The need for safe, robust updates and dependency management is a pressing issue of our time, and it's a tough problem to solve. While the Debian systems I use have proved to be impressively reliable, in particular never causing any sort of failure with their unattended upgrades in many years, that is unfortunately the exception rather than the rule.

Windows updates in previous versions have caused more downtime for my businesses than any other sort of technical failure. Sometimes that has included data loss.

Package managers for various programming languages are another recurring source of danger. They often have debatable architecture with limited security and sandboxing functionality, sometimes allowing any rogue package's installation script to damage the system or cause data loss.

Apple's style with iOS updates seems to favour bricking old (or not so old) devices or crippling reductions in performance over data loss, but they still have a pretty bad track record, and they still rely on a ratchet-style update system where you can't easily go back if something does break.

I still find it baffling that in 2018 we retain so much emphasis on things like complicated filesystems, applications built on top of shared libraries and dynamic linking, and complicated plug-in based architectures. There are remarkably few good arguments for these fragile, risky, over-complicated strategies on modern systems. It's just momentum, but the collective cost to society from all the things that break as a result (and worse, break but can't then easily be fixed again) must be staggering.