Do you think you could post a picture of the exact error message? Also you could check the Plex logs through the web app and you should see the exact error and what component caused it. If I had to take a guess, I’d say your uncompressed movie has something that’s causing the server to transcode (TrueHD audio or a forced HDMV subtitle stream) and the transcoding process is failing.

Life, that is. It would just make life a little easier.

Well dang, I guess that “learn about proxmox” line on my to-do list just moved a little higher. For the most part, I’ve enjoyed using ESXi and am sad to see it go.