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Research on court-imposed monetary sanctions has not yet fully examined the impact that processes used to manage court debt have on individuals' lives. Drawing from both interviews and ethnographic data in Illinois and Washington State, we examine how the court's management of justice-related debt affect labor market experiences. We conceptualize these managerial practices as procedural pressure points or mechanisms embedded within these processes that strain individuals' ability to access and maintain stable employment. We find that, as a result, courts undermine their own goal of recouping costs and trap individuals in a cycle of court surveillance.