This is what so many non-software people trying to make decisions on software fail to realize - every constraint added increases the complexity of software by an order of magnitude.
Me: FYI, in scenario xyz, I updated the documentation to do abc. It seems like the best balance of complication and doing the right thing, especially considering it will almost never come up.
Boss: why does it even matter what it does? It will come up maybe once per year. Oh, and it should do <this other really specific and complicated thing> instead, so do that.
Me: sigh....