For Russia, Kupyansk has been of strategic importance since the beginning of the war — it is an important logistical hub. The city stands at the intersection of two key highways — R-07 (connecting to Kharkiv) and R-79, as well as the railway with the Kupyansk-Vuzlovy junction.
Because of this, Kupyansk is a kind of gateway between Russia and the northeastern regions of Ukraine.
«Babel'»
In 2022, the Russians captured Kupyansk, but in the fall of that year, Ukrainian forces regained control of it in a major counteroffensive. Without occupying Kupyansk, it is almost impossible to surround Kharkiv.
So in June 2025, Russian forces intensified their offensive in this area. As along the entire front line, they took advantage of the moment when the corps reform was just beginning. The corps were advancing into their areas of responsibility, often not in full force.
From June to December 2025, the Russians advanced about 10 kilometers toward Kupyansk and partially penetrated the city. Almost 20 kilometers toward the city, the Russians crawled through underground pipes, in the section between Kupyansk and the village of Vilshana. At the exit from the pipes, they changed into civilian clothes in order to penetrate the city unnoticed.
By January 2026, Ukrainian forces had destroyed all such underground routes. Therefore, Russia is not currently attacking Kupyansk from the north (from the First Estuary or Vilshana).
The Russians who infiltrated Kupyansk itself were almost completely driven out by Ukrainian forces after long urban battles that had been going on since December. The front in this area has stabilized, and the Russians have been pushed back from the city all the way to the Oskil River, which is a natural barrier. This is exactly the situation in the Kupyansk direction that the “DeepState” map currently shows.
However, based on the “Suriyak” map, Russia has reoriented its forces to the southeast of Kupyansk, where it is making progress.
According to the map, two deep “pockets” have formed there: between Kucherivka and Kurylivka, and between Kurylivka and Kolisnykovka.
(The “DeepState” map gives different data.)
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Are the Russians really advancing in the Kupyansk direction now?
As Ukrainian units say, there is neither a major offensive nor a breakthrough. But there is no question of a deaf defense either.
The 33rd brigade specifies that the Russians are constantly trying to sneak into the rear of Ukrainian units and primarily damage logistics. The 43rd brigade adds that the Russians are mostly using the tactics of constant “probing” — local reconnaissance strikes, point assaults, and attempts to gain a foothold in weaker areas of the front.
However, they are not counting on a major offensive.
Where is it most difficult in the Kupyansk direction now?
The main Russian efforts in the Kupyansk direction are now focused on Pishchane. Russian forces have been able to gain a foothold in areas south of the village and build a foothold there.
Although this does not give them a direct bridgehead for an offensive, important commanding heights are located just south of Pishchane. The village itself, which is still held by Ukrainian forces, is located in a lowland.
Also a priority for the Russians is Kurylivka, from where they are trying to break through to Kivsharivka, gain a foothold there and then reach Kupyansk-Vuzlove. The last two cities actually merge with each other: they are logistically important, have many junctions and provide access to the river.
But for now, these cities are too distant a prospect for the Russians. As specified in the 33rd brigade, even at the stage of attempting to capture Kurylivka, the Russians came across defensive lines that did not allow them to do this.
«Babel'»
What are the Russian tactics in the Kupyansk direction?
They build up their strength and wait for bad weather (fog, clouds) when Ukrainian reconnaissance drones cannot observe the front line of defense. Then they move forward in small groups — twos or threes.
The 33rd Brigade says that Russian infantrymen often wander through the fields, looking for ways to infiltrate, especially in their unit’s lane. Here, the 33rd Brigade has an advantage: thanks to remote mining, the Russians come across mines, so they are afraid to enter the forest belts.
The Russians combine the tactic of “probing” lightly defended areas with artillery shelling, drones, and attempts to cross the Oskil River. They are constantly searching for targets with the help of reconnaissance drones, such as the “Orlan” and the “Prince Veshchiy Oleg”. However, as the 14th Brigade says, they destroyed six such devices in their unit’s area of responsibility in one day.
Is there now a threat that the Russians will infiltrate Kupyansk again?
Even though activity in the entire Kupyansk direction is likely to increase by summer, re-infiltration into Kupyansk is currently impossible. The city is difficult to reach, and all easy, i.e. underground, routes have already been cut off.
This is what representatives of all three brigades we spoke with say.