Kupiansk or Kupyansk (Ukrainian: Куп'янськ, IPA: [ˈkupjɐnʲsʲk]; Russian: Купянск, IPA: [ˈkupʲɪnsk]) is a city in Kharkiv Oblast, Ukraine. It serves as the administrative center of Kupiansk Raion. It is also an important railroad junction for the oblast. Kupiansk hosts the administration of Kupiansk urban hromada, one of the hromadas of Ukraine. It had a population of 26,627 (2022 estimate). In February 2024, more than 3,500 people remain in Kupyansk.

Until 18 July 2020, Kupiansk was incorporated as a city of oblast significance and the center of Kupiansk Municipality. The municipality was abolished in July 2020, as part of administrative reforms in Ukraine, which reduced the number of raions in Kharkiv Oblast to seven. The area of Kupiansk Municipality was merged into Kupiansk Raion.

Kupiansk is located on the bank of the Oskil River. Kupiansk is divided into three subparts, known as: Kupiansk (main part of town), Kupiansk-Vuzlovyi (where the train station is), and Kivsharivka.

Kupiansk is about two and a half hours from Kharkiv. The two cities are connected by train and bus.

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Kupiansk was occupied during World War II by Germany from 24 July 1942 to 3 February 1943.

Kupiansk was occupied by Russian forces from 27 February 2022 to 10 September 2022. 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 8 September 2022, a representative of the General Staff of the Armed Forces of Ukraine announced that Ukrainian forces had retaken more than 20 settlements in the Kharkiv Oblast and "in some areas penetrated Russian defence positions up to 50km". On the same day, the Russian occupation authorities claimed that "the Russian army began to defend the city" and that "additional reinforcements entered the region from Russia", indicating that Ukrainian forces were re-approaching the city from the west, after retaking the town of Shevchenkove earlier that day. 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. On 3 March 2023 Ukrainian authorities ordered an evacuation of civilians from the city due to advances of Russian Armed Forces around Kupiansk and Bakhmut.

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 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 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 14 November 2024, two Russian armoured vehicle columns advanced into the city from the northeast, though reportedly had tenuous control over the area. Russian forces made further progress into the city the following day, with fighting reportedly ongoing in the industrial area, and were reportedly setting up supply lines to assist in further offensive efforts.

Ethnic makeup of the city as of 2001:

Ethnic groups in Kupiansk percent Ukrainians   77.73% Russians   16.20% Belarusians   0.40% Armenians   0.18%

Distribution of the population by native language according to the 2001 census:

Language	Percentage
Ukrainian	78.03%
Russian	19.59%
other/undecided	2.38%

Media related to Kupiansk at Wikimedia Commons