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During the late 20th century, imprisonment rates in the United States saw unprecedented growth, leading correctional systems across the country to face widespread overcrowding and underfunding. Subsequently, policy makers sought out alternatives to incarceration for certain categories of offenses. Community supervision, such as probation, emerged as a popular solution to both reduce prison and jail populations as well as to generate revenue to fund the rapidly expanding legal system. With the rise in community supervision came increases in the number of people on probation for lower-level and non-violent offenses. The expansion of legal financial obligations (LFO) placed additional burdens on these persons, who disproportionately sit in lower socio-economic status brackets. Using data from the 1995 Survey of Adults on Probation (SAP), the current study adds to the literature on probation and LFOs in an important way. The SAP data contain information on the amount, frequency, and type of LFO. Thus, this paper examines the distinct types of LFOs to determine the differential burden that each type of LFO has on people on probation. This paper finds that of all types of fees, those associated with victim restitution are most likely to lead to missed payments, while those that generate revenues do not contribute significantly to missed payments. This paper discusses the implications of this for procedural justice and fairness.