The author details three case histories of prisoners, showing that the educational experience can promote a positive adjustment by inmates whose coping capacity is limited and whose careers include chronic misbehavior. The case histories reflect two sequences. In the first, the inmate as student becomes enticed by educational content or subject matter. In the second, the educational process provides the inmate with a supportive relationship with a teacher who is a prison staff member. The author argues that the regeneration of prisoners could be facilitated if prison staff members are perceived as generalists whose expertise can be used in a team approach to helping prisoners. Additionally, the author argues for better recordkeeping to document prisoners' positive behavior and a reward system for prisoners who demonstrate regenerative behavior.