Due to increasing recognition of the collateral consequences associated with monetary sanctions, fees have begun to occupy a prominent place in critical debates. This is especially true for community corrections, where multiple fees are assessed and collected. However, the agency-level perspective has largely been omitted, especially regarding how the current landscape may facilitate—or impede—reform. Using self-report data from a state-wide sample of Chiefs of Probation and Parole, this paper provides a new perspective on the complex interplay between the policy and practices surrounding monetary sanctions. Responses suggest that the practices and philosophies surrounding the collection of fees vary significantly between jurisdictions. This obligation is also reported to challenge the traditional roles of probation officers by limiting discretion and complicating the existing tensions between their treatment and control-oriented responsibilities. Some respondents indicated meaningful reliance on fee revenue for operational and treatment budgets. Implications for policy reform, especially considering the variation observed in this single state, are discussed.