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Staff members offer unique, and often unheard, perspectives on how reentry and desistance are framed in community corrections organizations. This qualitative study draws on semi-structured interviews and participant observation to examine how staff members shape trajectories to desistance through their interpretation of the program’s mission and their relationships with residents. Staff members at Smith House, a women’s halfway house in a major city in the northeast, were interviewed to explore their perspectives on the pathways women utilize on their journey to desistance. Results reflect that staff members differ on their definition of what it means to be “successful” at Smith House. Differences and similarities observed between line staff and administrative staff in terms of goals, job stressors, rule interpretation, and job satisfaction indicate the need for further research on how staff perceptions impact their clients’ reintegration process.