Microsoft engineer here. I would assert we want people upgraded more than anybody else on the planet. Our extended support contracts were designed to be cost prohibitive to encourage this point and were nowhere near a money-making venture. The engineering matrix (cost) for a fix across old versions was insane: IE6, 7, 8, 10, 10 touch; 32bit, 64bit, ARM; Windows XP, Vista, 7, 8, Server, Mobile, etc.; 5.5/7/8/9/10 browser document modes; etc. A "single" fix often meant weeks of porting work for engineers after the initial fix was written.

Note that the Jan 12, 2016 End of Support date means there are no more security updates, non-security updates, free or paid assisted support options, or online technical content updates. https://support.microsoft.com/en-us/lifecycle#gp/Microsoft-I...