Meh, Boeing is huge and I am a small specialized gear. In some ways I was happy I had one server that just balked at the install as it sat long enough to get security settings pushed before I ran the updates. Also they are a picky enough customer that where the driver did install but has a 'do you want to run this' pop up when trying to log into the server they want that properly gone as well so I had enough of a hammer to make the guys who are supposed to make sure this kind of thing does not get into production releases to wake up.
It was a nice change of pace for a few days what was truly annoying were the totally useless error messages from the installer, from windows, from the scripting logs, and nonexistent logging in the event logs. Do any of them say anything remotely related to 'untrusted cert, stopping now'. Nope, Sucks to be you doesn't it.