[hn_throwaway_99]

Couldn't agree with this more. While I think it's important to have good documentation, it is nearly always a very bad idea to rely on that documentation being 100% correct. Businesses simply have way too many moving parts to assume the state of the world is always up-to-date in the documentation.

You also highlight a very good point. Things like security software should "break loudly", i.e. beyond just sending alerts (which can be ignored), there should be some explicitly "painful" steps that occur if the security system is in a broken state for long.