“It looks like you’re writing a letter. Would you like help?” Before Alexa, Cortana and Siri, we had Clippy – the paperclip assistant included in Microsoft Office programs who Generations X and Y will know only too well. Designed as one of the earliest forms of contextual support, he had a real knack for annoying users with his somewhat intrusive and know-it-all nature. Since abandoning Word and Excel in the early 2000s, Clippy has been leading a new life as an internet meme. In early 2021, Microsoft announced his big comeback, only this time as a paperclip emoji for Office 365.