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Intensive supervision probation (ISP) programs achieve many correctional goals while maintaining public safety, regaining both popularity and promise in the correctional landscape. While widely adopted by correctional agencies and seeming to address public safety concerns, much remains to be unpacked regarding the process of this type of supervision. Prior research has indicated that supervisor/client dynamics can be indicative of successful supervision, where this research seeks to build upon exploring a more intensive model for a high-risk population. Relying on interview data from a sample of 25 individuals under probation and 19 supervising officers, this study explores the dynamics of the supervisor/client relationship within an intensive supervision with services program. With promising indicators of the value, time, and resources identified in this smaller caseload model, the study seeks to further explore how the relationship experience may vary by supervisor and client characteristics. Thematic analysis guides the research questions by exploring overall relationship experiences and conducting additional subgroup comparative analyses. Results indicate strongly perceived value of supervisor/client relationships, particularly in comparison to other supervision experiences. These findings provide an optimistic outlook toward the dynamic of supervision success and how positive supervision relationships may contribute toward longer-term success for individuals on probation.