This article examined differences between young women and men who were incarcerated juvenile offenders with disabilities in Oregon in terms of the barriers they faced in their transition from the correctional system back into the community. Data were gathered on 72 females and 276 males, all of whom presented disabilities and who were participating in a statewide project to support their transition from the juvenile correctional system back into the community. Logistic regression identified four barrier variables as more likely to be descriptive of female juvenile offenders with disabilities: (1) a history of running away from home or previous residential placements; (2) a history of suicide risk; (3) prior abuse or neglect; and (4) parenting responsibilities. Four other barrier variables were less likely to be descriptive of the female juvenile offender: (1) a specific learning disability; (b) Attention Deficit Disorder/Attention Hyperactive Disorder (ADD/ADHD); (3) retained a grade while in public school; and (4) an inability to maintain employment. The results are discussed relative to the development of gender-specific services in both the juvenile correctional facilities and in transition from the facility to the community. (Contains 2 tables.)