Best practices in juvenile probation focus on individualized treatment, yet youths’ perceptions of the role probation should play (e.g., law enforcement) have been largely overlooked in this process. This study used self-reported data from 110 racially/ethnically diverse youthful probationers in 2 jurisdictions. The youth reported their perceptions of the role probation plays, their beliefs about the role probation should play, their technical violations, and their delinquent offenses. The results of Poisson regression analyses indicated that when youths’ beliefs about the role probation should play aligned with their actual experiences on probation, they committed fewer technical violations and engaged in less delinquency. That is, compared with youth whose beliefs were incongruent with their experiences, youth whose beliefs and experiences were congruent committed fewer technical violations and delinquent offenses. Youth have varying expectations for how their juvenile probation officers will treat them, and individualizing treatment to ensure that probation officers and juvenile probationers are on the same page may reduce technical violations and delinquency. Altogether, this study suggests that youths’ perceptions of probation may matter in the probationary process. (PsycINFO Database Record (c) 2019 APA, all rights reserved)