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Criminal justice contact is a key stratifying institution in American life. By the close of 2020, almost 3.9 million non-incarcerated people were under community supervision (probation or parole), representing nearly 68% of the adult correctional population. Although the number of people incarcerated has declined since the Great Recession, alternatives to incarceration may introduce new pathways to inequality because compliance with court-ordered diversionary and rehabilitation programs rely heavily on access to resources such as money, information, and time. While there has been a considerable expansion of literature on the consequences of monetary sanctions imposed at sentencing, less is known about how alternatives to incarceration can produce other financial punishments that intersect and amplify inequality within the criminal legal system. In this paper, we show how shadow costs – i.e. financial outlays and expenditures not immediately quantifiable by the state but nevertheless ordered as a part of a reentry or rehabilitation treatment program -- financially burden defendants and probationers beyond the monetary sanctions imposed by courts. Our findings reveal that these shadow costs structure a bifuricated system of justice that facilitates the creation of markets for freedom that are dependent on poverty and inequality.