This study explores a generative co-design methodology to address a critical challenge in Type 1 Diabetes care: insulin pump infusion set leaks. These leaks can lead to life-threatening complications and often go undetected, especially in adolescent users. Through participatory sessions with teens managing T1D, the research uncovers lived experiences, emotional responses, and unmet needs, translating them into conceptual product ideas and early-stage prototypes. Grounded in co-design’s legacy and looking ahead to user-centered innovation in healthcare, this project demonstrates how collaborative design methods can inform more responsive, empowering, and safe diabetes management technologies.