This study investigates the association between the perceived impact of the COVID‐19 pandemic on skipped generation familial connections and subjective well‐being among grandchildren and grandparents across the United States. Guided by Walsh's family resilience model, this convergent mixed methods study drew on the survey responses of unrelated adolescent and young adult grandchildren (n = 66) and grandparents (n = 40). Correlational analyses revealed a significant association between perceived impact of COVID‐19 on one's skipped generation family relationships and subjective well‐being for grandchildren but not grandparents. The qualitative results demonstrate both a breakdown and build‐up of processes essential for family resilience: communication, organization, and belief systems. Together, these findings demonstrate the effects of COVID‐19 on skipped generation family relationships are complex, with ties between family members in younger and older generations being simultaneously strengthened and eroded. This study builds on our understanding of intergenerational familial contact when physical separation is present, allowing for more informed decisions as the effects of COVID‐19 on individuals, family systems, and relationships between family members—as well as geographic separation between generations more broadly—continue to evolve.