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Scholars and practitioners alike have noted a surge in the use of legal financial obligations (LFOs) in criminal justice processing. LFOs can be large, and the result is that outstanding balances often accumulate into unwieldy amounts of criminal justice debt. A small handful of studies have shown that these debts have adverse impacts on returning prisoners and their families, including increased stress, strained family relationships, worsened mental health, and longer periods spent under criminal justice surveillance. This paper expands on the major contributions of these recent qualitative works by addressing the lack of quantitative research in this area. Structural equation modeling is used to test whether LFOs indeed have adverse impacts on key outcomes of interest in reentry. Findings show links between correctional debt and reincarceration and the results generally reveal partial support for past research and theory.