Re: 20th century
It's a bit difficult to test an OS deployed on hundred of millions of machines with very different software configuration on them.
I updated my LAN machines - and but for an issue with Delphi (which tries to write a font from its resources to %temp%, and then try to add and remove it dinamically), I didn't find any issue.
But because those patches changed the way some font APIs work, I guess other software may be impacted. And if it happens in some drivers loaded at startup (it could be a video driver or printer driver, maybe), some really bad can happen.
Sometimes the large number of hardware devices and software Windows supports may become a double edged sword - it's impossible to test everything.
But it's silly to blame the support technician who asked for details - you really need a "sample" from an affected machine to understand what's wrong and fix it - until you have it, there's little you can do if on everything else you tested with it works...
For example on one of my machines I have a conflict between Asus USB 3.0 Boost software and the Epson Perfection 2400 Photo scanner driver, you really need them both to see the issue.