The introduction of Grade R (Reception Year) and its curriculum in early childhood education has been a key policy initiative, but despite the importance of this level of education the demands of the transition from Grade R to Grade 1 are not explicitly discussed. Official documents note the likely difficulties and challenges inherent in the transition of children from preschool and home into the primary school environment but they do not explicitly say how these difficulties can be dealt with. This study investigated the implementation of transition policy and existing practices for children transiting from preschool or the home into Grade 1 in South Africa’s schools. A case study of two purposively selected schools, from two different provinces, explored the impact of transition on both children’s adjustment to their new environment and the school itself. Key policy documents were initially analysed, and key informants in government and non governmental organisations (NGOs) were interviewed in relation to aspects of the policy guidelines and practices for transition to school. Participating principals, teachers, parents and children as subjects were interviewed to identify their perspectives about transition and how they deal with it. The social, behavioural and academic adjustment of 6 children from each of the two schools was investigated using the Social Skills Rating Scale (SSRS). The results show that although some differences in the adjustment of children between the two case study schools were noted, it appeared that preschooled children were more likely to make better adjustments than non-preschooled (home) children. The study also revealed that schools’ strategies for dealing with transitions are not informed by the government’s transition policies and guidelines. Instead, the two schools devised their own in-house strategies to deal with transitions and these differed from one school to another. The study also highlights that teachers are not familiar with policies governing their working lives. The schools studied also lamented the lack of continuity in the curricula and the way of life between the school and preschool despite policies enacted to deal with this disjuncture. Whilst the findings show a disparity between the adjustments of preschooled children and their home counterparts a longitudinal study involving more case schools would provide greater insight into preschool grade 1 transition in a developing South Africa. The educational and policy implications of the study are discussed with regard to important processes and structures put in place for the transition process of children entering into primary schools. While case study findings cannot be generalised the results can be beneficial in informing other similar contexts grappling with transitions. The study highlights important processes undertaken in the adjustment of children into primary schools, however it also revealed some shortcomings which have serious implications for policy and practice. “Policy literacy” should be embarked upon to familiarise teachers as end users with what policy entails. Every school should have a transition programme that would help orientate and settle in the new entrants into the school environment.