The only real issue I have with them using this method is whether or not Microsoft will then have a legal obligation to report the downloading of any software which could in the future become illegal, I'm thinking packages like Tor whcih can be used to directly contravene law inforcement efforts regarding things like child pornography.
I'm not saying I support it, but what I am saying is I would feel very uncomfortable knowing that my computer company would instantly inform the police if I downloaded "suspicious software" regardless of my purpose, but that's just a glimpse of where I see their next move being after the idiocy of ACTA and all the recent changes to privacy laws.
Furthermore, the intent of Tor is the empowerment of dissidents under oppressive regimes.
I imagine there's little likelihood that this capability could have impeded the Arab Spring since Microsoft wouldn't have cooperated, but it seems like this would create a vulnerability for Microsoft doing business in China. If China decided they wanted to more actively monitor software intended to bypass firewalls and circumvent censorship policies, I wonder how effectively could Microsoft could resist.
Tor's a bad example, Tor does not hide the fact you are using it usually. It simply hides what you are doing with it. Although I believe there is some sort of proxying system.
I'm not saying I support it, but what I am saying is I would feel very uncomfortable knowing that my computer company would instantly inform the police if I downloaded "suspicious software" regardless of my purpose, but that's just a glimpse of where I see their next move being after the idiocy of ACTA and all the recent changes to privacy laws.