iTunes Match doesn't allow album artwork changes in the cloud

I don't use Match but if these are songs that are matched with something that is in the iTunes Store, Apple will use that copy when you request a download. Obviously this won't have your artwork changes applied to it. If they aren't in the Cloud but are indeed your files uploaded then you probably have to somehow refresh any copies in the Cloud. I don't know how to do that, sorry, but it's probably possible.

In general, your custom metadata and artwork are retained even for matched tracks. The artwork is uploaded to Apple. However, this is not 100% accurate and sometimes the artwork will be from what is available on the store. One method to ensure you get your artwork is to turn off iTunes Match, reapply the artwork (making sure it conforms to at least 300x300 or 600x600 @ 72 DP), then reenable iTunes Match and let it does the scan, match and upload process.

In many cases when custom artwork doesn't show up it is because it falls outside the range of those criteria above.

What you'lll probably need to do is hit the "update iTunes Match" command from the Store menu after you apply your custom artwork. This is a guarantee to work, but it certainly won't hurt. For the moment iTunes Match is still a work in progress and I suggest you not expect perfection.

The only way I've been able to update artwork and get it to replicate in the cloud as well is to do the following:

First, this all should be done from the PC that holds your original iTunes library files (it's the only way I've tried doing it).

Select the album/tracks you want to change in iTunes and DELETE them from you library, make sure to also check the box "Also delete this item from iCloud." Obviously, on the next popup chose KEEP FILES.

I then use a third party tagging program called Tag&Rename to add the new artwork. Then re-add the files to your iTunes library and update update iTunes Match (will normally start automatically a couple minutes after you add the files back to iTunes).

Yes, it is a pain in the butt and a drawn out process for just updating the artwork but, it has worked for me every time. The key is, one way or another, you have to remove the files you want to update from the cloud, make the changes, then re-add them (unfortunately, to remove them from the cloud you also have to remove them from your library).

Still the same here too, waiting for Apple to fix this. iTunes Match is awsome, this is the only issue I have.

I can only confirm that this is an annoying bug. Apple, when will it be fixed?

I can confirm that this is still a bug that hasn't been ironed out. Considering iTunes match has been deployed for a year now, one would think this seemingly minor hiccough would have been cleared up already.

This bug is still present with iTunes 10.7 (21)

@see https://discussions.apple.com/thread/3546099?start=45&tstart=0

I feel your pain. I am a new user and am having the same issues.