Aims and objectives The findings presented in this manuscript address two key research questions: (a) What factors contribute to the initiation and maintenance of the caregiving role as performed by the grandparent‐caregivers; and (b) What are the perceived benefits of caregiving as reported by grandparent‐caregivers? Background Grandparents in sub‐Saharan Africa have cared for their grandchildren for generations, yet little is known about this role in the context of the HIV epidemic. Although the impact of the epidemic is overwhelmingly negative, specifically in Uganda, knowledge of familial context and underlying motivations and rewards that incentivise grandparent‐caregivers remains limited in the literature. Methods Using a constructivist grounded theory approach, we explored the experiences of 32 Ugandan grandparents of grandchildren affected by HIV. Data were collected using a semi‐structured and open‐ended interview guide, participant observation and fieldnotes. Data analysis included open, focused and axial coding. Findings The data revealed the influences of extended familial structures and of cultural and gender expectations on the decision‐making processes and rewards of caregiving as perceived by the grandparent‐caregivers. Discussion and recommendation These findings provide a broad foundation for policy, practice, research and education interventions needed to support grandparents so they can enjoy the benefits of raising their grandchildren. Implications for practice Our findings can guide education programs and clinical practice for nurses, nursing students, and other health providers on cultural considerations for holistic care provided for older adults—especially older caregivers.