Picture this. A man visits Air Canada’s website after his grandmother died to book a flight from Vancouver to Toronto. He uses the airline’s bereavement fares. He asks the site’s chatbot about the reduced fares. It tells him: he can book travel immediately; that he can retroactively apply to get a partial refund. What a compassionate chatbot that is!

But here’s where things get strange. Shortly after, as Gail J. Cohen reports, the airline denies the man’s claim, saying he did not follow the proper procedures to request the discounted fare.