Alternative: he is using software you’re familiar with to do something very specific that it can technically do but wasn’t designed for. Someone else hacked it together for him but now that system has broken down. He doesn’t know the names of any part of it, only that it used to do the thing and now it doesn’t. Also he is on the phone and you can’t see his screen.

There are five other people with equally obtuse problems waiting on five other phones, becoming increasingly frustrated and irrational the longer it takes to solve this one. There is no call waiting and the people have nothing else to do, so each phone never stops ringing until answered.