For the heck of it I created a new playlist with the same songs in one of the playlists where the artwork was not showing up and the same thing happened where there is no artwork.
I know the songs and albums have proper embedded artwork. When I view the album or any of the songs, the artwork is there, it just won’t populate on the playlist previews.
I’m not sure how to get this resolved. I can provide logs or any additional information needed to the plex team.