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The sharp rise of private security has considerably expanded social control from public towards private actors, challenging the nature of social regulation. These private actors implement a social order and enforce norms not just to prevent crime but also to defend private interests. Private security guards are present in many contexts where youths are in attendance, especially in large urban centers. However, studies about how youths view these guards and respond to their demands are scarce. This study examines youngsters’ compliance with three types of private security guards’ requests in a scenario-based survey. It explores the factors that influence the willingness to obey, particularly normative and instrumental ones. Findings from a sample of 631 high school students from the two larger urban areas in Portugal (metropolitan areas of Lisbon and Porto) suggest that perceptions about the role of private security guards in protecting public or private interests and normative judgments about these guards are important in shaping youths’ compliance. Interestingly, variations according to the type of demand made by private security guards were observed. The implications of these findings for security governance are discussed.