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This paper examines how Black Caribbean youth perceive and experience the state-endorsed ‘Stop and Search’ program in London and then-ongoing ‘Stop and Frisk’ practices in New York City while on route to and from public schools between 2007 and 2014. Despite a growing body of scholarship on the relationship between policing and schooling in the US and UK, comparative research on how school students experience Stop and Frisk/Search practices remains sparse. Drawing on the BlackCrit tradition of Critical Race Theory, in-depth interviews with 60 Black Caribbean secondary school students and 16 months of ethnographic observations at two large public schools in London and New York City, the article explores how adolescents experience adult-like policing to and from schools. The findings indicate that participants develop a strained sense of belonging in British and American societies due to a security paradox—a policing formula that promises safety for all in principle, but does so at the expense of some Black youth in practice. Participants learned that irrespective of ethnicity, Black youth are regularly rendered suspicious subjects worthy of scrutiny, even during the school commute. The article concludes with recommendations that can assist in improving students’ safety while on route to and from school.