Kupyansk: Why This Small Ukrainian Town Is Now the Focus of Brutal Russian Assaults

Russia has claimed for the second day running to have improved its fighting positions around Kupyansk, a small town in eastern Ukraine that in recent days has become the focus of a determined assault by the Kremlin’s forces.

Where is Kupyansk?

Kupyansk is a town located in the Kharkiv region of eastern Ukraine, with a pre-war population of around 28,000 people.

Why is Kupyansk important?

Kupyansk is a major rail hub with five different lines intersecting in the town– one of which leads directly into Russia – making it a hugely important strategic objective when Moscow launched its full-scale invasion of Ukraine.

The town was occupied just three days after the start of Russia’s offensive, largely thanks to its pro-Russian mayor Hennadiy Matsehora, who surrendered Kupyansk without a fight.

Ukrainian forces, fully aware of how important the rail link was to the Russians, destroyed a key rail bridge into the town attempting to slow the Russian advance. Matsehora allegedly helped them find another route into the town.

He was charged with treason but in a rather poetic twist, was later arrested by Russia for unknown reasons in July of the same year.

Meanwhile, Kupyansk became the de facto seat of the Russian-backed Kharkiv military-civilian administration.

Russia was shipping in badly needed supplies and reinforcements via the town for its ongoing offensive in eastern Ukraine, making it a prime target for Kyiv’s counteroffensives at the end of last summer.

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On Sep. 10, 2022, after a lightning offensive Kupyansk and many other towns and cities were liberated by the Ukrainian Armed Forces (AFU).

A Financial Times article on the battle for Kupyansk was titled: “The 90 km journey that changed the course of the war in Ukraine.”

But the joy of liberation was short-lived – Russian forces retreated and set up new defensive positions within artillery range of the town and Kupyansk has been shelled relentlessly ever since, killing and injuring hundreds of civilians.

What’s the situation right now?

Russia has dramatically increased its shelling of both Kupyansk and the AFU positions defending it in recent days.

On Friday, the Kremlin said its forces had improved their offensive positions around two settlements near the town and Russian forces had “continued offensive operations on a wide front and improved the tactical situation” in Vilshana and Pershotravneve, two settlements in the region.

Serhiy Cherevaty, spokesperson for the Eastern Group of the AFU, said on Friday that over the last 24 hours “the enemy tried to attack Kupyansk direction five times.”

He added: “The enemy shelled Ukrainian positions with all types of artillery – from mortars to MLRS – 502 times. They continue to use aviation more actively in this direction and launched 15 airstrikes.”

Cherevaty claimed 21 Russian soldiers had been killed and 91 wounded over the last day and Ukraine was reinforcing its positions around the town.

He said the situation “remains difficult but under control,” adding: “We know their plans, we know the composition of their grouping and their weak points.”

What about Kupyansk’s civilians?

In a sign of how difficult the situation is, on Thursday a mandatory evacuation was ordered in 37 settlements in the Kupyansk district due to the increase in Russian attacks in the region.

Oleh Synegubov, the head of the Kharkiv Regional Military Administration, said on Thursday afternoon the evacuation could affect more than 11,000 civilians, including approximately 600 children.

“The enemy has intensified shelling of border settlements and those close to the front line, and continues terrorizing the local population, including with airstrikes,” he said.

“Our goal is to save the lives of our civilian population, so this evacuation is carried out as a protective measure.”

Could Russia recapture the town?

At this stage nothing can be ruled out and retaking Kupyansk would clearly be a significant achievement for Russia.

Not only would it mean the reestablishment of the train link with Russia, but the Kremlin would be sure to make the most of the propaganda potential of recapturing territory liberated by Ukraine in last year’s counteroffensives.

At the moment, Ukraine’s forces appear to be withstanding the assaults but Russia's drive in Kupyansk has sought to draw Ukrainian troops away from Kyiv’s own counteroffensive operations elsewhere.

And according to Russian sources, a full assault is not yet underway. Prominent pro-Russian milblogger Rybar said on Telegram: “However, despite the tactical successes of the Armed Forces of the Russian Federation, it is premature to talk about the imminent assault on [Kupyansk] city.”