In 2010, Harriet Cleveland was imprisoned in Montgomery, Alabama for failing to pay thousands of dollars in fines and fees stemming from routine traffic violations. More than thirty years after a series of Supreme Court rulings outlawed debtor's prisons, Ms. Cleveland's case brought national attention to both the sheer amount of legal financial obligations (LFOs) that could be accrued, even in cases without a criminal conviction, and the potential consequences of non-payment. But it has been nearly impossible to know how common Ms. Cleveland's experience is because of a general lack of individual-level data on the incidence and payback of LFOs, particularly for non-felonies. In this vein, we gather about two hundred thousand court records from Alabama over the last two decades to perform the most comprehensive exploration of the assessments and payback of LFOs to date across an entire state. Consistent with conventional wisdom, we demonstrate that the median LFOs attached to a case with a felony conviction nearly doubled between 1995 and 2005, after which it has remained roughly steady. But a felony-centric view of criminal justice underestimates the extent of increasing LFOs in the United States. Our systematic comparison of LFOs in felony, misdemeanor, and traffic cases across Alabama demonstrates how the signficant debt Ms. Cleveland accumulated for a series of minor traffic offenses is not such an aberration. We show that only a minority of LFOs are assessed in cases where someone was convicted of a felony and incarcerated. Rather, most LFOs are assessed in cases without an imposed sentence, in cases with a misdemeanor or traffic violation, or even in cases that did not result in a conviction at all. These case records also reveal substantial heterogeneity in the assessment of LFOs - both within and across local judicial districts - even in cases in which defendants were convicted on exactly the same charge.