Ukraine Hit Russian Shadow Fleet Tankers, Undermining Moscow’s Sanctions-Evasion Fleet

UNSPECIFIED, UKRAINE – OCTOBER 17: A view of the SeaBaby naval drone on October 17, 2025 in Unspecified, Ukraine. The Security Service of Ukraine has unveiled upgraded SeaBaby naval drones. Ukrainian forces have been using them since 2022. The new version of the drones features more powerful engines, modern navigation and communication systems, strike FPV drones, turrets, and Grad multiple launch rocket systems. (Photo by Vitalii Nosach/Global Images Ukraine via Getty Images)

Global Images Ukraine via Getty Images

Ukrainian Sea Baby naval drones struck two Russian oil tankers operating in international waters off Turkey’s Black Sea coast on November 28, marking a significant expansion of Kyiv’s maritime drone campaign targeting the Kremlin’s oil revenue.

The attacks targeted the Kairos and Virat, both vessels flagged under Gambian registry but identified by Western authorities as part of Russia’s shadow fleet designed to evade international sanctions. A source from Ukraine’s Security Service told the Kyiv Independent that the domestically produced drones disabled vessels capable of transporting nearly $70 million worth of oil.

The strikes occurred approximately 28 to 35 nautical miles off Turkey’s Kocaeli province, well beyond Ukraine’s previous operational range in the northern Black Sea. The Kairos caught fire following the drone strike, with Turkish coast guard teams evacuating all 25 crew members. The Virat suffered damage but remained afloat.

It was likely intentional that Kyiv struck the vessels to damage them but not sink them, in order to avoid angering international partners. ChrisO_wiki, a military history author and researcher, wrote on X that targeting the stern suggests they were trying to wreck the propulsion and rudders, rather than sinking the ships outright.

Targeting The Shadow Fleet

The OpenSanctions database, which tracks entities involved in sanctions circumvention, identifies both tankers as participants in schemes designed to conceal ownership and disguise activities under flags of convenience. The United States sanctioned the Virat in January 2025, with the European Union, Switzerland, the United Kingdom and Canada following suit. The Kairos had been sanctioned by the EU in July 2025, followed by the UK and Switzerland.

Bloomberg reported that the Kairos was returning to Novorossiysk after delivering Urals crude to India, while the Virat had spent much of 2025 idle in the western Black Sea following its addition to US sanctions lists.

Olena Kryzhanivska, a defense analyst and author of the Ukraine’s Arms Monitor newsletter, previously told me, “When we see an armed conflict of such scale and intensity as between Russia and Ukraine, it’s an expected outcome that the entire wider region will be directly affected.”

Expanding The Campaign

Ukraine has conducted successful naval strikes against Russian shipping throughout the war, particularly using explosives-packed naval drones. However, Ukrainian operations had largely been confined to the northern Black Sea. The strikes off Turkey’s coast represent a dramatic extension of operational range, demonstrating improved drone endurance and Ukraine’s willingness to target Russian assets in international waters.

The Sea Baby drone platform has emerged as a key weapon in Ukraine’s asymmetric naval campaign against Russia’s Black Sea Fleet, combining long endurance with substantial explosive payloads. “Naval drones are now a crucial component of the Ukrainian navy and the primary strike weapon at sea,” says Serhii Kuzan, chairman of the Ukrainian Security and Cooperation Center and former Ministry of Defense adviser.

According to the Associated Press, Ukraine’s Security Service unveiled an upgraded version of the Sea Baby in October capable of operating anywhere in the Black Sea, carrying heavier warheads, and using artificial intelligence for targeting. The range had been expanded from 1,000 to 1,500 kilometers and the payload increased to around 2,000 kilograms, allowing for strikes far deeper into Russian-controlled waters.

These latest strikes reflect Ukraine’s intent to impose costs on Russia’s global oil supply chains, not just its military fleet. For the companies attempting to engage in supporting Russia’s oil trade, Kyiv is focused on changing that calculus. Oleksii Plastun, a professor at Sumy State University, told me there is a kind of risk-profit balance for companies.

Pressure On Russian Oil Infrastructure

The tanker strikes came the day before Ukrainian naval drones attacked the Caspian Pipeline Consortium’s marine terminal in Novorossiysk, forcing the facility to suspend all loading operations, the Kyiv Independent reported. The attack seriously damaged mooring point two, prompting port authorities to order all tankers out of the water area.

The pipeline terminal has now been struck three times in recent months, with previous attacks in September and November.

The latest attacks add mounting pressure on Russia’s ability to export oil, an economic lifeline that Ukraine has targeted with increasing frequency. By striking both transport vessels and loading infrastructure, Ukraine appears to be pursuing a coordinated strategy aimed at constraining Russia’s energy revenues while demonstrating its capacity to project power across the Black Sea region.

Ukraine’s strategy increasingly appears coordinated: degrading both the vessels transporting Russia’s oil and the infrastructure enabling those exports. Oil and petroleum products remain Russia’s single most important revenue stream. According to the International Energy Agency, Russia earned $13.1 billion from crude and oil product sales in October – still substantial, though down $2.3 billion from the same period last year.

According to Reuters, Russia’s oil and gas revenue is set to fall about 35% in November to 520 billion roubles ($6.59 billion), part of a broader 22% slide this year as cheaper crude and a stronger rouble squeeze the Kremlin’s most important income stream.

At the same time, the domestic political costs of the war are rising, with the Kremlin preparing an unpopular VAT hike and issuing guidelines to state media to blame the West, according to the Financial Times. It is part of a broader effort to shield Putin from public anger as Russia raises taxes to fund its war economy. Adding to those pressures, Kommersant reported on November 22 that Yakutia’s finance minister, Ivan Alekseyev, said payments to combat veterans serving in Ukraine have been suspended due to a lack of budgetary funds.

A Shadow Fleet Under Strain

The risks facing Russia’s shadow fleet are rising, not only from Ukrainian drones but from the fleet’s own deteriorating condition.

According to the Ukrainian outlet Censor.NET, the tanker M/T Mersin, which had regularly visited the port of Novorossiysk, sank off the coast of Senegal on November 30. Footage posted online showed the vessel slowly going under. The ship had called at Russia’s port of Taman in August before heading toward Africa, where it remained stationary for an extended period. Russia’s reliance on poorly maintained, under-insured and often aging tankers carries mounting environmental and economic risks.

Meanwhile, as the Trump administration is increasingly attempting to push Kyiv into what many analysts believe is a deal that favors Moscow, Ukraine is seeking to rebalance the negotiations. That means stepping up the pressure on the Kremlin.

Ukraine’s former foreign minister Dmytro Kuleba wrote in Foreign Affairs that Kyiv may not hold ideal cards, but it is far from needing to fold. Ukraine is counting on Europe to buffer any fallout from declining U.S. aid, and it knows the battlefield picture is less dire than portrayed.

Kuleba noted that Russia controlled about 42,000 square miles of Ukrainian territory in December 2023; by December 2024 that had risen only to roughly 43,600. As of late May, Russia’s gains remain nearly unchanged at around 43,650 square miles.

Ukraine’s naval drones have now shown they can reach deep into the Black Sea and disrupt ships far from the front line. The shadow fleet, built to slip past sanctions, is proving more vulnerable than expected. As these strikes extend farther from Ukrainian shores, the cost calculus changes for the companies and shipowners that have been willing to service Moscow’s oil trade. And with Kyiv increasingly willing to target the shadow fleet directly, that risk is only set to rise.