I’ve been having this issue for a few months now. After every update to the server, PMS does not automatically restart. I saw in another thread about it detecting if PMS was running before the update, that it would relaunch.
It will start back up without issues when I go and manually launch PMS.
In the Plex Update Service Launcher log it has an error:
"Apr 27, 2020 17:00:53.520 [12312] ERROR - Failed to start PMS. Exit Code: 0xdeadbeef - "
Ideas?