I always thought some three lettered agency must have encouraged MS to buy Skype from its foreign owners for precisely that reason. The first 10 years at least MS did absolutely nothing with the company, as if it never really wanted to buy it.
>An industry source disclosed that America's supersecret National Security Agency (NSA) is offering "billions" to any firm which can offer reliable eavesdropping on Skype IM and voice traffic.
And then Snowden revelations confirmed that MS was intercepting Skype [2]:
>Microsoft has collaborated closely with US intelligence services to allow users' communications to be intercepted, including helping the National Security Agency to circumvent the company's own encryption, according to top-secret documents obtained by the Guardian.
>In July last year, nine months after Microsoft bought Skype, the NSA boasted that a new capability had tripled the amount of Skype video calls being collected through Prism;
[1] https://www.theregister.co.uk/2009/02/12/nsa_offers_billions...
[2] https://www.theguardian.com/world/2013/jul/11/microsoft-nsa-...
Skype looked like a solid investment at the time. Microsoft makes a lot of money from corporate clients so it's probably just another strategic acquisition that they did not know what to do with.
There is a difference between being compelled to spend billions on a company just to provide wiretapping for feds, and buying a company with a wildly successful product then being asked to handle wiretaps after the fact. One of those is ridiculous, the other is expected.
That was immediately before O365, and at that point BPOS/Exchange online was starting to get traction with some governments. Microsoft was also ramping their OCS/VoIP business.
Government is a huge market for O365, they were able to get ATOs and go conquer most states and federal agencies. They also bought a huge VoIP play, learned how to operationalize it, quickly spun it into a service component that serves >100M people.
Microsoft, like any company, isn’t good or evil, but will do whatever is in the company’s best interests, and they’ll act appropriately when their interests align with the government.