A team of academic researchers, clinicians, prison administrators and undergraduate and graduate students came together to conduct an evaluation of a pre-release discharge planning program in a women's prison facility. This paper describes differences between academic and corrections systems, adaptations needed in order to work within the correctional system, pragmatic and ethical issues addressed by our team, and the joys and benefits we experienced doing the project. Team members who had not previously worked in a prison setting found it an extraordinary, transformative learning experience in spite of the challenges.