How Ukraine's Planned "Pearl Harbor-Style" Attack on Russian Airfields Was Delayed by Hungover Drivers

Operation Spiderweb represented the SBU's most audacious mission to date.

Ukraine was forced to delay its bold "Pearl Harbor"-style strike on Moscow's bomber fleet due to an unexpected prevalence of hungover Russian drivers, according to a newly released report.

Earlier this year, Kyiv secretly deployed drones into Russia, planning the unprecedented attack to coincide with Russian Victory Day on May 9, as reported by the Wall Street Journal. The assault, code-named Operation Spiderweb, was designed to cripple Moscow's air capabilities while simultaneously embarrassing the Kremlin.

Operation Spiderweb constituted the SBU's most daring undertaking ever, requiring 18 months of meticulous planning, strategic deception, cutting-edge technology, unwavering resolve, and an element of fortune.

The convergence of multiple holidays—including Victory Day, Russian Labour Day, and Orthodox Easter—resulted in a critical shortage of available drivers needed to transport the drones to their launch positions. Ukraine's plan relied on unsuspecting Russian truckers who believed they were merely transporting ordinary wooden cabins. SBU officials informed the American newspaper that the limited pool of available drivers made executing the mission too risky. It wasn't until late May 2025 that an ideal group of drivers was finally secured.

The SBU encountered additional complications throughout the operation. During one incident, a driver discovered that a cabin's roof had detached, exposing the drones concealed inside. The driver immediately contacted his employer, Artem Timofeev, a 37-year-old Ukrainian operating within Russia. Timofeev, who coordinated the ground operations and assembled the drones with his wife's assistance, had been coached by the SBU to feign ignorance.

When contacted by the concerned truck driver, Timofeev pretended to have no knowledge about the true nature of the cargo. Following SBU guidance, he provided a barely credible explanation, claiming the wooden structures were hunting lodges and the drones inside were used for tracking wildlife across vast territories, according to reports.

Other operational challenges included a truck experiencing mechanical failure, which the SBU and Timofeev resolved by transferring the sensitive cargo to an alternative vehicle, and a temporary communication loss with two drone-containing cabins. Attempts to remotely guide the driver failed, raising fears of compromise. Reports later revealed that the cabins had ignited, causing the drones to detonate and resulting in the driver's death.

Despite these obstacles, Operation Spiderweb ultimately succeeded. On June 1, over 100 drones were launched from cabins positioned on four trucks, targeting four Russian airfields. For the Kyiv-based drone operators, the exposed warplanes presented easy targets. Within a single hour, dozens of Russian military aircraft were either destroyed or significantly damaged.

The operation substantially enhanced the SBU's international reputation, helping to counter its long-established image as a corrupt KGB successor organization compromised by internal betrayal.