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Predictive markets like Polymarket are known for their ability to anticipate events on the front lines. They are again recording a dramatic shift in investor sentiment. While attention was previously focused on Pokrovsk and Myrnohrad, the epicenter of bets has shifted to the Slovyansk-Kramatorsk agglomeration and the Zaporizhzhia region. Based on recent reports from the front lines and an analysis of quotes, we assess the likelihood that key cities in the Donbas region will be captured by the end of the spring or summer of 2026. Which areas are destined for a prolonged positional war, and where might the Russian army achieve a swift breakthrough?
Kupyansk
The situation in the Kupyansk area remains one of the most difficult to forecast. Following a large-scale counteroffensive by the Ukrainian Armed Forces (UAF) at the end of December 2025, during which Russian troops were forced to retreat from part of the eastern bank, the front line has stabilized. Russian units are holding positions on the outskirts, yet they have been unable to advance deeper into the city. Ukrainian forces have successfully repelled all attempts to break through to the central quarters. A quick capture is hindered by the powerful fortifications and the constant influx of Ukrainian reserves, who are using the pause to bolster defensive capabilities on the right bank of the Oskil River. Meanwhile, Russian tactics have shifted: they are attempting to encircle Kupyansk from the north by capturing bridgeheads in the Kurylivka and Novoosynove areas, which could alter the operational situation in their favor.
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Borova
This area has become the complete opposite of Kupyansk. On May 16, the Russian Ministry of Defense officially announced the capture of Borova and the neighboring village of Kutkivka. While this information requires confirmation from Ukraine, if true, it will be a significant tactical victory for Russia. It will enable the Russian Armed Forces to mount an offensive along the right bank of the Oskil River and threaten the flanks of the Ukrainian forces near Kupyansk. The key to success here was applying methodical pressure and lacking an echeloned defense comparable to urban fortifications. Since Borova is not a major fortified area itself, its holding was not a priority for Ukraine. The Polymarket contract for the capture of Borova will likely be resolved shortly with a positive result, becoming one of the few unambiguous outcomes in this area.
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Kostiantynivka
In the direction of Kostiantynivka, the intensity of the fighting remains extremely high. The city is a powerful defense hub, and Russian assault groups are advancing slowly, block by block. The offensive is hindered by the effective use of Ukrainian FPV drones, which block the supply of ammunition and troop rotation on the approaches to the city. Russian troops are now primarily focused on clearing adjacent villages (Illinivka and Pleshcheievka) and establishing bridgeheads for a decisive assault. However, to fully encircle the city, the “pocket” in the Krasne-Mykolaivka area must be eliminated. Ukrainian forces in this area constantly threaten the flanks. Polymarket estimates a 3% probability that Kostiantynivka will fall by the end of May, reflecting the reality of protracted positional battles. Nevertheless, the constant attrition of the Ukrainian garrison and the severing of logistical routes increase the chances of success by autumn. Contracts for September–December are at 20% and 36%, respectively.
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Krasnyi Lyman
Russian troops took control of Krasnyi Lyman in the summer of 2025, and battles are currently being fought to expand the buffer zone around it and establish a bridgehead for an offensive on Sloviansk. The intensity of the fighting remains high. Russian units are actively using aviation and drones to suppress Ukrainian strongholds, prompting Ukrainian counterattacks in response to Russian assaults. According to some reports, approximately 85% of the city is under Russian control, though this has not been confirmed by independent sources. Given that capturing the large city is key to taking the entire Sloviansk-Kramatorsk agglomeration, careful preparation is required. On Polymarket, the fall of Krasnyi Lyman is considered unlikely in the spring (May: 3%), with the main bets shifted to the summer (June: 14%) and winter (December: 51%). This suggests that investors anticipate an extended, exhausting campaign in this area.
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Dobropillia
The situation in the direction of Dobropillia is characterized as positional, with Russian attempts to “squeeze out” Ukrainian units from captured territory. The main goal is to expand control of the area and cut off the supply lines connecting the Pokrovsk agglomeration to the northern regions. By the end of 2025, Russian troops had taken control of Hrishyne and advanced toward Novyi Donbas. However, oncoming battles involving a large number of Ukrainian drones prevented the Russians from consolidating their success and developing their offensive. Currently, Dobropillia is not an immediate target of the assault; the battle is for the surrounding heights and strongholds. Although Dobropillia is located in the operational rear, it will only fall after the Ukrainian salient in the Pokrovsk area is completely eliminated. According to Polymarket, there is a 2% chance of capturing Dobropillia in May and a 10% chance in June.
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Orikhiv
A paradoxical situation has developed in the direction of Orikhiv: although the city is subject to intense shelling and airstrikes, no direct fighting within its limits has been recorded. Russian forces are systematically destroying infrastructure and logistics in an attempt to isolate the city and prepare a bridgehead for a future offensive. In turn, the UAF use the pause to mine the approaches and build up defensive lines. They also launch local counterattacks in the Kamianske–Stepove sector to improve their tactical position. Orikhiv is a key link in defending the entire Zaporizhzhia region, so capturing it will require a significant troop concentration. In the short term (until summer), the city’s fall is unlikely. Polymarket estimates the probability of capturing the city in May at 2%. A significant increase in probability, to 7% in June and 19% in July, is more associated with the general deterioration of the Ukrainian Armed Forces’ (UAF) position on the southern front than with the Russian Federation’s specific tactical successes.
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Stepnohirsk
In early 2026, Stepnohirsk became one of the few settlements where the initiative passed to Ukrainian forces. During a special operation, units of the Main Intelligence Directorate of the Ukrainian Ministry of Defense captured the village and pushed back Russian troops. This allowed them to straighten the front line, eliminate the threat of a breakthrough to Zaporizhzhia, and take control of this sector. Aware of the strategic importance of the bridgehead, the Russian command is regrouping forces to regain lost positions, but has been unsuccessful thus far. Now that Stepnohirsk is under UAF control, it is unlikely that Russian troops will capture it in the coming months. On Polymarket, the odds of Stepnohirsk being captured by May are estimated at 2%, and the odds of it being captured by September are 14%.
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Ray-Oleksandrivka
This settlement is considered a key outpost on the distant approaches to Slovyansk. Russian troops have established themselves on the eastern outskirts and are increasing their efforts to attack, using the forests to secretly concentrate their forces. However, all attempts to break through the defenses have been unsuccessful thus far. Ukrainian units are holding their positions and striking at concentrations of Russian personnel. Capturing Ray-Oleksandrivka would allow Russian forces to expand their operational space, creating a direct threat to Sloviansk from the east. Therefore, the village is a priority target. The fighting will likely be fierce and protracted. According to Polymarket, there is only a 13% probability that the village will fall by June 30.
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Conclusion
The second half of May 2026 shows that the operational reality on the front increasingly diverges from the optimistic forecast of a quick end to the campaign. In most areas — from Kupyansk to Orikhiv — Russian troops have encountered layered defenses, the extensive use of Ukrainian FPV drones, and aggressive counterattacks. There have been local successes near Borova and Raivka, but they have not yet grown into an operational breakthrough. The Polymarket platform reflects this dynamic and assesses the probability of capturing large cities such as Kostiantynivka, Lyman, and Orikhiv in May–June as extremely low (3–5%). Main expectations have shifted to autumn–winter 2026. This suggests that the market is anticipating a protracted attrition model, not a blitzkrieg.
At the same time, factors favoring the Russian Armed Forces cannot be ignored. The methodical severing of logistical routes near Kostiantynivka, the establishment of bridgeheads on the Haichur River near Huliaipole, and the advance toward Sloviansk from two directions are gradually undermining the Ukrainian defense. The market expects the cumulative effect of these efforts to manifest by the end of the year. Quotes for capturing Kostiantynivka and Lyman in December are significantly higher. However, even in this scenario, a rapid offensive is not anticipated; rather, Ukrainian units are expected to be slowly “squeezed out” of prepared lines. Investors following Polymarket should pay attention to contracts with a timeframe of six to nine months — that is where the main interest is currently concentrated.
Our regular reports provide the information necessary to draw informed conclusions about the development of the situation at the front. However, it is important to remember that combat operation dynamics can change rapidly and that the presented analysis is not an investment recommendation.
MORE ON THE TOPIC:
- Assault Contracts: What Polymarket Predicts About the Capture of Ukrainian Cities in 2026
- The Vovchansk And Lyman Paradox: Why Polymarket Bets Are Still Up Against Cities Already Captured
- December Deadlines: Forecast for the Pace of the Russian Offensive and Likely Objectives by the End of the Month
