> Changing the boolean evaluation in this case is actually making the mess even worse. I don't see how that's possible. Assuming that using "if x:" is wrong (f

> Changing the boolean evaluation in this case is actually making the mess even worse. I don't see how that's possible. Assuming that using "if x:" is wrong (for some value of wrong) here, this issue only affects people who are using it wrong anyway. So all fixing it does is make the consequences of doing bad stuff less painful. I can't see how that would hurt things. Even if you think "if x:" should never be used on non-booleans, leaving land mines in there to hurt newbie (or lazy) developers is not a good way to enforce that convention. It just creates pain. Or more simply: whether having boolean coercion for conditionals is a good idea is orthogonal to how such a coercion should work. It sounds like Python should deprecate truthiness altogether. But it hasn't, so in the meantime truthiness should work in a reasonable way, and falsy midnights are not reasonable. Pointing out that it's documented is unhelpful (the documentation is just the wrongness restated in a different language), as is "That test does not mean what you are intending it to mean" (Tautological. The OP was suggesting changing what the test means).