Within the last decade, scholars and practitioners alike have noted a surge in the use of legal financial obligations (LFOs) in criminal justice processing. These include fines, fees, and costs that are applied to defendants’ cases from “upstream” agencies such as police departments to “downstream” agencies including jails, prisons, probation and parole agencies, and treatment centers. Legal financial obligations can be large, and the result is that outstanding balances often accumulate into unwieldy amounts of criminal justice debt. Recently, a small handful of qualitative studies have shown that these LFOs and debts can have adverse impacts on returning prisoners and their families, including increased stress, strained family relationships, worsened depression, and longer periods spent under criminal justice surveillance for those too poor to pay off outstanding balances. In addition, some of this work suggests that these financial obligations can increase the likelihood of returning to crime. This dissertation expands on the major contributions of these recent qualitative works by addressing the lack of quantitative research in this area. Toward this end, longitudinal data from the Returning Home Study (n=740) and structural equation modeling (SEM) techniques are used to test whether LFOs and debt indeed have adverse impacts on key outcomes of interest in reentry research, including family relationships, depression, justice involvement/entanglement, and recidivism. Findings reveal partial support for past research and theory. Legal financial obligations do not appear to have impacts on depression, family conflict, and several measures of recidivism on average. However, outstanding debt owed to community supervision agencies (i.e., probation/parole/mandatory community supervision) significantly increases the likelihood of remaining under supervision, which, in turn, increases the likelihood of returning to prison. Implications for decision-making bodies from state legislatures to corrections agencies are discussed. / Criminal Justice