When Canadian Jake Moffat’s grandmother died in late 2022, he was at least comforted by an assurance from Air Canada’s helpful AI chatbot that he could get a compassionate rebate for his airfare after the event. That was a nice thing for an airline to do, made all the easier with the help of a friendly AI, and it eased the sting of an unexpected expense. There was just one problem. Air Canada never had a policy of rebating airfares after the event on compassionate grounds. Passengers were required to obtain the compassionate discount before the event, not afterwards. Air Canada duly refused the post-event rebate, and Jake Moffat took them to court. He won the case, and Air Canada won a big black ...