In this study, the authors examined the facility-to-community transition experiences--focusing specifically on employment--of 531 incarcerated youth following their release from Oregon's juvenile correctional system. They gathered data on the sample while these youth were still in custody and then every 6 months through phone interviews to describe the participants' community work, educational, and living and social experiences of the study participants. The authors documented the participants' return to the juvenile correctional system and entry into the adult correctional system from extant state databases. In this study, being employed at 6 months postexit was related in a marginally statistically significant manner (p = 0.07) to remaining in the community and out of the correctional system at that same point in time. Generally, young men, participants without special education disabilities, those youth committed to the juvenile correctional system for person-related crimes, and individuals who were not gang members exhibited better employment outcomes. Services provided by mental health agencies and other social service agencies were inversely related to employment rate, but substance abuse treatment and completion of career/vocational classes while in custody were positively related to selected employment outcomes. The results suggest that individualized job placement and support services should be offered to members of this population upon their parole to the community--with special attention paid to distinct subgroups, such as young women, juvenile offenders with special education disabilities, gang members, and those with a history of property crimes.