I realize this question has been asked to death, but all the information I have found has not been helpful in solving the issue. I was running Plex Media Server on Windows 7 on a VM however for the longest time I just accepted that I could not update so I was stuck at v 0.9 something. In this version all artwork downloaded perfectly fine. I finally decided to update to Windows 7 SP1 and to the newest version of PMS and when I scan in my TV shows library it gets metadata (i.e. show descriptions, summaries, and ratings) however, season and show artwork does not download. I have searched everywhere for a solution to this and many forum posts say to have proper naming on your shows (which I know is not the issue as it worked on the earlier version of PMS).
Please help me as I have already spent way too much time on this problem.