Restoring people with mental illnesses to community life after detention in jail is fraught with significant challenges. Many of these challenges mirror those faced by anyone else who has been detained in jail. Among these are the particular challenge of seeking gainful employment and financial support for day-to-day life. This challenge is intensified when individuals return from jail to impoverished communities where employment prospects are already limited for residents, and where either a criminal record or a mental illness creates still additional barriers to work. To understand these barriers more fully, this study examined the process of seeking employment among people with mental illnesses leaving jail. Seventeen individuals with a history of mental health problems and with recent jail incarcerations were recruited from either a community based employment program or a mental health service setting. The informants were interviewed using life history interview techniques. Results show that connections to the paid workforce were tenuous at best for these respondents, both before and after their jail detention. While psychiatric symptoms, addiction, and the lack of productive social connections were individual-level factors that affected employment, the most pernicious impediments were rooted in policy, community structures, stigma and other social and economic realities.. If employment interventions are to have any traction at all in these settings, interventionists need to dig for innovative ways to address these factors, which are not complications, but bedrock realities that undergird all else.