> Bias towards authority in a way.
I think it's more "momentum". With a smaller company that affects a small number of users, the possibility of cutting your losses is quite feasible. On the other hand, with Outlook you've got your whole org using it, your servers running on it, your customers integrated with it, custom rules setup - a cut and run is just not simple.
Honestly though, I really don't get why rollback isn't more common for these larger pieces of software. Just some logic to detect multiple crashes, check if a rollback would break anything (i.e. dependencies) and then rollback. If you remove so much power from the average user in your OS, you ought to really have some amazing automated procedure for these scenarios.
I thought they also do limited roll-out as well? I think I remember the Windows anniversary bricked a bunch of machines in the limited roll-out and they just pushed it out anyway?
The complete lack of control as to when an update is performed is astounding - I know there are some settings to stop this, but apparently there are cases where that setting reverts back to auto or you need to switch it back on in order to manually update. I remember the last straw for MS and myself was accidentally clicking update just before a meeting whilst on very low battery, with no way to back out and no charger on hand. It didn't end well.
These days if something is "Windows only", it goes in a VM along with other software I don't trust.