• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 

2

Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'

3

Meet a 21-year-old community college student who's going to China as the first American woman welder in the trades Olympics

1

Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 

2

Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'

3

Meet a 21-year-old community college student who's going to China as the first American woman welder in the trades Olympics
TechAI

A customer support AI went rogue—and it’s a warning for every company considering replacing workers with automation 

Sharon Goldman
By
Sharon Goldman
Sharon Goldman
AI Reporter
Down Arrow Button Icon
Sharon Goldman
By
Sharon Goldman
Sharon Goldman
AI Reporter
Down Arrow Button Icon
April 19, 2025, 8:00 AM ET
Getty Images

AI startup Anysphere has been riding high over the past two months, thanks to the skyrocketing popularity of its AI-powered software coding assistant, Cursor. The company, which was eyed for acquisition by OpenAI and has reportedly been in funding talks for a valuation of nearly $10 billion, hit $100 million in annual revenue since Cursor launched in 2023. But this week, Cursor went viral for all the wrong reasons: Its customer support AI went rogue, triggering a wave of cancellations and serving as a cautionary tale for other startups betting big on automation.

Recommended Video

It all started earlier this week, when a Cursor user posted on Hacker News and Reddit that customers had started getting mysteriously logged out when switching between devices. Confused, they contacted customer support, only to be told in an emailed response from “Sam” that the logouts were “expected behavior” under a new login policy. 

But there was no new policy—and no human behind the support email. The response had come from an AI-powered bot and the new policy was a “hallucination,” an entirely made-up explanation. 

The news spread rapidly in the developer community, leading to reports of users cancelling their subscriptions, while some complained about the lack of transparency. Cofounder Michael Truell finally posted on Reddit acknowledging the “incorrect response from a front-line AI support bot” and said it was investigating a bug that logged users out. “Apologies about the confusion here,” he wrote. 

But the response seemed like too little, too late—with the AI support bot hallucination leaving Cursor seemingly flat-footed. Fortune contacted Cursor for comment but did not receive a response. 

LinkedIn tech influencers are already using the example to warn other startups. “Cursor…just landed itself in a viral hot mess because it failed to tell users that its customer support “person” Sam is actually a hallucinating bot,” Cassie Kozyrkov, an AI advisor and Google’s former chief decision scientist, wrote in a LinkedIn post. “This mess could have been avoided if leaders understood that (1) AI makes mistakes, (2) AI can’t take responsibility for those mistakes (so it falls on you), and (3) users hate being tricked by a machine posing as a human,” she continued. 

While customer support has been considered a top use case for generative AI ever since OpenAI’s ChatGPT chatbot debuted in 2022, it is also fraught with risks, said Sanketh Balakrishna, an engineering manager at cloud security platform Datadog. Customer support requires a level of empathy, nuance, and problem-solving that AI alone currently struggles to deliver, he explained. “I would be cautious about depending entirely on an AI bot for addressing user issues,” he told Fortune by email. “If I know that the only support available was an AI system prone to occasional errors, it could undermine confidence and impact our ability to resolve problems effectively.” 

Amiram Shachar, CEO of security company Upwind, pointed out that this isn’t the first time hallucinating AI chatbots have made headlines. Air Canada’s AI chatbot told customers about a refund policy that didn’t exist, while payment service provider Klarna did an about-face on replacing all of its human customer service agents in February after complaints about its AI chatbot’s hallucinations. “Fundamentally, AI doesn’t understand your users or how they work,” he told Fortune by email. “Without the right constraints, it will ‘confidently’ fill in gaps with unsupported information.” For highly-technical users like Cursor’s developer customers, “there’s no margin for sloppy explanations.” 

One Cursor customer agreed: Melanie Warrick, co-founder of healthcare AI startup Fight Health Insurance, said she found that Cursor offers great support to developers, but also growing friction. “Last week, I hit a persistent agent error (“try again in a few minutes”) that never cleared,” she told Fortune by email. “Support gave the same canned, likely AI-generated response multiple times, without resolving the issue. I stopped using it — the agent wasn’t working, and chasing a fix was too disruptive.” 

For now, headline-making hallucinations have been limited to AI chatbots, but experts warn that as more enterprises adopt autonomous AI agents, the consequences for companies could be far worse. That’s particularly true in highly-regulated industries like healthcare, financial, or legal—such as a wire transfer that the counterparty refuses to return or a miscommunication that impacts patient health. 

The prospect of hallucinating agents “is a critical piece of the puzzle that our industry absolutely must solve before agentic AI can actually achieve widespread adoption,” said Amr Awadallah, CEO and cofounder of Vectara, a company that offers tools to help businesses reduce risks from AI hallucinations. 

While not the fault of an autonomous AI agent completing tasks, Cursor’s snafu is “exactly the worst-case scenario” that is slowing adoption of agentic AI, he told Fortune by email. Businesses love the idea of autonomous AI agents that can take action on their own, thereby saving on labor costs. But, he said, companies are also “extremely worried that one incident of hallucination, paired with a disruptive or even destructive action by the AI, could deeply impact their business.” 

Join our exclusive webinar on May 28, featuring tech leaders from Orange, Mars, Reckitt, and Saint-Gobain. Apply to attend and receive Fortune’s editorial takeaways.
About the Author
Sharon Goldman
By Sharon GoldmanAI Reporter
LinkedIn icon

Sharon Goldman is an AI reporter at Fortune and co-authors Eye on AI, Fortune’s flagship AI newsletter. She has written about digital and enterprise tech for over a decade.

See full bioRight Arrow Button Icon

Latest in Tech

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Tech

Sheryl Sandberg tells Gen Z the 10-year career plan is dead as AI wipes out entry-level jobs: ‘Don’t script your career when the future is uncertain’
Successcareer
Sheryl Sandberg tells Gen Z the 10-year career plan is dead as AI wipes out entry-level jobs: ‘Don’t script your career when the future is uncertain’
By Orianna Rosa RoyleMay 21, 2026
58 minutes ago
Microsoft lost its way in the AI race. Can Copilot get it back on course?
MagazineMicrosoft
Microsoft lost its way in the AI race. Can Copilot get it back on course?
By Jeremy KahnMay 21, 2026
58 minutes ago
Samuel Corum/Getty Images
Big TechSpaceX
Elon Musk’s proposed pay package in SpaceX’s IPO filing reveals what the company actually is: a $1 trillion monster built to colonize Mars
By Eva RoytburgMay 20, 2026
8 hours ago
elon
SuccessIPOs
SpaceX IPO targets $28.5 trillion total addressable market, mission to ‘make life multiplanetary’ and understand ‘true nature of the universe’
By Nick LichtenbergMay 20, 2026
10 hours ago
Jensen Huang, chief executive officer of Nvidia
AINvidia
Nvidia tells skeptical investors that AI is ready to go mainstream
By Ian King and BloombergMay 20, 2026
10 hours ago
SpaceX finally files IPO prospectus, reveals revenue is up–but losses are too
Big TechSpaceX
SpaceX finally files IPO prospectus, reveals revenue is up–but losses are too
By Allie Garfinkle and Alexei OreskovicMay 20, 2026
11 hours ago

Most Popular

Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 
Workplace Culture
Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 
By Preston ForeMay 19, 2026
1 day ago
Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'
Success
Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'
By Preston ForeMay 20, 2026
17 hours ago
Meet a 21-year-old community college student who's going to China as the first American woman welder in the trades Olympics
Future of Work
Meet a 21-year-old community college student who's going to China as the first American woman welder in the trades Olympics
By Mike Householder and The Associated PressMay 17, 2026
4 days ago
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
8 days ago
Dr. Bernice King on why companies that walked back DEI were never truly committed: 'If you retreat that quick…that reveals who you really are'
Workplace Culture
Dr. Bernice King on why companies that walked back DEI were never truly committed: 'If you retreat that quick…that reveals who you really are'
By Preston ForeMay 19, 2026
2 days ago
Current price of oil as of May 20, 2026
Personal Finance
Current price of oil as of May 20, 2026
By Joseph HostetlerMay 20, 2026
18 hours ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.