The growth in the population of women on probation and/or parole has prompted the need for research that examines static and dynamic risk predictors for recidivism among them, particularly substance use and negative peer associations. Using a longitudinal study of 402 drug-involved and justice-involved women on probation/parole in 16 Michigan counties, this study employed the Dual-Role Relationship Inventory—Short Form (DRI-SF) and personal characteristics to examine how the perceptions of women under community supervision regarding their supervising officers correlated to risks for substance use and negative peer associations. We found those perceptions to be robust predictors of substance use and negative peer associations among our sample. The dynamics of that correlation are discussed, as are implications for practice.