Jun 21, 2026 · 20 min · 10 segments
A Canadian tribunal ordered Air Canada to pay 812 dollars and 2 cents after its booking chatbot invented a fare discount that did not exist, and the airline's argument that the chatbot was a separate…
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So I want you to imagine a scenario.
You're running a business, right? And you hire a brand new employee to handle your customer service.
Okay, pretty standard.
Right.
And this employee is enthusiastically talking to a customer.
But out of nowhere, they just confidently invent a fake discount.
Oh, no.
Yeah, they completely make it up on the spot.
So the customer, understandably, tries to use that discount.
And when you refuse to honor it, you get sued for the cost.
Which makes sense from the customer's perspective.
Right.
But now picture yourself standing in front of a judge and your official literal legal defense is, well, your honor, that employee is actually a separate legal entity.
So we aren't responsible for what they say.
I mean, you would be laughed entirely out of the courtroom.
No judge is going to entertain that for a second.
Exactly.
But that is exactly what Air Canada.
I mean, a massive global airline tried to argue in a Canadian tribunal regarding their own AI chatbot.
It's just why? It literally tried to claim their automated chatbot was responsible for its own actions independently of the airline.
Which, you know, gives us a really fascinating and frankly kind of terrifying glimpse into how confused some organizations actually are about the technology they're deploying.
Yeah, it really does.
And that confusion is basically the core of our agenda for today.
We have prepared an exploration of a recent Forbes roundup titled...
Five big AI failures that show what can go wrong.
So I want you to imagine a scenario.
You're running a business, right? And you hire a brand new employee to handle your customer service.
Okay, pretty standard.
Right.
And this employee is enthusiastically talking to a customer.
But out of nowhere, they just confidently invent a fake discount.
Oh, no.
Yeah, they completely make it up on the spot.
So the customer, understandably, tries to use that discount.
And when you refuse to honor it, you get sued for the cost.
Which makes sense from the customer's perspective.
Right.
But now picture yourself standing in front of a judge and your official literal legal defense is, well, your honor, that employee is actually a separate legal entity.
So we aren't responsible for what they say.
I mean, you would be laughed entirely out of the courtroom.
No judge is going to entertain that for a second.
Exactly.
But that is exactly what Air Canada.
I mean, a massive global airline tried to argue in a Canadian tribunal regarding their own AI chatbot.
It's just why? It literally tried to claim their automated chatbot was responsible for its own actions independently of the airline.
Which, you know, gives us a really fascinating and frankly kind of terrifying glimpse into how confused some organizations actually are about the technology they're deploying.
Yeah, it really does.
And that confusion is basically the core of our agenda for today.
We have prepared an exploration of a recent Forbes roundup titled...
Five big AI failures that show what can go wrong.
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