One approach to tackling problems of division in society has been to promote collaboration and engagement between schools separated on ethno-religious lines. Based on some variant of contact theory, the received wisdom is that inter-group encounters can contribute to prejudice reduction and promote more harmonious relationships. Evidence to support this analysis is convincing; however, relatively little is known about the environmental factors that impede or enhance the potential for contact in different contexts. The importance of understanding such factors is underscored in divided jurisdictions, where separate education has been linked to the perpetuation of division and hostility. This paper adopts a qualitative approach to exploring the impact of two inter-school initiatives in Northern Ireland. The projects are located in contrasting socio-political and demographic environments, and research findings point to very different contact outcomes for participants in each. Seemingly relevant factors include the degree of congruence between school and community norms and values, the opportunity to develop relationships outside the school context, the relationships developed between the schools and local communities and the historical, political and social referents used by individuals to navigate the contact experience. The paper concludes with some reflections on factors that may help foster social harmony and on potential policy implications of the findings.