We apply the continuum of moral harms as described by Litz and King (J Trauma Stress 32:341–349, 2019), ranging from moral distress to moral injury, to understand the impacts of correctional officer (CO) interpretations of prison, recognizing how experiencing prison work informs their personal views. In the current study, we analyze data from 93 COs with a maximum of 2 years of work experience, to understand how, reflecting on their occupational experience, they perceive the purpose of place of their work—the federal penitentiary. Findings reveal prison as a space that they believe should be rehabilitative but which is often adamantly perceived as not rehabilitative. Accordingly, these contradictory circumstances reveal most officers encounter workplace experiences that may be consistent with current conceptualizations of moral frustration, distress, or injury. Thus, we demonstrate how prison work can produce moral challenges for COs. We recommend further study into the conceptualizations of moral harm in prison work more broadly and how to inform proactive strategies to address sources of these deleterious experiences.