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In the UK, Classics fails to be inclusive of all students: the majority of students studying Classical subjects attend fee-paying schools (Hunt and Holmes-Henderson, 2021). This paper summarises the impact of an innovative online outreach initiative offered by the University of Oxford between January and July 2021 which successfully reached students traditionally underrepresented in Classics. Pre-pandemic, Classics outreach was predominantly delivered face-to-face in university buildings or in museums (Hackett et al., 2020, Holmes-Henderson et al., 2018). The ‘Classical Conversations’ initiative offered something new. It provided school students aged 6-18 and their teachers the opportunity to chat with an Oxford academic on a topic of their choice for approximately 30 minutes. The date, time, platform and topic were agreed in advance but the students, teacher and academic were free to ask questions as part of a natural, free-flow conversation, unlike a traditional prepared lecture. Afterwards, teachers and students were asked to reflect on their experience of these conversational interactions via online surveys. The resulting data illuminate not only what went well and where improvements can be made, but also indicate how Classics outreach in the UK could usefully adapt to changing curricular trends, student preferences and teacher needs. Both quantitative and qualitative data will be shared, together with some of the publicity which the initiative attracted. Based on this pilot programme, recommendations will shared with academics and outreach professionals in the international Classics community.