Plex server random crashes

Ok, in my case it was similar, when hover the icon disappears.
In the Task-Manager PlexMediaServer.exe was gone, but PlexTranscoder was still running.

Check if you really did this:
It’s important to create the folder manually:

%LOCALAPPDATA%\CrashDumps

this is where you should find the Dump for sa2000. - only send by PM because of sensible data.
Also set the registry key to enable the crash log.