Research increasingly points to the negative impacts of teacher absence from school on access to schooling and success in learning in schools, in particular in schools in areas of multiple-deprivation (including rural schools). South African schools are no exception. In this regard, like any other employer, the South African Department of Basic Education has a set of policies that govern teachers’ conditions of service. Among others, these include policies that govern leave and absence from school. While the policies are meant to enhance teachers’ conditions of service, they are also aimed at safeguarding the rights of learners to quality education by ensuring that teachers remain on task, and that teaching and learning is not interrupted. Using Lipsky’s theory of discretion, this paper takes the view that as street-level bureaucrats, principals use their discretionary power to manage teacher leave and absence from school, and that the strategies they employ are informed by their understandings and conceptualisations of policy. The paper reports on a study undertaken to explore teacher leave in South African schools. In particular, it critically examines principals’ use of their discretionary powers to make decisions about teacher leave-taking, and the coping mechanisms they use to manage teacher absence and to safeguard the rights of learners to quality education.