This project focuses on improving retention among young adults transitioning off their parents’ Kaiser Permanente plans, a moment where many disengage despite familiarity with the system. Research with 40+ Gen‑Z users revealed that confusing insurance terminology, competing financial priorities, and administrative hurdles cause significant friction, with most participants delaying action, misunderstanding plan options, or remaining uninsured past coverage end. Many lack guidance from parents or institutions and adopt a passive, reactive approach, treating insurance as a background safety net rather than an active tool for managing health. Our “Aging‑Off Hub” prototype addresses these challenges with a personalized, in‑app checklist, one‑click actions, and optional contextual reminders to guide users through the transition and increase confidence and timely completion of coverage steps.