This article reports findings from an ethnographic study aiming to deepen the understanding of the transition from preschool into school, with special regard to participation and learning, from the perspective of students and teachers involved. The results show that, although children appear well prepared and comfortable facing school, a system that requires two transitions within one year is problematic given the change in activities, roles, and relationships for children. In terms of literacy activities, preschool and Year 1 are weakly linked and there is no arena for teachers to develop a common ground for pedagogical discussion, a “borderland”.