How does helping behavior contribute to the health and the longevity of older helpers? From an evolutionary perspective, the ultimate cause may be rooted in ancestral parenting and grandparenting. These activities may have generalized to a neural and hormonal caregiving system that also enabled prosocial behavior beyond the family. From a psychological perspective, helping others may be associated with healthy aging, which, in turn, contributes to longevity as a proximate cause. Yet little is known about the extent to which mediating factors such as the health benefits of helping behaviors translate into enhanced longevity, particularly in regard to grandparenting. To fill this gap, we conducted mediation analyses (structural equation models) to examine whether grandparenting and supporting others in the social network contributed directly or indirectly (through better health 5-6 years later) to the longevity of older helpers. We drew on longitudinal data from the Berlin Aging Study (N = 516), in which older adults in Berlin, Germany, were interviewed at baseline (1990-1993, mean age at entry = 85 years) and continuously followed up until 2009. Results suggest that the associations of both grandparenting and supporting others with enhanced longevity are mediated by better prospective health (indirect effect). The effect of helping was not fully mediated, however-helping was also directly associated with increased longevity independently of the health indicators measured. The results were robust against effects of the helper's preexisting health status and sociodemographic characteristics of participants, their children, and grandchildren. We conclude that better prospective health contributes to the link between helping and longevity, but does not fully account for it. Other potential contributing mechanisms remain to be identified. As populations age across the globe, identifying mechanisms that foster health in old age can help to highlight potential targets for public health interventions.