This dissertation explores the experiences of individuals sentenced to private probation for misdemeanor offenses in the Municipal Court of Atlanta. Through 33 in-depth interviews with people placed on probation and over 50 hours of court observations, I investigate how perceptions of procedural justice and legal cynicism shaped views of system legitimacy. While the procedural justice and legitimacy framework suggests that perceptions of procedurally fair treatment leads to increased perceptions of legitimacy, my findings reveal a more complex reality. Namely, for my participants, the financial incentives of private probation exacerbate feelings of legal cynicism, which undermines perceptions of system legitimacy. At the outset of this research, I asked two related questions: 1) what role does legal debt play in shaping perceptions of procedural justice for people sentenced to misdemeanor private probation? 2) What impact does this perception have on the broader criminal legal system? To answer the first question, I identify three domains of procedural justice that matter to defendants: relational fairness (voice, impartiality, and dignified treatment), procedural fairness (transparency and accessibility, procedural hassle), and substantive fairness (outcome expectations and proportionality). These domains are conceptualized through participant responses to interview questions regarding their perceptions of procedural justice in the misdemeanor system. To answer my second research question, I draw on the interview data and previous literature to develop the concept of legal cynicism. Participants consistently distinguished between fines, which many viewed as legitimate consequences, and private probation fees, which most saw as exploitative. Even when defendants experienced procedurally fair treatment from individual system actors, the perception that “the system just wants money” created deep skepticism about its fundamental legitimacy. Subsequently, I propose that legal cynicism among participants is shaped by two primary factors: prior exposure to the criminal legal system and perceptions of financial exploitation. This cynicism created a lens through which even procedurally fair treatment could not overcome concerns about system legitimacy. These findings challenge traditional procedural justice theory by demonstrating that when the underlying financial structure of the legal system is perceived as exploitative, legitimacy is challenged despite procedurally fair treatment. The dissertation contributes to scholarly understanding of procedural justice by highlighting how outcome-based factors like financial sanctions interact with process-based elements to shape perceptions of legitimacy in the misdemeanor context, particularly when private profit is involved in punishment.