Ukraine has used drones four times in the past few weeks to hit oil tankers from Russia’s shadow fleet, escalating the war in the seas and showing that Ukraine’s security services agency feels increasingly emboldened to launch audacious attacks and claim them publicly.
One ship was struck by aerial drones on Thursday night in the Mediterranean Sea, more than 1,200 miles away from Ukraine. The other three were hit by sea drones in the Black Sea. The attacks are the first on Russia’s sanction-defying oil tankers that Ukraine has acknowledged since Russia’s full-scale invasion in 2022.
The security agency also said it had attacked Russian oil production platforms in the Caspian Sea four times in the past 10 days, including on Thursday.
The oil business fuels Russia’s economy and its war, and throughout the conflict, the West has tried to crack down on its profits with sanctions.
“No money, no war machine,” said Benjamin Jensen of the Center for Strategic and International Studies, a nonpartisan think tank in Washington.
To evade those sanctions, Russia has developed its so-called shadow fleet, a clandestine network of hundreds of dilapidated oil and gas tankers with hard-to-trace owners that covertly shuttle fuel to countries like India and China. Ukraine believes that if it can disrupt this business through attacks on the shadow fleet, as well as on oil refineries, it may gain leverage in peace talks now being pushed by President Trump by appearing to be on the attack against Russia.
In addition, Ukraine hopes to force Russia to the negotiating table by cutting its oil profits.
So far, President Vladimir V. Putin of Russia has given no indication that he is interested in ending the war. He says he is winning, and on Friday, he said Kyiv’s attacks on the shadow fleet would not have any effect. He also threatened retaliation. “We will definitely respond,” he said during his end-of-year news conference.
The recent attacks are part of a new front in the conflict. For years, the Biden administration had warned Ukraine against hitting Russia’s oil industry because of fears of driving up global prices and escalating the war. Ukraine’s public claims suggest that Mr. Trump might have known about them, as Ukraine would not risk angering Mr. Trump at this stage of negotiations.
The White House did not respond to a request for comment.
All four tankers disabled by Ukraine’s security services were empty. The security agency, known as the S.B.U., said the three vessels in the Black Sea were on their way to fill up with oil in Novorossiysk, the busiest port in Russia, on the sea’s northeastern coast.
The attack on Thursday night in the Mediterranean Sea, on a tanker identified as the Qendil, was the most surprising, as the vessel was so far from Ukraine. Officials did not say where the aerial drones were launched from.
Experts said the attacks were a signal to Russia that Ukraine was willing to escalate the war, and a message to Europe to enforce sanctions or face more problems in shipping lanes.
Ukraine “will pursue a decisive policy,” said Andrii Klymenko, who runs a group monitoring the shadow fleet for the Black Sea Institute of Strategic Studies, a Ukrainian think tank. He added, “That is, we will hit everyone who goes to Novorossiysk or to other Russian ports for oil — before they get the oil.”
The attacks have caused insurance rates to skyrocket for any legitimate tanker in the region. They have also raised fears in countries like Turkey about the war expanding into nearby waters, and prompted concerns about possible environmental damage.
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Russia developed its shadow fleet with old tankers sailing under the flags of other countries, similar to fleets that Venezuela and Iran operate. The ships have disrupted their tracking systems or turned them off. They operate with sketchy insurance, or none at all.
Tankers in the shadow fleet are now sometimes escorted by warships, a signal that “Russia is ready to face the West head on,” said Andrei Soldatov, a Russian journalist who reports on the work of Moscow’s intelligence organizations and who was an author of an article for Foreign Affairs on the shadow fleet. “It’s really, really new and very dangerous, what is going on,” he added.
Ukrainian intelligence shows that Russia launched drones into Europe from its shadow fleet tankers, President Volodymyr Zelensky of Ukraine said in September. Mr. Putin denied this.
Shadow vessels make up about 10 to 20 percent of the global tanker fleet, experts say. But estimates vary. There were 940 vessels this year, an increase of 45 percent from last year, according to S & P Global Market Intelligence, a research firm. The Black Sea Institute of Strategic Studies has identified about 2,100 tankers that carry Russian oil, Mr. Klymenko said.
The European Union has put more than 500 shadow fleet ships on sanction lists, some of which have been blacklisted by the United States and Britain. On Monday, the European Union announced sanctions against five people and four shipping companies connected to the shadow fleet.
Mr. Zelensky also recently announced Ukraine’s largest sanctions package to date against the shadow fleet, targeting 656 vessels.
The goal is to make ports stop working with the vessels. But the sanctions are tough to enforce, and Russia keeps adding ships.
The Trump administration is waging its own campaign against shadow fleets. On Tuesday, Mr. Trump ordered a blockade on sanctioned oil tankers going to and from Venezuela. On Thursday, the United States sanctioned dozens of ships and businesses linked to the Iranian shadow fleet.
Ukrainian strikes on shadow fleet tankers are unlikely to significantly dent Russia’s ability to export oil, said Hanna Notte, an analyst at the James Martin Center for Nonproliferation Studies, a California-based research body. Ukraine’s strikes on oil refineries and oil platforms in the past few months, along with sanctions against Russia’s two largest oil companies, are much more damaging, she said.
Russian oil exports dropped in November because buyers grew cautious over the risks linked to the more stringent U.S. sanctions, the International Energy Agency said in a market report this month.
On Sunday, the Institute for the Study of War, a Washington-based think tank, said Ukraine’s long-range strike campaign had continued to degrade Russia’s oil refining and military abilities. The Ukrainian military said on Wednesday that it hit two more oil refineries and an oil rig in Russia.
In highly produced videos of the recent tanker attacks, the Ukrainian security service included explosions of the tankers — the Kairos, the Virat, the Dashan and the Qendil — accompanied by songs such as “Empires Will Fall” by the Ukrainian band Beatbox. The S.B.U. said it had worked with the Ukrainian Navy to disable the three ships in the Black Sea with satellite-controlled speedboat drones called Sea Babies.
Other vessels connected to the shadow fleet have suffered strange explosions in recent weeks, including one off the coast of Senegal and one carrying sunflower oil off Turkey. Ukraine has not commented on the strike near Senegal and denied hitting the other ship.
The Kairos and the Virat, both sanctioned by the European Union yet sailing under the flag of Gambia, were hit on Nov. 28 off Turkey. A few days later, Mr. Putin termed the attacks “piracy” and threatened Ukrainian ports, ships using those ports and the ships of countries that help Ukraine.
“The most radical solution would be to cut Ukraine off from the sea, effectively making it impossible for it to engage in piracy at all,” Mr. Putin said.
The S.B.U. then claimed credit for a strike on Dec. 10 on the Dashan, a tanker sanctioned by the European Union that kept its transponder off as it sailed through Ukraine’s exclusive economic zone under the flag of the Comoros, a tiny country off southeastern Africa.
The Kremlin did not comment on that attack. But the next night, Russia started pounding Ukraine’s largest port city, Odesa, on the Black Sea with waves of drones and missiles. Those attacks have continued for more than a week. On Friday night, ballistic missiles hit the city’s port infrastructure, killing at least eight people.
On Monday, Mr. Klymenko, the shadow fleet analyst, said he had located the Virat at a shipyard in Turkey undergoing repairs. He was one of several open-source researchers to observe this. According to those experts, the vessel had a new name — Prometey — and was also flying a new flag — Russia’s.
Oleksandra Mykolyshyn contributed reporting.
Kim Barker is a Times reporter writing in-depth stories about the war in Ukraine.
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