No, MediaMonkey picks a first place Artwork from 1 file on the Album. However you can resize Artwork on Sync.

Is there a way to force the sync, or in general, the use of external covers? My entire database has embedded covers with a 500-pixel resolution. A leftover from the time when Mediamonkey couldn't change the resolution. Additionally, all albums/songs still have external covers (Cover.jpg) with a 1200-pixel resolution. However, I don't want to embed these into the files as it would be quite time-consuming and I'm afraid something might go wrong.