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Existing research has identified numerous collateral consequences and barriers that come as a result of felony criminal records. Those with records face discrimination from landlords and employers, social stigma, exclusions from government benefits, restrictions on civic participation, and a range of other obstacles operating to hinder (re)integration. Furthermore, extant research suggests that much of the behavioral- or skill-related reentry programming provided to this population is viewed pessimistically by participants. This paper contends with a relatively rare form of support for those with felony records: guaranteed income. Through a qualitative analysis of interviews with criminalized individuals receiving monthly cash transfers in Gainesville, Florida and Durham, North Carolina, this paper examines the promises and pitfalls of direct cash assistance. In particular, this paper explores both the material and non-material impacts of unrestricted financial assistance, while also illuminating the inadequacies of interventions designed to change people rather than their circumstances.