In practice, probation supervision involves integration of compliance monitoring, helping individuals achieve short-term goals (e.g., gain employment), and case management to address dynamic risk factors (Lutze, 2014; Taxman, 2002). The inclusion of practices related to evidence-based supervision creates challenges associated with managing a “dual-role” where officers are expected to engage in varying types of strategies that may at times be at odds with each another (Lutze, 2014). Regardless of the supervision style, probation agencies are required to manage compliance with the conditions of release and monitor individuals regarding adherence to their court-ordered conditions. Around 75% of individuals on probation and 62% on parole complete successful supervision (Kaeble & Bonczar, 2016). The number of supervision conditions affects completion rates, with the average individual having 13–17 court-ordered conditions and specific program requirements (see Taxman, 2012; Taxman & Thanner, 2004). With so many conditions to abide by, noncompliance is commonplace (Lattimore et al., 2016). When officers are able to incorporate evidence-based RNR practices in supervision rather than focus on compliance, they can improve success rates. In a meta-analysis of effective supervision models, Drake (2011) found that supervision aligned with RNR principles had a 16% reduction in recidivism compared with intensive supervision with treatment conditions or standard supervision frameworks. However, this study did not identify which supervision model contributed to positive outcomes or even identify the key characteristics regarding contacts, compliance monitoring, case management, or short-term progress strategies.