In nowadays increasingly ICT-related investments in an overgrowing competitive school setting, the deployment, maintenance, and particularly the effective use of ICT is in many ways a complex multifaceted managerial task involving several stakeholder groups. In a pilot study of a single school district in a Swedish municipality, we have interviewed representatives from the municipal board of education, the municipal IT-support for schools, and two principals. We have used Technology Acceptance Model (TAM3) as our analytical lens to explore how school principals’ and municipal IT-managers’ perceive ICT adoption, usefulness, and the potential role of ICT. We conclude that the barriers for a successful integration of ICT into school-related activities requires a holistic managerial thinking in order to overcome the lack of coordinated ICT investment strategy and tracking of ICT.