Orphans of the AIDS epidemic are a growing population in the U.S. but are sorely understudied. The current study is an empirical examination of the psychosocial adjustment of children whose mothers died from AIDS-related illnesses. Orphans were compared to two comparison groups of children from the same high-risk neighborhoods: children whose mothers were living with HIV and children whose mothers were non-infected. Comparisons between groups on child adjustment variables and correlates of child adjustment were examined. Adjustment was evaluated in four areas: internalizing and externalizing problems based on both child and mother/caregiver report, and social and cognitive competence as reported by the mother/caregiver. Assessments were conducted prior to maternal death, and at six months and two years following maternal death. Results indicated that, in general, the orphans were functioning more poorly than the comparison groups at the pre-death and second post-death assessment, while no differences emerged at the first post-death assessment. Furthermore, two between group differences for correlates of child adjustment emerged: both the soon-to-be orphans and their mothers rated their relationship as less positive than the non-infected group, and caregivers endorsed more depressive symptoms at the second post death assessment than the non-infected mothers. Finally, for the orphan group, significant associations emerged between quality of the mother/caregiver relationship and child adjustment at the pre-death and first post-death assessment, and between caregiver depressive symptoms and adjustment of the orphans at both post-death assessments. The results are discussed in terms of the anticipatory grief and delay effect for grief that may operate for these orphans. The clinical implications of the importance of the mother-child relationship prior to death and caregiver adjustment following maternal death as primary targets for intervention also are discussed.