I currently have Jenkins build an OS image every two weeks, just so our Deployment Server has an up to date image.
Ya, lots of tools have made this easier recently, but thinking about it, doesn't WSUS handle this?
I haven't been a Windows admin for a while, but I thought with WSUS it was install, join and forget while it did it's thing. Maybe it's been too long ...
It's a GPO that points your domains to the WSUS server. And I've only used Octopus to automate WU installs.
New updates do supersede others though, if they're marked to do so from Microsoft. That should cover at least some of the .Net point release updates and the like.
It is the second Tuesday of the month, not every Tuesday. They've only broken that pattern a handful of times in the years that they have been doing it when an "emergency" patch was required.
>It is the second Tuesday of the month
that's exactly what "every patch tuesday" means (notice the "patch" adjective).
It's one reason I liked service packs, new service pack comes out, generate a new install image.