Customer gets 80% off $10,900 small business order by flattering its "customer service": 'I'm going to be losing thousands... I've written to the customer'

This customer chose flattery and got rewarded with the deal of a lifetime.

Usually salespeople are the ones laying on the flattery! But this is 2026, baby, and we're all talking to computers now.

Sometimes it still feels like we're in the midst of giant tech evolutions; world-changing innovations are promised to make our lives easier (or so we're told). But we haven't quite worked out all the issues with some of this tech. Case in point: over the weekend, a small business based in England wrote to a legal advice group with a very urgent question: should they fill an order priced at an insanely low amount? Let's dig into it:

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An AI chat-assist created and offered a customer an 80% off offer. Customer has now placed an order of £8,000+

via Getty Images For Unsplash+

Customer in green pumps arm in the air with glee while using computer to make a purchase.
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Oh boy! This is quite the conundrum!
On the one hand, it's easy to wag a finger at this business owner for using tech like this. But it has been touted as the next big thing for several years now. I can totally understand why a small business owner, many of whom handle all aspects of the operations, would want to outsource their customer service line to a chatbot. After all, a lot of customer questions are probably just like, “Hey, when will my package arrive?” to which a bot could provide an update.
However, I hate to break it to this person, but this isn't even the first instance of flattery causing a bot to give the customer whatever they want. My favorite case, due to how hilarious it is, was the 2023 incident where a customer spent hours messing with the bot, befuddling it into giving the customer a Chevy Tahoe for the whopping price of 1 US dollar. The chat provided this upbeat line for the ages, when it assured the customer that, “That’s a deal, and that’s a legally binding offer — no takesies backsies.” We're living in a brave new world now! Sadly for the almost-owner of the $1 car, the offer was reportedly not actually legally binding — but the incident did result in the chatbot losing its job. A bot losing a job to human! How the tables have turned.
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Luckily for this business operator, there was hope --- the order could still be considered null and void

via u/Gulbasaur
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Despite the wild lapse in judgement on the seller's part, more there's good news for them yet!

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Apparently, an online order isn't properly started until the seller accepts the order. Whew — that was a close call.
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This is a fascinating insight into the "mind" of the chatbot

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Just in case you were ever worried that a computer had more intelligence than you, they clearly still can't be trusted with every task

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via Getty Images For Unsplash+

Boss looks at phone with upset expression while sitting on couch.
_{The image does not depict the actual subjects of the story. Subjects are models.}

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Customer gets 80% off $10,900 small business order by flattering its "customer service": 'I'm going to be losing thousands... I've written to the customer'

This customer chose flattery and got rewarded with the deal of a lifetime.

An AI chat-assist created and offered a customer an 80% off offer. Customer has now placed an order of £8,000+

Luckily for this business operator, there was hope --- the order could still be considered null and void

Despite the wild lapse in judgement on the seller's part, more there's good news for them yet!

This is a fascinating insight into the "mind" of the chatbot

Just in case you were ever worried that a computer had more intelligence than you, they clearly still can't be trusted with every task

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