The Second Chance Act and the Individuals with Disabilities Education Improvement Act encourage juvenile justice personnel to collaborate with not-for-profit organizations, employers, and community schools to provide incarcerated girls with disabilities transition support to reenter their community after incarceration. The "Career and College Fair" and "Dress Your Best" activities that are part of the Helping Offenders Prosper through Employment (HOPE) program are concrete examples of ways to prepare incarcerated girls with disabilities for employment while they are in custody. In this article, transition coordinators in correctional facilities and special educators will find recommendations they can use when working in juvenile justice settings to help girls with disabilities transition from confinement to their homes and communities, and to increase their chances of becoming employed.