• Russia
• Ukraine

June 4, 2025, 1:35 PM View Comments ()

During the night of June 1, Ukraine launched an audacious, long-planned drone operation deep in Russian territory, targeting Moscow’s strategic bomber fleet at multiple bases. Ukraine said the mission—codenamed “Spiderweb”—hit 41 bombers, with at least 13 fully destroyed. Reports suggest that Tu-95 and Tu-22M bombers were hit.

Notably, Ukraine apparently chose not to target Russia’s most modern, nuclear-capable Tu-160 bombers, focusing instead on the Tu-95 and Tu-22M, which have been used extensively in conventional cruise missile attacks on Ukrainian cities.

Ukraine reportedly deployed 117 kamikaze-style, first-person-view drones to strike multiple Russian air bases scattered across several time zones, from Murmansk near the Arctic Circle to the Amur region almost 5,000 miles from the Ukrainian border. The drones were covertly transported into Russia over many months, hidden inside wooden cabins mounted on the backs of trucks with remotely operated detachable roofs. Ukrainian intelligence operatives managed to smuggle the drones close to the air bases, and, in some cases, used unwitting Russian truck drivers to do so. Then, at the precise moment, the cabin roofs were opened remotely, allowing the drones to launch toward their objectives using commercial and open-source technology, including 4G LTE networks and ArduPilot software. Each drone had its own dedicated operator, reportedly based at a covert command center near a Federal Security Service (FSB) office inside Russia. According to Politico, Ukrainian intelligence said that some drones relied on artificial intelligence to complete their missions along preset routes when they lost signal, automatically activating their explosives as they reached and identified their assigned targets.

For all its complexity, creativity, and audaciousness, the raid’s immediate impact on Russian operations in Ukraine is likely to be limited. Russia typically employs between seven and 11 bombers per cruise missile salvo, and the loss of a dozen or more aircraft out of a total operable fleet of around 100 long-range bombers will not immediately halt cruise missile attacks on Ukrainian cities. The impact would have been greater in 2024, when Russia relied more heavily on bomber formations to strike Ukraine than it does now. With increased production of drones and ballistic missiles, air-launched cruise missiles have become less critical and are now mainly used for select high-value, stationary targets. Additionally, Ukraine might have hesitated to launch such a raid in 2024, when it was more dependent on U.S. aid and following U.S. concerns over previous attacks on elements of Russia’s nuclear deterrent.

Russia will now have to spend precious resources to harden air bases and other critical facilities by establishing robust, layered counter-drone defenses—combining electronic warfare, anti-air weapons systems, and physical barriers such as concrete hangars. This redeployment is unlikely to substantially impact air cover on the front line, however, given Russia’s relative abundance of air defense systems.

However, the long-term implications of the Ukrainian raid should not be underestimated. The Tu-95 and Tu-22M bombers are no longer in serial production, and their loss reduces Russia’s capacity for long-range force projection. The reported but still unconfirmed damage to A-50 aircraft would further degrade Russian air surveillance and command-and-control capabilities, complicating Moscow’s ability to coordinate complex air operations in a future war against NATO.

Psychologically, the raid is a major blow to Russian prestige and credibility. It undermines the narrative of Russian military prowess and demonstrates Ukraine’s ability to strike at the heart of Russian military power. The operation also illustrates once again that Ukraine does not need to have an equivalent arsenal to Russia’s: Small, low-cost platforms can inflict serious damage on high-value targets.

Yet raids alone do not win wars. Ultimately, the trajectory of the war in Ukraine will be determined by how well Ukraine can continue to attrit Russian forces along the front line in the coming months, thereby changing the Kremlin leadership’s mind about whether it is worthwhile to pursue the war given the high costs and limited gains. That said, last weekend’s significant loss of hard-to-replace strategic assets far from the front may, in the best outcome, nudge the Kremlin a bit closer to seeing that the costs of the conflict are becoming too much for Russia and the regime.

While some observers have heralded this operation as the advent of a new type of warfare, its true significance lies elsewhere. What the Ukrainians have done is adapt a classic tactic of European warfare—the military raid—to the 21st century.

Once the principal form of military engagement across Europe, raiding warfare typically unfolds in several phases: covert infiltration, a surprise assault, and a swift withdrawal. Underdogs have often employed the tactic to maintain pressure on a stronger enemy. The dawn of the modern raid can be traced back to British Prime Minister Winston Churchill’s order to his minister of economic warfare, Hugh Dalton, to “set Europe ablaze” following the devastating defeat of British forces in France in 1940; to that end, Dalton established the Special Operations Executive for sabotage and resistance in German-occupied Europe. But history abounds with other examples of such audacious operations. In October 1757, during the Seven Years’ War, Austrian forces under Andras Hadik executed a daring raid on Berlin using a small, fast-moving contingent of mostly Hungarian hussars. Despite being outnumbered by the city’s garrison, Hadik’s troops surprised the defenders, briefly occupied Berlin, and extracted a substantial ransom before withdrawing.

Modern raids involving air power were regularly employed for the first time in World War II. In November 1940, the British Royal Navy launched a surprise attack on the Italian fleet in the harbor of Taranto, Italy, using only 21 obsolete Fairey Swordfish biplanes from the aircraft carrier HMS Illustrious. The raid disabled three Italian battleships and damaged several other vessels, demonstrating how a small force in the air could achieve outsized operational effects. Similarly, in March 1942, British commandos assaulted the heavily defended dry dock at Saint-Nazaire, France, using a destroyer packed with explosives to deny the Germans a crucial facility for their battleships. And then there was the German Luftwaffe’s Poltava raid on the U.S. Air Force in 1944, when German fighters targeted Allied bomber formations stationed in Ukraine and inflicted heavy casualties and aircraft losses.

At its most basic level, therefore, Ukraine’s Operation Spiderweb belongs to a long tradition of daring raids. It does not mark the dawn of a new age—it is simply the latest adaptation of an enduring tactical approach.

On the one hand, however, the raid illustrates that high-impact, long-distance raids are made easier by new technologies like drones. Any assumption that military assets and infrastructure deep in the rear are immune from attack was just shattered by Ukraine. Russia will now have to spend precious resources hardening air bases and other critical facilities, as well as disperse its assets to reduce their vulnerability. The need for robust, layered anti-drone defenses—combining electronic warfare, kinetic interceptors, and physical barriers—will also become an urgent priority. The distinction between the frontline and the rear has blurred.

The raid also illustrated that a non-nuclear power could raid the strategic assets of a nuclear power. The only feasible way for Kyiv to do so safely was to consciously avoid targeting certain assets. The raid’s limitations—both in terms of the targets chosen and the damage inflicted—highlight the constraints imposed by the risk of escalation. Ukraine’s restraint in targeting nuclear-capable bombers and other sensitive infrastructure serves as a reminder that, in an era of nuclear-armed adversaries, even the most successful raids must be carefully calibrated to avoid crossing invisible but potentially disastrous red lines.

Russia’s nuclear doctrine, updated in late 2024, explicitly reserves the right to use nuclear weapons in response to attacks on its territory by a non-nuclear state that is backed by a nuclear-armed one. Although Ukraine is not directly backed in any strict sense by a nuclear state, the presence of NATO support and the risk of Western intervention looms large in Russian strategic thinking. The Kremlin’s repeated nuclear threats—including tactical strikes, high-altitude detonations, and missiles fired on European capitals—have been a constant feature of the war, even as most of the Kremlin’s supposed red lines have been crossed without triggering nuclear use.

This dynamic creates a paradox: the more effective Ukraine’s raids, the greater the risk of a disproportionate escalation by Russia. For some observers in the West, the fear of a severe Russian reaction almost overshadows the operational success of the raid itself. This plays into a culture of Western self-deterrence in response to Russian threats, whereby Russia actively uses nuclear and conventional saber-rattling not merely in a neutral strategic context, but also as a deliberate tool to manage and constrain Western behavior.

Operation Spiderweb will enter military history as one of the more daring raids and one of the first conducted with remotely controlled strike drones. But it does not herald the dawn of a new age. Rather, it is the latest iteration of the classic raid, adapted to the realities of 21st century warfare under the nuclear threat.