Formal systems and informal networks are presumed to be significant contexts that affect military families. Their effects on both parents and adolescents in active duty military families are examined (N = 236 families). Social organization and contextual model of family stress theories are employed as frameworks for the analyses of how dimensions of military culture influence parents’ life satisfaction, as well as key developmental outcomes of their adolescents (for example, mental health). Key findings from our analyses included a positive relationship between parents support from military leaders and fellow soldiers and parental well-being findings revealed the importance of civilian parents’ satisfaction with military life on adolescent outcomes for families that have experienced stressful military contexts. These findings provide support for the significance of multiple contexts for understanding resilience among military members and their families.