Ukraine’s Long-Range Strike Shakes Moscow and Exposes Deep Vulnerabilities in Putin’s Inner Circle

In the early hours of June 1, a grainy video began circulating across Russian social media channels. At first glance, it resembled the familiar footage of frontline skirmishes that have become routine since the start of Russia’s full-scale invasion of Ukraine. But this video had been recorded hundreds of miles from the nearest battlefield. It showed a small drone flying at treetop height across a military airfield deep inside Russia — and then striking a fully loaded Tu-95 strategic bomber, triggering an explosion that briefly illuminated the pre-dawn sky.

Seconds later, more footage appeared: another airfield, another bomber burning. Russian citizens awoke to scenes that military planners in Moscow had insisted could never happen.

What unfolded over the next several hours would come to be known as Operation Spider’s Web, a coordinated Ukrainian strike involving 117 long-range drones launched from within Russia itself and remotely piloted from Ukrainian territory. The attack hit five strategic air bases across five time zones, from the Kola Peninsula near the Arctic to the vast Siberian interior.

Satellite imagery later confirmed extensive destruction, including multiple Tu-95 and Tu-22M3 bombers and two A-50 airborne early-warning aircraft — platforms that Russia cannot easily replace. Even conservative Russian military bloggers acknowledged a loss of more than a dozen aircraft. Independent estimates placed the damage far higher.

At the center of the operation was a previously unknown Ukrainian weapon: the Flamingo cruise missile. Developed by a small defense startup, Firepoint, and built from carbon fiber, refurbished Soviet-era engines, and improvised warheads, the Flamingo had a range of roughly 3,000 kilometers and a payload exceeding that of an American Tomahawk. Ukrainian officials, speaking on background, described an 18-month effort to disperse production across the country and conceal testing from Russian intelligence services.

But the missile was only one part of a far broader covert program. According to Western analysts and Ukrainian officials, components for many of the drones used in the June attack had been smuggled into Russia piece by piece — hidden in trucks, shipping containers, and commercial cargo. Ukrainian operatives and sympathetic Russian recruits assembled them in safe houses before concealing them in innocuous wooden sheds mounted on vehicle roofs. On the chosen day, those roofs opened, and more than a hundred drones rose into Russia’s sky.

For the Kremlin, the implications were immediate and unsettling. A core assumption of Russia’s wartime strategy — that distance would shield its strategic rear — had been shattered. Within hours, emergency security meetings were convened in Moscow. Aircraft across the country were dispersed, and defenses were quietly reinforced. But the sense of vulnerability was harder to contain.

In public, senior Russian lawmakers demanded retaliation, some invoking the possibility of ballistic or even nuclear strikes. But the calls carried an unmistakable tone of alarm. With each passing month, Ukraine demonstrated the ability to strike deeper into Russian territory, hitting refineries, ammunition depots, logistics hubs, and even Moscow’s own suburbs. On March 11, Russian authorities reported the largest drone attack on the capital to date, briefly closing its major airports.

Inside Russia, these developments collided with growing social pressures. The Kremlin has spent years cultivating a sense of stability as the cornerstone of President Vladimir V. Putin’s legitimacy — a contrast to the chaotic 1990s and a reassurance that the costs of the war would remain distant. But as drone debris fell on Moscow neighborhoods and videos of burning Siberian airfields spread online, that narrative frayed. Local officials faced increasingly vocal demands from military families seeking information about missing or mobilized relatives. Social media platforms, despite tight state control, saw a rise in videos showing confrontations between residents and authorities.

For Putin’s inner circle, the threat was more direct. Many owned property in Moscow or its surrounding region — homes suddenly shown to be vulnerable to weapons Ukraine had produced domestically, outside Western restrictions and far from the reach of Russian intelligence. Security officials could no longer assure the president that key installations were beyond reach. The old assumption — that the war could be prosecuted without affecting Russia’s political elite — no longer held.

While Moscow scrambled to adapt, Kyiv pushed ahead. Firepoint reported rapid increases in production, supported by financing from European governments. New Ukrainian systems — shorter-range cruise missiles, hybrid drone-missile platforms, and possibly ballistic prototypes — were said to be entering testing. Western analysts noted that Ukraine was constructing not only an arsenal, but an entire industrial base capable of sustaining long-range warfare.

For Russia, the strategic dilemma remains unresolved. Acknowledging the scale of the losses risks undermining claims of military competence; ignoring them leaves key assets exposed. And both paths confront the same unanswered question: What else has Ukraine built in secret?

As the war enters its fourth year, the June attack stands as a stark reminder that the conflict’s geography — once assumed fixed — is rapidly evolving. The reach of Ukrainian weapons has redrawn the map, bringing the war into Russia’s interior and forcing the Kremlin to confront vulnerabilities it had long denied.