This policy brief uses data collected from the Returning Home study to examine the employment experiences of male prisoners returning to Chicago. Findings indicate that few prisoners had access to job training while in prison and the vast majority wanted job training and assistance upon release. Respondents expected that finding a job would be difficult, and these predictions were accurate, with relatively few sample members employed within the first several months after release. Over time, an increasing number of respondents found some type of job, although the share of those who were employed full-time did not increase. Respondents who had worked before prison, who had been on work release, and/or who thought their neighborhood was a good place to find a job had more success securing and maintaining employment. Those with a history of substance abuse and parole revocations were less successful at both finding and keeping a job. Most of the respondents who obtained employment after release reported satisfaction with their jobs in every area but pay.