This article presents the development and application of a model that can be utilized to compare the autonomy of principals in various historical and national contexts. Drawing on former conceptual work on autonomy in education, the model conceptualizes principal autonomy as two-dimensional. The first dimension is the decision making expected from principals, manifested on a continuum of being restricted or extended. The second dimension is the control imposed on principals, also varying between a restricted or an extended nature. In relation to each other, restricted/extended decision making and control can result in four different governance configurations that impact principals' work complexities. We apply the model for the description of the development of Swedish principals' work conditions over time and for a comparison of the autonomy of Nordic principals. With this endeavour, we demonstrate how historical and nation-specific particularities in educational governance interact with limitations and opportunities of educational leadership. Moreover, we argue that a focus on the autonomy of various stakeholders in schools might be a fertile strategy for further understanding the confusing concept of school autonomy.