Visma Wilma has become a standard in Finnish school system as the de facto school information system for teachers, parents and students to use. Whereas the digitalisation of the school system seems inevitable there have been some issues in the information system design to promote practices and values that are suboptimal – or even substandard for a school as an entity. In this paper we analyse the Wilma system from sociotechnical perspective with three different viewpoints: students’, parents’, and teachers’ and bring out requirements and recommendations on how Wilma should be constructed in accordance of the aforementioned practices and values in mind.