Ukrainian forces overran poorly prepared Russian defensive positions in September 2022, sweeping north, east, and south across the Kharkiv region, reaching all the way to the Oskil River and recapturing the rail junction city of Kupyansk.
It was a high-water mark for Ukraine, as much a sign of Ukrainian pluck as it was an symptom of Russian disarray.
Three years on, Kupyansk is on the verge of being seized by Russia once again. This time, it reflects Ukrainian struggles as much as it does Russian determination -- and the Kremlin’s willingness to absorb mind-numbing casualties.
As the fourth fighting season of Russia’s all-out war on Ukraine nears an end, the situation across the 1,100-kilometer frontline largely resembles the situation at the beginning of the season.
Russia has suffered more than 1 million casualties to date, with at least one quarter of those killed, according to Britain’s spy chief. Ukraine’s losses are fewer, but given its population size, arguably more onerous: an estimated 400,000 in total, with dead totaling at least 100,000.
“We are in a war of attrition,” said Thibault Fouillet, a military expert and deputy director of the Institute for Strategic and Defense Studies, a French think tank. “The decisive factor is only the capacity to endure, to patiently erode the enemy potential; all will be cumulative, not a decisive blow.”
Barring a major shift in fortunes, Kupyansk’s fall could coincide with onset of autumn rains and cold weather; for Ukrainian forces, a demoralizing coda 44 months into the invasion.
Here’s where things stand.
Kupyansk
Entrenched largely on the eastern banks of the Oskil River, Russian troops have slowly ground forward to the north for months, as commanders have prioritized other locations along the front.
The city is home to a major rail line that allows Ukrainian forces to resupply their positions from Kharkiv, the country’s second largest city.
Sometime in early September, Russian forces used parts of the underground gas pipeline network, creeping for kilometers underground, beneath the Oskil River, to bypass Ukrainian positions on the northern outskirts of Kupyansk.
It was at least the third time Russian troops had pulled off a tunnel ambush.
Ukrainian forces said they later destroyed the pipeline and killed or captured dozens of Russian troops. But they also acknowledged that an unknown number of Russian soldiers had slipped through and hidden – sometimes individually – in locations around the area.
"The enemy isn't conducting assault operations. They're infiltrating their personnel. They're not trying to storm our positions. They're simply bypassing them and trying to enter the city itself," Vitaliy Shum, head of the training group for the 151st Reconnaissance Shock Battalion of the 10th Army Corps, told Current Time last week. “The area is wooded, with lots of trees. And when there's a gap between our positions, they try to push their personnel through it.”
According to Deep State, a battlefield tracking group that has ties to the Ukrainian military, Russian forces have entered several northern districts of Kupyansk. And Russian officials claim Ukrainian commanders have already redeployed forces to keep the city from falling.
"The situation is critical; the enemy is still in the city. There are sabotage and reconnaissance groups in the city, and our special forces are undertaking counter-sabotage operations," Andriy Besedin, the head of the regional military administration, told a Ukrainian state broadcast on September 28.
Pokrovsk/Dobropillya
About a four-hour drive south in the Donetsk region, Pokrovsk – a bigger city with both road and rail junctions – has been under threat of encirclement by Russian forces for most of the year.
Driving the resupply route along a highway stretching toward the major metropolitan area of Dnipro, 180 kilometers away, became more dangerous earlier this year after Russian forces moved into the village of Kotlyne, to the southwest.
“Russian forces are pressed for time, because of worsening weather as well as the Kremlin’s political imperatives,” Lawrence Freedman, an emeritus professor of war studies at King’s College London, wrote in a recent analysis. Russia has “been targeting it for well over a year. Even if they can’t meet [President Vladimir] Putin’s ambitious timetable, capturing Pokrovsk would give them something to show for the year’s effort.”
Weather in recent days – in particularly high winds -- made it more difficult for both Ukrainian and Russian drone units to operate in the Pokrovsk area, according to Maksym Bakulin, a press officer with the National Guard’s 14th Operational Brigade.
The situation northeast of Pokrovsk is more problematic for the Ukrainians.
In early August, an unknown number of small-sized Russian units broke through porous Ukrainian defenses east of the town of Dobropillya.
The breakthrough highlighted both how stretched and understaffed Ukraine’s defenses are, and the tactic Russian commanders have relied on over the course of 2025: send small units, sometimes just one or two soldiers, possibly using motorcycles or all-terrain vehicles, to speed past or around Ukrainian trenches, and then dig in until Russia can reinforce or use artillery drones to batter nearby defenses.
It also forced commanders to redeploy troops from some of Ukraine’s most battle-hardened units, including the Third Separate Assault Brigade.
“Russian troops' primary method of operation is small infantry groups,” Denys Popovych, a Ukrainian military observer, told RFE/RL’s Ukrainian Service. “A process of infiltration, seeping in, and then creating these metastasizing pockets that then close in, and absorbing the enemy.”
“They create ‘kill zones’ where everything is destroyed,” he said.
Since the breakthrough, though, Ukrainian soldiers have managed to surround an unknown number of Russian troops. In some cases, experts point to defensive and offensive lines being dangerously entangled, with frontline soldiers unable to tell where enemy positions lie.
Captain Viktor Trehubov, a spokesman for the Dnipro regional command, told state TV that rear-guard Russian units had been unable to resupply the units that had managed to slip through Ukrainian defense.
The Russian “intestine,” Trehubov said, was now being “cut and dissected” by Ukrainian troops.
Zaporizhzhya
Further southwest, the front lines south of the city of Zaporizhzhya have been largely static for much of 2025, not to mention for much of the previous two years.
Over the summer, Ukrainian officials reported an uptick in small-scale infiltration tactics, again using motorcycles and off-road vehicles, along with drone units.
“We haven't witnessed this level of activity in the past three years," a battalion commander from the 65th Separate Mechanized Brigade told the online channel Espreso TV in July. He identified himself by the call sign “Forest” in line with military protocols.
In early September, Ukraine’s commander-in-chief, General Oleksandr Syrskiy, said that Ukrainian troops had thwarted a planned large-scale offensive in Zaporizhzhya, and Russian commanders redeployed marine infantry and other units east to the Donetsk region.
