OK thank you for that @OttoKerner I will study this and see if I can warm myself up to it. 
I had the same thing happen to me yesterday. After 2 or 3 attempts (PMS would not restart after āupdateā).
After the 3rd attempt restart, I started to get non-connect problems (referencing something about in-secure mode (which was already allowed)). I had to start PMS as administrator to even get clients to connect (Iām currently running in Admin).
Once I did that I search the db for any corrupt and malformed strings, none found. Ran Optimize db and Clean Bundles, restarted PMS and that time the update succeeded and PMS restarted (not sure if those did anything, but I thought I would mention it).
NEVER do that. It will mess up the access permissions in your Plex data folder, so that youāll have to run Plex as administrator in perpetuity. Which is a bad idea. Regular apps should never run with full administrator privileges.
You will have to repair the access permissions of every single file, folder, subfolder and all files contained therein if you want to go back to running Plex under a regular user account.
Well aināt that someā¦ I guess as āluck would have itā, I restarted PMS not elevated (after a server reboot) and all seems fine.
Itās not that simple. It wonāt show an effect immediately. Only it might happen that for instance one movie wonāt update its metadata or media analysis anymore. Caused by incorrect access permissions on this movieās metadata bundle.
@Mike-E for me it appears that the Plex for Windows is causing my problem because I see the same thing with this current update.
@Mike-E Normally, this is when I would just launch the update from my iPhone but this time I just launched the Chrome browser in Windows and logged into Plex from there and everything worked fine.
Thank you for the update @ralexlaptop so you are saying you updated from the browser and it worked as expected? The screenshots you provided appear to be from the Windows application so I am trying to understand this.
@Mike-E Thatās correct. Iām unable to update the PMS when using the Plex App for Windows because it gets hung on āChecking for Updatesā.
@Mike-E However, if I log into plex.tv and access my PMS settings from there, Iām able to get the option to āDownload Updatesā.
Thank you for that additional context @ralexlaptop. I do see Open Plex when I visit plex.tv but when I press this I do not see your screenshot window anywhere there. 
@Mike-E You are almost there.
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AHHHH I see my confusion now. Youāre using fancy dancy bordering for your screen captures. 
That was throwing me off. I see now that you clipped the a part of the General settings view and your screen clipping software beveled it to appear like a window.
So yes, unfortunately, when I press Check for Updates on that view the update process starts but never finishes for me, and I remain on the same version (after having to restart Plex as it does not restart after starting this process).
Iām sorry @Mike-E . It sounds like you are experiencing a different problem. I have no idea how to help you. Iāve never encountered that one.
@Mike-E Iām definitely not the person to tell you how to fix this problem but it appears that you may have to completely uninstall your PMS and start over with a fresh install. Unfortunately, uninstalling the PMS is not as simple as just clicking on uninstall application. It will require going into your Windows registry and deleting a key. Iām not a fan of messing around in the Windows registry but that is the only way to get into a state where you can do a clean new PMS install.
No worries, @ralexlaptop I appreciate you walking through with me to determine any possible leads. I am not exactly to the point of doing a full reinstall. In fact, I am considering reinstalling x86 as that is where it worked last. I do not have the motivation to do a full reinstall ATM. Weāve had this server since 2018 and itās taken forever to get it where it is now.
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Hey all, a quick update here. I think I figured out the reason why I am experiencing this problem:
It appears the 32-bit installer is running, but I am on a 64-bit instance of Plex. As mentioned, I did upgrade from 32-bit to 64-bit and that is when the problem started.
Is there a flip/switch I can toggle here to make sure the 64-bit installer is run instead of the 32-bit installer?
Reboot Windows. The installer should be gone after that. Then you are free to run the 64 bit installer.
Reboot Windows. The installer should be gone after that. Then you are free to run the 64 bit installer.
I have rebooted Windows several times since this issue started, which does not appear to address the problem. It appears it is running the 32-bit version of the installer from the web portal when it should be running the 64-bit version. 
What does this mean?
Are you still trying to update the server from the integrated update prompt in the web app?
Donāt do that. Download the 64bit server installer and start it manually.
