There are some decisions that you regret in life and for me, at the moment, going down the Plex route is one of them. It has been NOTHING but problematic ever since I started with it and I wish I'd just stuck with iTunes and syncing by cable rather then landing myself with this, at the expense of a Lifetime Pass (big mistake) to encounter problem after problem after problem.
Having got remote access working once I set up manual port mapping as opposed to relying on UpNp (which despite seeming to be an extremely flaky option, still seems to be the default recommendation for setting up remote access) I now encounter the certificate signing issue EVERY SINGLE TIME the Mac server I use goes down for whatever reason, requiring me to log into it, remotely if I'm not around and click YES!!! There have been previous threads on this that seem to have just died a death rather than getting anything by way of a definitive answer.
I have tried all the fixes listed such as deleting the media server, doing a fresh install, typing in the sudo command line etc etc etc but EVERY SINGLE TIME the server goes down I have to open it up and tell is YES EVERY SINGLE TIME. So is there any definitive working fix for this problem or not?
At home Plex does NOTHING for me that iTunes doesn't do (and on the ATV 4 iTunes does it with a less confusing interface) and I bought the Plex Pass because I thought I needed it for remote access and to add my wife's user account to give HER remote access (both of which don't seem to require a Plex Pass) and thus I find I actually ONLY need it for the sync, maybe once or twice a year. For all the hassle and time Plex sucks from my life trying to GET it working and KEEP it working reliably, seriously, if I could get the money back I paid for the Pass I'd bin Plex and walk away.