Don’t believe the bot: When AI confidently gets things wrong

September 11, 2026 — 4:00pm SaveYou have reached your maximum number of saved items. Remove items from your saved list to add more. Share AAA Care for a drop of Sahara Silk? Or maybe a splash of Oasis White? Each name is a would-be brand for camel milk, put forward . Not bad for a lactose-intolerant chatbot. The exercise arose from my talk with Paul Martin, the founder of Summer Land Camels, who’s selling his milk to the world, presuming he can pick the right label. Though at this stage, with sales going well, Camel Milk nails it. Nonetheless, it was fun watching AI Overviews deliver such gems as Nomad Nectar and Simoom Smooth. Even Humpilicious had a flair unthinkable – machines are getting craftier. I set the parameters – “give me 20 names for camel milk” – and awaited the results. While none astonished, each had a playful word-feel, that spooky knack we humans own to conjure crisp phrasing. AI might be smart, but don’t rely on it for help with the cryptic crossword. Getty ImagesIt stands to reason then that AI is up to cryptic thinking. If Overview and every other virtual brain can tackle camel milk, then surely decoding puns and anagrams is in reach. Tom Hawking explored that premise for Gizmodo, a tech-science website. Based in New York, Tom is an Australian journalist with a love of twisted clues. Explaining why he picked five of my Friday clues from “the most perverse and human of puzzles, the cryptic”, a chance to test three LLMs (Large Language Models): ChatGPT, Claude Sonnet 5 and Oreate AI. The toughest clue read: January 15, 2000? (9) The wordplay relies on Roman numerals, and our home calendar, pointing to MIDSUMMER (where MM – or 2000 – mirrors the date’s seasonal position.) In short, the chatbots struggled. Claude imploded; Oreate entered a fugue state, while ChatGPT claimed the answer was HEWITT WON. “A terrible answer,” Tom wrote. “HEWITT WON is two words for a start. Yet, ChatGPT was so confident of this wrong answer!” That last remark echoed an experiment a friend did last week. A cryptic fan, Stuart McArthur challenged AI with his own clue: Bill Gates driving almost erratically (11) Claude replied with BILLIONAIRE, claiming “the clincher is the right letter tally, and it’s an obviously witty description of Bill Gates himself.” But Claude was wrong, as Stuart explained, showing how the anagram (mixing GATES + DRIVIN/g) yields ADVERTISING, a synonym of bill.