This article reports the findings of a qualitative study that examined what it means to be a principal in the context of rurality. We argue that principals in the 21st century encounter complex work situations that make it hard for them to manoeuvre. Furthermore, for principals in the context of rurality, such complexities pose multiple dilemmas, given that rurality exposes principals to multiple challenges. Using a case study within an interpretive paradigm, we interviewed and observed five principals from rural schools in the Limpopo province. The study found that principals’ leadership focuses dominantly on administrative tasks. It further identified social and institutional complexities that principals encounter and argues that these complexities compel to treat rural schools as systems. While we hail this view of schools, it emerged that some units of the system appear to be thwarting the progress of principals in leading rural schools. We conclude that, at times, principals’ leadership in the context of rurality can be defined as a leadership that shuns policies and issues of social justice for the purpose of finding what works in their contexts.