The Missouri State Penitentiary is a historical landmark in Jefferson City, Missouri (United States), being utilized for various purposes. The condition and aesthetics of the prison led to concerns in the community, creating a division of those in support of keeping the prison open for tourism and those in favor of demolishing it. This chapter documents various aspects of dark tourism, service operations management, and humanistic tourism management as it relates to the motivation to restore, or demolish, landmarks and cultural heritage sites. More specifically, elements of the prison’s operations and their impact on the community are explored.