The family stress model proposes economic hardship results in caregiver distress and relational problems, which negatively impact youth outcomes. We extend this model to evaluate the impact of coronavirus disease 2019 pandemic-related family hardships on caregiver and youth stress, and, in turn, youth’s psychological well-being. We also investigate how social supports moderate this relationship. We used 2 samples of cross-sectional survey data collected between May 2020 and May 2021: children aged 2 to 12 years (n = 977) and adolescents aged 11 to 17 years (n = 669). Variables included pandemic-related family hardships, stress, social support, and youth life satisfaction. Data were analyzed using structural equation modeling. Experiencing more pandemic-related family hardships was associated with increased caregiver and youth stress (b = 0.04 to 0.21, SE = 0.01-0.02) and, in turn, decreased youth life satisfaction (b = -0.36 to -0.38, SE = 0.04-0.07). Social connectedness (b^ = 0.11-0.17, SE = 0.04) and family engagement (b^ = 0.12-0.18, SE = 0.05-0.06) had direct positive associations with life satisfaction; for children aged 2 to 12 years, greater family engagement was associated with decreased effect of child stress on life satisfaction (b^ = 0.15, SE = 0.05). For adolescents, females had higher levels of stress compared with males (b^ = 0.40, SE = 0.6), and having anxiety and/or depression was associated with decreased life satisfaction (b^ = -0.24, SE = 0.11). Caregivers and youth who experienced more coronavirus disease 2019 pandemic hardships had higher levels of stress, particularly adolescent females. Although stress negatively impacted life satisfaction across all ages, family engagement was a protective factor for children aged 2 to 12 years, whereas having anxiety and/or depression was a risk factor for adolescents. For all youth, however, being more socially connected and engaged with family promoted life satisfaction.