The battle for Kupiansk

Kupiansk today is the site of one of the longest, bloodiest and least decisive battles of the war, and the public picture is unusually muddied by propaganda on both sides. What follows is as up to date as open sources allow, to early December 2025, with the inevitable caveat that local tactical control may be shifting almost daily.

Why Kupiansk matters

Kupiansk is a small rail and road hub on the Oskil River in Kharkiv oblast. Before the full-scale invasion she was principally known as a junction through which fuel, ammunition and other supplies moved from Russia into the Donbas. When Russia first occupied much of Kharkiv oblast in 2022, Kupiansk became one of Moscow’s main logistics hubs for operations around Izium and Lyman.

Ukraine’s lightning counteroffensive in September 2022 broke that system. Russian forces abandoned most of Kharkiv oblast and fell back to the eastern bank of the Oskil; Kupiansk was liberated, and the river became a rough front line.

From late 2024 onwards, however, Moscow made the “Kupiansk direction” one of her principal axes of renewed attack, alongside Avdiivka and later Pokrovsk. The aim has been:

• to push Ukrainian forces back from the Oskil,

• to retake Kupiansk itself, restoring a supply axis into Donbas, and

• potentially to create conditions for a future push further into Kharkiv oblast.

In Ukrainian terms, the battle is existential for the region. If Kupiansk falls decisively, the door opens for Russian artillery to reach deeper into Kharkiv oblast and complicate the defence of the Donbas from the north.

The offensive: from river crossings to urban combat

Establishing bridgeheads (late 2024 – early 2025)

In November 2024, Russian forces began systematically crossing the Oskil using small boats and establishing bridgeheads west of the river near Dvorichna, Masiutivka and Zapadne. Ukrainian observers initially assessed these as company-sized incursions, fragile and heavily dependent upon vulnerable boat logistics.

Throughout winter 2024–25 these bridgeheads were fed by infantry rather than vehicles. Russian armoured units repeatedly failed to cross in strength; Ukrainian artillery, drones and special forces raids turned the bridgeheads into what one Ukrainian account called a “fire pocket”, in which small forward elements could be chewed up without allowing Russia to consolidate a stable line.

A grinding Russian campaign, high casualties, few gains

Through 2025 the Russians persisted, reinforcing the Kupiansk axis with elements of the 6th Combined Arms Army and other units. Euromaidan Press, drawing on geolocated footage and Ukrainian sources, has described Kupiansk as a “graveyard” for Russia’s 6th Army after some twenty-plus months of offensive efforts that yielded negligible territorial gains at the cost of whole brigades.

Russian tactics shifted over time:

• assault infantry advancing through forest belts near Synkivka and Pishchane;

• motorcycles and buggies used for quick dashes across open ground;

• occasional armour-supported pushes;

• heavy use of glide bombs and artillery to erase Ukrainian positions before infantry moved in.

Ukrainian forces responded with “active defence”: letting some Russian groups penetrate into salient areas and then isolating and destroying them with artillery, drones and counter-attacks, particularly around the “Pishchane funnel” west of the Oskil, a narrow wedge of territory that has changed hands repeatedly.

By mid-2025 one informed assessment held that this approach had largely blunted the Russian push, turning it into a costly attritional battle that did little more than drain Russian manpower and material.

Russian adaptation: infiltration and pressure on the city

Infiltration into Kupiansk (late summer – autumn 2025)

In August–September 2025 Russian forces began a pattern of infiltration operations, slipping small groups into industrial and residential zones on the eastern side of Kupiansk while maintaining pressure from the north near Synkivka and from the east near Petropavlivka and Pishchane.

Open-source mapping projects such as DeepState and analytical groups like ISW and Critical Threats tracked incremental Russian advances:

• Russian forces entered parts of the city’s outlying districts in late summer;

• they briefly reached lines close to the H-26 highway south of the city;

• Ukrainian counter-attacks repeatedly pushed them back to the eastern outskirts.

Russian military bloggers claimed partial encirclement of Ukrainian troops near Kupiansk, and Moscow’s Ministry of Defence has periodically announced that the city is either surrounded or effectively taken.

Street-to-street fighting

By late November 2025, independent Ukrainian-leaning outlets reported continuous street fighting “day and night” inside Kupiansk, with heavy bombardments and drone strikes lighting up the city as Russian assault groups tried to dislodge Ukrainian defenders house by house.

Reuters, citing Ukrainian Commander-in-Chief Colonel General Syrskyi on 28 November, reported that Ukrainian forces were still fighting in the city and its surroundings, contradicting statements by President Putin that Kupiansk had been fully captured.

On 2 December Ukraine’s General Staff again publicly rejected Russian claims of having captured Kupiansk, insisting that Ukrainian units continue to hold positions both in the city and on nearby lines, a message amplified by Defence Ministry communications and social media postings.

The current situation (early December 2025)

Because both sides see propaganda value in Kupiansk, one has to triangulate between official communiqués and independent analysis.

Key points that appear consistent across multiple sources as of early December:

1. The front line runs through or immediately around the city.

   
   

   Russian forces hold portions of the eastern and possibly some northern districts; Ukrainian forces hold central and western neighbourhoods and key crossings over the Oskil. The city is effectively a contested ruin.

   
   

2. There is no confirmed encirclement.

   
   

   Russian sources talk of a “cauldron” and surrounded Ukrainian troops; Ukrainian General Staff and independent mapping projects show Ukrainian formations still maintaining supply lines from the west and south-west.

   
   

3. Ukrainian command insists Kupiansk remains under Ukrainian defence.

   
   

   Syrskyi and the General Staff have publicly stated that Russian incursions into the city have been “largely pushed back” and that statements about full Russian control are disinformation.

   
   

4. Russian advances elsewhere have shifted some pressure away.

   
   

   Since mid-2025 the Russian main effort appears to have pivoted towards Pokrovsk and Huliaipole, where they have made more visible gains. Analysts argue that to replicate that success near Kupiansk Russia would need to redirect substantial reserves, which she has not yet done on the same scale.

   
   

5. Kupiansk is still described as “held” by Ukraine by front-line commanders.

   
   

   A recent Associated Press / Defence News report quoted a Ukrainian drone brigade commander saying that, despite intense pressure, Ukrainian forces continue to hold Kupiansk and Vovchansk, both of which Russia has been trying to seize for more than a year.

The Ukrainian General Staff’s daily bulletins still list airstrikes and shelling against Kupiansk and nearby Kivsharivka, but not as a fully lost locality, again implying ongoing defensive presence.

Given the intensity and fluidity of fighting, one must be cautious about any precise map line; but it is fair to say that Kupiansk is neither securely Ukrainian nor truly Russian-controlled at this time.

Tactics and technology: drones, artillery and river crossings

The Kupiansk sector epitomises the technological character of the 2025 front:

• Drones dominate reconnaissance and strike.

  
  

  Both sides use quadcopters and fixed-wing drones for artillery spotting and kamikaze attacks on small infantry groups, dugouts and vehicles. Ukrainian drone brigades, such as the Achilles UAV Brigade, have been specifically mentioned as operating in this area, using drones to interdict Russian concentrations and supply routes.

  
  

• Artillery remains the main killer.

  
  

  Russian forces employ massed artillery and glide bombs to grind down urban blocks before sending assault groups, while Ukrainian batteries respond with counter-battery fire and pre-registered kill zones along likely assault corridors, particularly around Synkivka and the Pishchane funnel.

  
  

• River crossings as a weakness.

  
  

  The Russian need to cross the Oskil has forced reliance upon small-boat logistics and improvised pontoon bridges, which are highly vulnerable to drone-directed artillery. Several assessments note repeated destruction of Russian bridging attempts and the consequent fragility of Russian bridgeheads west of the river.

  
  

• Manpower constraints on the Ukrainian side.

  
  

  Reporting from multiple sectors indicates that Ukraine is suffering from a chronic shortage of infantry, forcing her to man long sections of front with fewer troops and to rely increasingly upon drones, mines and artillery rather than dense trench lines. This applies particularly in sectors like Kupiansk where there is no political decision to withdraw but insufficient manpower for offensive counter-operations.

The net effect is a battle that progresses at walking pace, if at all, but remains extremely lethal for small assault groups attempting to cross open ground or rivers.

Humanitarian and urban impact

Kupiansk has been subjected to almost continuous shelling and glide-bomb attacks since 2022, with intensity rising again from late 2024. Population decline has been dramatic: large portions of the civilian population have fled, leaving behind a small, vulnerable community living under daily fire.

A recent Guardian report portrayed the city’s “slow demise”, with most streets damaged or deserted, public services largely destroyed, and surviving residents living in basements or temporary shelters, without any realistic prospect of normality whilst the front line cuts through or around the city.

Ukrainian authorities periodically announce mandatory or strongly encouraged evacuations from Kupiansk and surrounding villages as the fighting intensifies. Survivors’ accounts describe a landscape of burned-out vehicles in the forest belts around Synkivka, ruined apartment blocks, and a pervasive sense of exhaustion, as a battle “going nowhere” grinds on.

The humanitarian consequences are not limited to direct casualties. The destruction of rail and road infrastructure reduces the capacity to move goods into the wider region, complicating reconstruction efforts elsewhere in Kharkiv oblast and forcing Ukraine to use longer, more vulnerable logistics routes.

Strategic and diplomatic significance

Despite its modest size, Kupiansk has outsized strategic and political importance.

1. Operational leverage in the north-east.

   
   

   If Russia could secure the Oskil line and fully capture Kupiansk, she would gain a more defensible jumping-off point for any future offensive towards Kharkiv city or deeper into Ukrainian-controlled Donbas. Conversely, Ukraine’s continued hold on at least part of the city denies Russia this platform and keeps Russian supply lines in the region more exposed.

   
   

2. Symbolism of “momentum”.

   
   

   Moscow has sought to present Kupiansk, along with Pokrovsk and Vovchansk, as evidence that her forces are regaining the initiative. Hence the eagerness to declare the town captured even when independent evidence points to ongoing fighting.

   
   

3. Bargaining chip in peace talks.

   
   

   As various peace proposals are floated, each side will want to enter negotiations with the most favourable map possible. A clearly Russian-held Kupiansk would strengthen Moscow’s claim to the entire belt of territory linking Russia to Donbas, whereas a contested or Ukrainian-held Kupiansk makes any partition line more ambiguous and potentially more favourable to Kyiv.

   
   

4. Domestic perception inside Ukraine.

   
   

   For Kyiv, maintaining control over towns in Kharkiv oblast liberated in 2022, including Kupiansk, has major psychological significance. Losing such a town would feed narratives of reversal and failure; holding it, even partially, supports the claim that Ukraine is still capable of effective defence despite shortages of men and ammunition.

Likely trajectories

While prediction is hazardous, several trends seem plausible if current conditions continue:

• Russia is likely to keep attacking, but at the current rate of attritional operations her ability to achieve a clear breakthrough around Kupiansk remains in doubt without major reinforcement and redeployment from other sectors.

  
  

• Ukraine, facing acute manpower shortages, may continue to trade space for attrition, allowing limited Russian advances into pre-registered kill zones whilst avoiding encirclement. Kupiansk may remain a fragmented, contested ruin for months, as Bakhmut did before, rather than falling in a single decisive action.

  
  

• Any political deal that freezes lines will hinge upon who can plausibly claim control of Kupiansk at the moment of agreement. This may incentivise both Moscow and Kyiv to maintain or increase pressure until the very last moment of any diplomatic process.