Russia’s last footholds in Kupiansk are crumbling, Ukrainian military says

Weeks of grinding combat may soon end as Russian holdouts face inevitable elimination.
russia’s last footholds kupiansk crumbling ukrainian military says · post situation kharkiv oblast 27 2025 isw kupyansk-city-december-27-2025 ukraine news reports
Situation in Kupiansk, Kharkiv Oblast, as of 27 December 2025. Map: ISW.
Russia’s last footholds in Kupiansk are crumbling, Ukrainian military says

Ukrainian forces continue systematically clearing Kupiansk in Kharkiv Oblast, where small Russian units remain trapped without reinforcements, according to Suspilne. Though urban combat slows progress, Kyiv’s troops now control nearly the entire city.

Kupiansk, a key rail and highway hub in eastern Kharkiv Oblast, has been a recurring target for Russian forces since Ukrainian troops liberated it in 2022, months after Russia’s full-scale invasion began. In recent months, Russian units advanced from the north and managed to seize several neighborhoods. However, Ukrainian forces encircled them shortly after, cutting off ground supply lines and blocking any chance of reinforcement.

Russian pockets of resistance remain in Kupiansk

Ukrainian forces are eliminating the last Russian positions inside Kupiansk, where small enemy groups are reportedly hiding in isolated urban areas. Viktor Trehubov, head of communications for the Joint Forces Grouping, told Suspilne on 28 December that these remaining “pockets” could take up to two more weeks to fully clear.

The cleanup in Kupiansk is going rather slowly because civilians remain in the city,” Trehubov told Suspilne. "Secondly, it’s urban combat — it always goes slowly — but the overall situation in the city is developing quite positively."

The spokesperson stressed that Russian troops have no realistic path to relieve their stranded units.

Trehubov added that Russia had made multiple failed attempts to break the encirclement but lacked the capacity to succeed.

“There were a few attempts, but given that the Russians are failing, there’s no prospect of unblocking these pockets,” he said. 

The main axis of remaining Russian activity in the broader Kupiansk area lies across the left bank of the Oskil River. However, even if those operations succeeded, they would not affect the status of Kupiansk itself, Trehubov explained, according to Suspilne.

Russian defeat previously acknowledged even by pro-Kremlin milbloggers

A Ukrainian military spokesman recently said Russian troops are struggling to regroup east of Kupiansk following their failed offensive. Kyiv’s forces are continuing to clear the city, which is now nearly fully under their control. 

These recent Ukrainian gains prompted even Kremlin-affiliated Russian milbloggers to acknowledge defeats and accuse their own military command of spreading false battlefield reports, according to the Institute for the Study of War (ISW). The bloggers are now publicly blaming Moscow’s chain of command for misleading the Russian leadership and misrepresenting the situation to President Vladimir Putin.

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