FYI, I am running 0.9.9.5.411-da1d892, Server Essentials 2012 fully patched, unchecked startup automatically, exited PMS, installed PMS service from this thread. Strange that it just drops at no specific time. If it does drop I have to reboot to reconnect.
This was the problem relating to tcp/winsock that I was thinking of
https://forums.plex.tv/topic/75484-windows-server-essentials-pms-freezing-fix/
https://forums.plex.tv/topic/52700-pms-crash-on-windows-server-2012/?p=425764
Confirmation here later in that thread that Windows Server Essentials 2012 R2 fixed the problem
https://forums.plex.tv/topic/52700-pms-crash-on-windows-server-2012/?p=464185
There were also confirmations elsewhere that disabling the Windows Server 2012 built-in vpn 'Anywhere Access' fixed the problem
It might not be your problem - but could be
