I have a handful of old machines I use for Tribblix testing. One of them was originally installed with Tribblix m8 (that's a long long time ago) and has been upgraded through every release since. (That's about 40 upgrades, I reckon.)
Something was bound to break eventually. In the recent past, it managed to lose the eventfd and timerfd devices. Which would have gone unnoticed, but getaddrinfo() stopped working, which broke curl, which broke the next upgrade as it couldn't download anything.