This paper describes headmasters’ perceptions of digital school administration in terms of whether it is productive, destructive or irrelevant for the school. Their accounts are then analysed by relating them to theoretical categories, illustrating the differences between practitioners’ view and a theoretically founded understanding of what that is productive, destructive or irrelevant. Intuitively, we may expect that headmasters’ ideas of how digital school administration affect school work corresponds to the schools’ capacity to interact with students. The presented idea is that such a correspondence exists, although the links are not as straightforward as expected, rather counter-intuitive, which is also the main point for practitioners.