How Kyiv has withstood Russia’s attacks

Written Anjali Singhvi, Charlie Smart, Mika Gröndahl, James Glanz and Guilbert Gates
Kyiv is the ultimate prize for Russia: the heart of Ukraine and the seat of a government it has sought to replace. For weeks, Russian troops have pressed in on the city from both sides of the Dnipro River.
But the bigger the city, the more difficult it is to seize. And Kyiv is enormous — larger in land area than New York City and five times the size of Mariupol, which Russian troops have been trying to capture for weeks.
Russia vastly underestimated Ukrainians’ resolve to defend their homeland. And a Russian military trained for open spaces has also struggled with basic realities of urban warfare. Even a finely orchestrated military would be challenged the block-to-block fighting required to secure Kyiv. The Russian army has failed to even surround it.
Early Missteps
The campaign went wrong on Day One, when Russian helicopters assaulted the Hostomel airfield on the outskirts of Kyiv and were met with stiff resance.
Because the military failed to hold the airport, it could not quickly build up the airborne forces needed to invade the capital.
The next day, Russia sent a small force directly into Kyiv anyway, seemingly intent on quickly toppling Ukraine’s government.
But fighting for a major city like Kyiv is notoriously difficult, bloody and time-consuming.
There are plenty of places to hide. Opposing forces can camp out in tall buildings. Rubble hides fighters as well as standing structures do.
A column of Russian trucks and tracked vehicles managed to move straight down Peremohy Avenue, a main thoroughfare leading to the center of Kyiv.
Tanks and other armored vehicles are useful to armies attacking cities if they are well supported infantry and air power. But this column was largely on its own.
Several vehicles were destroyed from above before the Russians were forced to retreat.
Russian leadership was deluded that Ukraine would collapse at the first sign of fighting, and that President Volodymyr Zelenskyy would flee, said Nick Reynolds, a military analyst at the Royal United Services Institute.
“That was a catastrophic failure to understand Ukrainian society and the Ukrainian state,” Reynolds said.
Even outnumbering Ukrainian fighters 10-to-1 might not be enough to take the city, given Russia’s inability to coordinate its ground forces with intelligence, air power and engineering, some analysts said.
“You need to be good at this,” said Scott Boston, an analyst at Rand Corp. who studies the Russian military and land warfare. “And I don’t think I have any real evidence that Russia has trained to do large-scale urban warfare.”
Encircling the City
After the disastrous initial attempt on Kyiv, Russia resorted to a different strategy: encircling it.
An outer ring would block crucial weapons and supplies from getting in. An inner ring would seal off opposing forces and provide a solid base for a more robust attack.
But the Russian offensive stalled without completing either ring, preserving Ukrainian supply lines.
Even in places where Russians got closer, they had few major routes to enter the city.
That predictability is part of what makes a well-defended city so difficult to capture. Key lines of attack can be blocked, fortified and barricaded, said Anthony King, the author of a book about urban warfare and a professor at the University of Warwick.
Ukrainian forces relentlessly attacked Russian positions along major roads. Lt. Tetiana Chornovol, commander of an anti-tank missile unit, said she blew up a Russian tank near Brovary.
“We look for firing positions where we can see a stretch of road,” Chornovol said, adding that “we know a column will drive on the road” eventually.
In a fight outside of Brovary last month, seen in footage released Ukrainian forces, Russian tanks were sitting ducks, ambushed and destroyed Ukrainian artillery fire and anti-tank missiles.
Even if the Russian military had entered the east side of the city, another defensive resource loomed: the Dnipro River, which splits the city in two. Bridges further limit the Russian advance.
“It’s easy to see when they’re coming across,” said retired Col. Liam Collins, who has served as a military adviser in Ukraine. “Ukraine would blow bridges at the latest time possible to maintain resupply.”
After crossing one of the bridges, Russian forces would still need to climb a steep slope to get up the western side, which acts as natural cover for the center of the city.
Among the biggest surprises of the battle is that the Russian military has never fully controlled the airspace over the capital.
Ukrainian forces concentrated their air defenses in the city, and they used the urban terrain to provide cover, said Michael Kofman, research program director in the Russia Studies Program at CNA. The Russian air force has been mysteriously absent, he said.
“It became, in some ways, mutually denied airspace,” Kofman said.
The Russian advance was also weakened a series of puzzling logical failures.
Thousands of troops advancing west of the Dnipro River had to follow a narrow road. Lacking a railway, they trucked in supplies from Belarus on convoys that were repeatedly ambushed.
Ukrainians appeared to further constrain the Russian advance blowing up bridges and dams, flooding areas north of Kyiv.
The Russian army got close to Kyiv in suburbs northwest of the city. But in some of the most critical battles of the war so far, Ukrainian forces stalled the advance, ambushing columns of armored vehicles and causing heavy losses.
Russian troops east of the river struggled with their own supply problems. An advance from the north failed to capture the city of Chernihiv, leaving Ukrainians room to fight north of the city.
A separate, fragile advance from Sumy — some 175 miles to the east — never secured a consent line of attack. It was subject to frequent, debilitating counterattacks from Ukrainian forces.
The stalled offenses around Kyiv reflect Russia’s wider strategic failures planning the war, analysts said.
Numerous lines of attack across the country stretched the military too thin. Soldiers were thrown into battle without enough support. The smaller Ukrainian force was vastly underestimated.
“It’s really been kind of astonishing, in the sort of the cynicism, the stupidity with which the operation was carried out,” said Boston, the Rand analyst.
On Tuesday, Moscow promised to reduce the intensity of its military activity around Kyiv, in effect acknowledging that its advance toward the capital had stalled. Ukrainians reclaimed a series of towns outside the capital, signaling at least a partial Russian retreat.
Both sides have taken heavy losses, and the fight for Kyiv could still restart. Russians could dig in, keep Ukrainian forces pinned down and besiege the city. Air attacks could destroy civilian infrastructure and kill thousands of people. Or the Russian army could try to muster forces to attack the capital once again.
But for now, Russia’s prized target appears out of reach.