The North Carolina Workplace and Community Transition Youth Offender Program (YOP), recently renamed the Incarcerated Individuals Program (IPP), has proven to be effective in terms of its growth and expansion, the support of education directors across the correctional facilities, university collaboration, student evaluations, and a low recidivism rate. This article, drawn from a multiyear evaluation, explores what has contributed to that effectiveness. There are six major contributing factors: (1) Case managers actively including the YOP into case plans for students; (2) Education directors recognizing the effects the program had on students; (3) Instructors keeping on-campus course content in prison courses and accepting the demand to be "real" in their interactions with students; (4) Students articulating better educational experiences than ones they had before and using the coursework to critically understand their situation and, thus, motivate themselves to learn; (5) Program participation mediating the effects of prison by reducing opportunities to incur infractions and by helping to manage the stigma of prison post-release; and (6) The program using the annual evaluation to improve operations as well as to understand program outcomes. Analyses of other programs are needed to better understand higher education in prison, we think the experience of NC YOP is instructive for other programs in their efforts to promote effectiveness. (Contains 2 figures.)