Specifically, a dedicated server running Debian 12.
After a monthly sudo apt upgrade? (Is a monthly upgrade even necessary?)
Never? (unless there is a security update?)
Edit: I may be missing kernel upgrades. Those are probably good... I can't remember if I installed a LTS kernel. I imagine it would be unsecure to post an exact kernel version, however.
are you able to move production traffic onto a different webserver?
Like a load balanced situation? Unfortunately, no. The app supports only a single server setup.
Not necessarily load balanced I suppose but say spinning up a new server and switching over using dns or something could work too. Then you keep both running while the first one drains. If thats not possible idk probably put up a notice on your site and do it at like 2am on a weekday
I could do that, but the server reboots faster than DNS records can update.
Sure but its less disruptive
Less dread that it won't come back online.
The high availability dilemma. Hardly ever need that hot spare. If 0 downtime isn't a requirement w/e