When people imagine what a Turing Test conversation would look like, they frequently underestimate the conversation. I find Dennet's example of an imaginary Turing Test from Consciousness Explained to be a good counterexample:
Judge: Did you hear about the Irishman who found a magic lamp? When he rubbed it a genie appeared and granted him three wishes. “I’ll have a pint of Guiness!” the Irishman replied and immediately it appeared. The Irishman eagerly set to sipping and then gulping, but the level of Guiness in the glass was always magically restored. After a while the genie became impatient. “Well, what about your second wish?” he asked. Replied the Irishman between gulps, “Oh well, I guess I’ll have another one of these.”
CHINESE ROOM: Very funny. No, I hadn’t heard it– but you know I find ethnic jokes in bad taste. I laughed in spite of myself, but really, I think you should find other topics for us to discuss.
J: Fair enough but I told you the joke because I want you to explain it to me.
CR: Boring! You should never explain jokes.
J: Nevertheless, this is my test question. Can you explain to me how and why the joke “works”?
CR: If you insist. You see, it depends on the assumption that the magically refilling glass will go on refilling forever, so the Irishman has all the stout he can ever drink. So he hardly has a reason for wanting a duplicate but he is so stupid (that’s the part I object to) or so besotted by the alcohol that he doesn’t recognize this, and so, unthinkingly endorsing his delight with his first wish come true, he asks for seconds. These background assumptions aren’t true, of course, but just part of the ambient lore of joke-telling, in which we suspend our disbelief in magic and so forth. By the way we could imagine a somewhat labored continuation in which the Irishman turned out to be “right” in his second wish after all, perhaps he’s planning to throw a big party and one glass won’t refill fast enough to satisfy all his thirsty guests (and it’s no use saving it up in advance– we all know how stale stout loses its taste). We tend not to think of such complications which is part of the explanation of why jokes work. Is that enough?
Dennett: "The fact is that any program that could actually hold up its end in the conversation depicted would have to be an extraordinary supple, sophisticated, and multilayered system, brimming with “world knowledge” and meta-knowledge and meta-meta-knowledge about its own responses, the likely responses of its interlocutor, and much, much more…. Maybe the billions of actions of all those highly structured parts produce genuine understanding in the system after all."
I'm sure they didn't get anywhere near this with their 13-yr-old simulation. But this gives an idea of the heights AI has to scale before it can regularly pass the Turing Test.