Prior studies establish a link between incarceration and stress-related health, but relatively little is known about perceived stressors among current and former prisoners. To better understand the stress-related experiences of this population, in-depth interviews were conducted with 25 former inmates in upstate New York and northeast Ohio in 2012 and 2013. Participants were asked about their health during and after prison, with all participants describing aspects of their incarcerations as stressful. The most commonly identified primary stressors (i.e., stressors while incarcerated) were interactions with correctional officers, interactions with medical staff, and fear of other inmates. Post-release, employment troubles emerged as the most cited secondary stressor. Surprisingly, few participants described feeling stigmatized following their imprisonment. Findings carry implications for the long-term health and well-being of ever-incarcerated individuals and point to the need for further research, both quantitative and qualitative, on stress-related health among correctional populations.