Plex not playing anymore but thinks it is

I have a recent install of Plex that has stopped working for some reason but it thinks it is.

On the server itself it plays fine and it was playing fine on the internal wifi on a laptop via browser.

Now it seems to connect, the timer spins a bit but nothing displays.

If I leave it a 2 minutes and try to refresh the browser or go to the server and click the same movie showing on deck it asks if I want to carry on from 2 minutes. If I click at 11:16 (already buffered) it shows the pause button as if it is playing. If I click refresh and select the movie from the a minute later it asks if I want to carry on it asks if I want to carry on from 11:16.

I do not get any errors saying that server can’t cope

It seems to be in last stage of playing that it fails.

If I play on Chrome and then access server from Firefox it lists the movie under now playing (plex web via Chrome) but nothing is showing in in the Chrome session.

This is the Alerts Tab of the Status on the server

6:27 PM User1 started playing Movie Name on Plex Web (Chrome).
6:27 PM Finished processing Movie Name in Movies
6:27 PM Loading metadata for Movie Name in Movies
6:26 PM Finished processing Movie Name in Movies
6:17 PM Opened connection to MyPlexServer, listening for events.