This qualitative study investigated the experiences of two pairs of boys (one pair typically developing, one pair 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 did the typically developing boys at preschool (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. The data suggests that specifically it was the nature of relationships in each context that affected inclusion and exclusion, more so than the setting (preschool or school) or the presence of DS. These relationships were shaped at all levels of the centre or school's educational culture and ethos. (Contains 2 figures.)