In prison and jail, individuals with mental illness often experience a series of traumatizing (or re-traumatizing) events that increase their mental and emotional vulnerability. These experiences can create challenges with re-entry into the community. This training is designed for those who are or will be working with individuals living with mental illness who have a justice-involved history. Specifically, it explores cultural adaptations common during incarceration, and how these behaviors can influence the adjustment to “living on the outside”; it then provides tools for engaging and assisting these individuals as they transition back into community settings. Case scenarios are presented, as well as a “Prison Survival Quiz” that reviews some of the situations/decisions that an inmate may encounter when incarcerated, and the impact of those decisions after. Attendees of the training will leave with a clearer understanding of what it means to be acculturated into prison life, and the steps that direct service staff can take to help individuals re-acclimate after release.