Related is William Gibson's idea of "the Jackpot", or a "multicausal appocalypse", where a large catastrophe is caused not by a single major factor but by several smaller ones accumulating and interacting over time. Gibson talks about it in https://vimeo.com/116132074.
A good book in this space is Normal Accidents[0], which describes (among others) the impressive cumulative failure that caused the Three Mile Island incident. Fascinating read and applicable to software systems as well.
If this is the kind of thing you find interesting, you should also read How Complex Systems Fail (http://web.mit.edu/2.75/resources/random/How%20Complex%20Sys...).