My take away from this is that Air Canada would rather fight a customer in court than suffer a few hundred dollar refund as the cost of figuring out they have a flaw in the consistency of their system. (And in the face of an extreme unlikelihood of winning against prevailing common sense, too.)
Because if they win this, they get to keep the good and ignore the bad.
They get to automate a large chunk of their customer service and when the chatbot does something really stupid they can tap on the sign that says "We're not legally bound by our chatbot"
But anything output by your chatbot is no different from something you put onto a billboard, or into a flyer or any other communication. The idea that a discount offered by a chatbot is not valid in the same way as one written on a coupon is nonsensical.
Maybe they were thinking, if we spend a bit more money on lawyers, we can try this crapshoot.
i imagine that paying out would set a precedent or provide future discoverable evidence that they want to avoid. fighting (and winning) might have allowed them to continue their chat bot system without needing to change anything.
