In the race to perfect the first major artificial intelligence-powered search engine, concerns over accuracy and the proliferation of misinformation have so far taken centre stage. But a two-hour conversation between a reporter and a chatbot has revealed an unsettling side to one of the most widely lauded systems – and raised new concerns about what AI is actually capable of. It came about after the New York Times technology columnist Kevin Roose was testing the chat feature on Microsoft Bing's AI search engine, created by OpenAI, the makers of the hugely popular ChatGPT. The chat feature is currently only available to a small number of users who are testing the system. While admitting that he pushed Microsoft's AI "out of its comfort zone" in a way most users would not, Roose's conversation quickly took a bizarre and occasionally disturbing turn.