Purpose: Grandparents are common providers of childcare within the Caribbean region. Yet research on the implications of grandparent caregiving for older adults’ well-being is limited. This study examined gender differences in the relationship between grandparent caregiving and the life satisfaction of older adults in Jamaica. Methods: Using a sample of 1,622 grandparents 60 years and older drawn from the 2012 study “The Health and Social Status of Older Jamaicans,” we estimated binary logistic regression models to examine the association between the frequency of grandparent caregiving and the life satisfaction of grandparents. Findings: Grandmothers were more likely than grandfathers to provide care. We did not find a statistically significant gender difference in the life satisfaction of caregiving grandparents. Yet, gender differences in the patterns of association between grandparent caregiving and life satisfaction were evident. Among grandmothers, both occasional and regular caregiving was associated with higher life satisfaction relative to non-caregivers. Among grandfathers, however, only regular caregiving was positively associated with life satisfaction. Originality: This is the first population-based study within the Caribbean to examine gendered patterns of grandparent caregiving and the association with grandparents’ well-being. The findings of this study suggest that grandparent caregiving is beneficial to the well-being of older Jamaican men and women. This study challenges assumptions of gender norms that typically do not position men to be involved in caregiving roles, and to derive satisfaction from such roles, within Caribbean households. The authors suggest more attention should be given to interventions to encourage men to be actively involved in family caregiving.