Transfer (or waiver) of juveniles to criminal court is one of the most extreme responses to serious youth crime. Although many states have recently revised their transfer statutes, and the number of juveniles prosecuted as adults increases each year, little research has been conducted to assess the correctional experiences of delinquent youth convicted in criminal court and sentenced to adult prison. Evaluations of such experiences are important to policymakers and juvenile justice officials who are considering juvenile transfers as a strategy for securing longer and harsher confinement for offenders. Based on interviews with 59 chronic juvenile offenders placed in state training schools, and 81 comparable youths sentenced to adult correctional facilities, this article presents a comparison of offenders' perceptions of their correctional experiences. Juveniles incarcerated in training schools give more positive evaluations of treatment and training programs, general services, and institutional personnel than do those youths in prison. Juveniles housed in institutions which emphasize security over treatment — i.e., prisons — are more often victimized during their confinement than youths in the treatment‐oriented training schools. Once placed in prisons, adolescent inmates are more likely to be victims of prison violence and crime from both inmates and staff. These research results suggest some paradoxical effects of the treatment‐custody distinction implicit in judicial waiver practices. The differential socialization into crime and violence for youths in adult prisons may increase the risks of having these types of behavior repeated by transferred youths once released.