I should add here that the "antiquation" case is the one that has caused the most observed grief in my career. The forces causing failure are coming from outside the code/business (dependence on an outside vendor), and sometimes collide with forward momentum of other parts of the code (i.e. that graph library will never, ever work with Java 7, to name an example). These become life-or-death situations, and the tendrils of the product dependency are often deeply integrated. It might be easier to rewrite than to fix.
Also, this case can impact not just products, but organizations. You can still find teams dependent on an antique commercial version control system or IDE that greatly slows down or even stops work. I've tech-led jumps to new version control systems a few times, and it's always riddled with anxiety, strain, and management angst. (And it always makes the team far happier and more productive!)