Previous research has demonstrated that family transitions, specifically births and deaths of preceding and following generations within families, are associated with individuals' later-life wellbeing and health. However, lifecourse, family systems and role theories suggest that this relationship might be complex because, as individuals age, they can experience multiple such events and their effects might be interconnected. Therefore, this study asks whether and how transitions into and out of multiple intergenerational family roles are associated with later-life wellbeing and health. We account for the occurrence, timing and ordering of the parents' death and the birth of the first child and grandchild. To this end, we use the concept of ‘generational placement trajectories’. They capture the vertical position of individuals in their intergenerational family over age and reflect the changing family roles and kinship reservoir of individuals across their lifecourse. Applying sequence, cluster and regression analyses to data from the German Ageing Survey (N = 3,617), we investigate associations between generational placement trajectories from birth to age 60 and four dimensions of later-life wellbeing and health, namely life satisfaction, depressiveness, functional limitations and physical health problems. Results support, first, the notion of salutary effects of a larger kinship reservoir and multiple social roles in the family and, second, indicate that ‘off-time’ transitions are associated negatively with various later-life wellbeing and health outcomes. Importantly, the effect of temporal deviations from the ‘normative’ family lifecourse might be affected by individual socio-economic differences. We enhance previous research by demonstrating that the occurrence, timing and ordering of transitions into and out of multiple kin relations and family roles across the lifecourse relate to individuals' later-life wellbeing and health.