When incarcerated youth face the prospect of reentering the community, they have many obstacles to overcome. There are often employment requirements in the terms of their parole or aftercare and if they fail to obtain and maintain employment, they may reenter the justice system instead of successfully reentering society. While research shows employment matters significantly for a successful transition from incarceration back in to the community, there is limited information on which programs or supports positively impact post incarceration employment. Practitioners have the challenge of locating and choosing curriculum, interventions, or supports with little to go on as to which are the best choices for their population in terms of teaching employability skills. This article focuses on services and supports for teaching employability skills at each of the stages of the juvenile justice process – before, during, and after incarceration. The psychological damage to youth resulting from incarceration is examined as well as the impact on obtaining and maintaining employment post incarceration. Resources are provided for practitioners to find evidence-based interventions and supports for the youth with whom they work. Calls for future research are detailed in the areas of programs and practices, desistence and recidivism, and community-based alternatives.