This research brief discusses the health challenges faced by male prisoners being released to Chicago, Illinois. Three out of ten survey respondents reported having a chronic physical or mental health condition, but it is likely that even higher shares have health problems, given that many diseases can remain undetected in the absence of routine screening and medical care. Study participants had high expectations for maintaining good health after release, but few means of doing so: fewer than 10% reported a referral to health care from prison and over 80% were uninsured. One year after release, health problems were not linked to recidivism, but mental illness was associated with increased substance use and unemployment.