This paper examines the multilayered dynamics behind the drivers of overdose deaths, criminal legal-system involvement, and the drug war infiltration of people’s everyday lives—especially for people under community supervision. While incarceration receives more media and academic attention because of its particular cruelty, almost twice as many people—3.7 million, or one in every sixty-nine U.S. adults—are under community supervision. Probation and parole are commonly understood as “alternatives to incarceration” or “lenient sentences,” but people on supervision must endure constant monitoring, perpetually under the threat of incarceration. Drug war policies and practices have profoundly shaped probation and parole. Regardless of someone’s original sentence, abstinence from drugs, drug testing, submission to warrantless searches, and court-ordered treatment are routine features of supervision. The putative goal of community supervision is to ensure successful reintegration; yet drug war surveillance enacts extensive barriers, while not reducing drug use or drug-related harms like overdose. In order to ensure health, financial security, and overall well-being of those under supervision, policymakers, probation and parole officers, clinicians, service providers, and researchers must work to identify and remove barriers to care, including routine drug testing, substandard or forced substance use disorder treatment, and poor-quality services and support.