From the origin of Colorado prisons in the territorial facility established in 1871, notions of rehabilitation have existed—and they have repeatedly changed. “Defining Rehabilitation” looks at the broad scope of rehabilitative ideology and practice over time, including education, mental health treatment, parole and probation, and art therapy. “Prison Education” then delves into forms of schooling offered to historical prisoners. “Mental Health Treatment” uncovers how prison physicians and other personnel have dealt with mental health issues within the walls. “Parole and Probation” describes alternatives to incarceration and the barriers to success in such programs, especially probation and parole. “Art Therapy” concludes this section of our broad investigation by assessing the benefits of this often underutilized and underfunded method of rehabilitation.