This study gathered information about adults with disabilities who were served with special education services during high school and incarcerated after high school, on their job preparation plan and explored the effects of that preparation on the individual's perception of successful transition after high school. It also investigated what, if anything, could have been done in high school to prevent their entrance or continuation in the criminal justice system. Due to the difficulty in accessing this population, only three individuals were interviewed. However, the rich information provided from this study indicated that to help them live independently and successfully transition into adulthood and avoid incarceration, they needed the following supports: more teaching of practical skills while in high school to help them have better control of their anger and emotions, and help obtaining a job of interest, that would allow financial stability and skills. This information may be beneficial to teachers developing appropriate Individualized Transition Plans. This information could allow educators to more effectively prepare their students to transition effectively and prevent them from becoming incarcerated.