Since the promulgation of the South African Schools Act in 1996 it has become illegal to exclude pregnant girls from school. Influenced by feminist research, policy has sought to assist pregnant girls and young parents to continue and complete their schooling on the understanding that having children often terminates school-going limiting future employment and work opportunities. This paper seeks to examine how the new policy has been understood and implemented. We focus on the views and experiences of principals and teachers as they are the authorities at school with the responsibility for ensuring that the policy is implemented. The paper draws on qualitative data collected by a larger study on being and becoming a parent at diverse group of schools in Kwazulu-Natal and the Western Cape. In the paper we investigate the extent to which schools’ responses to pregnancy and parenting reflect and/or reproduce normative gender roles and practices with respect to schooling and parenting in contemporary South Africa. We show also that despite familiar stereotypes about young parents and pregnancy, both teachers and principals take their pastoral responsibilities seriously. They do care and do try to help. But many teachers were judgemental and moralistic particularly in response to young girls.