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This paper explores the influence of a first arrest on secondary delinquency among a cohort of first-time arrested youth in Florida. Specifically, we advance current empirical research on youthful offending and labeling theory by comparing the effects of first arrests that occur in school with those that occur outside of school on subsequent delinquency and school-based incidents and discipline. In general, prior research that examines the labeling effects of juvenile arrests on recidivism has assumed that any youthful arrest will have the same effect on recidivism. However, there are reasons to suspect that where youth offend—either on school grounds or in the community—may affect pathways to continued offending. Location of youthful offending may lead to variation in awareness of the deviant label, label internalization, and varying stigmatization or types of exclusion youth face after arrest (e.g., whether they are suspended or expelled from school). We explore these potential differential labeling effects of first arrests using unique longitudinal administrative data from Florida’s Department of Juvenile Justice and Department of Education. Based on the study’s findings, implications for future research, policy, and practice will be discussed.