--- - |2 Abstract During the last few decades, criminologists have identified several adult roles and statuses, including employment, positive family relations, and economic stability, as critical for promoting successful reintegration and desistance. Very few researchers, however, have investigated the conditions that serve to bring about these transitions and successes crucial for behavior change. As a complement to a burgeoning amount of literature on the impact of incarceration on health, we emphasize the reverse: Health has important implications for reentry outcomes and reincarceration. Informed by multiple disciplines, we advance a health‐based model of desistance in which both mental and physical dimensions of health affect life chances in the employment and family realms and ultimately recidivism. Investigating this issue with longitudinal data from the Serious and Violent Offender Reentry Initiative (SVORI) and structural equation models, we find overall support for the health‐based model of desistance. Our results indicate several significant pathways through which both manifestations of health influence employment, family conflict, financial problems, and crime and reincarceration. The findings highlight the need for implementation of correctional and transitional policies to improve health among the incarcerated and avert health‐related reentry failures. - 'Criminology, Volume 57, Issue 3, Page 544-573, August 2019. '