The study of depressive symptoms among caregivers raising HIV/AIDS-orphans is emerging as an important area of research. However, it has not been explored at length in generational and cultural contexts. In this study, the authors explore the role of financial strain, raising a HIV-infected and/or impacted child, and caregiver knowledge on the depressive symptoms of 89-older caregivers raising HIV/AIDS-orphans in Namibia, Africa. In this study, we found elevated levels of depressive symptoms among this population. Using hierarchical regression, a significant positive association between financial strain and depressive symptoms was found. A significant negative association between caring for an HIV-infected orphan and depression was shown. Our work suggests the need for economic assistance programs and psychosocial interventions for older caregivers.