<p>Extant research on reentry and reintegration increasingly recognizes that both are processes unfolding over varying lengths of time after contact with the criminal legal system. Yet, reentry research, including theory building, empirical work, and policy analysis, typically frames reentry as a singular event or a series of discrete episodes, missing reentry’s cumulative impacts over the life course. For example, studies compartmentalize reentry experiences along various dimensions, including type of facility (jail or prison), length of reentry period, or supervision status. Such distinctions, however, miss the person-centric conceptualization of reentry, meaning that any given study participant has potentially experienced one or more combinations of reentry over their lifetime, with varying degrees of success and challenges across multiple and intersecting life domains. Analyzing in-depth interviews with 20 formerly incarcerated men in the Northeastern United States, the present study advances understanding of the multidimensional pathways of reentry experiences. Our findings demonstrate that reentry is an ongoing process rather than a singular event, that reentry has cumulative impacts across intersecting life domains such as employment, housing stability, and family support, and that gradual shifts in outlook during reentry may lead to desistance. Our work contributes to theoretical and empirical understandings of the cyclical and perpetual nature of reentry and reintegration experiences across the life course.</p>