Objective: This paper examines how formerly homeless adults with serious mental illness living in Housing First (HF) and “treatment first” (TF) supportive housing programs experience employment. Research questions include: How do these individuals experience employment in the context of their mental health recovery? What do they perceive as the benefits of and obstacles to attaining employment? Are there programmatic differences in their employment experiences? Method: Case study analyses of data from a federally funded qualitative study were conducted of 40 individuals purposively sampled from HF and TF programs. Data were independently analyzed and consensually discussed to develop cross-case themes. Results: Three themes emerged: (a) the meaning of work, (b) working within the system, and (c) balancing treatment requirements and work. While none of the study participants had full-time jobs, more HF program clients had part-time employment than their TF counterparts. Of the 12 employed participants, all but 2 worked within their respective programs. Participants in both groups described similar benefits of obtaining employment, but TF program requirements inhibited job-seeking. Conclusions and Implications for Practice: These findings provide insight into the challenges of obtaining employment for formerly homeless individuals with serious mental illness residing in supportive housing. Despite the motivation to work, individual, structural, and organizational factors impeded employment. To address this problem, factors at each of these levels will need to be considered. Interventions such as supported employment offer promise to supportive housing programs committed to employment as a contributor to recovery.