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Putin promised to make Ukraine pay for its airbase attacks. What does he have left?

Last updated: June 9, 2025 12:54 pm
Oliver James
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10 Min Read
Putin promised to make Ukraine pay for its airbase attacks. What does he have left?
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For more than three years, Russia has used its fleet of bombers to rain hellfire on Ukraine. On June 1, Kyiv responded by going after those bombers.

Contents
Tit for tat?Grinding on

The operation, codenamed “Spiderweb,” was 18 months in the making. Dozens of hidden drones emerged from trucks parked in Russia, racing to airfields thousands of miles from Ukraine and destroying at least 12 bombers.

Although the operation was a huge boost for Ukrainian morale, many in the country braced for Moscow’s retaliation. Their fears sharpened when Russian President Vladimir Putin told his US counterpart Donald Trump on Wednesday that the Kremlin would “have to respond” to the attack.

Russia’s initial retaliation began Thursday night, in the form of a massive drone and missile strike on Kyiv and across the country. Russia’s Ministry of Defense described the strikes as a “response” to Kyiv’s “terrorist acts.” The attack was punishing, but not qualitatively different to what Ukraine has grown used to over three years of war.

Olha, a 67-year-old resident of Kyiv who asked to be identified only by her first name, told CNN that if Thursday night’s strikes were Russia’s retaliation, then Ukraine faces “many such retaliations – once a month, even more.”

Russia’s response so far to Ukraine’s extraordinary operation has raised questions about Putin’s ability to escalate the war and exact the retribution that many of his supporters have clamored for. And it has left Ukrainians wondering if it has already felt the brunt of Russia’s response, or if the worst is yet to come.

In determining Russia’s retaliation, analysts say, Putin has faced several constraints. One is political: Mounting a large-scale, innovative response to the “Spiderweb” operation would be akin to admitting that Ukraine had inflicted a serious blow against Russia – an impression the Kremlin has been at pains to avoid, said Kateryna Stepanenko, a Russia analyst at the Institute for the Study of War, a think tank in Washington DC.

Locals clean up after a Russian drone struck an apartment building in Kyiv on Friday. - Thomas Peter/ReutersLocals clean up after a Russian drone struck an apartment building in Kyiv on Friday. - Thomas Peter/Reuters
Locals clean up after a Russian drone struck an apartment building in Kyiv on Friday. – Thomas Peter/Reuters

In a meeting with government ministers on Wednesday, Putin received a lengthy briefing on recent bridge collapses in Kursk and Bryansk, blamed by Russia on Ukraine. Yet, aside from Foreign Minister Sergey Lavrov’s reference to recent “criminal provocations” by Kyiv, there was no mention of the “Spiderweb” operation.

In Russian state media’s coverage of Putin’s call Wednesday with Trump, little was made of the Russian president’s pledge to “respond” to Ukraine’s attack. Instead, the reports focused on the outcome of recent peace talks in Istanbul.

Stepanenko said this is part of a deliberate strategy. “Putin is trying to make this go away and hide this failure yet again,” she told CNN. She said a high-profile response “would contradict the Kremlin’s strategic objective of making it all go away and sweeping this under the rug.”

Tit for tat?

Putin has also faced material constraints. Whereas Russia’s near-daily strikes on Ukraine used to involve just dozens of drones, they now routinely use more than 400. A day before Ukraine’s “Spiderweb” operation, on May 31, Russia launched 472 drones at Ukraine – a record in the three-year war, which was surpassed again during Sunday night’s attacks, which used 479 drones.

“Russia’s response is constrained by the amount of force they’re constantly using,” said William Alberque, a former NATO arms control official now at the Stimson Center think tank.

“How would you know if Russia was actually retaliating? What would be more brutal than them destroying apartment flats or attacking shopping malls? What would escalation look like?”

Firefighters respond to a Russian drone and missile strike on Kyiv on Friday. - Valentyn Ogirenko/ReutersFirefighters respond to a Russian drone and missile strike on Kyiv on Friday. - Valentyn Ogirenko/Reuters
Firefighters respond to a Russian drone and missile strike on Kyiv on Friday. – Valentyn Ogirenko/Reuters

Russia’s pro-war community of Telegram bloggers was not short of ideas. Some prominent channels said that Kyiv’s strikes on Moscow’s nuclear-capable bombers warranted a nuclear strike on Ukraine. Others called for a strike using the Oreshnik ballistic missile, which was unveiled by Putin last year, and has so far been used only once against Ukraine.

Although Putin often praises his new missile, it has limited uses, said Mark Galeotti, a leading Russia analyst.

“The Oreshnik is really geared for a particular kind of target. It’s not that accurate… and it’s not a bunker-buster,” he told CNN, meaning the missile would struggle to take out key manufacturing and decision-making hubs that Ukraine has moved deep underground. “If you’re going to deploy it… you want it to have a target that’s worthy of the name.”

One target could be Ukraine’s security services, the SBU, which masterminded the “Spiderweb” operation, he said.

“But that’s not something you can do quickly,” he cautioned. “In some ways, Putin has already swept away most of the escalation rungs at his disposal, which means that he doesn’t have the option for clear punishment.”

In a sign that Moscow’s “retaliation” may be ongoing, Russia’s Ministry of Defense said it had struck a Ukrainian airfield in the western Rivne region on Sunday night – a week after Ukraine’s attacks on Russian airfields.

The ministry said the attack was “one of the retaliatory strikes” for Kyiv’s “terrorist attacks” against Russia’s airfields, suggesting there may be more to come. Yuriy Ihnat, a spokesperson for Ukraine’s air force, said the attack on the airfield was “one of the biggest ever carried out by Russia.” Although air defenses “performed very well,” he said it was “impossible to shoot down everything.”

Grinding on

Although Putin may be constrained in his ability to respond to Ukraine’s spectacular operation with one of Russia’s own, this may not matter on the battlefield, said Galeotti.

“From a political perspective… it’s the Ukrainians who demonstrate that they are the nimble, imaginative, effective ones, and the Russians are just thuggish brutes who continue to grind along,” he said. “But from the military perspective, in some ways, that’s fine.”

While Ukraine may have the initiative in terms of headlines and spectacle, Russia still has the initiative on the battlefield. Russian troops have opened a new front in Ukraine’s northern Sumy region and are now just 12 miles from the main city. And on Sunday, Moscow claimed that its forces had advanced into the central Ukrainian region of Dnipropetrovsk for the first time, after months of clashes.

Police officers stand at the site of a Russian missile strike on Sumy on June 3. - ReutersPolice officers stand at the site of a Russian missile strike on Sumy on June 3. - Reuters
Police officers stand at the site of a Russian missile strike on Sumy on June 3. – Reuters

The question is whether “Putin is willing to accept whatever damage happens on the home front, precisely for his slow attrition grind forward,” said Galeotti.

Alberque, of the Stimson Center, said a lot rests on whether Ukraine has been weaving more “Spiderwebs,” or whether its drone attack was a one-off.

“The fact that this operation was a year- and-a-half in the planning – how many other operations are a year-in right now?” he asked.

Two days after the drone attack, Ukraine’s SBU unveiled another operation – its third attempt to blow up the bridge connecting Russia and the occupied Crimean Peninsula. The bridge over the Kerch Strait was not significantly damaged, but the attack reinforced the SBU’s commitment to impressing upon Moscow that there are costs to continuing its war.

If “humiliating” operations like those continue, Putin will come under greater pressure to deliver a response that is different in kind, not just degree, Alberque said.

“Putin is such a creature of strongman politics,” he added. “(The Kremlin) is going to look for other ways to strike back, to show the Russian people that Putin is a great wartime president who is inflicting horrible damage on his enemy, rather than a victim of these spectacular Ukrainian attacks.”

CNN’s Kosta Gak and Victoria Butenko contributed reporting.

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