Parole officers are an integral part of parolees’ reentry process and success. Few studies, however, have examined whether the quality of the relationship between parolees and their parole officer influences outcomes such as recidivism. This study assesses how recidivism is affected by the quality of the relationship that parolees have with their parole officers. Using the Serious and Violent Offender Reentry Initiative (SVORI) dataset, we use parolees’ perceptions of their relationship with their parole officer to determine whether they have established a positive or negative relationship, and whether these types of relationships differentially affect recidivism. Results show that parolees who have a negative relationship with their parole officer have higher rates of recidivism, while a positive relationship lowers parolees’ likelihood of recidivating. An implication of this study emphasizes parole officer training that develops positive, high-quality relationships with parolees. Further implications are discussed below.