It's pretty ironic to have problems with audio not recognizing headphones... on WINDOWS.
Multi-trillion (10^12) dollar company, btw.
(Both laptops are reasonably new.)
Setting up new laptops at work is similarly annoying even with every trick we keep up our sleeves. Naturally Microsoft does bypass some portion of that BS if you happen to be connecting to to an AD or Azure account because they don't want to completely piss off their core userbase