what’s the most unhinged thing you’ve seen a company do with AI?

March 15, 2026
what’s the most unhinged thing you’ve seen a company do with AI?

Here's something that’ll make you do a double-take — an AI overhaul gone totally off the rails at a mid-size SaaS company. According to Reddit user /u/kubrador, about six months ago, their leadership decided to go all-in on AI after their CEO returned from a conference raving about automation. The first move? Replacing a 12-person support team with a chatbot. Sounds promising, right? Well, this bot was trained on outdated help docs, leading it to direct customers to non-existent features and broken links. But here’s where it gets wild — its default answer for anything it couldn’t handle was 'Have you tried restarting your device?' — even when asked for refunds! As /u/kubrador reports, support scores plummeted, churn doubled, and some customers posted hilarious viral screenshots. Yet, leadership still calls it a win because support costs dropped 80%. So, what’s the real price of 'AI success'? Probably not what they expected. And honestly, this is a cautionary tale — sometimes, AI can be unhinged in all the wrong ways.

i’ll go first. i work at a mid-size SaaS company and about 6 months ago leadership decided we were going to be an AI-first company because the CEO went to a conference and came back speaking in tongues about automation and efficiency.

first thing they did was replace our entire 12 person customer support team with an AI chatbot. they laid off all 12 people on a friday and chatbot went live on monday.

the chatbot was trained on our help docs which sounds fine except our help docs haven’t been updated since 2023 and half of them reference features we don’t offer anymore. so from day one this thing was confidently directing customers to buttons that don’t exist and pages that 404.

but the real problem is the fallback response bc whoever set it up made the default response for anything the bot can’t answer “have you tried restarting your device?” everything and every question. someone literally asked for a refund and the bot told them to restart their computer.

it’s been 6 months and our CSAT score has dropped 40% so does our churn rate doubled. we’ve had 3 customers post screenshots on twitter of the bot giving unhinged responses and one of them went viral lol

the best part is leadership still calls it a success because we reduced support costs by 80%. yeah we also reduced our customers by 30% but nobody’s put that in the quarterly deck yet. the CEO still opens every all-hands by saying our AI transformation is ahead of schedule. ahead of schedule toward what like bankruptcy pls

what’s the worst AI implementation you’ve seen?

submitted by /u/kubrador
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Audio Transcript

i’ll go first. i work at a mid-size SaaS company and about 6 months ago leadership decided we were going to be an AI-first company because the CEO went to a conference and came back speaking in tongues about automation and efficiency.

first thing they did was replace our entire 12 person customer support team with an AI chatbot. they laid off all 12 people on a friday and chatbot went live on monday.

the chatbot was trained on our help docs which sounds fine except our help docs haven’t been updated since 2023 and half of them reference features we don’t offer anymore. so from day one this thing was confidently directing customers to buttons that don’t exist and pages that 404.

but the real problem is the fallback response bc whoever set it up made the default response for anything the bot can’t answer “have you tried restarting your device?” everything and every question. someone literally asked for a refund and the bot told them to restart their computer.

it’s been 6 months and our CSAT score has dropped 40% so does our churn rate doubled. we’ve had 3 customers post screenshots on twitter of the bot giving unhinged responses and one of them went viral lol

the best part is leadership still calls it a success because we reduced support costs by 80%. yeah we also reduced our customers by 30% but nobody’s put that in the quarterly deck yet. the CEO still opens every all-hands by saying our AI transformation is ahead of schedule. ahead of schedule toward what like bankruptcy pls

what’s the worst AI implementation you’ve seen?

submitted by /u/kubrador
[link] [comments]
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