Momentum Shift: In May, Russia Lost Double the Ground It Lost In April

The overarching strategic question is no longer whether the Russians can turn this situation around - because it is increasingly apparent that they have neither the resources nor the leadership to do so - but at what point losing the territory they have remaining becomes irreversible. JL

Mick Ryan reports in Futura Doctrina:

Russian forces surrendered a net 93 square miles of Ukrainian territory over the four weeks to 3 June, double their losses in the preceding month. Ukraine’s drone strikes in the Pokrovsk sector destroyed 105 Russian artillery systems in May, twice April’s tally, and a Kremlin-affiliated milblogger conceded Ukrainian drones are preventing Russian forces from rotating troops. Ukraine  announced fire control over the Crimea to Donetsk corridor on 29 May. Open-source analysis has logged more than a thousand geolocated Ukrainian strikes in the Russian rear since the start of 2026, with 35% hitting ammunition, fuel and equipment depots, 20% hitting transport and 7% striking air defences. Western analysts count more than 125 destroyed trucks on the route.

For all the action in the skies and behind the frontlines, there was minimal exchange of territory in the past week. From Russia Matters, Russian forces surrendered a net 93 square miles of Ukrainian territory over the four weeks to 3 June, roughly double their losses in the preceding month, while Ukraine’s own DeepState monitors recorded a near-static line, a net Russian gain of about three square miles. Over the year to early June, Russia’s net territorial gain is 1,427 square miles, around six tenths of one per cent of Ukraine.

Source: Russia Matters

The decisive ground remains the Donbas, where Russia’s summer campaign is once again organised around the Pokrovsk, Kostiantynivka and Sloviansk axis and the fortress belt that anchors the roughly one fifth of Donetsk Oblast still in Ukrainian hands. The clearest Russian progress this week lay in the Kostiantynivka to Druzhkivka tactical area, with the Russians seeking progress against the fortress belt on several axes concurrently.

While it is true that drones cannot seize and hold ground, they still play a crucial role. Ukraine’s 7th Rapid Reaction Corps reported that its drone strikes in the Pokrovsk direction destroyed more than 105 Russian artillery systems in May, twice April’s tally, and a Kremlin-affiliated milblogger conceded that Ukrainian drones are preventing Russian forces from rotating troops into their forward infiltration positions, blunting the advance before it begins.

Strangling the Road to Crimea. If Russia’s focus this week was terror raining down from the skies, Ukraine’s was Russian operational logistics. The most important development on the Ukrainian side is the maturation of what Ukrainian planners now call the “middle strike,” the systematic destruction of Russian supply lines in the operational depth between roughly fifty and two hundred and fifty kilometres behind the front. On 27 May, Defence Minister Mykhailo Fedorov announced a “logistics lockdown,” allocating an additional five billion hryvnia, around 112 million US dollars, directly to brigades to buy mid-range strike drones through a points-based system that rewards the most effective units.

The campaign’s effects are now visible along the land bridge connecting Russia to occupied Crimea. Ukrainian drones have taken aerial control of the R-280, M-14 and N-20 highways running through Berdiansk and Melitopol, turning the corridor into what one analysis described as a road of burning fuel trucks. In May alone, observers counted at least seventeen destroyed fuel and military trucks on the Melitopol to Crimea stretch, and occupation authorities in Sevastopol and across Crimea imposed fuel rationing.

The French open-source analyst Clément Molin has logged more than a thousand geolocated Ukrainian strikes deep in the Russian rear since the start of 2026, with around thirty-five per cent hitting ammunition, fuel and equipment depots, twenty per cent hitting transport and seven per cent striking air defence. Western analysts count more than 125 destroyed trucks on the key route, and the Washington-based CEPA aptly titled its assessment “Russia’s Land Bridge is Becoming a Highway to Hell” which noted that:

With no single point of failure, the Kremlin believed its logistics network was more secure. But certainties don’t last long in the Ukraine war. Hornet drones were initially used selectively and in limited numbers. Their widening use by more brigades now suggests production is increasing and access is spreading.That advantage may not last forever. Russia will almost certainly develop countermeasures over time, making the current period especially important.

Ukraine’s military intelligence directorate announced fire control over the Crimea to Donetsk corridor on 29 May, and the 3rd Army Corps reported strikes in Luhansk Oblast as far as 205 kilometres from the front on 31 May. The Institute for the Study of War has geolocated drone flights along highways in Donetsk Oblast roughly a hundred kilometres deep, assessing that the strikes complicate Russia’s use of the Rostov to Crimea route. Its analyst George Barros argues that these mid-range strikes degrade Russia’s ability to mass forces and sustain the front, with Ukraine holding a slight but meaningful advantage in drone innovation.

In a 4 June article, military expert Viktor Kevliuk estimates that Ukrainian drones have already destroyed something on the order of seventy-five thousand general-purpose vehicles in the Russian rear, achieved by AI-guided systems which acquire and home on targets autonomously in the terminal phase even under electronic-warfare suppression.

This mid-range strike campaign is not just focused on military vehicles. It is also hitting Russian ships carrying cargo into occupied ports in southern Ukraine. On the evening of 6 June, the Ukrainians hit five Russian vessels in the Sea of Azov, as part of this campaign.

This is operational art. And it is integrated with tactical ground operations and long-range strategic strike to form a unified military strategy.

As reported by Fortune, long-range strikes reduce the volume of fuel Russia can refine, while mid-range strikes degrade its ability to move what remains. Gasoline shortages in occupied Ukraine are, for now, having only a limited effect on Russian forces, but the analysts noted that “more militarily consequential diesel shortages are beginning to materialise.”

The week also brought a strike that Ukraine called the first of its kind in modern history, the destruction of a Russian drone base at the occupied Donetsk airport.