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Understanding the processes and policies that undergird diversion program implementation is key to identifying and contextualizing potential areas of concern, including racial/ethnic or socioeconomic disparities that are linked to legal financial obligations (LFOs). This study assesses the flow of cases through Philadelphia’s ARD diversion program, with an emphasis on reasons for initial ineligibility determinations and program attrition (e.g., LFO non-payment), and potential sources of racial/ethnic and economic inequality. Combining data from the Administrative Office of Pennsylvania Courts (AOPC), Common Pleas Criminal Court Case Management System (CPCMS), District Attorney’s Office (DAO), and Adult Probation and Parole Department (APPD), we determine key factors that influence the rate of ineligibility determinations and program attrition for ARD referrals (and by demographic subgroups). Qualitative analyses of program documentation, stakeholder meetings, and ARD participant interviews and surveys further contextualize these results, which show that many individuals are determined ineligible for ARD or leave the program before completion (and for myriad reasons). The results support that there are actionable steps that can improve program entrance, completion, and expungement rates within diversionary contexts. This has important implications for reducing the collateral consequences of justice involvement, particularly for marginalized groups.