From empty to enemy-held: A day in the fight to save Ukraine's Kupyansk from Russian reoccupation

"This is putting out a fire that has already started"

From the monitor in the drone operators' dugout, the center of Kupyansk is visible, shrouded in fog and smoke from strikes.

"There is always fog over Kupyansk," comments drone operator Passenger.

Together with his brothers-in-arms — FPV operator White and sapper Marlin — they are watching the morning streams from the units defending the city. The drone operators of the Black Wing company of the 116th Mechanized Brigade have a broken retranslator, which helps FPV fly farther than with a stationary antenna. Waiting for their brother-in-arms, the "fixer," to arrive, they have nothing left to do but watch the war-torn Kupyansk in the morning.

"This is the very center of Kupyansk. At the beginning of summer, we were sitting there," says White.

"A little farther," clarifies Passenger.

Russians have started burning through positions in the city — and this UAV unit had to pull back to the southern outskirts of Kupyansk, where we are talking. Having entrenched themselves in the city center, the enemy is already seeping in this direction, approaching the final capture of the city.

Kupyansk is a key logistics hub in Kharkiv Oblast, where nearly 60,000 people lived before the invasion. Understanding its important significance, the Russians occupied the city in the first days of the full-scale war. However, in September 2022, Ukraine's Defense Forces triumphantly liberated Kupyansk. Since then, despite shelling, Kupyansk lived until the summer of 2025.

The situation for the city began to worsen in June, when the Russians captured the village of Dvorichna and the village of Zapadne, north of Kupyansk. This allowed them to deploy crossings over the Oskil River — a key natural obstacle that divides the axis.

"And the situation in which we all find ourselves now is the result of the fact that some did not hold [the line], others are only coming in to cover it all. They (Russians — ed.) need to be pushed back and then build a certain line of contact, so that they no longer seep through," explains Valeriy Kyseliov, press officer of the 116th Mechanized Brigade.

"This is putting out a fire that has already started. This could have been done earlier too, but that is already philosophy," adds drone operator White.

"There is no proper line of contact"

Despite the fact that the Russians are not bypassing Kupyansk from the flanks but have entered the city itself, classic urban battles like those in Bakhmut or Avdiivka are not developing. As Ukrainian troops explain, those Russians who manage to enter the city hide in basements and from there transmit information about the movements of Ukrainian defenders, less often — they knock out vehicles and engage in small-arms battles.

"They act like sabotage and reconnaissance groups. They do not walk [through the city], do not shoot. They hide and wait for others to come closer. Two or three people enter. They even crawl in one by one!" Passenger recounts.

The same way, the soldier adds, Ukrainian infantry operates: they clear buildings in small groups. In particular, Scarab — commander of a platoon in the 151st Separate Reconnaissance and Assault Battalion — works with his brothers-in-arms. Since the end of summer, with his fighters, he has been participating in the liberation of Kupyansk and stabilizing the situation in the city. Doing this is especially difficult in conditions where it is unclear which section the enemy controls.

"There is no full knowledge of where they might be sitting, there is no proper line of contact, so that you know: here are friends, there is the enemy. This morning, there is no one here, you checked the building, and by afternoon, the enemy is already entrenched there," Scarab recounts.

During one of the missions, Scarab and his brothers-in-arms had to clear a building. The scouts received a warning that the enemy might be there. When the first group entered, they came under fire. It became clear that there was an enemy in the building.

Russian servicemen transmitted over the radio that they were being stormed, and immediately the scouts came under shelling from a mortar and FPV. But the Ukrainian fighters managed to establish control over the building. They eliminated three Russians and captured one. It turned out that the prisoner had entered Kupyansk through a gas pipe.

From 50 to 70 Russians entered through the pipes

At the beginning of September, Russian troops were spotted at the exit of a gas pipe in the village of Radkivka, near Kupyansk. The Russians entered the pipe in Lyman Pershyi, which they control on the left bank of the Oskil, and exited near the city, remaining unnoticed.

"The situation worsened when Holubivka came under their control. They got access to the pipes, and the situation with Kupyansk itself began to deteriorate. First of all, the fact that they crossed the river played a role. But the pipe also played its big role," says Donor, platoon commander of the 151st Separate Reconnaissance and Assault Battalion.

Enemy infantry exited the pipe in a very convenient place — near a forest in which they could disperse and then move further into the city.

"See what a little hole? It was hit. And right away the trees start farther on. They can run across to the forest, and catching them farther is very hard. There are a lot of trees. They have places to hide. We were just trying to catch them near the trees," drone operator White recounts, showing a video of strikes on the pipe exits on his phone.

The prisoner captured by Scarab's group while clearing Kupyansk said that it was very stuffy and dark in the pipe, and when the Russians exited it, they felt disoriented. The prisoner, according to him, was given the task to hole up in Kupyansk and transmit information. He had been in the city for about a week.

According to Ukrainian scouts, the Russians exited the pipe in several places. Approximately 50–70 people managed to use the pipe before they were detected. As Donor from the 151st Reconnaissance and Assault Battalion recounted, soon most of the enemy infantry was detected, and all the pipe exits were put under surveillance.

"If not destroyed, then controlled. Those on our side, inside with razor wire and already controlled from above either by machine gun or infantry group," Donor assures.

"We still need to dig up the potatoes"

"A guided aerial bombKAB hit here. Minus six houses," Passenger shows the smashed mess of what was once houses.

In the cameras of the Mavic quacopters, locals keep appearing. You can make out a grandmother in a robe on the porch of a house or a woman walking with bags in the direction of the exit from the city. The soldiers assume she will try to reach an evacuation point.

In Kupyansk, nearly 700 residents remain. Evacuations from there are no longer being conducted. Officially, Kupyansk is closed to entry. Only fighters can get there. The only way for civilians to get out of the city is to leave on their own or ask the military for evacuation.

"In this house, they were doing repairs, fixing the roof a month ago. The owners came and say: 'We still need to dig up the potatoes.' I say: 'Maybe not today.' Such optimists," Passenger marvels.

Ukrainian troops complain that civilians in the city complicate their work, since Russians sometimes also dress in ordinary clothes. Donor from the 151st Reconnaissance and Assault Battalion recounts that some locals even help the invading forces. One of the prisoners said that two local women brought him food.

"The Russians have contacts of people who were under occupation in 2022, they contact them. Also, already in Kupyansk proper, they can meet in the yard like that and make friends," Donor says.