iOS made them pretty seamless and second-nature, and I can’t recall macOS ever ruining my day because of forced updates.
Maybe even 98 didn't have automatic updates, but I won't be surprised if 98SE already had this capability in some form.
For whatever reason it hasn't impacted me, and that's also having a laptop that only gets irregular use as well as my regular desktop, but I'll be more observant about this going forward.
Updates may have an "on startup" component to them. If you shut down, currently you are forced to install updates on the shutdown - this happens silently, without permission. But: It will just do the shutdown side - so that the next time you start, you're stuck there looking at the "startup part" where updates continue to install.
MS ought to fix this, either by changing how updates are installed in two phases, or to incorporate an automatic "shutdown/install"=>"start windows, run updates"=>"shut down" option.
Also they should let you just shut down the PC without having to install updates, especially if you don't have time to do so.
Currently, as a user, the only really safe thing to do would be to "update and restart" followed by a shutdown.
Since when?
With a little creativity, one can redecorate routine maintenance into a parade of glorious futurism. And of course that parade needs to be the first you experience on the computers return to conciousness.
Something similar happens on Surface updates.
See, turning on a computer is an explicit declaration that you want to use it. Windows updates ignores this declaration by taking that time to itself. It doesn't matter if I can defer the update by how many days if one day it will stop/delay me from using my computer when I want to. Almost no one outside of IT Administrators turns on computers solely for updates and maintenance.
Contrast that with Linux (Ubuntu distro in mind) where updates happen when the computer is shutting down. In contrast with turning your computer on, shutting down is a declaration that you no longer need your computer. That's the OS' cue to chime in and perform some routine maintenance.
I wonder how much of this is an architectural problem. The first time I remember being frustrated with this Windows behavior was in Vista. Someone correct me if I'm wrong but I seem to recall that 95, 98, and XP used to do updates on shut down. I know Vista isn't fondly remembered but, gee, did they deliberately make it so that it updates when you start your computer? Why couldn't a company who takes pride in backwards compatibility keep the old update behavior?
To wit, people make a big deal about how immediately can you use your computer (i.e., start-up times) but all your fancy-schmancy SSD + hyperthreading set-up is useless if Windows decides to update just before that one presentation you've spent weeks on. Updating on shut down is the user-friendly way.