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High Quality relationships between officers and supervisees in probation and parole are posited to promote positive outcomes. However, only a few studies have attempted to characterize their relationship features to allow empirical assessment of the impact of relationship quality. This may stem from the challenges that probation officers assume two distinct and sometimes conflicting roles: law enforcers (compliance) and social workers (connecting with resources). Even fewer studies look into relationship change overtime, and our study fills in this gap. We examine 1266 unique video interactions of 467 unique officer-supervisee pairs in a 12 month period. Of these, 168 officer-supervisee pairs have 4 videos whereas the remaining pairs have at least 2 videos. We will present findings comparing a) how do officer-supervisees with different length of relationship differ in the DRI scores; b) how do scores of the three dimensions on DRI change over time for the same pair of officer-supervisees in a 12-month period controlling for their length of relationship. These findings offer empirical insight into the temporal dynamics of officer–supervisee relationships and have the potential to inform training and policy efforts aimed at enhancing supervision effectiveness and outcomes