iTunes dropping album artwork

That's OK. The delay between when you post and when your post shows up can make things very confusing. I was in a bit of a hurry when I typed my response. The reason I suggested you try all of that, is sometimes things like external HD's don't fully boot up fast enough. So if your OS and iTunes get ahead of your HD it can cause all kinds of problems. Missing artwork is a very common result when this happens.
Some of the other posts talk about tagging issues. They're absolutely correct. That can be your problem, as well.

Thanks Kijanki - Like you, I have some albums where only track no. 1 has the artwork so now I know how to remedy that.

All of my artwork is showing now since spending hours re-populating the artwork from the internet. It looks like all the ones that I just re-populated have artwork for each track. That is a new development so things are improving.

Puerto, You can open properties by right clicking and selecting "Get Info". You can do that to one song or more if you mark them. Sometimes only one song has artwork. I don't know why, perhaps this song was highlighted/selected when I was dragging artwork into album (blank) icon. Strangely, when I click on "Get info" for the album artwork/icon it has none.

Another confusing thing in Itunes is fact that I cannot see my albums as tiles. Remedy for that is to set "Smart PlayList" with "Genre contains xxxxx" where I set xxxxx to genre like "Classical" etc. Later I added "- " in front of the name to have them appearing together (not mixed with other playlists). Playlist still allows to change properties but does not allow to delete - good protection.

Zd542 I responded to your suggestion with a "Thank you I will try that" but I did not see my post in the thread - so, Thank you, I will try that! (again).

Kijanki: Are you referring to an iTunes properties location? Not sure what you are referring to there.

I had this problem when one song was selected. During playback artwork was shown only for one song. I fixed it by marking all songs and pasting artwork in properties.

Try turning on your external HD before you boot the OS. If your drive does not have a power switch, unplug it and plug it back in again. Wait a few seconds for the HD to fully start up and then power up your computer. Once the OS is booted up, make sure you see the drive mounted in your file system and then start itunes. There is a good chance that this will fix your problem.

All of my files are in aiff. I get the album artwork by click and drag from the internet. Yes I use an external HD.

What format are your files? How do you add artwork to your iTunes files?

Are you using an external HD? Also, what format are you using for your music files?