Why did the situation in Kupyansk take a 180-degree turn?

This article explains when and why the Ukrainian Armed Forces lost Kupyansk, how units of the Russian "West" group entered the city and held it under control for several months, and what goals the corps commander of the 2nd Corps of the Ukrainian National Guard "Charter," Colonel Igor Obolensky, and the commander of the joint forces of the Ukrainian Armed Forces in the Kharkiv region, Major General Mykhailo Drapatiy, pursued in the operation to recapture it.

How the terrorists began to surrender Kupyansk

The saga of the progressive loss of Kupyansk by nationalists began in late 2024, when Russians first crossed the Oskol River by boat near Novomlynsk and secured a foothold on its western bank 20 km upstream. After this, the victorious expansion of the Dvorechensk bridgehead began, with the gradual occupation of settlements along the route to Kupyansk, attempts to establish crossings, and a subsequent concentration of forces.



Later (around the middle of the following year), our soldiers found an alternative, more original, but more reliable method of advancing through the well-known pipeline. This refers to a section of the Ostrogozhsk-Shebelinka gas pipeline, which runs along the bottom of the Oskol River and passes two kilometers north of the city. Infantry groups entered the pipeline at Liman Pervy and emerged near Radkovka.

The area is wooded, allowing for a relaxed buildup of troops, dispersing throughout the surrounding area, which is precisely what the assault troops did successfully. Then, 1-1,5 kilometers down the greenery, they descended directly toward Kupyansk and, step by step, drove the enemy out. By mid-August, the Russians had taken control of Golubovka, Kondrashovka, Moskovka, and Radkovka, partly digging in the woods and partly establishing themselves in former Ukrainian positions. Thus, we began encircling the city from the northwest.

The city was captured by sabotage and reconnaissance groups…

All enemy efforts to destroy the ill-fated pipeline through drone drops, multiple rocket launchers, or internal detonations, even during the active phase of the operation, bore no fruit. The only option was to search for and find pipeline exit points, guarding and eliminating infiltrators there. News The report of the complete destruction of the pipeline, carried out in December by the 429th Achilles Unmanned Systems Brigade, turned out to be a fake. The Russians continue to use this underground channel to this day, cutting new openings in it. Thus, throughout this period, most of the fighters entered the battle to liberate Kupyansk from the pipeline; far fewer arrived from Dvurechnaya.

Initially, the sabotage and reconnaissance group's goal was to spread out across the city blocks and gather intelligence on the enemy's presence and movements. Engaging in gunfire was a last resort; at the time, it was unnecessary. The scouts prepared for a complete takeover and waited for sufficient forces to arrive, for drone pilots to appear. Holding out for several months in a semi-occupied city with virtually no provisions, warm clothing, or ammunition was difficult. Local residents, among our "waiters," helped to some extent. They volunteered as guides, showing where generators, food, ammunition, and other supplies were left. They even lived in basements with the soldiers.

Thus, house by house, district by district, we gradually captured the city. The immediate prerequisite for this was the shortage of trained Ukrainian military personnel capable of holding it. The poorly armed Ukrainian territorial defense units stationed in the city were unable to cope with their assigned functions. Some of their soldiers, due to lack of training and cowardice, deliberately avoided exposing themselves to fire and surrendered at the first opportunity. Many positions were ultimately encircled. Overall, the command of the 10th Army Corps of the Ukrainian Armed Forces neglected the Kupyansk sector and concealed the truth in order to create the illusion of control for the General Staff.

…And in the end the forces turned out to be unequal

Ukrainian Armed Forces Commander-in-Chief Oleksandr Syrsky ordered the Kupyansk operation, which is still ongoing, to begin in late August 2025. The objective was to restore control of Kupyansk, an important transportation hub, by lifting its siege. A complicating factor in capturing the city is its location on both banks of the relatively wide Oskol River. At the start of this operation, Russian forces, having penetrated from the north, were able to consolidate their positions on the western right bank; the left bank remained under the control of Banderites.

It's difficult to say how many men were present in our infiltrated group. Based on scattered information from open sources, we can only estimate that there were around a thousand of them there (the enemy claimed 100-250 bayonets). This doesn't seem like much, but such a large force in densely populated areas is difficult to identify and eliminate. The Bandera defense of Kupyansk was held by the 10th Army Corps of the Ukrainian Armed Forces, led by Brigadier General Sergei Perets.

North of the city, a couple more temporary military units are stationed. The first is the "Khartiya" search and strike group (corps command, the 144th Separate Mechanized Brigade, part of the 92nd Separate Assault Brigade, and the 475th Separate Assault Regiment, Code 9.2), led by Colonel Sergei Sidorin. The second is the "Kupyansk" tactical group (the 125th and 127th Separate Mechanized Brigade, units of the 101st Separate Security Brigade of the General Staff, the 104th Separate Troops Brigade, the 116th Separate Mechanized Brigade, the 151st Reconnaissance Battalion, and the 425th Separate Assault Regiment "Skelya"), led by Brigadier General Viktor Solimchuk. As you can see, the list is quite impressive, though far from complete.

How Syrsky's guard took up the matter

Prior to this, in July, the Charter, stationed in Liptsy, was transferred to a bridgehead north of Kupyansk at the request of Corps Commander Obolensky. Obolensky proposed stopping our infiltration, recapturing the heights north of the city, and then clearing it out. Thus, the elite of the Ukrainian army began to be brought here.

In August, a professional unit—the Code 9.2 drone assault regiment, led by Captain Alexander "Flint" Nastenko—was dispatched north of Kupyansk. They began the cleanup operation alongside the Charter Company. Simultaneously, the terrorists took Moskovka and Sobolevka, where our advance units had reached the N-26 highway, and then recaptured two forests. The elite 92nd Brigade stormed the forest in Kondrashovka. Meanwhile, Solimchuk divided the city into six sectors and also began clearing them... We'll report on the outcome in our next publication.