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Update on Russia-Ukraine War: Ukraine is Slowly Gaining the Upper Hand, But That Does Not Mean Peace is Closer But That Escalation Risks Are Rising

Published on May 29, 2026

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By

Jacob Funk Kirkegaard

I was in Kyiv last week and weekend to work with a large group of senior Ukrainian government officials, so was able to get a first-hand impression of the state of affairs in the war, and can confirm recent week’s more positive media reporting (See ISW here or Financial Times here) of Ukraine’s situation in the conflict: Ukraine is slowly due to a number of factors gaining the upper hand in the war against Russia, but this trend risks pushing Vladimir Putin into attempting to expand the scope of the war, rather than seriously pursue a ceasefire or broader peace process.

Today’s impact by a Russian drone on a Romanian residential block is indicative of the types of operations that Russia may begin to implement across a number of neighboring NATO countries. The aim will be to test NATO responses to such incursions and weaken public support for the Ukrainian cause.

Several important trends have recently begun to trend slowly in Ukraine’s favor in the fight against Russia’s invasion.

First of all, Ukraine has achieved an at least temporary technological advantage in tactical and medium-range (up to 150-200km range) drones, enabling Ukrainian forces to more effectively target Russian frontline infantry infiltrations and logistical supply routes behind the frontline. Particularly in the South of Ukraine along the “land-bridge” to Crimea, this has enabled Ukrainian forces to successfully target Russian air defense, electronic warfare systems, and supply lines in operations what will over the coming months both enable further attacks on Russian deep targets, and also gradually degrade the overall supply situation for Russian frontline troops in the South.

The situation has now deteriorated enough for also well-known Russian military commentators to openly discuss it. Here is a recent map presented by the Russian military blogger Rybar of strikes on Russian logistics since March 1st 2026.

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The Ukrainian drone advantage is likely to gradually enable Ukrainian forces to engage in localized offensive operations along the Southern frontline, where the Russian supply situation can be expected to have deteriorated the most. The Russia-Ukraine War is characterized by continuous innovation, and it must be assumed that Russia will over time succeed in developing countermeasures to Ukraine’s new drone advantages

Secondly, Ukraine now has gained access to the first tranches of the €90bn EU loan, of which 2/3rds are earmarked to the expansion of Ukrainian military and especially drone production. This will finally enable Ukraine to go to full utilization of its rapidly expanding domestic drone production capacity, unleashing a further significant increase in Ukrainian drone production. Complementing this expected increase in now fully funded domestic Ukrainian drone production, an increasing number of other NATO (and now Japan, too) countries are making locations available for the production of Ukrainian designed drones to supply the frontline.

Overall, Ukraine will increasingly going forward be able to match Russia’s drone quantities and will hence be able to continue to scale up its strikes against both frontline and deeply located Russian targets. This is a strategic and lasting shift in relative military production capabilities in Ukraine’s favor.

Thirdly, Ukraine has progressed in its reform of armed forces personnel allocation. This does not imply that Ukraine has “solved” its structural manpower problem, as it will after 4+ years of all-out war against a much larger neighbor always have a manpower shortfall, putting significant constraints on Ukraine’s ability to launch large future offensive operations. Ukraine has, however, significantly improved its allocation of scarce manpower between successful and unsuccessful units, leading to an improvement in the “average performance” of frontline units, as poorer performing ones have gradually been “swallowed up” by the better commanded ones.

This has been a crucial factor in the improved overall defensive performance of Ukrainian frontline units in recent months, where Russian territorial gains have slowed to a near standstill. It is also a qualitative organizational improvement on the part of Ukraine’s armed forces that will be lasting in duration. Moreover, given the ongoing very high attrition rate among Russian forces, leading to evidently lower average force quality from short training periods for new troops and depletion of NCO and officers’ numbers, Ukraine is likely to achieve a relative force quality advantage over Russia going forward.

Ukraine’s gradually improving situation should not be assumed to lead to any near-term or decisive battlefield breakthroughs. Russia remains a far larger and more powerful force, with a fully committed Russian economy sustaining it. It is, however, increasingly likely that the coming “summer fighting season” over the next 4-5months will not see Russian forces make any material territorial gains, while continuing to suffer high personnel and equipment losses.

This would, come September and October 2026, see Russia having suffered easily another 100,000 troops killed or seriously wounded for essentially no gain on the battlefield. While Vladimir Putin’s decision-making process is difficult to gauge, such an outcome ought rationally to lead him to “try to do something differently” to change what is otherwise an increasingly disadvantageous war trajectory for Russia.

“Doing something differently” would logically include switching to suddenly seriously engaging in peace negotiations, which could likely given Ukraine’s acceptance of an unconditional ceasefire lead to a quick end to the fighting. However, this would require that Putin abandons his still expansive war goals with regards to annexation of Ukrainian territory and broader control over Ukraine’s sovereign political decisions.

It would also compel Putin to contemplate the future economic direction of a Russian economy currently fully committed to producing the needs for a war effort to now be concluded. Both of these political considerations may lead Putin to disregard possible negotiated solutions to the conflict.

“Doing something differently” might also include decisions to reduce the scale of current scale of the fighting to a shorter frontline (similar to what Russia did early in the war, following the defeat around Kyiv and in the North as fighting shifted to only the Eastern part of Ukraine), or perhaps a less intense ongoing Russian offensive effort.

Such changes would though implicitly entail an acceptance by Russia of its inability to achieve its stated war goals and especially acquiring control over all unilaterally annexed territories in Ukraine. This may prove politically unacceptable to Putin, too.

Russia may also, after a summer of military stalemate and high losses, decide to militarily escalate to try to force its demands on Ukraine. This could involve another round of involuntary mobilization of a potentially large number of new soldiers for the Russian army, similar to what Russia carried out in the Fall of 2022 following the first successful Ukrainian counteroffensives in Kharkiv and Kherson. Carrying out another mobilization, after almost 5years of war and rising losses, would though likely be accompanied by significant political risks for Vladimir Putin.

It would also further aggravate continuing labor shortages inside Russia from both new call-ups to the front and emigration out of Russia by Russian men eligible for mobilization. In short, manpower mobilization remains a high-risk strategy both politically and economically for the Russian government.

The recent restrictions put on internet and social media inside Russia may be related to fears in the Kremlin about the public’s reaction to highly unpopular new measures, including possibly new mobilization orders.

Following the successful example from Iran of “geographically expanding the war”, Russian armed forces may also continue and expand its practice of firing drones into neighboring NATO countries, and (again) seek to attack Ukraine directly from Belarus territory. Recent months have seen repeated drone incursions into Poland, the Baltic countries and today Romania.

While some of these may have been cases of “accidents happen in war”, they are at a minimum testament to a complete disregard by Russia of any risk of its weapon systems hitting inside NATO territory. As there to date has been no forceful NATO response to these Russian violations of the alliance’s territory, it likely follows that Moscow will feel it can escalate this way with more frequent drone and other weapons’ based violations.

The aim here would be to gradually undermine public and business sentiment among neighboring NATO members (forcing populations not at war to go to shelters repeatedly would have this effect), and in time eroding economic support for Ukraine.

Russia may also become even more audacious and perhaps attempt to strike directly against energy or other critical infrastructure in a NATO member in the hope that the alliance – given the distraction/indifference of its largest member in the United States – would fail to mobilize a coherent and forceful response.

This may not seem like a “short-term winning strategy” for Vladimir Putin but might by “rule of elimination” become the least bad way of “doing something differently”.

In sum, Ukraine is gradually gaining the upper hand in the war against Russia, but rather than lead to an accelerated peaceful solution, this trend may invite Russia come the fall to try to escalate the war by implementing more frequent incursions into NATO countries, too.

Ukraine’s improved circumstances may therefore usher in a more unpredictable, unstable and unconstrained period in the war.

Jacob

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