‘Uncanny Parallels’: How Ukraine’s Operation Spiderweb Echoes SAS Daring of WWII

When Ukraine unleashed its audacious Operation Spiderweb in June 2025, military historian and author Damien Lewis could hardly believe what he was seeing.

A strike 18 months in the making saw 117 drones roar to life from lorries deep inside Russia, hitting 41 high-value bomber targets across multiple airbases and time zones. It was a devastating blow to Moscow’s air power, and a £5 billion loss, according to Ukraine’s Security Service. But to Lewis, it was more than just a modern-day military triumph. It was history repeating itself.

“When I saw the breaking news of Spiderweb,” Lewis told reports, “I thought, Oh my God, this is like Paddy Mayne and his raiders in the North African desert, translated to the modern day.”

Doing the unthinkable

For those familiar with the Special Air Service’s exploits in the Second World War, the similarities are striking. The SAS built its reputation on impossible missions, acts so bold even some senior figures balked.

Lewis, whose books include The Ministry of Ungentlemanly Warfare, SAS Daggers Drawn, and SAS: The Great Train Raid, says Ukraine’s tactics mirror those of Britain’s most elite warriors eight decades on.

Take Operation Loco, the SAS’s secret 1943 raid revealed only decades later. The mission, led by Major Oswald Cary-Elwes, involved hijacking a train, driving 120 kilometres behind enemy lines, and using it to evacuate prisoners from the concentration camp at Pisticci in Italy.

Eighty-two years on, Operation Spiderweb saw Ukrainian forces commandeer trucks instead of trains, drones instead of incendiary charges, but the spirit was unmistakably the same: deep penetration into enemy territory, high-risk strikes, and total surprise.

From Lewes bombs to drones

Back in 1941 and ’42, SAS raiders in North Africa would travel thousands of kilometres in jeeps, sneaking into Axis airfields under cover of darkness. They planted Lewes bombs, small incendiary charges, on German and Italian aircraft before vanishing like ghosts.

Lewis says Ukraine’s drones did the exact same thing, just without the human cost.

“The only difference in terms of the modus operandi,” he explained, “is that it’s a drone carrying out the kill rather than a man with a Lewes bomb.”

Even their navigation technique, dead reckoning, a method based on speed, distance and direction, is straight out of the SAS playbook. This old-school system made Ukraine’s drones far harder to intercept electronically, echoing the ingenuity that once helped British commandos outfox Nazi forces in the desert.

Nowhere is safe

Churchill’s approach was to unleash chaos, to make sure Nazi Germany never felt secure. He wanted Hitler’s troops to feel that danger could strike from anywhere, at any time.

“Surprise,” Lewis said, “is the golden elixir of guerrilla warfare behind enemy lines.”

That philosophy now runs through Ukraine’s defence strategy. Just as the SAS made the Luftwaffe uneasy in their bunkers, Ukrainian forces have targeted senior Russian commanders, shattering morale and spreading fear through the ranks.

Since Putin’s invasion began in 2022, at least 11 senior Russian officers have been killed, according to Reuters. After Operation Spiderweb, paranoia reportedly swept across Russia, every lorry on the road became a potential drone carrier.

Lewis is clear about the lesson:

“The Ukrainians have taken that SAS spirit, to think the unthinkable and then do the unthinkable, and made it a reality.”

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