ROKU and Cloud Sync

I asked this question last week in the ROKU section but it only got 24 views so I’m asking again here.

I am a PLEX PASS Lifetime member and I’ve signed up for AMAZON’s unlimited cloud service. I’ve successfully linked the accounts and SYNC’d my libraries to the cloud. I have no problem watching my Cloud Sync Libraries on a computer, but when I try to play them on my Roku I get the “Your plex media server doesn’t support video transcoding” error. Now if I keep trying, I’ll get a movie to play every now and then after using the “brute force” method. Am I doing something wrong? Do I need to change my settings (Direct play, Direct Stream, etc?)? Thanks in advance!