For Russia, Kupyansk has been of strategic importance as a logistics hub since the beginning of the war.
The city is located at the intersection of two key highways — R-07 (connecting to Kharkiv) and R-79, as well as an important railway with the Kupyansk-Vuzlovyi junction. Because of this, Kupyansk is a kind of "gateway" between Russia and the north-eastern regions of Ukraine.
In 2022, Kupyansk was captured by the Russians, and in the fall of the same year, Ukrainian troops regained control of it during a major counteroffensive. Without taking Kupyansk, it is almost impossible to surround Kharkiv.
So in June 2025, the offensive in this area intensified. The Russians, as on the entire front line, took advantage of the moment when the corps reform was just beginning, and the corps were advancing into their areas of responsibility, often not in full force.
The area of responsibility of the 10th Army Corps is marked approximately*.
«Babel'»
Since June, the Russians have advanced about ten kilometers toward Kupyansk and have partially penetrated the city, although they do not have full control over it. This is only the "on the ground" advance that is visible on combat maps.
At the same time, as the Ukrainian military notes, the Russians crawled through underground pipes for almost 20 kilometers towards the city, in particular on the section between Kupyansk and the village of Vilshana.
This is not the first attempt. Previously, Russian troops used similar tactics in Avdiivka (Donetsk region) and near Sudzha (Kursk region). At the exit from the pipes, they allegedly change into civilian clothes in order to penetrate the city unnoticed.
The first mention of the movement through the pipes in the Kharkiv region was in September. At that time, the General Staff of the Armed Forces of Ukraine stated that the pipeline, through which the underground groups were allegedly advancing, did not lead directly to the city.
The head of the “Achilles” drone regiment Yuriy Fedorenko wrote that the main entrances to the underground routes are located in the area of Lyman Pershyi, and movement to Kupyansk through them takes about four days. The diameter of the pipes allows the use of specially designed beds on wheels and the arrangement of places for supplies.
According to him, three of the four pipelines were destroyed by Ukrainian troops back in September. However, Russian infantry continued to arrive on the outskirts of Kupyansk through the last remaining one, hiding from the drones in the forest.
The front line on November 27, 2025.
«Babel'»
Fedorenko explained that Ukraine needs to block underground pipes in advance so that the Russians cannot infiltrate their groups with them. To do this, military-civilian administrations should review maps of the gas transportation system, assess the diameter of the pipes, and block them as needed.
For example, in safe areas, “dangerous gas pipelines” can be dismantled or blocked. This is impossible to do on the front line — equipment and people would be under fire, so Ukrainian units only mine such networks and keep them under fire control — which turns out to be insufficient.
The situation "on the ground" is not much simpler. The main threat in the Kupyansk area is the Russian bridgehead north of the city, on the Oskil River.
From this bridgehead, the Russians are constantly attacking and conducting "infiltration" — moving small groups of infantry into the cityʼs borders unnoticed in order to penetrate the city and gain a foothold there.
The Zapadne — Holubivka — Radkivka — Kindrashivka area is important for Russian forces.
They use it to transfer ammunition and reinforcements to units in Kupyansk. It serves as a flank cover and a supply corridor. But there is also a weak spot for the enemy there.
The area is small — at its widest point, approximately 4.3 kilometers (from the forward positions near Kindrashivka to the Oskil River). Small Russian infantry groups were able to “infiltrate” west of the R-79 road (south of Tyschenkivka, to Myrne, and even to the northern outskirts of Sobolivka), but they are unable to gain a secure foothold there.
The front line on November 27, 2025.
«Babel'»
Russian forces hold the northern and partly central parts of Kupyansk.
On the map, their advance looks like a narrow pocket going deep. However, over the past week, the Russian offensive has slowed down — they are now trying to hold on to the areas they have already occupied.
The Ukrainian Armed Forces are gradually pushing them out, especially in the west of the city, operating in small assault groups that conduct raids and knock Russian units out of individual neighbourhoods.
The Ukrainian Armed Forces have advanced in the area of Kindrashivka. Assault groups entered the outermost buildings on the southern side and began to knock Russian units out of their shelters.
The “gray” zone is noticeably shifting to the southeast and east — where the Russians felt stable yesterday, today the situation is unstable for them. If the Ukrainian units continue to advance in the same coordinated manner, they can cut off the supply routes of the Russian troops. This will allow them to take control of Kindrashivka and level the front line.
At the same time, Russian forces are losing positions near Radkivka, where the “gray” zone is also growing.