How often should you reboot a production webserver?
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.
Some packages managers, including Debian APT, create a /var/run/reboot-required file when an upgrade requires a reboot (like a kernel upgrade). If you have other reasons to reboot, it's up to you to find the best interval between reboots.