Single-site Housing First (HF) is associated with reduced publicly funded service utilization and costs and alcohol-related harm for chronically homeless individuals with severe alcohol problems. Many residents, however, continue to experience alcohol-related problems after their move into single-site HF. Thus, it is necessary to explore areas for program enhancement after individuals move into single-site HF. To this end, we collected qualitative data via 30 hours of naturalistic observation, staff focus groups (n = 3), and one-on-one interviews with single-site HF residents (n = 44), program staff (n = 7), and agency management (n = 4). Qualitative analyses were used to construct a conceptual or thematic description of residents’, staff’s, and management’s suggestions for program enhancement, which comprised 3 areas: (a) enhancing training and support for staff, (b) increasing residents’ access to meaningful activities, and (c) exploring alternate pathways to recovery. Development of programming addressing these areas may help residents continue to reduce alcohol-related harm and improve health and quality of life after their move into single-site HF.