Artwork does not automatically copy to iPod classic

We have 3 ipods in our hosuehold, one classic photo, one 3rd generation photo, and a nano from the latest generation.
All are managed manually.
On the older 2, artwork does not automatically copy across from itunes to the ipod when songs are added. Instead, I have to select each song or album on the itunes library, manually copy the artwork, and then paste it into the iPod. while not crippling, it is certainly annoying.
The nano does not seem to have this problem.
ANybody else have this problem, and is there a way around it?
Of course I have "display artwork" enabled on all ipods, and the software is up to date, on all ipods and on the mac.

I don't manually manage, so my apologies for not being really familiar with it. But my question is, have you noticed that the addition of artwork depends on if the artwork was there from the beginning or not?
In other words, I wonder if when put in a new CD, tracklisting is looked up, you import and artwork gets automatically added. You then drag and drop those tracks to your iPods. Does the artwork show up on the iPod or do you have to do a secondary addition of the artwork?
Versus, if you already had the songs on your iPod, then LATER added artwork to the tracks in itunes, I could see where unless you resynced the songs to the manually managed iPods, that the artwork wouldn't go onto the iPod automatically and would have to be manually added.
I mention this because your Nano is the newest one and I am wondering if the issue is that you have stuff on the older iPods from back before artwork was added to your library. You are now adding artwork, but the songs on the old iPods still have older versions without artwork. The Nano, being brand new, you are probably adding tracks that have since had artwork added and so it maybe seems like it is being automatically added to that iPod and not the others when maybe you just need to re-sync the same tracks to the others?
Again, just some random streams of thought and guessing.
Cheers,
Patrick

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