Transitioning from jail or prison to community living frequently results in homelessness and recidivism. Access to benefits such as Supplemental Security Income (SSI) and Medicaid can increase access to housing and treatment and reduce recidivism. The authors review best practices for prerelease access to these benefits by using examples from five jails and four state prison systems. In these settings, approval rates for SSI applications averaged 70% or higher, with evidence of improved access to housing and reductions in recidivism. Success depends on the commitment of resources and leadership, ongoing communication, and monitoring of results.