[vkou]

>How is this different from me getting one of my friends to work at Air Canada and promise me a billion dollars to cancel my flight?

There is a common misconception about law that software engineers have. Code is not law. Law is not code. Just because something that looks like a function exists, you can't just plug in any inputs and expect it to have a consistent outcome.

The difference between these two cases is that even if a chat bot promised that, the judge would throw it out, because it's not reasonable. Also, the firm would have a great case against at least the CS rep for this collusion.

If your friend of a CS agent promised you a bereavement refund (As the chatbot did), even though it went against company policy, you'd have good odds of winning that case. Because the judge would find it reasonable of you to believe and expect that after speaking to a CS rep, that such a policy would actually get honored. (And the worst that would happen to the CS rep would be termination.)