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Background: People face numerous barriers to reentry and community integration following incarceration, and these obstacles manifest themselves as barriers to economic stability, housing security, healthcare, community acceptance, and educational attainment, ultimately leading to poor health. This study aims to understand healthcare needs of reentrants post release within the unique political and service context of Miami Dade County, FL, and seeks to uncover the structural facilitators and barriers to sustaining health during reentry. Methods: We report on a subset of data from a larger reentry asset mapping project. We conducted a qualitative thematic analysis based on 12 semi-structured interviews with community stakeholders, including reentrants who were released in the past year (n = 5) and with community providers who have provided support services to returning citizens for at least one year (n = 7). Narratives were coded through an iterative process using NVivo software and were analyzed using the general inductive approach. Results: Three themes emerged from the analysis: (1) social and structural barriers and facilitators to health during reentry, (2) challenges with medical care following release, and (3) long-term impacts of receiving poor healthcare in prison. Reentrants describe the carceral environment as non-conducive to health and cite an urgent need for systemic change within correctional institutions to promote their well-being. Respondents identified substance use disorder (SUD) treatment, trauma informed therapy, and chronic disease management as the primary healthcare needs of reentrants, and cite social support, stable housing, education, and employment as the key social and structural needs upon release. Conclusion: This study identifies prevalent resource gaps in Miami Dade County during reentry. Respondents advocate for more inclusive governmental housing programs, Medicaid expansion, and more holistic reentry programs to support reentrants. Understanding the barriers and facilitators to health during reentry can inform future interventions to better support reentrants in their transition post-incarceration. [ABSTRACT FROM AUTHOR]