Server breaks after auto update

Server Version#: 1.16.5.1488-deeb86e7f (Now, no idea before the auto update)
Player Version#: https://app.plex.tv/desktop version.

I have been having this issue for some time now with my server but every time it does an auto update, it fails to start properly and just gives me the local GUI but fails when I try to see settings or remote access settings. I have to usually exit the app from the taskbar, download the latest version of PMS, run the install, and open it again and it works as if the issue never happened. The server completes the auto updates I assumed as after a minute or two, the icon comes back to the taskbar when it closes it for the auto update but for some reason, when it comes back it doesnt do anything other than show me my dashboard and none of my server settings. As I said, downloading the latest and installing it usually fixes it but, what is the point of auto update if I still have to do a manual update to fix the failed auto update? I first noticed this issue in January of this year (2019),

In this instance of tonight, I had to reinstall it manually, but this time it broke even worse. Now when I try to open the server, I get a 404 Not Found. I opened it by double clicking the icon in the taskbar. It brings me to 127.0.0.1:32400/web/index.html but does not do anything.

I had to run the just now downloaded PMS update installer a second time and hit the repair button to remedy the issue. So this time I had to reinstall the manually downloaded update twice because of a failed auto update. Might have to go back to manually updating it again. Oh wait, it didn’t fix it. I had to uninstall it, reboot, reinstall, and reconfigure EVERYTHING again. This has happened about 4 times since the first time it failed from an auto update.

I am having similar issue following latest update on Ubuntu Plex server. I can watch video for about 15 minutes, then it shuts. I cannot play it even direclty on server, have to reboot whole machine and reinstate the connection.

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