For maybe a few years now my Plex server will notify me of an update, but it never finishes the update
this is the message that stays forever
The server “Acer Plex” is installing an update
Grab a cup of tea. This may take a couple of minutes.

For maybe a few years now my Plex server will notify me of an update, but it never finishes the update
this is the message that stays forever
The server “Acer Plex” is installing an update
Grab a cup of tea. This may take a couple of minutes.

which one are you on currently? if you are on something super old it might not update. I would just download it manually and run the installer.
Version 1.13.8.5395
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