With the recent approval of the Second Chance Pell Program and a proposal to reauthorize the Higher Education Act, a shift is occurring in favor of expanding educational opportunities to incarcerated adults. As reform to the criminal justice system becomes a focus, there is an immediate need to study the dynamic relationship between community colleges and correctional facilities. In response, this study set out to understand how a partnership between a community college and county sheriff's department can affect the daily decisions and implementation of a vocational program. This study asked: How do a community college and the local sheriff's department partner to make decisions and implement a correctional education program? Additionally: What factors facilitate or impede the success of the partnership? This study used the case study approach to better understand the implications of a longstanding partnership between a community college and county sheriff's department that oversees the jail operations. Four key administrative staff members were interviewed, and numerous administrative documents were analyzed. Results highlight how the collaborative decision making nature of this partnership contributes to decision making. Secondly, interview and document analysis exposed how cultural differences impact decision making. This study adds to the limited research on partnerships between community colleges and correctional facilities; therefore, informing policymakers and administrators on how to best serve incarcerated students. This study also provides implications for future partnerships between community colleges and county sheriff's departments. Suggestions on how to leverage collaborative decision making to battle cultural differences are discussed.