Kupiansk and Pokrovsk, the Winter Battles 2025/26

Both Kupiansk and Pokrovsk remain pivotal in the eastern theatre of operations. Their capture (or successful defence) influences not only momentum and logistics, but morale, media messaging, and downstream diplomatic implications. The attacker in each case remains the Russian Federation (Russia) seeking operational advantage; the defender remains Ukraine seeking to hold and/or counter-attack.

Kupiansk

Located in Kharkiv Oblast on the western bank of the Oskil river, Kupiansk is a key railway/road junction and has been contested since spring 2025, after previous liberation by Ukraine in 2022. Control of the city and nearby logistics nodes would allow Russia to threaten deeper into Kharkiv region and to interdict Ukrainian supply and reinforcement flows.

Pokrovsk

Pokrovsk, in western Donetsk Oblast, lies at a nexus of highways and supply routes for Ukrainian defence in Donetsk. Its fall would open greater space for Russian manoeuvre, threaten other centres such as Chasiv Yar, and deliver a symbolic and material blow to Ukraine’s industrial base (for example the coking-coal mine at Pokrovsk).

Thus both battles have high strategic value: Kupiansk for the northern Kharkiv front and potential Ukrainian counter-thrusts; Pokrovsk for the Donetsk front and Russia’s aim to degrade Ukraine’s defence network and economy.

Assessment: Kupiansk

Current situation (to 5 November 2025)

According to the latest assessment by the Institute for the Study of War (ISW) as of 4 November 2025, Russian forces continue offensive operations in the Kupiansk direction, but no confirmed advances into new major terrain have been reported recently. Ukrainian sources report that on 4 November 2025, in the Kupiansk direction, there were five enemy assault actions near the settlements of Pishchane, Borivska, Andriivka and Petropavlivka — which Ukrainian defenders repelled. Moreover thousands of civilians around Kupiansk were ordered to evacuate in mid-October due to the worsening security situation. 

Russia is pressing toward Kupiansk, applying sustained pressure, but has not yet announced or achieved an operational breakthrough as of early November. Ukraine’s defensive posture remains intact, although under stress.

Key determinants

• Logistics and terrain: The Oskil river remains a natural barrier; Russia has established and maintains bridgeheads west of the Oskil but sustaining supply across the river under Ukrainian artillery and drones remains difficult.

  
  

• Force strength and attrition: Russian units continue to press, but the lack of confirmed territorial gains suggests attritional slowing. Ukraine appears capable of local defence and repulsion of assaults in targeted sectors.

  
  

• Ukrainian counter-defence: Ukraine continues to hold key settlements west of the Oskil river and repelled enemy attacks on 4 November (see above). This suggests that Ukraine retains enough defensive depth and reinforcements to forestall collapse for now.

  
  

• Morale and population: The evacuation orders indicate that civilian presence is reduced, reducing constraints on Ukrainian defensive fires but also signalling elevated risk.

Likely outcomes and time-scales

Short-term (next 1–3 months: Nov 2025–Jan 2026)

Given the current data, it remains plausible that Russia will continue to gain ground in the outskirts of Kupiansk and key junctions (e.g. the railway at Kupiansk-Vuzlovyi). However a full Russian claim to the city proper by January 2026 now appears less certain than earlier models suggested. We would now assess a moderate-high probability (~60–70%) that Russia will control significant parts of the Kupiansk urban area by March 2026, but the probability of full control by January has reduced.

Medium-term (3–9 months: Feb–Aug 2026)

Assuming the city or major parts fall, Russia may attempt to use Kupiansk as a springboard westwards. But a full operational breakthrough into Kharkiv Oblast remains unlikely without Ukrainian collapse or diversion of large Ukrainian force commitments elsewhere. The fighting may stabilise around Kupiansk with heavy attritional combat until late 2026.

Long-term (9–18 months: Sep 2026–Apr 2027)

If Russia holds Kupiansk, the strategic payoff will depend on how effectively she can exploit the junction. Ukraine’s likely posture will be to fortify the next lines and exploit drones/long-range fires to make further Russian advances very costly. A protracted stalemate through 2026 and into early 2027 appears likely under current trends.

Probability assessment

• Russian capture of Kupiansk city (completely) by March 2026: moderate to high (~65–75 %)

  
  

• Russian use of Kupiansk as basis for significant deeper advance by end 2026: moderate (~40–50%)

  
  

• Ukrainian counter-recapture within next 12 months: low to moderate (~20–30%)

Assessment: Pokrovsk

Current situation (to 5 Nov 2025)

Recent reporting underscores that the battle for Pokrovsk has intensified. Ukraine’s President Volodymyr Zelenskyy reported that Russia has deployed approximately 170,000 troops in the Donetsk region, focused on the Pokrovsk axis. Meanwhile on 2 November Ukrainian forces deployed special operations units into Pokrovsk to bolster defences that were under very heavy pressure. Russian authorities claim their forces have “penetrated multiple parts” of the city and are clearing Ukrainian units. Ukrainian sources report that, on 4 November, Ukrainian defenders repelled 52 enemy assault actions in the Pokrovsk direction across multiple settlements. 

The situation is extremely contested, with Russia making infiltration and penetration efforts, Ukraine reinforcing and holding for now, and logistics and supply under stress.

Key determinants

• Strategic pressure: Russia is clearly placing heavy emphasis on the Pokrovsk axis, using large formations and seeking to make a major battlefield gain.

  
  

• Attrition and manpower: With around 170,000 Russian troops deployed to this sector, Ukraine faces a quantitative disadvantage in some sectors (some reports suggest up to 1:10 ratios in infantry density). Ukraine is therefore under heightened risk of being overwhelmed in some local sectors.

  
  

• Terrain and fortifications: Pokrovsk’s built-up area, mines and urban environment favour the defender somewhat, but infiltration tactics by Russia and concentrated assaults raise the risk of collapse.

  
  

• Supply routes and highways: Russia is reported to be aiming at cutting Ukrainian supply routes into Pokrovsk and its environs. Ukraine claims reinforcements are arriving but the risk of encirclement remains.

Likely outcomes and time-scales

Short-term (next 1–3 months: Nov 2025–Jan 2026)

Given the intensity now reported, there is a significant risk that Russian forces might capture large parts of Pokrovsk (for example southern districts or key transport nodes) by January 2026. We estimate a moderate-high probability (~55–65%) of partial Russian control of the city by that date. However full capture remains less likely in that timeframe given Ukraine’s reinforcements and defensive preparations.

Medium-term (3–9 months: Feb–Aug 2026)

Should Russia maintain momentum, a full Russian capture of Pokrovsk by mid-2026 (say June–August) appears increasingly plausible. We assess a higher probability, ~70% — of Russian control of the city by that point. Once captured, the Ukrainian defensive line in western Donetsk will be significantly stressed and may force a re-posture.

Long-term (9–18 months: Sep 2026–Apr 2027)

If Russia holds Pokrovsk, she may then attempt to exploit the victory to push further west or south-west into Donetsk, though the success of such a push would depend on Russia’s ability to sustain momentum, logistics and Ukraine’s resilience. For Ukraine, the loss of Pokrovsk may mean a strategic shift in the Donetsk sector defence, and could have significant morale, economic, and diplomatic ramifications. A full Ukrainian recovery of Pokrovsk within 12-18 months looks increasingly unlikely unless major external support or opportunity arises.

Probability assessment

• Russian capture of Pokrovsk city by August 2026: moderate-high (~70%)

  
  

• Russian consolidation and further operational breakthrough in Donetsk by end of 2026: moderate (~50%)

  
  

• Ukrainian successful counter-attack to hold Pokrovsk into 2027: low (~30–35 %)

Comparative assessment and broader implications

• The defence of Kupiansk remains slightly more favourable for Ukraine than Pokrovsk, thanks to terrain (Oskil river) and slower Russian advance; however the Russian pressure remains real and sustained.

  
  

• The situation around Pokrovsk has deteriorated for Ukraine compared with earlier projections: the concentration of Russian troops, the intensity of assault and the infiltration reports mean that the time-scale for its capture has been shortened somewhat.

  
  

• The fall of Pokrovsk would have a more profound strategic effect for Ukraine’s Donetsk defence and could create material/logistic crises more swiftly than a fall of Kupiansk would affect the Kharkiv axis.

  
  

• Even if one or both cities fall, this does not guarantee a decisive operational breakthrough by Russia; rather the likely pattern remains attritional. Ukraine’s ability to hold adjacent lines, use long-range fires, drones and fortifications means the fighting may become slower and more grinding.

  
  

• Diplomatically and morally, success by Russia at Pokrovsk would yield a stronger bargaining chip than at Kupiansk. For Ukraine, holding either or delaying their capture is strategically and symbolically important.

Key uncertainties

Recent developments have revealed several major uncertainties that could tip the balance:

• The volume and quality of Western military support Ukraine receives in the coming months (e.g. heavier artillery, air defence, replenishment of infantry manpower) remain critical.

  
  

• Russia’s reserve resources, logistics, and ability to sustain 170,000 troops on the Pokrovsk axis or large numbers on the Kupiansk axis may be constrained by attrition and supply lines.

  
  

• Winter weather and seasonal terrain (mud, snow - record cold is predicted for the 2025/26 winter season) may slow operations, especially river crossings near Kupiansk or built-up movement near Pokrovsk.

  
  

• The possibility of Ukraine launching local counter-offensives (or diversionary operations elsewhere) which could relieve pressure on one of these axes.

  
  

• Morale, manpower exhaustion and civilian evacuation (especially around Kupiansk) may degrade Ukrainian defensive capability; similarly Russian casualties may impose limits.

  
  

• Broader strategic shifts — e.g. if Russia diverts forces to another front or if Ukraine receives a major new weapons package — may reset the dynamics.

Conclusions

With the benefit of recent November 2025 data, our best estimate is:

• On the Kupiansk axis: Russia is likely to continue gradual gains but has not yet achieved major breakthrough. We now estimate a ~65–75% chance of full capture of the city by March 2026, with deeper advance into Kharkiv region remaining uncertain.

  
  

• On the Pokrovsk axis: Russia has the momentum, large troop concentrations, and is pressing hard. We now assess a ~70 % chance that Russia will capture the city by August 2026, and a ~50 % chance that she uses this as a basis for a broader operational advance in Donetsk by end 2026.

  
  

• Neither outcome is immediate or guaranteed; attritional warfare, Ukrainian defence, external support and logistics will all play decisive roles. The battles remain of strategic importance not only militarily but for humanitarian, morale and diplomatic consequences.