Implementation research is emerging in the field of corrections, but few studies have examined the complexities associated with implementing change among frontline workers embedded in specific organizational cultures. Using a mixed methods approach, the authors examine the challenges faced by correctional workers in a work release correctional facility during their transformation into a reentry center. Findings reveal that staff report a low readiness for change while observational and interview data confirm that staff attitudes and accompanying behaviors undermine efforts to provide a humane environment for reentry. This study illustrates the value of using quantitative and qualitative methods to understand and measure key organizational issues that affect the ability to alter the milieu for delivering services. The authors examine how inertia regarding reforms is not due to the nature of the reform but rather to the culture of the organization and how important it is to address organizational culture. They also highlight the importance of integrating interactional and routine practices among frontline workers as part of a strategy to reform correctional facilities. (Contains 5 notes, 1 table, and 2 figures.)