Both personal experience and parental attitudes shape youths’ attitudes toward the justice system. The present study tested the influence of (a) youth rearrests and (b) parents’ attitudes toward police on trajectories of youthful offenders’ attitudes toward police over 3 years. Among a sample of 317 first-time male juvenile offenders and their mothers, group-based trajectory modeling identified 4 trajectories of youths’ attitudes toward police over the 3 years since the youths’ first arrests. Mothers with more positive initial attitudes toward the police were more likely to have sons who were part of 1 of the 2 positive attitude trajectory groups than the 2 negative attitude trajectory groups. In contrast, youth rearrests were rarely associated with trajectory group membership, suggesting that a mother’s attitude toward the police may outweigh a youth’s own experience (via arrests) with the justice system in determining trajectories of his attitudes toward the police. Additionally, the present study tests whether parents’ own attitudes toward police are predicted by their children’s rearrests. We found that mothers whose sons were rearrested during the study period had more negative attitudes toward the police. The results add a novel component to our understanding of family attitude dynamics as related to perceptions of law enforcement and juvenile arrests. Overall, a family level perspective is necessary when considering the effects of rearrests on youths’–and their parents’–attitudes toward the police. (PsycINFO Database Record (c) 2019 APA, all rights reserved)