Sir Keir Starmer's threat to seize sanctioned Russian tankers has been directly defied by Vladimir Putin after Moscow sent a warship to escort two vessels through the English Channel.
Admiral Grigorovich, a Black Sea fleet frigate, accompanied sanctioned ships in British waters earlier today.
A British naval vessel trailed the boats, with The Telegraph witnessing the Russian flotilla sailing past RFA Tideforce.
However, today's sighting in the Channel came just weeks after Sir Keir granted special forces the authority to capture two sanctioned Russian vessels.
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The Prime Minister, who is currently in the Middle East, pledged to hit the shadow fleet "even harder" if it sailed through British waters.
However, the UK is still yet to seize a single Russian vessel.
The Russian warship's journey through the English Channel marks another blow for Sir Keir, with the Prime Minister facing criticism after an Iranian-made drone hit RAF Akrotiri.
HMS Dragon's arrival in the Middle East was also delayed by as much as three weeks after Britain's lone deployable destroyer suffered from water supply issues.
Sir Keir Starmer is currently in the Middle East
|GETTY
The Russian warship, which weighs in at 3,620-tonne armed with anti-ship missiles, was spotted sailing between Universal and Enigma tankers shortly after 9am as the flotilla headed west towards Plymouth.
Universal is believed to have departed the Russian port of Vyotsk on January 18.
Meanwhile, the Cameroon-flagged Enigma is bound for Turkey and left the port of Primorsk on March 29.
Both vessels were sanctioned by the UK for pumping money into the Kremlin's coffers.
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Admiral Grigorovich was spotted sailing between the two 600ft tankers Universal and Enigma shortly after 9am
|GETTY
Andrew Fox, a retired major in the Parachute Regiment who is now a senior fellow at the Henry Jackson Society, said: “The Russians are desperate to keep that oil flowing and keep the war in Ukraine going. They are running rings around Starmer right now.
“If we’re really serious about helping Ukraine, we need to clamp down on these shadow fleet ships.
"That would send a message... It would embarrass Putin. At the moment, we’re not sending that message."
Sir Keir had announced his crackdown on sanctioned Russian ships in March, with around 544 vessels being identified by the UK.
PICTURED: A suspected 'shadow fleet' tanker - Russian oil companies are using a complex network to obscure ownership and evade sanctions
| GETTYThe Prime Minister said: “Putin is rubbing his hands at the war in the Middle East because he thinks higher oil prices will let him line his pockets.
“That’s why we’re going after his shadow fleet even harder, not just keeping Britain safe but starving Putin’s war machine of the dirty profits that fund his barbaric campaign in Ukraine.”
Sir Keir added: “He and his cronies should be in no doubt, we will always defend our sovereignty and stand with Ukraine for as long as it takes.”
The Prime Minister's plan allows the Royal Navy and National Crime Agency to capture the tankers under sanctions legislation passed in 2018.
Vladimir Putin is believed to have mocked Sir Keir Starmer
| REUTERSSpecial forces personnel from the Special Boat Service and Special Air Service could be used to seize tankers if armed guards are spotted onboard.
Meanwhile, the Royal Marines have been granted the power to take action if the vessels do not pose a danger.
However, the Kremlin continues to threaten to retaliate if the UK deploys the military to seize sanctioned ships.
Russia's ambassador to the UK Andrei Kelin said: “The appropriate measures are being developed. Let this come as a surprise to the British people.”
A spokesman for the Ministry of Defence said it would not comment on ongoing operations.