This research explored the delay of grandparenthood in East and West Germany, investigating how the timing and life-course context of this transition have changed across cohorts. The authors estimated the timing of passages into the grandparent role as well as demographic overlap with worker, parent, and filial roles. Data from the German Aging Survey (N = 3,628) revealed a rise of 3 months per birth cohort (1929–1958) in the median age at grandparenthood. As a result, the grandparent role decoupled almost entirely from active parenthood. Overlap with worker and filial roles was frequent and remained stable across cohorts. The findings direct attention to a neglected demographic trend that is striking in scope and precipitates change not only in the grandparent role but also in kinship structure.