Studies on the experience of reentry following confinement in a correctional facility for youth offenders is limited, and often quantitative. Using qualitative data gathered through structured interviews with 43 youths, this study examined potential risk and protective factors connected with parole revocation. For this sample, the most significant risk factors experienced were related to substance use, failure to receive needed mental health services, and poor relationships and communication with their parole officer. The findings underscore the importance of social support for youth recently released from secure care confinement, and specific examples of actions and approaches that can interfere with youths’ feelings of support are provided. Multiple policy and programming recommendations for the juvenile justice system are offered.