Of all the applications of psychoanalysis to various fields, perhaps none has been as important – or as fraught – as the application of psychoanalytic insights to education. This paper re-constructs some of the early debates around psychoanalysis and pedagogy that Anna Freud engaged with during the 1920s in Vienna, when the whole question of what education should be became a central issue for politicians, pedagogues and psychoanalysts alike. The paper focuses on the period leading up to the creation of the so-called ‘Matchbox School’, operating under Anna Freud's guidance between 1927 and 1932, and describes the influence of pioneers such as Seigfried Bernfeld and August Aichhorn. Compared to her more well-known work at the Hampstead War Nurseries during the Second World War, Anna Freud's involvement with this earlier educational experiment is relatively neglected. Yet one can argue that this short-lived project not only laid the foundation for much of Anna Freud's later work; it also had some far-reaching consequences, both for psychoanalysis and for the practice of progressive education.