This article examines staff discretion in permanent supportive housing facilities run by a nonprofit agency claiming to use a Housing First approach. Field observation, archival data, and individual and group interviews with staff and clients were examined to better understand agency processes involved in intake, sanctions, and disposal of clients to evaluate Housing First fidelity. In their day-to-day interactions with clients, frontline workers' discretion is affected by working conditions such as lack of resources and heavy workloads, as well as by demands placed on the agency by members of its task environment. Implications for Housing First programs and homeless clients are discussed.