This article presents accounts regarding Digital School Administration (DSA) from Polish and Swedish principals and analyse them from a conceptual and a contextual perspective. The accounts were categorized in productive, destructive or irrelevant representations of impact on schools, and first analysed using concepts from a Human Service Organization (HSO) perspective; professional capital, entrepreneurial role and decoupling. From this first analysis, a counter-intuitive rather than straightforward pattern between the principals’ native view and the conceptual view is made visible. The second round of analysis was based on the context of the principals, comparing features of the Polish and Swedish school systems, and relating these features to the results of previous analysis. The article concludes that school system marketization and whether principals teach themselves are key factors for if DSA works productive, destructive or irrelevant for schools.