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Incarcerated individuals with sex offense histories present a unique and distinctive set of challenges for correctional staff who support discharge and reentry planning. This paper will present a review of current challenges and practice strategies focused on safely and effectively transitioning individuals with sex offense histories from prisons and jails back into the community. Using multiple methods, including a scan of departments of correction policies and procedures, and interviews with key informants from an array of jurisdictions, we focus on best and promising practices, and accompanying evidence, across the discharge and reentry process: 1) the programming available to prepare individuals for release, 2) case planning strategies to support a “warm hand-off", 3) assessing systems and processes for the exchange of information between prison-based and community-based sex offender treatment providers and supervision personnel, and 4) practices to ensure continuity of care and supervision. We also explore practices designed to address the unique discharge planning and reentry challenges posed by special populations, including women, those in need of nursing home care, individuals with significant mental health and/or substance abuse treatment needs, and neurodivergent populations such as those with autism spectrum disorders or intellectual disabilities. Findings reveal best and promising practices in this critical period of corrections and rehabilitation.