Warning shots fired from a Russian military frigate, the Admiral Grigorovich towards the civilian yacht Bright Future in the English Channel have demonstrated how close Russia and the European coalition have come to the possibility of a military confrontation over Russia’s shadow fleet.
The first phase of escalation was initiated by Moscow. Until late 2024, Western countries had made little effort to obstruct the activities of the shadow fleet, despite being fully aware of its scale and role in circumventing sanctions. This changed when evidence emerged that vessels associated with the fleet were also being used for sabotage and intelligence-gathering operations in the Baltic Sea. These developments led to the first detentions of vessels.
In 2025, the Western coalition began systematically increasing pressure on the shadow fleet by placing its vessels on sanctions lists and threatening sanctions against jurisdictions that provided Russian tankers with flags and fictitious registrations. In the middle of the same year, a coalition of Northern European states also developed legal grounds for detaining vessels sailing under foreign flags without genuine registration, in accordance with the United Nations Convention on the Law of the Sea.
Russia was consequently forced to return some of its vessels to the Russian flag in order to ensure their legal status and the possibility of physical protection. Currently, approximately one quarter of the vessels transporting Russian crude oil and petroleum products operate under the Russian flag. A substantial number of tankers, however, continue to sail under false flags.
The Russian authorities are seeking to broaden the quasi-legal grounds for protecting such vessels by passing a law on the use of armed forces to protect Russian citizens detained pursuant to court rulings in foreign states. The law could be invoked to justify the protection of vessels that do not fly the Russian flag but carry Russian crew members. However, such an interpretation is clearly untenable under international law and would not be recognised by European states.
Thus, Russia and the European coalition have reached a critical juncture in their confrontation over the shadow fleet. The shots fired by the Admiral Grigorovich frigate served as a symbolic indication of this reality. Whether Europe will retreat in response to this signal, and whether Russia is prepared to employ something more substantial than small arms, are questions that are likely to be answered in the near future.
On 16 June, the Russian warship Admiral Grigorovich fired warning shots from small arms in the English Channel at a yacht that had allegedly approached it to an unsafe distance. Subsequent reporting indicated that the yacht, ironically named Bright Future, carrying a retired couple on board, had not in fact approached the warship. The distance between the vessels exceeded 400 metres and the yacht posed no threat. It appears instead to have been used as a pretext to demonstrate the seriousness of the intentions of the Russian vessel, which has effectively maintained a near-permanent presence in the Channel. The incident involving Admiral Grigorovich therefore marked another step in the escalating confrontation between Moscow and Europe over Russia’s shadow fleet.
It should be noted that responsibility for the early stages of escalation rested largely with Russia. During 2023 and 2024, neither Europe nor the United States attempted to impede the operations of the Russian shadow fleet, despite understanding its scale and its importance for sanctions evasion (see Appendix for a broader timeline of the confrontation). More decisive action by Western governments was prompted not primarily by sanctions concerns but by evidence that Russia had begun using oil-transporting vessels for sabotage and intelligence purposes, creating clear security risks, as RAND analyst Henri van Soest notes, in particular.
Between 2024 and 2025, a series of incidents occurred in the Baltic Sea involving commercial vessels suspected of links to Russia and China. The most notable case concerned the tanker Eagle S, which on 25 December 2024 severed a power cable and several telecommunications cables connecting Finland and Estonia. Finnish special forces subsequently boarded the vessel and detained the crew. Several days later, Finland denied the tanker permission to operate after identifying serious safety deficiencies. In January 2025, the oil-laden tanker Eventin, which had departed from the Russian port of Ust-Luga under the Panamanian flag, lost propulsion in the Baltic Sea. German authorities towed the vessel to port in order to prevent an environmental disaster and later announced its confiscation on the grounds of documentation irregularities, although legal proceedings on this matter remain ongoing.
Pressure on the shadow fleet intensified during the first half of 2025, when the United States and subsequently the European Union began adding shadow fleet vessels to sanctions lists. By July 2025, the EU list contained more than 440 vessels, rising to over 550 by October. Estonia and France meanwhile detained two additional vessels in April and October respectively. In the first case, investigators identified a fraudulent registration in Djibouti. In the second, authorities cited suspicions that the vessel had been involved in launching drones used in sabotage operations that temporarily disrupted civilian air traffic in Denmark.
As later revealed by an OCCRP investigation, from mid-2025 onwards Baltic tankers associated with Russia’s shadow fleet systematically carried individuals with links to the Wagner Group or the GRU who lacked maritime qualifications. In addition to providing security in the event of vessel seizure, these individuals reportedly conducted signals intelligence activities, monitored NATO force movements, and potentially coordinated with Russian naval assets. The presence of militarily affiliated personnel without maritime qualifications provided European authorities with legal grounds for detention. The militarisation of a crew undermines a vessel’s status as an ordinary commercial ship and may deprive it of the right to peaceful passage under the United Nations Convention on the Law of the Sea (UNCLOS).
However, the principal legal justification for action against Russian vessels was developed in June 2025 within the framework of a coalition of 14 Baltic and North Sea states. The coalition declared its intention to step up its efforts to counter the shadow fleet within its waters, particularly against vessels operating under false flags. Such vessels lack genuine registration and therefore may fall outside the protections afforded by the Convention. European authorities have relied on Article 110 of UNCLOS, which provides for action against vessels of this kind. At the same time, during the second half of 2025, EU officials undertook extensive diplomatic engagement with so-called ‘flag states’, jurisdictions that had provided fictitious registrations to shadow fleet vessels, as part of preparations for the nineteenth sanctions package. Bloomberg reported, citing an internal European Commission document, that these jurisdictions were pressured to remove vessels linked to the shadow fleet, and included on the sanctions list, from their registries.
In December 2025–January 2026, the escalation at sea received a significant boost from the United States, which launched a stringent maritime blockade of Venezuela and detained or intercepted seven tankers linked to Russia in one way or another. The operation, combined with Russia’s notably restrained response, largely because Moscow was seeking Donald Trump’s support in exerting pressure on Ukraine and therefore wished to avoid confrontation with Washington, helped to normalise the practice of vessel detentions.
In the first half of March 2026, France and Belgium, followed by Sweden on two separate occasions, detained three vessels in quick succession: the Ethera, the dry cargo ship Caffa and the Sea Owl I, on charges of operating without valid registration. The vessels were not listed in the registries of the countries whose flags they were flying. The EU’s foreign policy envoy, Kaja Kallas, thanked the countries that carried out the detentions and called for consistent action along the same lines. On 25 March, the British Prime Minister authorised the UK armed forces to stop and inspect shadow fleet vessels. The EU’s twentieth sanctions package against Russia, published on 23 April, further expanded the legal basis for action against Russian tankers. Finally, in implementation of these measures, EU defence ministers meeting in Nicosia in early June expanded the mandate of Operation Irini, originally established to enforce sanctions on Libya in the Mediterranean. The mission was granted authority to monitor sanctions compliance in relation to Russia, and member states agreed procedures for the detention and inspection of Russia-linked tankers.
However, only five vessels were detained in European waters between 20 March and 15 June. The most high-profile operation was the boarding of the tanker Smyrtos by British Royal Marines on 14 June. Altogether, 22 vessels associated with Russia’s shadow fleet have been detained since December 2024, of which nine were detained by European states in 2026. Detentions therefore remain relatively rare, despite the fact that hundreds of vessels transporting Russian oil continue to transit the same routes every month. According to CREA’s estimates, in May 2026, a total of 337 vessels were involved in the maritime transport of oil and petroleum products, of which just under half (147) belonged to the shadow fleet. As before, the principal legal basis for detentions in international waters remains the absence of genuine registration in the state whose flag a vessel claims to fly.
As early as 17 February 2026, shortly after the French Navy boarded the tanker MV Grinch, the former Secretary of the Russian Security Council, and now the President’s aide on shipbuilding and head of the newly established Maritime Board, Nikolai Patrushev, stated that Russia considers such detentions to be illegal. He characterised them as piracy and stated that Russia could employ naval forces to counter them.
In reality, however, Russia’s shadow fleet faced a genuine legal dilemma. Under pressure from the EU, flag states began removing sanctioned tankers from their registries, thereby creating the legal basis for their detention. As a result, Russian authorities were compelled to return an increasing number of vessels to the Russian flag. According to a review by the Kyiv School of Economics (KSE), there were 75 Russian-flagged tankers at the beginning of 2022. As the shadow fleet expanded, this number fell to 48 by the fourth quarter of 2024. During this period, Russian-flagged vessels accounted for only 7% to 12% of all ships transporting Russian energy exports. During 2025, however, the number of tankers flying the Russian tricolour increased to 77, with roughly two-thirds of all reflagging occurring in the fourth quarter alone, when 18 tankers switched to the Russian register. A further five vessels were added during the first quarter of 2026, bringing the total to 82. According to slightly different data compiled by S&P Global Market Intelligence and cited by The Wall Street, 25 tankers switched to the Russian flag during the fourth quarter of 2025 alone, including 18 in December. As a result, the share of Russian-flagged tankers within the overall fleet transporting Russian crude oil and petroleum products rose to 12%, while their share within the shadow fleet reached 24%. According to KSE calculations, Russian-flagged tankers transported 56.5 million barrels of oil cargo during January-March 2026, 3.5 times more than during the corresponding period a year earlier.
Perhaps the most controversial example of an emergency change of flag was the case of the tanker Bella-1, which was pursued by US vessels in December 2025 for its involvement in the transport of sanctioned oil from Venezuela and Iran. During this chase, the crew painted the tricolour on the ship’s hull, whilst Moscow retroactively approved the vessel’s registration without inspecting it. This constitutes a violation of Article 92 of UNCLOS, which prohibits a change of flag without a genuine transfer of ownership, as noted by Jose M. Masias of the Centre for Strategic and International Studies (CSIS).
Whatever the legal merits of such cases, the transfer of vessels to the Russian flag is intended to achieve a dual effect. First, it raises the risks for states seeking to detain tankers. The first instance of military escalation linked to a vessel detention occurred as early as May 2025, when Estonia attempted to stop the tanker Jaguar in the Gulf of Finland. The interception was abandoned after a Russian Su-35 fighter aircraft approached the scene. Second, reflagging deprives such detentions of their principal legal justification under international law. Because European, British and American sanctions against Russia have not been authorised by the United Nations, detaining vessels solely on the basis of those sanctions may conflict with UNCLOS. At the same time, operating under the Russian flag creates practical difficulties for shipping. The EU has intensified pressure on organisations and ports that assist sanctioned tankers. On 15 June, the Council of the EU imposed sanctions on 24 legal entities and two individuals involved in facilitating shadow fleet operations. Even broader sanctions against ports and port infrastructure in third countries involved in supporting the Russian shadow fleet are expected to be included in the EU’s 21st sanctions package. These measures, however, would apply only to assistance provided to vessels that appear on EU sanctions lists.
This legal contradiction is well illustrated by previous episodes involving Russian vessels transiting the English Channel under the protection of Admiral Grigorovich. According to information from the British military, the frigate has been operating in the area for an extended period and has recently escorted a Russian submarine and at least six shadow fleet tankers through the Channel. According to a report in London’s The Telegraph, on 8 April, shortly after Sir Keir Starmer authorised the detention of Russian-linked vessels, the frigate escorted two tankers through the Channel: Universal, sailing under the Russian flag, and Enigma, sailing under the Cameroonian flag, most likely a flag of convenience. Both vessels were subject to British sanctions. Formally, the warship was escorting the first vessel, and such an action is entirely lawful under international law. In practice, however, the second tanker also benefited from the protection afforded by Admiral Grigorovich. Notably, the Russian-flagged vessel had departed from the port of Vysotsk as early as 18 January, while the second vessel left Primorsk on 29 March. This suggests that the first tanker may have deliberately waited for the second in order to transit the Channel together under naval protection.
However, the Russian authorities are seeking to expand the quasi-legal grounds for protecting vessels that do not fly the Russian flag as well. On 18 March 2026, immediately after three Russian-linked tankers had been detained in European waters, a bill on extraterritorial protection was introduced in the State Duma. The legislation authorises the use of Russian armed forces abroad to protect Russian citizens. Russian officials have occasionally described the measure as an analogue of the American Servicemembers’ Protection Act (ASPA). In reality, however, the Russian legislation is both broader and largely without precedent. Whereas the American law concerns the non-recognition of certain international judicial bodies, the Russian law rejects the authority of ‘decisions of courts of foreign states vested with criminal jurisdiction by other foreign states without the participation of the Russian Federation’. In other words, the law may be invoked whenever a foreign court orders the detention of a Russian citizen. This could include the detention of shadow fleet vessels that do not sail under the Russian flag but carry Russian nationals among their crew. The law was adopted and signed by Vladimir Putin on 25 May and entered into force on 5 June.
The seizure of the tanker Smyrtos by the British Royal Marines took place after this date. However, the vessel was flying the Cameroonian flag, and there were no Russian citizens amongst its crew, a fact promptly confirmed by the Russian Embassy in London. Nevertheless, the Russian response was asymmetrical. Shortly afterwards, warning shots were fired in the direction of an unsuspecting British couple aboard the yacht Bright Future. The more serious confrontation would emerge if the circumstances of April were repeated, involving two tankers under the protection of a Russian frigate. Under the British legal framework, armed forces would be authorised to detain a tanker sailing under a non-Russian flag. Under Russia’s revised legislation, however, a Russian warship could claim the right to protect the same vessel if Russian citizens were present among the crew.
Russia and the European coalition have therefore reached a critical juncture in their confrontation over the shadow fleet. The position of European governments is that vessels lacking valid registration cannot benefit from the right of innocent passage and may therefore be detained. Russia, by contrast, has declared that it does not recognise the decisions of European courts and has signalled its willingness to oppose their implementation by military means. Whether Europe will retreat in response to the symbolic warning shots fired by Admiral Grigorovich, and whether Russia is prepared to employ something more substantial than small arms, are questions that are likely to be answered in the near future.