This paper analyzes the relationship between orphan status, household wealth, and child school enrollment using data collected in the 1990s from 28 countries in Sub-Saharan Africa, Latin America, the Caribbean, with one country in Southeast Asia. The findings point to considerable diversity—so much so that generalizations are not possible. While there are some examples of large differentials in enrollment by orphan status, in the majority of cases the orphan enrollment gap is dwarfed by the gap between children from richer and poorer households. In some cases, even children from the top of the wealth distribution have low enrollments, pointing to fundamental issues in the supply or demand for schooling that are a constraint to higher enrollments of all children. The gap in enrollment between female and male orphans is not much different than the gap between girls and boys with living parents, suggesting that female orphans are not disproportionately affected in terms of their enrollment in most countries. These diverse findings demonstrate that the extent to which orphans are under-enrolled relative to other children is country-specific, at least in part because the correlation between orphan status and poverty is not consistent across countries. Social protection and schooling policies need to assess the specific country situation before considering mitigation measures.