On the web (and also formerly on the Roku until a recent update looks like it broke it…), I can just click on a TV Season (or entire series) and play, and it will play all unwatched episodes.
On the Playstation (3 or 4, either one), it always starts at Episode 1, no matter what is marked Watched/Unwatched.
Is this a bug (in either the PS App, or the version of Media Server I’m on, 0.9.14.4), or a possible configuration issue? This has been broken on PS3/4 for a while, and just recently broke on the Roku as well.
