Hi @ezman
Mike wrote this earlier (back in March) in this topic:
Roon does allow one to select from the list of files to change which file is being used but it is performed by editing each album individually … it works but is a lot of effort.
As a workaround, assuming you want Roon to select cover.jpg … how about temporarily renaming (programmatically) all the non cover.jpg image files to say .jpgXXX then let Roon import. Then once complete rename those files back.
What I’m not sure about is whether on renaming back, or a file re-scan, Roon would still revert to using the largest file… so best to try with just a couple of albums first.
Let’s see if @Mike has any more thoughts on this.