At the present time there is common agreement among academics and practitioners that the notion of inclusion means more than simply access to education. The mere placement of children in mainstream educational environments does not suffice to foster participation and equal opportunities for success. In Greece, this is particularly the case for children with challenging behaviour, the majority of whom are educated in mainstream classrooms. Personal experience shows that students and experienced kindergarten teachers feel ill prepared to manage these children. This, in most cases, results in the children being isolated from the pedagogical process. This form of internal segregation, in addition to the fact that the teacher's role, and consequently teacher education, is key in promoting inclusive practices, provides the overall rationale of this study. Initial teacher education is a context in which changes in professional values, knowledge and beliefs can and do occur. Within this frame, the present study examined the initial kindergarten teacher education provided to kindergarten teachers with an aim to shed further light into how they can be better prepared to accommodate the needs of their hard-to-manage pupils within mainstream settings. Using an activity theory perspective, the study was designed in such a way so as to allow student teachers to be followed in their transition between university and school through their school placement. This allowed for a coupling of the university and school contexts and thus provided a means of analysing contrasting practices in order to find possible misalignments and contradictions between these two contexts. The aim was to learn more about how these two systems can be better aligned with implications for improving the initial kindergarten teacher education curricula and pedagogy. A qualitative multiple case study design was employed in order to explore student teachers' experiences of their teaching practice. The participants in the study were drawn mainly from student teachers on a four-year teacher education programme at one of the universities in Greece. Beginning teachers were also observed and asked to reflect retrospectively on their transition from university learning to actual teaching at school. Inadequate preparation, lack of relevant modules and the gap between theory and practice were a few of the constraints that were pointed by this study. However the interest focused on the way these elements were located in concrete contextual conditions. The constraints students and beginning teachers face in developing inclusive practices for their challenging pupils are located at the level of the contrasting practices and discourses of the school practicum. Within these constraints students and beginning teachers adopt particular student teacher/teacher identities with ramifications on the children who have challenging behaviour.