Youth resilience is the product of multiple systems. Still, the biological, psychological, social, and environmental system factors that support youth resilience are incompletely understood. How these factors interact, and the situational and cultural dynamics shaping their interconnectedness, are also under-researched. In response, we report a multi-site case study that is instrumental to understanding multisystemic resilience. It draws on the insights of 52 youth from stressed, oil and gas communities in South Africa (13 young men; 8 young women; average age: 20.28) and Canada (19 young women, 12 young men; average age: 20.77). Deductive and inductive analyses show that youth resilience is informed by a biopsychosocial-ecological system of interacting resources that fit situational and cultural dynamics. This has implications for society's championship of youth adaptation to stressed environments, including less emphasis on individual resources and more on contextually responsive, systemic changes that will facilitate meso- and macro-system resistance to significant stress.