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Prior research about prisoner reentry has identified an array of needs for formerly incarcerated men. In addition to concerns such as finding employment, securing housing, and complying with supervision requirements, they must find ways to form new identities and meaningful interactions with their families and communities. Termed strengths-based approaches to understanding prisoner reentry, scholars have examined the assets and resilience mechanisms that help people through the challenges of reentry, as well as how generativity, or a future orientation, and the desire to “give back” contributes to the desistance process. Yet, important questions remain about how men recently released from prison, as well as those who have been released for longer periods of time, identify opportunities for pro-social engagement with their families and communities. In addition, how do the men conceptualize notions of giving back to others, in contrast to the narratives of taking, and being a burden, during periods of offending, incarceration, and reentry? Through analysis of in-depth interviews with formerly incarcerated men, this paper examines how they identify and utilize avenues for giving back to their families and communities, and how expectations for masculinity frame their experiences.