Server Version#: 1.16.2.1321 running on windows 10
Player Version#: Chrome 75.0.3770.100 running on windows 10
After a few hours of plex running, the Remote Desktop connection fails with Internal Error has Occurred. The workaround to getting rdp working again is to restart the Plex Media server. To make that possible I’ve been using Chrome’s Remote Desktop extension. Doing a plex update also resolves the problem since the plex service gets restarted during that process. Same problem occurs whether I’m on the same subnet as plex or outside. Once the failure happens, it is persistent until the Plex media Server is restarted. Attempting rdp reconnects do not help. It’s not necessary to restart rdp on the server to resolve the issue.
Obviously, something different in the configuration. I suspect it’s some kind of resource issue. It would be nice if it were possible to restart the Plex service from the web client. This is a common feature in routers. That would eliminate the need for Chrome Remote Desktop which other forum members have also alluded to using for recovery.
Have you considered using separate accounts to see what happens? I use a local account to automatically log in and load Plex, while using my Microsoft account via RDP when I need to do any maintenance. RDP Wrapper can be used to allow both accounts to be logged in simultaneously.