When returning to their communities after incarceration, individuals face elevated rates of mortality and other poor health outcomes. The reentry period provides a critical opportunity for interventions to improve health, but, historically, a prohibition on federal Medicaid coverage during incarceration has created barriers to care after release. To address these barriers, many states have applied for Medicaid section 1115 reentry waivers to expand access to Medicaid coverage for certain pre- and post-release services. These waivers present an important opportunity to improve care access during reentry, but, if driven by carceral entities, they run the risk of replicating carceral systems that harm health. This article advocates for an alternative approach: centering the perspectives of people with lived experience of incarceration in all aspects of waiver design, implementation, and evaluation. Drawing on personal and professional experience, the authors explore the value of centering lived experience in health policy and identify successes, challenges, and lessons learned from California’s waiver. This article also explores the importance of centering lived experience in information sharing and privacy practices in waiver implementation. Across these areas, waivers driven by lived experience can promote dignity, autonomy, and wellbeing, dismantling carceral approaches that reinforce stigma, erode trust, and perpetuate inequities.