For what it's worth, I have trouble seeing this as anything but a bug. I understand the motivation of trying to catch user errors, but in doing so, you're breaking with the behavior of every other option parsing library that I'm aware of, in favor of an arbitrary heuristic that sometimes guesses wrong. That's not the kind of behavior I expect from my Python libraries; I want them to do what I ask them to, not try to guess what I probably meant.