Okay, trying the exact same file on a Mac, I see your a Windows User and possibly on Plex Media Server 1.40.1.8227, there have been a couple Beta since which may have addressed some Windows issues. Check them out in Announcements.
Give me 30 minutes or so, also which player are you using? Example WebOS,Roku ?
Update: This exact same file (info provided ) has no issue loading and playing on all my Player apps with a PMS on Mac. My suggestion, if you feel the need Update to the Pass for a Month $4.99 fee and download the latest Beta. You can always roll back, Instructions are available on the forums if it does not work out, which I doubt.
So to guess I would say this is a Transcoder Issue on some Windows installations.
