Economic sanctions targeting North Korea have recently focused on regulating international trade infrastructure through restrictions on maritime transport. In response, vessels with a nexus to North Korea have engaged in deceptive maritime practices designed to circumvent the sanctions and keep illicit trade flowing. These strategies include manipulation of vessel-tracking identification systems, illegal ship-to-ship transfers at sea, and various identity laundering techniques designed to conceal the nature of shipping transactions. As North Korea has achieved some level of success in sanctions-busting, enforcing actors have enhanced scrutiny over commercial shipping activities and even directed industry participants to aid law enforcement through compliance programs, commercial intelligence gathering, and risk mitigation techniques. Exploring these developments, this article examines North Korea’s practices employed to evade economic sanctions and surveys recent enforcement efforts designed to bolster private sector coordination. It evaluates the controversies surrounding this approach, analyzes best practices, and also highlights the enhanced risks it generates for commercial actors attempting to engage in legitimate trade in the Asia-Pacific and beyond.