In this chapter we examine how family, extended family, culture, and social context influences resilience building of Palestinian youth in the West Bank and Gaza Strip, in a sociopolitical context of chronic adversity. Our discussion analyzes the effects of exposure to chronic, anticipated political violence, continuous tensions and periodic conflicts within the context of ongoing Israeli-Palestinian aggressions. Analyses focus on the interplay of complex trauma, resilience and associated dynamic cultural, collective, and situational influences which contribute to the paradoxical expressions of resilience in youth, their parents, families and communities under conditions of chronic and complex trauma which differs from communities where tensions and violence require less energy devoted to perpetual adaptations to shared pain and suffering. Expressions of resilience are interpreted within a cultural context that evidences elements which are both traditional and dynamic. Our thesis is that interventions which support healthy, adaptive, and conflict-mediating resilience will be dependent on a multi-layered approach that supports healthy family resilience, community resilience, and socio-political cooperation in change as an expression of societal resilience.