Operation Spider’s Web shows how creative Ukraine can get in taking fight to Russia

Ukraine’s brazen, multifaceted attack on Russian military bases over the weekend was more than a year in the making and demonstrated its creativity in picking up battlefield victories against a much larger and better-resourced military.

The full extent of Operation Spider’s Web, as it was called, demonstrated Ukraine’s evolving tactics, the significance of drones in the conflict, and possibly a more aggressive campaign if the ceasefire negotiations fail.

Ukrainian officials said 117 drones were used during the simultaneous attacks at four military bases across three time zones, and that 41 Russian aircraft, or roughly one-third of Russia’s entire fleet, were damaged or destroyed in the weekend attack. The strikes did an estimated $7 billion in damage, according to Ukraine’s domestic intelligence agency, known as the SBU.

The Ukrainians smuggled the small, first-person-view drones into Russia near the four bases they targeted, and the unmanned aerial vehicles armed with explosives were hidden until they were activated on Sunday. The drones then hit the airfields at Belaya, Diaghilev, Olenya, and Ivanovo bases simultaneously.

“This was an ingenious creative attack,” retired Rear Adm. Mark Montgomery, now a senior director at the Foundation for Defense of Democracies, told the Washington Examiner. Some Russian military bloggers have likened the surprise attack to the Japanese bombing of Pearl Harbor during World War II.

Russia “bombed our state almost every night from these planes,” said Lt. Gen. Vasyl Malyuk, the head of the Security Service of Ukraine.

Ukrainian President Volodymyr Zelensky supervised the planning of the attack, which began more than 18 months ago.

The Ukrainians proved they “are capable of creating strategic level effects with these cheap rinky-dink tactical FPV drones that the Ukrainians have really stunning range and reach into deep interior Russia in the Arctic and in Siberia that we previously assessed were basically safe havens for Russia,” George Barros, an expert with the Institute for the Study of War, told the Washington Examiner.

Sneaking the drones across the border removed one of Ukraine’s greatest obstacles when it comes to hitting targets in Russian territory: Russia’s air defense systems.

Instead of trying to intercept every Russian missile fired from fighter jets overhead, this operation targeted the aircraft that carry and ultimately deploy the munitions. So, even if Russia is able to salvage some of the damaged aircraft, it has fewer operational bombers, which it has used to relentlessly bomb civilian infrastructure across the country.

“The hardest part of [Ukraine’s] long-range drone strikes is getting through the jamming curtains, getting through the air defense systems,” Montgomery said. “They removed the Russian obstacles to the strikes by putting the drones inside the inner ring.”

The drones also hit targets much farther from the Russia-Ukraine border, in part because they were launched from within Russian territory. The Belaya air base, which is close to the Mongolia border, was successfully hit.

“So this has to be taken as a collective approach by Ukraine to make it harder and harder for the Russians to launch,” Montgomery said. “They’re hitting the archer instead of the arrow, and so that makes it cheaper. This is part of an integrated approach to lessen the pressure on their integrated air missile defense systems, to impose cost on the Russians.”

However, Russia has other ways to carry out its attacks on Ukraine, including via drones and ground-launched ballistic missiles. Ukraine has struggled to thwart drone attacks, including this weekend, when Russia launched one of its largest drone attacks during the war.

From a battlefield standpoint, Russia will likely need to be more careful with its shipping and logistics to ensure it is not unknowingly transporting Ukrainian weapons to targets, though Barros said it will likely only have “a marginal effect on the drone and missile strike campaign.”

Ukraine has a smaller military and arsenal, and Russian leaders have shown a much stronger willingness to risk the lives of their troops. U.S. officials have likened Russia’s strategy to sending troops into a meat grinder.

The war has largely become one of attrition, and that is a battle the Ukrainians will lose given their disadvantages on the battlefield and in the defense industrial base. Ukraine, even with Western support, still struggles to stop Russia’s aerial campaign, so it has sought to conduct special operations that can, in effect, hit the Russians in unexpected ways.

In addition to this attack, Ukraine has conducted multiple brazen surprise attacks to varying successes, though each case demonstrates ways it is trying to level the playing field. Ukraine targeted Russia’s Moskva, the flagship of Russia’s Black Sea Fleet, in April 2022, and in August 2023, Ukrainian forces launched an incursion into Russia’s Kursk Oblast and held territory there for more than six months until they were pushed out.

Russia will likely respond in kind to the unprecedented attack, as it has in the past in the aftermath of Ukrainian victories on the battlefield. It has already begun spinning the attack in the information domain.

“Kremlin officials are already discussing and putting out their red herrings about how striking elements of Russia’s nuclear triad pushes the West closer toward World War III, and it undermines Russian nuclear doctrine and stability,” Barros added. “I think the Russians are going to try to play this nuclear destabilization card in a way that’s really just ridiculous.”

Montgomery likened the creativity and brazenness of Ukraine’s drone attack to Israel’s beeper and walkie-talkie operations against Hezbollah last year. In both instances, Ukraine and Israel carried out meticulous operations that took more than a year to configure and made their respective enemies question their own national security and defenses.

“I put this on par in terms of creativity and planning with the Israeli beeper and walkie-talkie attack,” Montgomery added.

Negotiations continue

Russian and Ukrainian officials met Monday in Turkey to discuss a possible end to the war that has been going on for more than three years.

The two sides have met before and done so with mediators, including the United States, multiple times over the last several months. However, there has been little progress to show for it so far, other than prisoner-of-war swaps.

The low-level Russian officials who traveled to Monday’s meeting were the same who participated in the first round of talks, which Barros said was an indication of their insincerity in the talks.

“Sending senior officials who can make senior decisions would be an indicator that this would be a substantive talk, but they sent the same low-level guides that they sent for the last meeting where nothing happened,” Barros added, calling the meeting “a nothing burger.

Wes Rumbaugh, an expert with the Center for Strategic and International Studies, said it is “clear that Ukraine wanted to strike to send a message of Russian vulnerability prior to the talks.”

RUSSIA BOMBARDS UKRAINE OVERNIGHT AS TRUMP’S PATIENCE WITH PUTIN WEARS THIN

Ukrainian officials have presented the U.S. with a term sheet detailing their positions on how to end the war, while the Trump administration is awaiting Moscow’s response, though its offer was published in Russian media on Monday after the meeting.

Russian leaders want the international community to recognize Russian-occupied Ukrainian territory as Russia’s, and they also call for Ukrainian forces to withdraw from those areas.