A tenet of the juvenile justice system is to rehabilitate adjudicated youth and set them back on a path to productive citizenship. Sadly, however, the structures used to support this aim often result in continued movement away from value and contribution. At its most fundamental level, youth incarceration increases exposure to deviance which is known to reinforce negative attitudes and behaviors (Nance, 2016). In addition, juvenile incarceration can deter employment (Fedders, 2016) and heighten the chances of a youth becoming a school dropout (Farn & Adams, 2016). Fortunately, the utilization of transition practices can alter this course trajectory. Need for Transition Services Adjudicated youth often struggle with transitioning from a secure placement back to school. Many students face emotional hardships and stigma due to treatment from peers and instructors (Nance, 2016). Such circumstances can result in the reinforcement of a youth's negative behaviors and his or her resentment toward authority (Fedders, 2014). Factors such as these make school achievement a seemingly insurmountable task, particularly for those who already struggle academically. Consequently, researchers estimate that as many as two thirds of adjudicated youth drop out of school after being released from custody (Sweeten, Bushway, & Paternoster, 2009). Characteristics of Juvenile Offenders Estimates show that youth with special needs are between one-and two-thirds of the incarcerated juvenile population, the majority qualifying under the emotional disturbance (hereafter referred to as emotional and behavioral disorders [EBD]) and learning disabilities (LD) designations (Mallett, 2009). In fact, individuals in the juvenile justice system are 6 times more likely to have EBD than their nonadjudicated peers (Gagnon, Barber, Van Loan, & Leone, 2009), a factor that correlates with low academic achievement. Overall, only 20% of adjudicated juveniles graduate with a traditional or general education diploma (GED; Farn & Adams, 2016). Youth with EBD, however, trail even further behind as they are 61% less likely to earn a traditional diploma or GED in custody as compared with their peers without disabilities (Cavendish, 2014). Mental health is also a concern for many individuals in the juvenile justice system. Estimates reveal that between 60% and 70% of adjudicated youth have mental health disorders (Skowyra & Cocozza, 2006). In their review of the literature on risk factors of incarcerated youth, Pyle, Flower, Fall, and Williams (2016) reported that adjudicated youth were often victims of trauma and were highly susceptible to conduct disorder, anxiety, depression, and substance abuse. Youth with EBD in particular often have histories of abuse, neglect, and experience with the child welfare system (Malmgren & Meisel, 2004), all of which can contribute to or catalyze mental health disorders.