Much recent, national attention has centered on financial sanctions and associated debt burdens related to criminal justice. Scholars and practitioners alike have argued that financial debt among the incarcerated, in particular, exacerbates a transition home already defined by difficulties. This article takes a step back and assesses who is at risk of these adverse consequences in reentry by examining the extent of debt burdens that resulted from financial sanctions, its sources, and the individual-level factors that are associated with owing criminal justice debt. Relying on the Returning Home data (N = 740), results from descriptive analyses, logistic regression, and negative binomial models show that a large proportion of respondents owed debts and that debt was strongly linked with being mandated to community supervision. In addition, debt amount was predicted by employment, income, and race. Policy implications in the realm of financial sanctioning by courts and correctional agencies are discussed.