Earlier quoted context omitted.
The way around this is to update your deployment images from time to time. It's one reason I liked service packs, new service pack comes out, generate a new install image.
Right, and that takes care of the 'big ones', but you still have tons of other minor updates that are released every Patch Tuesday. 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 ...