Although prior research revealed that in noncorrectional and correctional settings, staff relationship style affects client outcomes, there has been little study of this effect for women offenders. The present study investigated effects of two dimensions of relationship style (probation or parole agent–reported supportiveness and punitiveness) on female clients’ reports of responding to interactions with their agents with anxiety, reactance, and a sense of self-efficacy to avoid a criminal lifestyle. Results of a longitudinal study of 330 women on probation or parole revealed that agent supportiveness elicited lower anxiety and reactance and higher crime-avoidance self-efficacy. Agent punitiveness elicited greater anxiety and crime-avoidance self-efficacy. Moderation effect analysis showed that punitive style was most related to anxiety and reactance for women at lowest risk for reoffending. In contrast, supportiveness was most related to positive outcomes for the highest risk women. The research findings suggest areas for future theory development and approaches to effective correctional practice.