bad ones, and also had it convert links to tags. Not sure if that made things worse or better. What I do know is that Album Art that was displaying for songs before I opened it with MM are now showing the music note.

Not saying MM's fault; iTunes is a POS which has probably impacted MM's ability to work with it properly.

I used MM to edit the files on the iPod.

Did MediaMonkey sync/copy files to the device and/or did you use MediaMonkey to edit the files on the iPod? In other words, how was MediaMonkey involved in this?

Hello-

I have an iPod Classic, which still works great. However, iTunes is, as the French say, "A POS". I can't tell you how many times I've had to go and re-delete the Album Art cache on my Win 10 PC, re-copy album art over, etc.

Rather than keep using a soon-to-be deprecated poorly-designed database, I decided to go with MM.

I opened all my songs in MM, and started updating some of the album art. However, now that I'm playing my iPod, I noticed lots of album art that was present before is now displaying the gray "music note" icon. The strange thing is that not all album art is affected; some songs still have their art.

Note that most of the album art I use is from external sources such as Amazon (I used mp3Tag to update the metadata and images before copying songs into iTunes). I do not auto sync, I do all the work manually because I don't trust iTunes.

Sorry for the long message, but has anyone ever seen this happened before? if so, how did you fix it?

Thanks,

-Steve