Youth offenders often struggle to successfully return to their communities and schools after release from confinement. The reasons for this struggle are well documented, as is the fact that school engagement and success (before and after confinement) are closely associated with delinquency and recidivism. Despite this, little attention has been given to examining the specific school reentry challenges that reentering youth offenders face, as well as the supports and motivating factors that enabled some to succeed. In response, this dissertation analyzed the success stories of former youth offenders who returned to their schools from confinement, graduated, and remained out of the justice system. To do this, a single case study was conducted with four "successful" former youth offenders. Data were analyzed using thematic analysis, with this analysis yielding four central themes: (1) Managing and Balancing: Dealing with School Reentry Challenges; (2) I Did It, With Help: The Types and Role of Social Support; (3) No Other Choice: Motivating Factors for Reentry Success; and (4) It’s a Process: Sustaining Motivation for Reentry Success. The findings illustrated the school reentry challenges for former youth offenders and how social supports and motivation are both critical, and complement each other, for those achieving success. Furthermore, it was revealed that because reentry is a process with many challenges, failures, and setbacks, motivation must be sustained and persistent. This is done, in part, through embracing weakness and a lack of confidence in the ability to be successful in isolation. The participants in this study did not necessarily expect success, which led them to be more diligent in setting boundaries, sticking to strategies, and leaning upon others for help. In the end, the findings and recommendations provided in this study allow for schools to imagine how to improve their services for youth offenders and ensure that they become the protective factor that is so desperately needed. Doing so could significantly reduce the recidivism rates for youth offenders and provide significant cost savings to broader society.