Ukraine is “regaining tactical initiative” in its war against Russia, building on gains made in April and achieving its first net territorial gain in two years, according to analysis from the Institute for the Study of War (ISW) published on May 20.
“Ukrainian forces have conducted a series of counterattacks in different areas across the theater in recent months, having made their most significant gains on the battlefield since Ukraine’s incursion into Kursk Oblast in August 2024,” the ISW report showed.
These attacks have forced Russia into difficult resource-allocation choices during its Spring-Summer 2026 offensive against Kyiv’s “Fortress Belt,” with Moscow facing a dilemma in whether to defend against Ukrainian counterattacks or allocate manpower and resources to priority sectors such as the Kharkiv and Donetsk oblasts.
Key recent Ukrainian advances include recapturing much of Kupyansk, an offensive which began in November 2025, with the ISW now assessing the city as Ukrainian-controlled after clearing remaining Russian sabotage elements; the liberation of more than 400 square kilometers in southern Ukraine last winter and in spring this year; and, most recently, recapturing several settlements in western Zaporizhzhia Oblast since late April, according to the ISW analysis.
This recapturing of settlements in Zaporizhzhia Oblast has halted the Kremlin’s advances toward both Orikhiv and Zaporizhzhia City.
In addition, Ukraine’s intensified mid-range strike campaign against Moscow’s logistics, command posts, and rear areas since early this year has further degraded Moscow’s offensive momentum, the ISW reports.
Kyiv says that offensive actions now exceed Russian ones, with drone strikes alone accounting for over 19,000 Russian personnel casualties in the first 19 days of May, according to a May 20 Telegram post from Ukrainian Armed Forces Major Robert Brovdi.
Ukraine aims for circa 50,000 Russian casualties per month—above Russia’s current recruitment rate, according to a May 5 Telegram post from Ukrainian Defense Minister Mykhailo Fedorov.
In addition, the ISW analysis published on May 21 states that Ukraine’s ongoing strikes are also constraining Russia’s oil refining and energy revenues, a key source of income for Moscow’s military. However, the reported loss in capacity due to the strikes is not leading to the revenue loss it would otherwise have, due to a spike in prices and demand for Russian energy caused by the ongoing Iran war.
American political scientist Ian Bremmer has also asserted that the “tide is turning” in Ukraine’s favor in the more than four-year-long conflict.
“For the first time since the Ukrainian counteroffensive three years ago, the tide of the war is turning in Kyiv’s favor,” Bremmer wrote for Geroz Media on May 20.
He argued that Ukraine’s long-range missile and drone strike capabilities are “not only pressuring Russia’s economy but bringing the war home to ordinary Russians and, for the first time since [Russian] President Vladimir Putin launched his full-scale invasion of Ukraine in 2022, risking political trouble for the Kremlin.”
Bremmer also asserted that this fresh Ukrainian offensive was having a “debilitating” psychological effect on “poorly-trained Russian conscripts, fighting for a land that isn’t theirs.”
“The number of deaths has far exceeded any other Russian war since World War II. Russian desertions are surging accordingly,” he wrote.
Not all analysts share the view that the situation on the battlefield has shifted in Kyiv’s favor; however, American political scientist John Mearsheimer issued a note of caution during an interview with Australian writer Tom Switzer, broadcast on May 18.
Mearsheimer said that the idea that the Russians are losing massive numbers of people and territory to Ukrainian attacks was “just not true,” and asserted that it was Kyiv facing issues with recruitment and desertion, rather than Moscow.
“I think if you look at what’s happening on the battlefield, the idea that the Ukrainians are on the march and the Russians are on their back foot is simply wrong. The Russians are on the march,” he said.
Mearsheimer further said that if one were to criticize Russia’s performance, it was that they are still only moving forward slowly, rather than in a “blitzkrieg” fashion, but stated that not only were Moscow’s forces in better shape than Kyiv’s, but that “if the war were to stop today, Ukraine would have lost the war because they would have lost about 1/5 of their territory, and they have no way of regaining that territory.”
“Russia has won the war. The only question is, what does the victory look like now?” he added.
Neither Russia nor Ukraine publishes official figures for the casualties they have sustained on the battlefield.
The political analyst also highlighted that both Ukraine and its European allies had a “deep-seated interest in making the argument, regardless of what’s happening on the battlefield, that Russia is losing, that Putin’s in trouble, and the Ukrainians are on the march.”
He said that this vested interest meant one had to be “very suspicious” of claims of Ukrainian success.
Mearsheimer said that these interests were born of a Ukrainian desire to keep its Western allies funding and arming it, and, from Europeans, a wish to keep their publics and the United States interested in the war.
This comes amid attempts by U.S. President Donald Trump to shift more of the burden of the war, and Europe’s defense as a whole, onto NATO allies in Europe rather than allowing them to rely on the might of the American military.
For the time being, support from Washington continues to flow to Kyiv, with the U.S. State Department on May 21 announcing that it has approved the approximately $108.1 million sale of equipment to sustain Ukraine’s Hawk Missile System.
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