Less educational investment in orphans has become a serious concern in Sub-Saharan Africa, although the findings of the existing literature are mixed. This paper explores the factors that shape the dynamics of educational attainment for orphaned children and adolescents. A theoretical model predicts that there are three phases of orphans’ educational progression; 1) orphans may experience an immediate negative impact (grade repetition) associated with parental death, 2) yet continue to attend school up to a threshold age, 3) after the threshold age, however, they are more likely to drop out of school. Empirical analysis examines this prediction and shows that in Malawi the patterns of educational progression for female orphans follow the predicted pattern, whereas the patterns for male orphans are more heterogeneous. This paper aims to provide a theoretical framework to correctly evaluate the long-term impact of parental deaths on children’s educational achievement in Sub-Sahara Africa.