Can't Update Plex Server

I am having problems displaying on the TV correctly, and checking the server tells me that I have an old version of the server. Version 1.20.1.3252. - so I attempt to upgrade the server first.

Opening the server, I see that there is an update in progress, which I started hours ago. The message showing in the left column is “Once the server “DESKTOP-HTB0RCB” has finished installing the update, Plex will automatically try to reconnect to this server.”

How long should this take? Should I just “try again”? I have done this a number of times, and I will see:
Update available for Plex Media Server
You are currently running version 1.20.1.3252 on the server “DESKTOP-HTB0RCB”.
Version 1.21.1.3876 is now available.
Download Now

Press Download now and immediately (no time for a download) appears the next text:
Update available for Plex Media Server
You are currently running version 1.20.1.3252 on the server “DESKTOP-HTB0RCB”.
Version 1.21.1.3876 is now available.
Install Now

I click on Install Now, and get
The server “DESKTOP-HTB0RCB” is installing an update
Grab a cup of tea. This may take a couple of minutes.

Immediately the text appears “Retry Connection” - I don’t know if I should press it, or wait…

An idea of how long to wait before retrying would be appreciated.

Meanwhile, the system runs, with the bug “Playback Error” appearing at odd times whilst watching a video. Buffering before playing seems to take a lot longer than it used to.

The message is “Connection failed. The transcoder exited due to an error” - I need to disconnect the TV from the mains to make this screen disappear. I mention this, as it may be relevant to the upgrading.

Whilst waiting for a reply (anyone?) I thought that I might as well try to update the server again.

Now, I on the settings/update page I see Version 1.20.1.3252, followed by a greyed out/inactive message “Checking for updates”

Help!

An update should only take a few minutes. If it’s taking longer than that, then something went wrong with the update. Uninstall PMS, download the latest from our website, and install manually.

Thanks, will try that…

In the future, just let it run, don’t watch it. When it’s done it will bring up the server without you clicking retry.

I left it for hours… nothing seemed to happen…

Normally it only takes a few minutes, less than 10.
Did you try @anon18523487 's suggestion?

Yes, but I am in Europe (different timezone) and was too late to start last night

Did it this morning. The update appears to be OK.

Later I will see if this has resolved the playback issues.

I have resolved the server upgrade issue - delete everything and reload.

It didn’t resolve the playback issues, though, so I will create a new thread.

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