Ukraine has attacked two Russian shadow vessels and an oil terminal, and may also have been behind an explosion onboard a Russian-linked vessel off the coast of Senegal last week. It’s a dramatic turn of events in the already intense drama involving Russia’s shadow fleet—a group of mostly old vessels of uncertain ownership, flag status and insurance protection—and was a clever way for Ukraine to demonstrate its abilities ahead of the Trump administration’s latest peace talks with Moscow.
The Kremlin made a fateful choice when, in December 2022, western governments imposed a price cap on Russian oil to prevent oil exports from funding the war against Ukraine: it turned to the shadow fleet, which provides services to sanctioned countries. North Korea, for example, receives western luxury goods via shadow vessels, and Iran uses the fleet to export oil. Apartheid South Africa similarly bypassed sanctions using this method.
Unsurprisingly, Russian demand caused the shadow fleet to grow extensively; these days, it includes almost 1,000 oil tankers plus other cargo vessels. That means that more than 1,000 ships sail through other countries’ waters, especially in the Baltic Sea, whose surrounding nations have diligently tried every legal avenue available to stop the scourge. Most vessels are of questionable seaworthiness, possess no valid accident insurance, disguise their movements and sometimes even lack flag registration—a cardinal sin in shipping. Their crews and owners are, alas, unfazed by a few inspections and documentation requests. The ships have kept sailing.
But on 28th November, two such vessels erupted in flames off Turkey’s Black Sea coast. Both ships were quintessential shadow tankers: sanctioned, flagged by The Gambia (a flag of extreme convenience), owned by tiny entities in China and Hong Kong, respectively, and with a history of transporting sanctioned Russian oil. Hours after the incidents, news arrived from Kyiv: the Security Service of Ukraine, or SBU, claimed responsibility for the attacks. The shadow vessels had been targeted with naval drones that “successfully completed their work on the ships”, an SBU official told the Kyiv Independent, adding that the attacks had dealt “a significant blow to Russian oil transportation”.
Then, in the middle of the night between 28th and 29th November, an oil terminal at Russia’s Novorossiysk port was hit by Ukrainian naval drones. Russia complained, but the Ukrainian government was unapologetic. To top off the dramatic sequence of events, it emerged that a Turkish-owned tanker known to transport Russian oil had exploded off the coast of Senegal while carrying a load of oil. Kyiv said nothing, but by that point, everyone assumed Ukraine was involved.
Kyiv has, in fact, triggered an extremely high-stakes game. Until now, western governments have let sanctions-busting ships traverse their waters because under the United Nations Convention on the Law of the Sea (UNCLOS), coastal nations have only limited rights outside their territorial waters—and the shadow vessels take great care to sail outside these zones and in international waterways. Western governments could do what many a social-media commentator has suggested and seize or even sink the ships. That would violate international legal obligations, but proponents argue that could be acceptable since Russia also breaks such rules.
Western governments have refrained from such radical measures, perhaps in order to maintain the rules-based international order—and because they know that rejecting international rules would expose ships from their own countries to immediate risk. On their journeys across the oceans, western vessels traverse the waters of numerous hostile states, and there are already plenty of perils. One needs only to remember the Houthis’ recent attacks in the Red Sea or Iran’s seizure of the British-flagged Stena Impero six years ago.
But Ukraine clearly feels it can’t afford to observe such niceties. What’s more, the peace talks involving the United States, Russia and Ukraine are at a crucial stage. This week Donald Trump’s special envoy, Steve Witkoff, travelled to Moscow accompanied by the US president’s son-in-law, Jared Kushner, to negotiate with Vladimir Putin, who rejected most of their peace proposal. Indeed, Ukraine has ample reason to be concerned about the US-Russia talks. Given that Witkoff has turned out to be decidedly sympathetic to Russia, going so far as to coach his Russian counterpart, and that Trump himself has often seemed more willing to listen to Moscow than Kyiv, hoping that the US and Russian negotiators will grant concessions in Ukraine’s favour would be unrealistic.
Instead, Kyiv appears to have decided to demonstrate that it can cripple Russia’s main source of income. In the past decade, oil and gas have made up between 30 and 50 per cent of Russian government revenues. The attacks on the shadow fleet certainly put Ukraine in a better negotiating position than it was a month ago. Which shipowners would want to transport sanctioned Russian oil if doing so brought the risk of a naval drone attack or explosion? Besiktas, the owner of the tanker struck of the Senegalese coast, has already announced it will no longer carry Russian oil. The Ukrainian negotiators meeting Witkoff for peace talks in Florida today carry a new trump card, so to speak.
Putin may have rejected most or all of Witkoff’s plan, but he appears rattled. He told Russian media this week that If Ukraine continues to strike Russian-linked vessels, the Kremlin may attack merchant vessels from countries supporting Ukraine. Doing so would be blatantly illegal, but Moscow has already demonstrated that it cares little about international law.
With Ukraine strengthening its negotiating position by striking Russian shadow vessels, and Russia responding by ominously threatening western merchant shipping, spare a thought for western governments. They naturally support Ukraine’s efforts to hit back at its aggressor and improve its negotiating position, but if those efforts put western countries’ own shipping at risk, it’s a very different equation. Then again, Russia being forced into a just peace would be the best possible news.
