Not all bad
Assuming the upgrades work (and they usually don't bork a machine these days) I think this is a good thing from the perspective that it forces normalisation of upgrading. This means admins will practice, finally implement proper automation, and stop falling behind. It also means the boss will have to listen.
Yes, it's a pain. But if you concentrate on the good aspects of this it's not quite as bad as it looks on first sight.
Biting the hand that feeds IT
