More than 8 in 10 returning prisoners have chronic physical, mental, or substance abuse conditions. This research report demonstrates how each of these health conditions is associated with distinct reentry challenges and service needs. Using a representative sample of men and women from the Urban Institutes multistate Returning Home study, we assessed health status at release and gathered data on reintegration experiences through multiple postrelease interviews. We present typologies of reentry experiences by health status, detailing individuals' success finding housing and employment, reconnecting with family, abstaining from substance use and crime, and avoiding reincarceration. Using these typologies, we conclude with targeted strategies to improve service delivery and reentry outcomes.