Alerts that I need to Reboot at every reeboot

I have a fresh install of Lubuntu 20.04 on an Intel NUC hosting my Nextcloud server.
Ever since a resent update I have experienced multiple issues, of which I will describe one in this post.
I am alerted by a a popup window telling my my system needs to reboot. I need to click OK 4 times before the window closes. At this point I initiate a reboot, and am greeted with the same popup after the reboot.
I ran sudo apt update, and it tells me the system is up to date.
If I try to run update in Discover it tells me that it is unable to authenticate.
The following is system information and syslog: