Children and youth with mental health issues and learning difficulties are common in the juvenile justice system and finding ways to effectively rehabilitate, treat, and educate them is complicated, yet imperative. In this article, we examine the prevalence rates of mental health disorders in youth involved in the juvenile justice system, discuss the myriad challenges involved youth face, present differences related to gender and race/ethnicity as well as provide information associated with how best to assist these youths. Additionally, significant influences such as cultural, behavioral, and educational issues related to detained youth will be presented. Developing a better understanding of the challenges faced by detainees as well as recognizing barriers to treatment and rehabilitation are key. Further, identifying effective support systems for rehabilitation and transition are addressed.