Development policymakers and child-care service providers are committed to improving the educational opportunities of the growing population of 153 million orphans worldwide. Nevertheless, the relationship between orphanhood and education outcomes is not well understood. Varying factors associated with differential educational attainment in multiple contexts leave policymakers uncertain where to intervene. Positive Outcomes for Orphans (POFO) is a longitudinal study, following a cohort of single and double orphans and abandoned children (OAC) in institutional and community-based settings, that aims to better understand the characteristics associated with child well-being. Using cross-sectional and child-level fixed effects regression analyses on 1,480 community based children, this manuscript examines associations between emotional difficulties, cognitive development, educational attainment, and a variety of correlates including trauma. Results show that factors such as trauma and lower socio-economic status are correlated with higher emotional difficulties, and that increases in emotional difficulties are associated with lags in cognitive development. In contrast, wealth and caregiver literacy rates hold stronger associations with a child’s grade for age than the level of emotional difficulties experienced by the child. These findings suggest that interventions targeting both the psychosocial development of the child and the socioeconomic status and education of the caregiver may help to reduce barriers to a child’s educational attainment. Family based interventions to stabilize socioeconomic conditions or increase caregiver education may also help overcome psychosocial challenges that otherwise would present as barriers to the child’s educational advancement.