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Automated enforcement of commercial vehicle regulations is one potential method through which states can generate revenue and improve safety compliance by more efficiently directing the attention of law enforcement and state Department of Transportation (DOT) officials to non-compliant carriers and identifying carriers who may be evading taxes. This paper estimates the potential benefits of remote enforcement of weight–distance tax regulations in Kentucky, United States (U.S.) using data from camera-equipped Kentucky Automated Truck Screening (KATS) systems and PrePass weigh stations in Kentucky, and links these data sources with administrative tax returns and Kentucky State Police citation data. This research estimates that remote enforcement and identification of tax evaders could generate up to $10.4 million annually in revenue. Implementation of KATS weigh stations increases monthly impounds by approximately $5,000 per station, or about 160%. Overall, the results indicate that remote enforcement can assist state DOTs and law enforcement agencies targeting non-compliant carriers and may be an effective tax enforcement tool for states.