Illinois’ prison work release centers, called Adult Transition Centers (ATCs), connect incarcerated people to vocational opportunities to support successful community reentry. As part of a larger process and outcome evaluation of Illinois ATCs, we conducted 16 interviews with Illinois Department of Corrections administrators and ATC program staff to understand their perceptions about ATC operations and purpose as well as their perspectives on ATC effectiveness, strengths, and weaknesses. Participants noted that ATCs offer individualized behavioral health treatment, build educational and vocational skills, and provide promising employment prospects upon release. Interviewees believed they fostered positive relationships with work release participants, contributing to their success. However, interviewees believed the effectiveness of work release programs may be reduced when participation is relatively short and community-based social support services are insufficient. Relevant research and some considerations of our findings are discussed.