This paper reports on a one-year project in a Singapore 'neighbourhood' school where the researcher was invited to assist the teachers of two secondary English classes to incorporate drama strategies to enliven their pedagogy. Few teachers involved had any prior experience of drama in schools and none had studied drama during pre-service teacher education. The project was faced with a number of challenges, most significantly the extent of teacher 'buy-in' for the research; this was influenced by the hierarchical nature of school administration, teacher resistance, teacher and community pre-conceptions about drama, and the degree of willingness to engage with change practices within the school. This paper discusses the challenges facing long-term intervention research in schools. It addresses issues of teacher commitment to the research, teacher-researcher relationships, and the challenges that impeded significant change taking place in this particular school context. It considers methodological issues for researchers who wish to engage in schooling contexts which are by nature complex, chaotic and diverse.