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Decades of hyper-incarceration have resulted in a generation of Americans living behind bars well into middle-age. Moreover, many of these older incarcerated individuals are now reentering their communities having to reestablish social, economic, health, and housing connections that withered during extended confinements. In this chapter, we overview the aging of the American incarcerated population and the challenges that older incarcerated men, in particular, face upon reentry. To give the issue voice, we present an interview with Kurt Danysh, executive director of the non-profit organization Tomorrow’s Neighbors, focused on the reentry challenges and promising solutions for older incarcerated men. Both Mr. Danysh and the interviewer, Divine Lipscomb, have lived incarceration experience and share their thoughts on how this has shaped their post-incarceration advocacy and support for peer-led reentry programming. In the past year, Mr. Danysh opened a unique peer-led reentry residence, The Cumberland House, to provide reentry services and informal social support for older, recently-incarcerated men. We conclude with an update on the house and how an interdisciplinary group of Penn State researchers are evaluating the network mechanisms underlying this unique program.