The South African Department of Education is working with multiple non-governmental organisations (NGOs) to transform schools into "caring schools" that emphasise: health promotion, safety, care for orphans and vulnerable children, quality education, community engagement and respect for rights and equality. Using a qualitative case study of a primary school and a secondary school in a Johannesburg township, as well as a review of caring school models currently operating in South Africa, this research explores the degree to which the caring school philosophy can be translated into practice. Findings suggest that educators accept the caring schools theory; however, most doubted that their schools could serve such a function at present. Educators named entrenched obstacles such as teacher burden, over-sized classes, inefficient governing bodies and support teams, and inadequate training and funding to deal with learners' psychosocial issues as the main shortcomings in their schools. This research illuminates the realities of transforming schools into sites for children's services, while contributing to the debate about the function of schools in social development programming. (Contains 1 figure and 6 footnotes.)