The same way you test any system - you find a sampling of test subjects, have them interact with the system and then evaluate those interactions. No system is guaranteed to never fail, it's all about degree of effectiveness and resilience.

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.

temperature 0 and 10,000,000 mischievous prompts