It'd also be nice if Microsoft shipped an easy-to-install plugin for IIS. I know, I know, they have this ... design ... where that handling is done by HTTP.SYS

It'd also be nice if Microsoft shipped an easy-to-install plugin for IIS. I know, I know, they have this ... design ... where that handling is done by HTTP.SYS in the kernel. But their technical decisions like that shouldn't impact how they deliver updates.