People often assume a very benign, civilized environment for AI. In ordinary life, human beings (on the internet or off) take an adversarial approach to other people modeling the logical framework behind an utterance. They either subvert it for amusement (trolling or comedy) or profit (politics, propaganda, sales), and a tremendous amount of effort goes into it, much of which is very effective.

As people have observed, it can be very easy to convince a human that a machine is intelligent, as with ELIZA. But if you violate the presumptions of trust that a machine is designed with, it's going to be surprisingly vulnerable. To be superior to humans, a machine would have to be able to fend off an intelligent person trying to undermine it, not just work when it is spoon-fed.