Juvenile crime and violent victimization continue to be significant social problems (Fitzpatrick, Piko, Wright, & LaGory, 2005); in that, adolescents, females in particular, are likely to participate in health related risk behaviors as result of having been victimized or exposed to a violent environment. Specifically, abuse, neglect, sexual molestation, poverty, and witnessing violence are well known risk factors for the development of trauma-related psychopathology and poor outcomes relative to delinquency, drug and alcohol abuse, and HIV risk behaviors (Steiner, Garcia, & Matthews, 1997). HIV infection is a common public health concern disproportionally affecting adolescent African American female detainees. This unique population has a serious history of violence exposure, which subsequently tends to lead to engaging in risky sexual behaviors, mental health problems, and abusing substances. Also, as a result of little to no intervention, this population is recidivating at an alarming rate, a problem that may further exacerbate the expression of health-related risk behaviors among African American adolescent female detainees. The authors briefly describe a pilot program to be implemented in the juvenile justice system that is based on the Model of Accumulated Risk (Garbarino, 1996), Bronfenbrenner's Ecological Model (1994), and the Positive Youth Justice Model (Butts, Bazemore, & Meroe, 2009). The program proposes to reduce risky sexual behaviors, teach alternatives to abusing substances, treat mental health concerns, and reduce the rate of recidivism through "positive youth development", PYD (Butts, Bazemore, & Meroe, 2009). Tying elements of wraparound services and reeducation together, this program addresses salient concerns that may have an impact on an adolescent detainees' success following their release from prison in a holistic manner.