Children's early experiences of educational transition can be a critical step in their life-long learning journey, yet we know very little about their perceptions of this experience. This paper draws on the findings of a participatory study, which identified rules and rewards as being significant factors for children transitioning from an early childhood education setting to the first year of primary school in a European school in a major city in Belgium. This case study accessed the voices of six children, their parents and the teaching staff. The findings indicated that the children perceived both sanctions and rewards to be important in the enforcement of classroom rules. However, the children expressed concerns about their ability to adapt their behaviour to meet the cultural expectations of the setting and were troubled about the impact this could have on their social belonging. Furthermore, learning dispositions were found to be inhibited by both ambiguous criteria for success and the desire to earn rewards. This paper recommends that educators give careful consideration to the ways in which rules and rewards impact upon children's experiences of transition.