https://www.theguardian.com/world/2013/jul/11/microsoft-nsa-...
https://www.theguardian.com/world/2013/jul/11/microsoft-nsa-...
If the NSA wanted to intercept or forge Skype conversations and had access to Microsoft to do so, they would have a much easier time doing so on the server side.
Despite the tone of the article, there is nothing to suggest that anyone at Microsoft was doing anything more than creating the most cost-effective method to handle requests it was coerced to fulfill.
Alternatives to "collaboration":
1. Deny all requests. Get held in contempt of court. Go out of business.
2. Have dedicated staff to manually dig through every data repository to handle each request in a bespoke manner.
In many other cases technology transfer, joint management/ownership, market access, political favors, lucrative contracts, direct infiltration, nationalist instincts, and bribery are all reasons for Microsoft to work with the NSA and other intelligence agencies. They were caught providing backdoor access along with Google to all outlook (and gmail) emails to the FBI, for example.