i've definitely had it happen with some software so i can understand that.

i guess my frustration was coming from trying to support old outdated software that microsoft itself has stopped supporting. I had to keep xp machines alive during my last sysadmin job. I get not updating critical software there are a lot of solid applacations that dont work on win10+. but if it's just a box that you use for office work....i dunno just fucking update? I had to lower the minimum allowed ssl version so he could connect..