The focus of this article is on how the relative autonomy of middle managers is expressed in the context of local education administrations. In the Swedish education system, middle managers often constitute the link between principals at schools and local government education administrators. Little is known about what such middle managers do and why. To fill this knowledge gap, this article presents and discusses the results of interviews with middle managers, chief education officers and principals linked to four local education administrations in Sweden. A previously developed analytical model has been adapted to facilitate the interpretation of results and how they relate to the concept of autonomy in education administration. The framework encompasses four cognitive domains: educational, social, developmental, and administrative. The results display middle manager autonomy as fostered and limited by all four domains and how the use of relative autonomy varies between middle managers. There are differences between middle managers in separate local education administrations and middle managers working in the same organization. A major finding is that autonomy is always conditioned, not only by organization but significantly also by cognition and administrative interaction.