2009 - NSA offering 'billions' for Skype eavesdrop solution [1]
2011 - Microsoft buys Skype for $8.5 billion. Why, exactly? [2]
2012 - Skype replaces P2P supernodes with Linux boxes hosted by Microsoft [3]
2013 - Microsoft handed the NSA access to encrypted messages Subhead: Skype worked to enable Prism collection of video calls [4]
1. https://www.theregister.co.uk/2009/02/12/nsa_offers_billions...
2. https://www.wired.com/2011/05/microsoft-buys-skype-2/
3. https://arstechnica.com/information-technology/2012/05/skype...
4. https://www.theguardian.com/world/2013/jul/11/microsoft-nsa-...
Skype used to have a ton of issues with certain features requiring both parties be online. For instance, since it was peer-to-peer, sharing pictures and/or file attachments would fail if you weren't online at the same time as the other person, and of course, you were subject to the their upload speed for you (and each other person in a chatroom) to download it.
https://en.wikipedia.org/wiki/Skype_Technologies#P2P_licensi...