The thing is (and maybe this is what parent meant by non-determinism, in which case I agree it's a problem), in this brave new technological use-case, the space of possible interactions dwarfs anything machines have dealt with before. And it seems inevitable that the space of possible misunderstandings which can arise during these interactions will balloon similarly. Simply because of the radically different nature of our AI interlocutor, compared to what (actually, who) we're used to interacting with in this world of representation and human life situations.