Teenage pregnancy in South African schools poses a serious management and leadership challenge. It calls for school management teams (SMTs) to acquire critical skills to manage teenage pregnancy within the requirements of the Constitution of the Republic of South Africa, 1996 and the South African Schools Act 84 of 1996. Little, if any, research has been conducted on learner pregnancy as a hurdle toward the achievement of millennium development goals (MDGs) and EFA goals. Drawing on literature, this article will (1) explore policy on teenage pregnancy from a South African perspective; (2) look into the trends and challenges of teenage pregnancy in a schooling context; (3) reflect on policy implications of teenage pregnancy in a schooling context; and (4) capture information on teenage pregnancy in schools as it relates to MDGs and EFA goals.