Server Version#: 1.31
Player Version#:NA
After upgrading 1.31, when I see that a server update is available, I attempt to install it, but the screen sits at the Retry Connection view and the application never updates. I have to restart the PMS exe and the version is the same as before, with a prompt still to upgrade to the new version.
First: verify that your server database is not damaged.
Or inspect them yourself. Take a look at the Plex Media Server.log file and seek for messages about database corrupt or malformed.
If you find these, you may have to repair your database.
https://support.plex.tv/articles/repair-a-corrupted-database/
After you have verified that the database is in good health, perform a āmanualā update.
All you need to do is:
(If you want to install an older version of PMS, take a look into %LOCALAPPDATA%\Plex Media Server\Updates)
Keep in mind that the current Plex server version doesnāt support Windows 7 and 8 anymore.
If you are running on Windows 10 or 11, use the 64bit build of Plex server.
Thank you for your assistance @OttoKerner. I did take a look in the logs as suggested and I do not see these words in any of my Plex Media Server.log files.
Additionally, I forgot to add, I have already done the manual install as you suggested and it is still prompting me to the autoinstall/upgrade screen on the next version. So, this is the second time I have encountered this issue, if that makes sense.
Did you uninstall the old server version first, as indicated above?
Have you ever used CCleaner or Revo Uninstaller or similar software on this machine?
Thank you for your patience @OttoKerner I did misread the instructions. However, the results are the same, unfortunately:
Updates folder shown above)PMS loads up and when I load the dashboard in web it says thereās an upgrade to 1.32. I attempt to install this but the screen again sits there with the Retry Connection screen.
To answer your questions, no I have not installed or used CCleaner/Revo. However, I did have x86 at one point and installed x64 after uninstalling x86. Perhaps this has something to do with it?
The third step was actually to install the new, manually downloaded version.
I was following this step because I want to see the upgrade work from 1.31 to 1.32. Otherwise I will have to wait until 1.32+.
Sorry, I donāt follow.
Uninstall the old, download and install the new.
This is what I did, but instead of of install the new I followed this earlier direction of yours here:
If I install the absolute newest, then I will no longer have an upgrade notification and I cannot test the upgrade process and see if this is fixed until the next version is released. With 1.31 I get the upgrade notification and when I test it by following the prompt to 1.32, it does not upgrade.
So I guess put simplerā¦ if I install the latest, how do I test that the upgrader now works as expected?
You wait until the next server update.
Why did you list the older installs as an option then if that is not really an option here?
A post was split to a new topic: Plex tells me my 30 days Plex pass trial are up
Alrighty, yesterday I installed the latest 1.32.0.6950. This morning I see there is a prompt for 1.32.0.6973 ā¦ I attempted to install this and ran into the same problem.
Any further guidance/suggestions would be appreciated. 
Have you ever started Plex server with āRun as Administratorā (if you have never, donāt try it now!)?
Are you actually running Plex regularly or are you using the āPlex as a Serviceā wrapper?
Thank you for your continued assistance @OttoKerner it is appreciated
I have not, not to my knowledge/recollection. 
I am unfamiliar with Plex as a Service, but I do run it on every startup. This is a dedicated server for this application.
Iād like to re-iterate that I did not have this problem with x86 but since removing it and installing x64 this problem seems to have presented itself. Not sure itās related but wanted to make sure thatās known. 
At this point there is not much left which I can recommend.
Try this:
Backup the Plex registry branch (just in case something goes horribly wrong, while performing the next steps)
https://support.plex.tv/articles/201539237-backing-up-plex-media-server-data/
Uninstall Plex Media Server using the Microsoft Troubleshooter: Fix problems that block programs from being installed or removed - Microsoft Support
You may have to run it several times, in order to remove remants of both the x86 and the x64 edition of Plex server, as well as the service named āStopping Plexā/āPlex Updaterā.
Then reboot the machine and run the latest installer by hand.
Reboot the machine again and hope for the best.
@Mike-E Iāve been noticing the same problem on my Windows PMS but I only see the problem when using the Windows Desktop client to start the upgrade. Each time Iāve encountered this problem, I just get my phone and launch Plex in my Safari Browser (it never occurred to me to try from a Windows browser until just this moment while typing this response) and from there I have no problems launching the PMS upgrade. I kept thinking it was a Windows Desktop client problem but each time I check, Iām on the latest client.
@Mike-E I will be sure to try from a Windows browser before I pick up my phone next time.
Thank you for the suggestions @ralexlaptop, to be certain I am only using a Chrome browser on my server, I RDC into it from my local machine. I start the process and in Task Manager I see the Plex Setup exe start, and then it closes, and then that is that. Nothing else happens after this.
