This study evaluated the characteristics related to a successful reintegration among youth from a residential facility. Specifically, this study describes the transition skills of youth at departure in five areas: (a) education and employment goals, (b) self-determination skills, (c) social support, (d) life skills, and (e) hopefulness. Further, self-report and teacher ratings of youths' self-determination and life skills were examined to determine possible differences in perception between youth and their school and Family Teachers (house-parents). One hundred four youth departing the Boys Town Treatment Family Home residential program participated in the study. The majority of youth reported average to above average skills in the five domains. However, significant differences were found between youth and schoolteacher reports of self-determination skills. The results indicate the need to provide transition services related to success post-discharge, including individualized transition plans and family involvement during treatment.