The purpose of this study using a qualitative methodology was to investigate the process of transition from preschool to school at an in-depth level for three children with Down Syndrome (DS) and two typically developing children with a view to ascertaining factors associated with effective and ineffective transitions. This begged the question, 'What constitutes an effective transition/what is the purpose of the transition process?' Attention, therefore needed to be focused on identifying the meaning of inclusion at the 'chalk face' of the preschool and school, and identifying the processes underlying it. Bearing in mind that disability theorists argue that it is not so much individual impairments that disable, but society's response to them, this study investigated the range of roles in which the children were included in each of their two settings (preschool and school) and the contextual factors which contributed. Findings indicated that at preschool the children with Down Syndrome (DS) were engaged in a narrower range of roles than their typically developing peers. Essentially they were included in level 1 type inclusion (interactions which did not involve any emotional connections with particular 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 type inclusion). Furthermore, one of the typically developing children who was included at preschool was excluded at school and experienced mostly interactions characteristic of level 1 type inclusion at school. He was unable to become part of a particular peer group or dyad due to the social dynamics of the classroom at the time. Investigation into the processes underlying each outcome indicated that to be included as a valued member in the full range of roles characteristic of that setting required that the processes involve reciprocal, equal and valuing relationships irrespective of disability. However, these processes were shaped by all levels of the schools' educational culture and beliefs, which permeated through the curriculum, pedagogy, assessment procedures and ethos of the institutions, which in all but one school were based on an absence of diversity as a prevailing norm. For children to experience facilitative inclusion requires schools to adopt a philosophy of difference, which embraces disability and other differences such as race and gender as valued attributes, as opposed to deficiencies or problems.