Artwork ok in iTunes but 50% of it not syncing

99% of the songs in my iTunes library have artwork, largely from google. Until recently, all of my songs synced to my 4th gen Nano complete with their artwork. However, now only about half of the songs have their artwork when viewed on the iPod. The artwork is still there in iTunes, it hasn't gone anywhere. I've clicked "Get Info" on individual songs to make sure they've got artwork and not just some songs on each album. I've also tried replacing artwork on some albums and making sure songs don't have several images. I think the problem may have arisen since I chose to let iTunes convert my songs to AAC before syncing to save space (it can't be a space issue because now I've got over a Gb free).
None of this has worked, can anyone help my artwork sync again?

The iPod stores album art differently than on the computer, in an optimized database, to save space.
If something has gone out of sync, you may be able to fix the problem if you connect the iPod to computer, select the iPod under DEVICES, go to the Music tab, and uncheck the box for +Display album artwork on your iPod+. Then click the Apply button.
This will remove the album art on the iPod. Now check that box again, and click the Apply button. This will put the artwork back on the iPod. Hopefully, the image will now be in sync with the songs being played.

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After importing my music from an external hard drive backup, I have a problem with ~5% of my music. The songs are listed in iTunes as "Unknown Artist" and "Unknown Album". However, if I find the file within my iTunes folder, all of the artist information tags are listed if I use "Get Info" --> "More Info" in the Finder. Back in iTunes, the album artwork is there, but the tags are missing. These are for .m4a, Apple MPEG-4 audio files. How can I get iTunes to recognize the tags that are obviousy still present in the file?
There are too many songs like this to relabel the, realistically.
I have tried deleting the songs from my library and re-importing them into iTunes, but this does not fix the problem. I cannot find any logic as to which songs this affects.
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Artwork ok in iTunes but 50% of it not syncing

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