Across sub-Saharan Africa, the AIDS pandemic has impacted children in a myriad of ways, from parental loss, to HIV infection, to increased poverty and marginalization. These children have been labeled orphans and vulnerable children (OVC) in the international development literature, and a range of interventions have provided services aiming to mitigate the impact of the crisis on human development outcomes, including education. Now, a decade after the term OVC entered the policy lexicon, it is possible to reflect on the “orphan crisis” and the policy response, and examine how ‘vulnerability’ has shaped the educational outcomes and experiences of African children. We pose the question: is ‘orphan’ a meaningful category in understanding child vulnerability in the context of schooling? This paper examines access to schooling and educational experiences of orphan youth, moving from a macro lens—analyses of household survey data from Lesotho, Malawi, Tanzania, Uganda, and Zambia—to a micro lens—an in-depth secondary school survey and ethnographic study from Lesotho. We find that orphanhood itself is not predictive of lower levels of school attendance, and that there are generally more orphans enrolled in school now than there were in the past. In addition, female orphans have higher primary attendance rates than their male counterparts. A closer look at barriers to school attendance in Lesotho shows that orphans do face certain economic disadvantages, though ethnographic findings identify the lack of adult care, leading to perceived behavioral problems at school and in the community, as a key local measure of child vulnerability. In sum, it appears that orphanhood itself is an inadequate measure of vulnerability that does little to describe the complexity of challenges facing children in eastern and southern Africa—a finding that policymakers and development practitioners would do well to consider. However, other indicators, such as the quality of adult care in the case of Lesotho, might potentially offer more meaningful measures of child vulnerability.