Ukraine claims 400 sq km of southern territory and most of Kupiansk since winter, largest gains since Kursk
Ukrainian counterattacks have retaken more than 400 square kilometres in southern Ukraine since winter, recaptured most of the eastern city of Kupiansk, and seized settlements in western Zaporizhzhia Oblast since late April, according to a 20 May Institute for the Study of War assessment. Commander-in-Chief Gen. Oleksandr Syrskyi told the defence outlet Militarnyi in a 15 May interview that, as of 14 May, the count of Ukrainian offensive actions exceeded Russian ones — a shift Ukrainian officials are pairing with intensified deep-strike drone operations. The advances are the largest Ukrainian territorial gains since Kyiv's incursion into Russia's Kursk Oblast in August 2024.
The Institute for the Study of War reported on 20 May 2026 that Ukrainian counterattacks since winter have liberated more than 400 square kilometres in southern Ukraine, recaptured most of the eastern city of Kupiansk, and taken settlements in western Zaporizhzhia Oblast since late April. The gains are the largest Ukrainian territorial recapture since the Kursk Oblast incursion of August 2024 and present Moscow with a strategic choice: reinforce the southern flank or sustain the Spring-Summer 2026 offensive aimed at the Donetsk Oblast cities Russian planners label the "Fortress Belt."
Commander-in-Chief Gen. Oleksandr Syrskyi told the defence outlet Militarnyi in a 15 May interview that, as of 14 May, the count of Ukrainian offensive actions exceeded Russian ones. Syrskyi did not provide absolute figures but cited precise strikes on Russian reserves and "constant pressure" on Russian assault units. The recapture of much of Kupiansk began in November 2025; since early 2026 Ukrainian forces have widened a mid-range strike campaign against Russian logistics, equipment and manpower across the theatre.
The data Ukrainian commanders are pointing to come from the Delta battlefield-management system. Unmanned Systems Forces Commander Maj. Robert Brovdi, known by the call sign "Magyar," said on 20 May that Ukrainian drones struck 19,203 Russian personnel in the first 19 days of May, with formations under his own command accounting for more than 6,000 of those losses. Brovdi forecast that drone strikes alone would inflict more than 34,000 Russian casualties by the end of May, excluding losses from artillery shelling, rear-area strikes and frontline ground combat.
Those figures, if accurate, outstrip Russia's reconstitution rate. The Russian Ministry of Defense signed 70,500 military service contracts in the first quarter of 2026 — roughly 23,500 per month, below the monthly quota of 33,500 to 34,600. Ukrainian Defense Minister Mykhailo Fedorov said on 5 May that Ukrainian forces had already met an April 2026 target of inflicting casualties at a rate exceeding Russia's recruitment and had set a new objective of 50,000 Russian casualties per month.