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While some individuals have never been stopped by the police, others report frequent involuntary police stops from an early age. In over-policed neighbourhoods, some adolescents experience several police stops on a weekly basis. Such cumulative experiences at a young age can shape legal socialisation and have long-term unintended consequences. Drawing on data from four large-scale national cohort studies that surveyed individuals born in the UK in 1958, 1970, 1990, and 2000, this study examines whether repeated police stops during adolescence are associated with long-lasting traits related to trust in legal authority and cynicism about social norms in adulthood—and whether such consequences vary across different birth cohorts and socio-political contexts. Using group-based trajectory modelling, I analyse cohort differences in police stop trajectories from 1969 to 2019, as well as their association with developmental trajectories of legal cynicism. Findings underscore repeated police stops during adolescence as a form of cumulative disadvantage with significant life-course implications.