Wait, your work laptop only lets you perform administrative tasks on the local machine if it can connect over the internet to corporate, and that includes being unable to modify certain network settings without first having a working network uplink? That sounds like something that was always guaranteed to break in an awkward way, not a particular problem with the DNS server that you happened to be using that day.
Yeah exactly! Just once (every x hours) but always required for anything sudo, and it's really buggy, too. Restarting stuff, installing some stuff with brew sucks especially, even updating some apps all require sudo. I've resulted to stack the prompts in my lower right corner until I have to do to