Two things irritate the shit out of me. First, the "wait while we report this to Microsoft" dialog comes up and implies its transmitting immediately, even for trivial issues, without asking for your confirmation and without indicating what, exactly, it's sending. (I guess that's the point of this meme. But a yes/no prompt would be nice?)
Second is that it does it for absolutely trivial things. Like, the crap point of sale software we use at work can be easily and repeatably made to go into an infinite loop state if you know how to do it, and you have to kill it via Task Manager or whatever. But then this stupid "we're reporting this to Microsoft" dialog comes up. Oh yeah? You're reporting it, are you? What the fuck is Microsoft going to do about it, exactly? Send a helicopter so Bill Gates himself can rappel down and bust through the skylight at the office of this two-bit POS software company, guns blazing, hack into their mainframe, and fix their code?
What a useless thing to show the user.