This article is based on a qualitative multi-case study carried out in southwestern Kenya along the border areas of Nyanza and Rift Valley province. The purpose of the research was to examine the challenges public secondary school principals faced in their leadership roles and suggest efforts they might adopt to minimize the effects of these challenges. Data was drawn from interviews with six secondary school principals, document analysis as well as participant observation. Findings indicated that principals of public secondary school are faced with challenges associated with overdependence, uncertainty and vulnerability.