Most of the respondents had some employment experience prior to entering prison, typically in low-paying jobs for short periods, supplemented with illegal income. While in prison, less than one-third of respondents participated in programs designed to improve educational levels and job skills. All respondents participated in a prerelease program, with the majority reporting having received information on finding employment. Less than half of respondents believed it would be easy to find a job after release, and the majority wanted help in job training and finding employment after release. In the first few months after release, very few respondents were employed for any period of time. Those who did find employment were in low-skilled, low-paying jobs. Over time, the number of respondents who found jobs increased, although the job types remained the same. At each interview, respondents who were employed were satisfied with their job, except for the low pay. Respondents who had been involved in work-release jobs while still in prison worked more weeks after release, suggesting that expanding work-release programs to more inmates might increase workforce participation after release. Respondents with substance abuse problems and posttraumatic stress disorder were more likely to have difficulty becoming employed. Clearly, gainful employment is a significant issue for released prisoners returning to Chicago, and they want help in dealing with this problem. These findings are based on data collected at the prerelease interview (n=400), 4 to 8 months after release (n=205), and 16 months after release (n=198). 1 figure, 1 table, and 14 notes