After Western sanctions capped Russian oil prices at $60 per barrel, Russia responded by building a 'shadow fleet' of over 600 aging tankers to bypass restrictions. These vessels operate under fraudulent flags, disable GPS tracking, and rely on opaque ownership and non-Western insurance networks to avoid detection. Maritime pilots like Bjarne Caesar Skinnerup have observed their suspicious behavior firsthand, raising alarms about safety, environmental risks, and complicity in funding war. Despite international regulations, enforcement remains weak due to jurisdictional limits and geopolitical tensions—exemplified when France detained a tanker and Russia called it piracy. The shadow fleet has redirected global oil flows, boosting Russian revenue through discounted sales to China and India, while increasing shipping costs and creating a dangerous, uninsured maritime network. This underground market undermines sanction goals and threatens ecological disaster, all while frontline workers grapple with moral dilemmas about their role in enabling these shipments.