Plex issue

I've got a video file that I encoded via Handbrake (AppleTV 3 preset with Quicksync turned on). I believe this is an MP4 file encoded H.264 with AAC audio. It plays on my Tivo Mini but when I try it on the Roamio, it just boots me out of Plex back to the main menu. I did not choose Web Optimized so maybe this is the issue but the part that's bothering me is why did it work on the Mini?