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The importance of family within the process of reentry has been well documented. Returning individuals often rely on family for material support, such as housing, and immaterial support, such as emotional bonding. Not surprisingly, research shows that high levels of family support and bonding significantly relate to successful reentry. Yet, with a small number of exceptions, few studies have assessed how family conflict—and not just the absence of, or changes in, support—relates to reentry outcomes. This gap in the literature is especially important to address as we know that individuals can experience family support and conflict at the same time. Using longitudinal data from the Returning Home Study, results of mixed-effects models show that family conflict is significantly related to increased odds of arrest during the reentry process, decreased odds of employment, and increased odds of substance abuse. Family support, on the other hand, did not significantly relate to these outcomes once family conflict was included in the models. These findings suggest that we need to consider how negative family dynamics may contribute to reentry outcomes differently than simply the absence of positive family dynamics.