The transition from preschool to primary school began attracting attention in Icelandic educational research shortly after the turn of the twenty-first century. This chapter examines multiple studies that have explored different aspects of the transition from preschool to primary school and leisure centres in Iceland. While various studies have advanced empirical understandings of this topic during the past quarter century, others report that transition practices in preschools and primary schools have largely remained the same throughout the period as have challenges to further collaboration between the two levels. Current laws and curriculum guidelines and research on transition from the perspectives of educators, parents, and children all emphasise democratic approaches, play, wellbeing, and belonging. Despite this, the research reviewed indicates trends that are antithetical to these values, such as a lack of professional collaboration, dialogue, and development; the pressure of formal learning at a younger age; and an education system that still needs to adapt to recent demographic and social developments. The chapter concludes with a set of key principles which highlight aspects to be addressed, considered, and integrated into transition to school programs in Iceland.