This article addresses a particular area of research in the field of education and child protection: the protective role of schools in the contexts of HIV/AIDS and poverty. Such adverse situations may lead children not to enroll in school or to drop out of school and subsequently to be subjected to abusive child labor and, in some cases, the worst forms of child labor (WFCL). I argue that the mutually reinforcing relationship of HIV/AIDS and poverty in many countries is leading to increasing child labor and that schools need to respond to this situation through policies that protect vulnerable children from dropping out and from abuse when they are at school. Further, I demonstrate that the HIV/AIDS pandemic has led to a breakdown of traditional and family-based safety networks in many communities, adding to the difficult situation experienced by orphans, children who are heads of families, and children who are caregivers to sick parents. The school emerges as the institution that can take over some of the protective and socializing roles that parents and the community have traditionally provided. The education literature discussing the relationship between the role of schools in child protection and child labor is limited. This gap is surprising, especially in the contexts of extreme poverty and high rates of HIV/AIDS, since these phenomena result in many children who do not attend school or drop out of school and become involved in abusive forms of labor at an early age. Many impoverished families are challenged to bear the direct and opportunity costs of children’s schooling (ILO 2006). This situation is exacerbated in the context of the HIV/AIDS crisis in that, when parents are incapacitated or die from the disease, there is an even greater need for children not to attend school. Pressure mounts for them to work as agriculture workers, as herders, or—especially for girls—as caregivers for parents and younger siblings (ILO/IPEC 2003). Therefore, child labor, and specifically WFCL, is increasingly a focus for many governments and development agencies (USDOL 2008). Hence, the research question that I address is, in societal contexts that are characterized by high levels of HIV/AIDS and poverty, what can schools do to encourage enrollment and to prevent dropout, outcomes which in many cases lead to abusive child labor? To respond to this question, I conducted case studies in two countries in sub-Saharan Africa, Namibia and Swaziland.