Education of democratic citizens is a fundamental aspect of Danish primary and secondary schooling. However, policymakers push school principals' agency towards professional leadership by encouraging specific methods for assessing student learning outcomes. Enactment of a learning management system (LMS) supports the transition towards professional leadership and leads to self-regulation by all actors within schools. While supporting the professional agency of school principals, this transformation is at the expense of core elements of democratic practice. This article argues that schooling's democratic purpose tends to be forgotten in the shift towards the professionalization of principals' agency. In this process, an LMS is a powerful tool because principals can keep track of what teachers are doing digitally at all times. The concept of professional agency is used in this article to denote how the actions of school principals become distanced from the educational practice within the schools. The article is based on a qualitative study at four schools, comprising 31 semi-structured interviews with principals, teachers, and civil servants. Bourdieu's thinking tools--field, habitus, and capital--will be used along with the concept of governmentality to explore principals' professional agency and self-regulation and to conduct a thorough analysis of practice.