When Henry VIII married Anne of Cleves, historical records state he was so appalled that her beauty did not match the portrait by Hans Holbein the Younger that his fourth wife became widely known as the “Flanders mare”. Now, Holbein’s pictures of another of Henry’s wives, Anne Boleyn, have been called into question using a more scientific method of analysis: artificial intelligence (AI). Researchers used facial recognition tools to establish that a sketch of a previously unknown woman could be of Henry VIII’s doomed second wife. Meanwhile, a drawing previously thought to be of Boleyn by Holbein in the Royal Collection has probably been misidentified and is more likely to be a picture of her mother. Academics used AI to re-examine the second drawing, known as the Windsor Sketch, which for 200 years has been assumed to be the Tudor queen based on an 18th-century inscription that says it is “Anna Bollein Queen”. The portrait, labelled as Anne Boleyn (c.1500-1536), depicts a blonde woman with a double chin. This contradicts contemporaneous accounts of Boleyn, which describe her as slender, dark-haired and with a distinctive “little neck”, a feature she reportedly referenced before her execution. Using facial recognition software, experts went on to suggest that another drawing by Holbein the Younger in the Royal Collection is more likely to be Boleyn. Karen L Davies, a historian who led the study, which is published in Nature Heritage Science, said: “I’ve spent many years researching Anne Boleyn, and what ultimately drove me to this project was a growing dissatisfaction with the long-accepted identification. There were simply too many contradictions. “The drawing didn’t align with the primary sources and each proposed explanation seemed only to generate further inconsistencies rather than resolve them.” Davies and academics from Bradford and Stanford Universities set out to use