A growing body of literature has documented the dismal outcomes of youth placed in juvenile correctional facilities (JCFs) upon their return to the community. However, very little is known as to how well equipped are the youth with the necessary skills for reintegration. In the current study, the authors examine self-reports of readiness for independent living among adolescents in correctional settings on the verge of leaving care, and explore how individual, placement, and social support characteristics predict such perceived readiness. A sample of 116 adolescents (aged 15-20) placed in Israeli JCFs responded to structured self-report questionnaires. The results indicated that most adolescents perceived their readiness to leave care as high, with girls showing significantly lower levels of perceived readiness when compared with boys. Higher levels of self-esteem and optimism as well as support from peers and staff were related to better readiness. From these findings, implications for theory and practice are proposed.