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The school leader task is complex and has since 2017 been expanded with the task of leadingthe digitization in school. The purpose of this study is to make visible and problematize thechallenges school leaders face in their mission to lead digitization in schools. Through focusgroup interviews where school leaders at upper secondary school level talked about the workat their own school and their own role in the work of leading the digitization, challenges havebeen identified. These are set in relation to theory of how successful (distributed) managementof digitization ought to take place and in relation to the National Agency for Education'sexpectations of school leaders in the task of leading the digitization.The results show that an already complex assignment has become even more challenging. Thedigitization assignment affects almost all areas of the school's activities and, as a result, theschool leaders express difficulties in formulating clear goals with the digitization. They alsodescribe limitations in the conditions, both in terms of teachers' time but also personnelresources in the form of IT educators or development leaders and support. Technology is alsoa challenge because development is progressing so fast. In parallel with the internal activities,there is a debate about the effects of digitization on the individual and the learning that schoolleaders need to relate to.The challenges are many and it is important to continue the discussion about how school leaderscan be supported in their mission to lead digitization in schools.