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The toll of the opioid overdose crisis in the United States generated efforts to decriminalize drug possession to protect the health of people who use drugs by reducing their involvement with the justice system. These efforts culminated in Oregon’s statewide decriminalization in 2021, a measure substantially reversed in 2024 after a series of negative outcomes. In demonstrating the potential of such reforms, the most frequent point of reference is Portugal, which decriminalized drug possession nearly 25 years ago. While Portugal’s pioneering drug policy has been frequently analyzed, significant gaps remain in our understanding of its implementation and practice, especially how the nation’s police have experienced decriminalization and reconciled it with their responsibility to deliver public safety and maintain order. Drawing on key informant interviews with a wide range of Portuguese police and other public officials, this paper examines aspects of Portugal’s approach to decriminalization that made it acceptable and sustainable from the perspective of the nation’s urban police force. It finds that Portugal’s decriminalization policy was more modest in scope than popularly assumed, especially in contrast to North American attempts to emulate it, and that police were integral to its effectiveness and success.