Modern “Trojan Horse”: Ukraine's secret operation strikes at Russian heartland

Russia, which continues to cling to its imperialist ambitions, was stunned by Ukraine on June 1. Ukrainian special services carried out an operation across the vast territory of Russia that could serve as a ready-made script for a Hollywood film — one that Christopher Nolan himself might be tempted to direct, if only he could bring it to the screen.

The operation, conducted in various remote regions of Russia, is likely to impress powerful intelligence agencies such as the CIA, MI6, and Mossad. It serves as a manual for inflicting billions of dollars in damage on Russia within hours by striking key strategic assets. In doing so, Ukraine’s special services demonstrated the culmination of their knowledge and capabilities, both past and present.

Modern “Trojan Horse”

Historical sources suggest that around 1200 BC, the Greeks invaded Troy on the Aegean coast, seeking plunder. They fought there for a decade, most of which proved fruitless. In the epic Iliad, the ancient Greek poet Homer recounts the events of the tenth year of the war, detailing how the Greeks finally infiltrated the city through deception. According to the legend, they feigned retreat, offering a large wooden horse as a gift of peace. Unbeknownst to the Trojans, Greek soldiers were hidden inside. That night, the soldiers emerged, opened the gates, and captured Troy. Since then, the term “Trojan Horse” has come to symbolize deceptive tactics masked as goodwill. Whether the Trojan Horse incident actually occurred is a matter of historical debate. But the essence of that story came to life in a modern form during Russia’s ongoing invasion of Ukraine, which has now entered its fourth year.

On June 1, Ukrainian drones, launched from within Russian territory and hidden in a truck, inflicted significant damage on Russia’s military infrastructure — evoking the concept of a modern Trojan Horse. The resources needed for this mission, codenamed “Spider Web,” had been covertly smuggled in, with preparations carried out inside Russia.

A day earlier, on May 31, Russia had launched its largest airstrike on Ukraine since the start of the war, deploying 472 drones. In response, Ukraine struck back with an unprecedented counterattack. Airfields in Russia’s Amur region, Belaya in Irkutsk, Diaghilev in Ryazan, Olenya in the Murmansk region, and another in Ivanovo region were targeted. The Russian Defense Ministry confirmed the airstrikes. While Russia claimed that the attacks in Ivanovo, Ryazan, and Amur regions were repelled, reports indicated that several aircraft were destroyed in Murmansk and Irkutsk regions.

According to Ukraine’s security service, 34 percent of Russia’s strategic aviation fleet was taken out in Operation Spider Web — including long-range cruise missile carriers based at major airfields. Kiev estimated the total financial impact of the operation at \$7 billion. Sources reported that 41 Russian aircraft were damaged, including an A-50 reconnaissance aircraft, and Tu-95 and Tu-22M3 strategic bombers, which had been used in regular assaults on Ukrainian cities.

Reports also indicated that Kiev carried out the operation independently, without notifying the White House. As some Ukrainian officials implied, there was little point in briefing a U.S. administration led by a president perceived as unpredictable. Ukrainian President Volodymyr Zelensky confirmed the success of Operation “Pautina” — the Ukrainian word for “Spider Web” — and praised Vasyl Malyuk, head of Ukraine’s Security Service, along with all those involved in the mission. Zelensky described it as a “unique operation,” reaffirming that Ukraine would do whatever it takes to end the war on its own terms.

“Cobweb” – a script worthy of an Oscar

More than three years of relentless defense and sustained pressure appear to have elevated Ukraine’s security service to a level comparable with Israel’s Mossad and the CIA of the United States. Kyiv is increasingly becoming a vault of strategic secrets. By striking Russia from within Russian territory, the Zelensky administration offered a forceful rebuttal to former U.S. President Donald Trump’s remark that Ukraine had “no cards in its hands.” After Operation “Cobweb,” Trump may not repeat those words. Here's a closer look at how this unprecedented operation unfolded.

The operation, prepared over a span of one year, six months, and nine days by Ukraine’s Security Service (SBU), involved smuggling 117 drones hidden in the backs of trucks and deploying them near four key Russian air bases. President Zelensky revealed that the command center for this operation was located near a Federal Security Service (FSB) office in one of Russia’s regions. However, he did not disclose further details. What is clear is that Ukraine’s secret services managed to execute a highly complex and wide-reaching campaign that temporarily paralyzed Russia’s strategic air forces. Among the targets were locations spanning vast distances — one near Finland, another near Mongolia. These airfields are thousands of kilometers apart, indicating Ukraine’s capability to strike deep into Russian territory.

All of the targeted airbases lie far from Ukraine’s borders. For example, the Olenya base, located near Murmansk in the Arctic Circle, is about 2,000 kilometers from Ukraine. The Belaya base in Irkutsk is roughly 4,500 kilometers away. The Diaghilev base in Ryazan, a key training center for Russia’s strategic bomber fleet, is located 520 kilometers from Ukraine, while the Ivanovo airfield, a base for military transport aircraft, sits around 800 kilometers away. As a result, Operation “Cobweb” unfolded across three different time zones. This made the mission extremely complex in terms of coordination, timing, and logistics — but Ukraine succeeded. The drones, hidden inside mobile wooden cabins mounted on trucks, were concealed beneath remote-controlled roofs. At the designated time, these roofs were opened, and the drones launched toward their targets, aiming to disable Russian bombers.

Footage from the attack shows drones rising from truck-mounted launchers, and in another clip, a detached roof lying on the ground after being opened. Perhaps most remarkably, Ukrainian officials stated that all personnel involved in this highly sophisticated operation have already returned safely to Ukraine. While only a few local residents were seen on the ground during the attacks, the vast majority — including Russian security agencies — were unaware of the tactics being used. This operation has undoubtedly opened a new chapter in the evolution of modern warfare.

“If necessary, we’ll go underground” – SSU

Following the success of Operation “Cobweb,” Ukraine’s Security Service (SSU) issued a strong warning to Russia: “If necessary, we will reach them even underground.” Indeed, after a string of Russian failures in Ukraine and the aborted march on Moscow by the late Yevgeny Prigozhin, the myth of Russian invincibility has begun to unravel. Last summer marked the first time since World War II that Russian territory came under siege, and President Vladimir Putin’s defensive image started to look increasingly fragile. Today, it is clear that Ukraine’s intelligence services are capable of inflicting multibillion-dollar losses on Russian military infrastructure, regardless of location.

Several Russian military commentators and pro-war “Z” bloggers have compared Operation “Cobweb” to Japan’s surprise attack on Pearl Harbor during World War II — an assault on one of America’s most strategic military hubs. A senior U.S. defense official told CNN that Ukraine’s operation was unlike anything they had ever witnessed. This context lends new weight to President Trump’s recent statement that “the United States is studying Russia’s attack on Ukraine and learning from it.” Ironically, as Washington learns lessons from Ukraine, it may well be Russia that finds itself left behind in the process.

Russia in mourning

From June 2 to June 4, an official mourning period was declared in Russia. However, it was not related to the Ukrainian drone strikes that damaged Russian military aircraft, but rather to a tragic accident that occurred just hours before those events. In Russia’s Bryansk region, a passenger train en route to Moscow derailed after a road bridge collapsed onto the railway line. The incident took place on May 31 at 22:44 local time, along the single-track railway section of the Pilsino–Vygonichi route. The upper structure of a road bridge suddenly gave way, causing debris to fall directly onto passenger train No. 86, which was traveling in the Klimovo–Moscow direction. The collapse resulted in the derailment of the locomotive and several carriages. Seven people were killed, and approximately 90 others were injured. During the mourning period, the Russian national flag, as well as regional and local flags in the Bryansk region, will be flown at half-mast. In addition, all cultural institutions and entertainment programming on television and radio have been suspended out of respect for the victims.

This was not the only bridge-related incident in Russia during that period. A similar accident occurred in the Kursk region, where a railway bridge collapsed while a train was passing over it. The collapse happened at the 48th kilometer of the Trostna–Kalinovka route. One locomotive driver sustained leg injuries. Local authorities stated that the cause of the collapse is still under investigation. However, according to Russian Telegram channels, the incident may have been the result of sabotage. Reports claim that two explosive devices were found — one on the bridge pillar and another about 30 meters away under the railway track.

These incidents have raised suspicions due to their proximity in both time and location to Operation “Spider Web” — a large-scale Ukrainian drone operation targeting Russian military airbases. Notably, the Bryansk bridge collapse took place just as Ukrainian operations intensified. Nevertheless, there has been no official statement linking Ukraine to the railway incidents. Kyiv has only acknowledged its role in Operation “Pautina” (“Spider Web”).

Regardless of official confirmation, May 31 and June 1 will likely be remembered in Russia as days of mourning not only for the victims of the Bryansk accident but also for the heavy losses suffered by the country’s strategic aviation and security services.

These developments highlight the growing capabilities of Ukraine’s intelligence services. As the saying goes, “Backward countries collect information about their own citizens, while powerful countries gather intelligence on others.” Ukraine’s Security Service has set a new benchmark, serving as a case study for intelligence communities around the world: the focus should not be on surveilling one’s own people, but rather on understanding potential adversaries.