In August 2015, the U.S. Department of Education announced an experimental program that would allow higher education institutions to offer postsecondary educational programs inside adult prisons. The U.S. Department of Education's Second Chance Pell Grant Experimental Sites Initiative would allow state and federal incarcerated students to apply for federal financial aid. On June 26, 2016, the University of Baltimore (UB) was selected to participate in this program in partnership with the Maryland Department of Public Safety and Correctional Services. UB was among 67 other colleges/universities selected nationwide to offer a postsecondary correctional education program through federal Pell Grant funding. As a new program at the university, UB's Second Chance College Program, required a major process of planning and implementation. As such, the implementation of one of the first Experimental Sites programs successfully launched in August 2016. This article provides an overview of the history of postsecondary correctional education programs, a review of the literature on the effectiveness of these efforts, an overview of our program, and a description of our implementation process, challenges, and lessons learned on how to maintain a successful program.