This article focuses on special education as cultural representation and explores how it is fashioned by the realities of the Caribbean diaspora. These realities are framed within the context of the Caribbean's response to the global agenda of education for all and the development of learning support systems that are relevant to regional and national circumstances. Historical and contemporary accounts of policy development are discussed to exemplify the link between colonialism and the construction of difference. Particular consideration is given to how specific groups have been historically marginalized within an ideology of normalization. Identity accounts provide insights into how disabled girls and those labelled as having learning difficulties experience education and show how the expansion of special education through strategies for education for all provide social challenges and possibilities. Further, constraints on expansion of special education are considered in light of the socio-economic developments of Caribbean countries.