Used to work IT at a university during the transition time from Win 3.11 to Win95. The amount of emotional hand-holding (not even so much technical support) involved in getting the admin staff through the process was unbelievable to me at my young age. Now I understand, but back then I was expecting way more “this doesn’t work” or “I can’t find this program” and way less “I don’t know how I’m going to do my job.”