I don't really expect this to go anywhere until Python 4 (*maybe* 3.9 after a deprecation period), but it seems like it would have been a good idea to make NotImplementedType's __bool__ explicitly raise a TypeError (rather than leaving it unset, so NotImplemented evaluates as truthy). Any correct use of NotImplemented per its documented intent would never evaluate it in a boolean context, but rather use identity testing, e.g. back in the Py2 days, the canonical __ne__ delegation to __eq__ for any class should be implemented as something like:

    def __ne__(self, other):
        equal = self.__eq__(other)
        return equal if equal is NotImplemented else not equal

Problem is, a lot of folks would make mistakes like doing:

    def __ne__(self, other):
        return not self.__eq__(other)

which silently returns False when __eq__ returns NotImplemented, rather than returning NotImplemented and allowing Python to check the mirrored operation. Similar issues arise when hand-writing the other rich comparison operators in terms of each other.

It seems like, given NotImplemented is a sentinel value that should never be evaluated in a boolean context, at some point it might be nice to explicitly prevent it, to avoid errors like this.

Main argument against it is that I don't know of any other type/object that explicitly makes itself unevaluable in a boolean context, so this could be surprising if someone uses NotImplemented as a sentinel unrelated to its intended purpose and suffers the problem.