This qualitative study investigated the experiences of 2 pairs of boys (1 typically developing, 1 with Down Syndrome) during their transitions to school. The boys were observed using continuous narrative recordings during all aspects of the curriculum. Their teachers, parents and peers were also interviewed. Results indicated that the boys with Down Syndrome (DS) engaged in a narrower range of roles than the typically developing boys at preschool. Essentially, they were included in level 1 type inclusion (interactions that did not involve any emotional connections with specific children). However, observations at school indicated that inclusion or exclusion were not within-child characteristics, but largely dependent on the context. By the end of the first week of school, one child with DS was actively included in the full range of roles characteristic for that setting (levels 1 and 2 inclusion). Furthermore, one typically developing child who experienced both forms of inclusion at preschool was excluded at school. He experienced mostly interactions characteristic of level 1 type of inclusion at school. The data suggest that the nature of relationships in each context affected inclusion and exclusion more than the setting (preschool or school) or the presence of DS. These relationships were shaped by all levels of the centre or school’s educational culture and beliefs, which permeated through the curriculum, pedagogy, assessment processes and ethos of the institutions, which in all but one school were based on an absence of disability as a prevailing norm.