This paper develops two sets of concepts to theorize why students engage differently in Geographical Information Systems (GIS). These theoretical concepts are used as an analytical lens to explore empirical data on the experiences and engagement of students enrolled in an undergraduate GIS course in planning and management. The analysis shows that both the theoretical perspectives and the custom and didactical contract are important to understand students' engagement in GIS. However, it is the personal desiderata that are the key to understanding the students' different engagement. Further, a temporal dimension and contextual awareness are important in understanding students' engagement in a broader perspective.