HumanPrint: How to Use AI Without Losing Yourself
Jun 25, 2026 · 12 min · 9 segments
## **What this episode is about** ## In 2024, Air Canada's chatbot gave a customer the wrong information about bereavement fares — and when he filed a claim, the airline tried to argue the chatbot…
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Christine WhitmarshHostSo in February 2024, a man named Jake Moffitt was booking a flight to go to his grandmother's funeral.
He found the customer service chat bot and asked about bereavement fares.
The bot told him he could apply for a discounted bereavement rate retroactively after he'd traveled, as long as he submitted the request within 90 days.
So he went ahead, he traveled, he submitted the claim, but then Air Canada was like, sorry, yeah, no.
So Moffitt took his case to British Columbia's Civil Revolution Tribunal, and here's where it gets interesting.
It was like a separate entity, and the airline could not be held responsible for what it said.
Air Canada was responsible for everything on its website, whether it came from a static page or a chat bot.
So Moffitt was awarded exactly $650.88. Now, obviously, $650 is not a huge amount of money in the grand scheme of airline litigation, but that ruling is a big deal because what the tribunal was really saying is you don't get to outsource the judgment and keep the authority.
You built the system, you deployed it, you put your name on it, whatever it says, you said.
And I want to be clear, what happened to Air Canada isn't really a story about a company trying to cheat anyone.
The story was more about what happens when a company delegates a judgment call.
In this case, what fair policy applies to this specific customer in this specific situation.
So the judgment call to the system that really isn't equipped to make it.
It just, well, it could generate an answer, but what it couldn't do was evaluate whether that answer was correct.
And that gap, the gap between generating an answer and being able to evaluate whether it's correct, that's what we're gonna talk about today.
So in February 2024, a man named Jake Moffitt was booking a flight to go to his grandmother's funeral.
He found the customer service chat bot and asked about bereavement fares.
The bot told him he could apply for a discounted bereavement rate retroactively after he'd traveled, as long as he submitted the request within 90 days.
So he went ahead, he traveled, he submitted the claim, but then Air Canada was like, sorry, yeah, no.
So Moffitt took his case to British Columbia's Civil Revolution Tribunal, and here's where it gets interesting.
It was like a separate entity, and the airline could not be held responsible for what it said.
Air Canada was responsible for everything on its website, whether it came from a static page or a chat bot.
So Moffitt was awarded exactly $650.88. Now, obviously, $650 is not a huge amount of money in the grand scheme of airline litigation, but that ruling is a big deal because what the tribunal was really saying is you don't get to outsource the judgment and keep the authority.
You built the system, you deployed it, you put your name on it, whatever it says, you said.
And I want to be clear, what happened to Air Canada isn't really a story about a company trying to cheat anyone.
The story was more about what happens when a company delegates a judgment call.
In this case, what fair policy applies to this specific customer in this specific situation.
So the judgment call to the system that really isn't equipped to make it.
It just, well, it could generate an answer, but what it couldn't do was evaluate whether that answer was correct.
And that gap, the gap between generating an answer and being able to evaluate whether it's correct, that's what we're gonna talk about today.
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