Contextual factors linked to behaviour problems in schools include leadership, school culture, and levels of teacher stress. Efforts to improve the school environment, reduce teacher stress, and improve student outcomes, often have a singular focus on behaviour management policy. The series of studies reported here present an alternative perspective on the environment-behaviour equation, in terms of the direction of effects from leadership, culture, and teacher stress factors. That is, while student misbehaviour is most often viewed as a producer of teacher stress and school level problems, it could, paradoxically, be viewed as a product. Differences in school leadership styles, as well as characteristics of different school cultures, appear to explain some of the variation in the numbers of students referred for behaviour management. Interestingly, and somewhat unexpectedly, teacher stress does not always add explanatory variance. In the present monograph, leadership style and school culture emerge as the most important factors in student behaviour outcomes, and may be pivotal in considerations of school-based approaches to behaviour management.