I did a completely fresh install after removing an older version of the server. I followed the instructions to remove the registry key and Plex folder from the users directory. I started from scratch on a new server, version 1.0.3.2461. The reason I did a fresh install is that I upgraded previously and had this same issue, described below. All videos played without issue on server version 0.9.1211.1406, it's only after the upgrade that these problems started.
Every time I go to play a video in Chrome, regardless of the file type, I get the same error message, "There was a problem playing this item". When watching from my Galaxy Android phone, a few of the movies will play, but not most. Same issue on Roku, some will play, but most will not. I've tried to see if there is a correlation between the videos that play and those that don't, and there is none. Two videos with the same file type and encoding, one will play and the other will error.
I've gone through the log file, but not really seeing error messages, at least not directly related to what I'm trying to watch, but I've added it here if anyone can find something I'm missing.
Your help would be greatly appreciated!