The federal criminal justice system routinely requires convicted individuals to pay fines, restitution, and special assessments as part of their sentence. These criminal justice payments are an obligatory condition of federal community supervision, which a vast majority of convicted individuals are compelled to undergo. Although some of these legal financial obligations are intended to hold people accountable for criminal behavior and address crime victims’ financial losses, they also create a significant barrier to supervision success by imposing heavy economic burdens on those least able to afford them. The financial obligations imposed on the majority of federal criminal defendants both frustrate the practice of community supervision as well as create onerous and long-lasting criminal debt. The government’s inability to recover most financial legal obligations demonstrates the futility of continuing our current supervisory debt practices. Permitting courts to determine a financial assessment of a defendant’s ability to pay, allowing partial debt waiver, and creating an income-based fines and fees system would help ameliorate some of the crushing debt obligations resulting from community supervision. Unpayable criminal justice debt serves no one.