This article draws on data collected from a wider, longitudinal life history study conducted in South Africa between 2010 and 2014. The study focussed specifically on the personal and professional pathways to principalship of a sample of women leaders of co-educational high schools in South Africa, in both rural and peri-urban provinces: a role that, in gender terms, remains a minority position in South Africa and internationally. The data revealed valuable insights into how two of the women experienced principalship of high schools in multiply deprived rural areas. This article focusses only on these two women's experiences of, and not their pathways to, principalship. The women, one black and one white, work in rural schools which, through historic demographics, still serve black communities only. Their leadership roles are beset by the problems of the multiple deprivation prevailing in their school and community contexts. Though the findings are not generalisable from this small sample, they indicate that there are commonalities of experiences in two key areas: issues of authority and power contestation, and the manifestation of deeply entrenched cultural traditions and patriarchy. These impact adversely on the execution of principalship for women leaders in deeply rural, traditional communities.