Sylvia Ashton-Warner’s New Zealand educational context has been – and continues to be – misrepresented as antithetical to her creative methods. Sue Middleton, a professor of education, locates Sylvia’s educational ideas within the national and international Progressive Education movement, indicating that key education officials in post-war New Zealand encouraged creativity and self-expression. This chapter makes the case that, as a teacher, an educational writer and theorist, Sylvia Ashton-Warner grew in, and not in spite of New Zealand. My argument unfolds in two parts. The first reviews theoretical ideas in the local and international educational environment in which Sylvia lived and worked. Sylvia and Keith Henderson taught in what was referred to until 1946 as the Native School system (and from 1948 until its abolition in 1968 as the Maori Scholl system). They trained and began work as teachers during the Great Depression; and Sylvia began serious writing during World War Two. The war and the Native Scholl system interested in complex ways with the wider international Progressive Education movement and its promotion ‘from the top’ in New Zealand’s public schools. An overview of Progressive (or New ) Education, the changing theories of culture and race in the Native School system, and relations between these during World War Two, opens a wide-angled aperture through which to read Sylvia’s early writing.