Ancient settlements Human settlement in the area dates back over 6,000 years. A
Neolithic settlement from circa 5000-4000 BC and four
Bronze Age burial mounds from 2000 to 1000 BC were discovered near Kupiansk. It was a typical military Ukrainian Cossack settlement. Although the Ukrainian Army had destroyed a railway bridge to slow the Russian advance three days earlier, Kupiansk Mayor
Hennadiy Matsehora, member of the
Opposition Platform — For Life party, surrendered the city to the
Russian Army in exchange for a cessation of hostilities, as the Russians threatened to take the city by force. As a result, the Ukrainian government
indicted Matsehora for
treason the next day. On 28 February 2022, Matsehora was arrested by Ukrainian authorities. Later Kupiansk became the
de facto seat of the Russian-backed
Kharkiv military-civilian administration and an important logistical supply route. At Kupiansk town hall, the
Ukrainian flag continued to be flown for 6 weeks, and at the medical school for 3 months. Locals were forced to work for the occupation force, paint bridges in the colours of the
Russian flag and perform railway repair for alleged salaries that were never paid out. On 9 September 2022, Ukrainian forces re-entered the outskirts of Kupiansk and its administrative borders, starting the
battle of Kupiansk. By the morning of 10 September 2022, Ukrainian forces had recaptured the city council building. Later that day, a Ukrainian official confirmed that the
Ukrainian Armed Forces had liberated the city. By September 26, Ukrainian Forces liberated Kupiansk-Vuzlovyi, the sister city of Kupiansk, located on the left bank of the Oskil River. After retreating from the city, Russian troops repeatedly shelled it. In particular, the central city hospital, high-rise buildings and a lyceum, the Kupiansk-Vuzlovyi railway station and others were damaged. The first strikes against the town were on 13 September, which killed two civilians. The next day, one person was wounded from airstrikes. On 18 September, five people were injured from shelling in Kupiansk. Two days later, two civilians were killed and five injured after Russian shelling on the city. On 22 September, a woman and two children were injured by shelling. On 26 September, Russian forces
shelled a convoy of civilians escaping the villages of Kurylivka and Pishchane near Kupiansk, killing 26 civilians. Signs of torture were discovered in Russian administration centers throughout the city. On 27 September, five civilians were injured after a Russian strike on a church in Kupiansk. On 3 October, Russian shelling of a hospital in Kupiansk killed a doctor and injured a nurse. One woman was injured on 5 October by an airstrike. Kupiansk's bridge over the Oskil River was partially damaged in combat, and became suitable only for use by pedestrians. Russian forces bombed the local meat factory of Kupiansk, killing around a thousand pigs. On 14 November 2024, two Russian armoured vehicle columns advanced into the city from the northeast, though reportedly had tenuous control over the area. After facing logistical problems, Russian forces withdraw from Kupiansk in late November. At the end of November 2024, a Ukrainian official confirmed that Russian troops recently crossed over to the west bank of the Oskil River north of Kupiansk near the suspension bridge south of Novomlynsk. At the same time, Ukraine's General Staff admitted that Russian forces launched attacks on the west bank near Fyholivka, Holubivka, and Kindrashivka
. The fighting continued into December 2024, when Ukrainian troops reported that Russian forces were attempting to cross the Oskil river a few kilometres north of Kupiansk city. At the end of January 2025, the
Institute for the Study of War assessed that Russian forces are attempting to use their bridgeheads across the Oskil river to support their advances and encircle Kupiansk from the northwest, as well as set the ground for future advances and offensives into Kharkiv Oblast. In September 2025, the Russian Ministry of Defense stated that the seizure of Kupiansk would support Russian efforts to advance toward
Sloviansk and
Kramatorsk (both south of Kupiansk) and seize Ukraine's fortress belt in Donetsk Oblast, which further highlighted the strategic importance of the city during the war. On 24 May 2025,
Ukrainska Pravda reported that over 90% of Kupiansk is destroyed or damaged from the bombardment. During the
Kupiansk offensive, misinformation and false intelligence reports from the Russian Ministry of Defence have sparked friendly fire incidents among Russian troops. By early October 2025 the city was again partially occupied by Russia. On 20 November 2025, the Russian Defense Ministry announced the full capture of Kupiansk, although the Ukrainian military denies this. On 12 December, President Zelenskyy confirmed with his visit that the city is not captured. Uawire reports that "The operation to liberate Kupyansk remains far from complete", and that "Clearing continues “house by house,” complicated by the presence of civilians “whom the Russians use as human shields."" == Population ==