Purpose This study examines the effect of arrest on delinquency at a salient transition during adolescence: the move from middle to high school. The effects of arrest on delinquency via deviant attitudes, attenuation of prosocial bonds, and involvement with deviant groups are examined to determine whether labeling processes and consequences vary for youth in 7th, 8th, or 9th grade. Methods Longitudinal data from a school-based survey are used to estimate the direct and indirect effects of arrest on delinquency for youth in 7th, 8th, and 9th grades. Wald tests are used to determine whether there are significant differences across cohorts. Results While arrest is associated with increased delinquency for all three grade cohorts, effects are most detrimental for 7th graders. For these youth, arrest exerts a significant, direct effect across all intermediate outcomes and accounts for increased delinquency via neutralizations, weak school commitment, delinquent peers, and negative peer commitment. Although some of these mediators explain increases in delinquency among 8th and 9th graders, effects are smaller in magnitude. In total, arrest is associated with a 132 % increase in delinquency among 7th graders, but only a 55 % increase among 9th graders. Conclusions The findings indicate that the effects of arrest become less severe as youth age and delinquency becomes "normative." It is recommended that the unintended consequences of arrest should be carefully considered-particularly for younger youth as they relate to deviant attitudes and commitment to and involvement with delinquent peers-and interventions should be coupled with efforts to improve prosocial attitudes and relations to prevent future delinquency. Although the effects of arrest wane over time, they do not disappear, and youth continue to experience consequences associated with arrest after they transition to high school.