Using extensive census data from Russia and Estonia and employing a synthetic cohort approach, I conducted the first origin-destination comparison of key life-course statuses during the transition to adulthood to provide holistic insights into the demographic dynamics among Russian-origin Estonians (aged 15–35). The analysis scrutinized the degree of similarity or dissimilarity between Russian-origin Estonians and their native counterparts in Russia and Estonia across three dimensions: timing (i.e., age-specific status prevalence), ordering (i.e., proportions of noncompleted status pairs), and heterogeneity (i.e., age-specific status combinations). Overall, findings suggest a semblance of demographic similarity between Russian-origin Estonians and native Estonians in family domains (i.e., union status and parenthood), indicating an adaptation to family life-course patterns. Dissimilarities in the timing, ordering, and heterogeneity of key statuses between Russian-origin and native Estonians predominantly manifest in nonfamily domains. Descriptively, I observe signs of immigrant disadvantage (pertaining to school attendance and employment) alongside facets of cultural maintenance (regarding residential independence).