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This study explores how housing-insecure high school students develop coping strategies while navigating formal schooling. Using a narrative inquiry approach, the study draws on interviews and classroom observations with students enrolled in Chicago Public Schools. Preliminary findings reveal that students cope through informal networks, community and cultural practices, and future-oriented “dream-making” behaviors that support academic persistence. These early insights highlight coping as a developmental and identity-forming process rather than a deficit response. The next phase of research will expand the study to include additional interviews and classroom observations to inform the design of learning environments that cultivate positive coping mechanisms and foster resilience among housing-insecure students.