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This paper examines the intersection of legal financial obligations (LFOs) and financial precarity among U.S. parents involved in the criminal legal system. Drawing from interviews with 135 parents across Georgia, Minnesota, Missouri, and New York, the current study highlights how LFOs exacerbate existing economic challenges, affecting caregiving responsibilities and the ability to meet essential family needs. By centering parenthood in the analysis, the research provides a nuanced understanding of how LFOs disproportionately harm families. The study reveals that for many parents, LFOs force a choice between legal debt repayment and providing for their children, which can lead to further penalties, including extended supervision or incarceration for nonpayment. Findings from this study underscore the critical need for policy changes to reduce LFO burdens on parents, including transparency in determining ability to pay and exemptions for those reliant on public assistance. This research contributes to a broader understanding of how criminal legal debt may impact family financial precarity and intergenerational poverty in the United States.