Geopolitics · 2026-10-11 · 13 min read · By Vsevolod

Which Cities Will Russia Enter in 2026? Odds & Analysis

Which Cities Will Russia Enter by December 31? The Board as of October 2026

Prediction markets price Druzhkivka as the only city on this board that Russian forces have a real chance of entering before the end of 2026. As of October 2026, the "Which cities will Russia enter by December 31?" odds are: Druzhkivka 38.5%, Kramatorsk 15%, Sloviansk 11.5%, Sumy 3.85%, Zaporizhzhia 2.95%, Kherson 2.15% and Kharkiv 1.45%. An eighth contract, Dobropillia, has already resolved Yes. Each city trades as its own Yes/No contract, and each one can also be traded with leverage on PredMart, which suits a board where a single ISW map update can reprice a contract overnight.

The level matters less than the direction, and the direction since mid-September has been down. A month ago Druzhkivka traded near 47.5%, Kramatorsk near 30.5% and Sloviansk near 23%. All three fell sharply in the second half of September, when Ukraine's counteroffensive north of Lyman removed the Russian salient that was supposed to form the northern arm of a pincer around the Donbas "fortress belt." Druzhkivka has recovered part of that drop in the past week, while Kramatorsk and Sloviansk have stayed near their lows. The event has drawn about $1.68 million in trading volume since it opened on May 11.

The resolution rules are what make this market different from the "capture" markets on the same war, and they explain why the prices are higher than a casual reader might expect. A city resolves Yes if, according to the Institute for the Study of War (ISW) map, any part of its municipality is shaded under one of three layers: "Assessed Russian Infiltration Areas," "Assessed Russian-Controlled Terrain," or "Assessed Russian Advances." The shading has to survive the next full ISW daily update. Shading under "Claimed Russian Territory" does not count, so a Russian Ministry of Defense announcement is not enough. Once a city qualifies, a later Ukrainian recapture does not reverse it. Municipal boundaries are the ones in ISW's "Ukrainian Settlements" layer, and a negotiated settlement that hands Russia actual control would also count, though a paper agreement giving de jure control would not. The deadline is December 31, 2026 at 11:59 PM ET.

In plain terms, the market asks whether ISW will assess that Russian troops, even a small infiltration group, have operated inside the city limits, not whether Russia will take the city. That is a much lower bar, and the Dobropillia contract showed how low it can be.

The Precedent: How Dobropillia Resolved Yes

Dobropillia opened near 43% in May. It rose through the summer, reached about 74% in early August and about 90% by September 20, and resolved Yes on September 22.

The resolution did not mean Russia captured the town. On September 22, Russia's Ministry of Defense announced that it had encircled Dobropillia. ISW's September 24 assessment said it had "observed no evidence to support these Russian MoD claims of advances within or surrounding Dobropillya" and put the nearest Russian-held territory 10.2 km from the town's southeastern outskirts. But ISW had observed Russian infiltrators operating east and northeast of the town on September 19 and 20, and on October 6 it reported that Russian forces had "recently conducted infiltration missions within and south of Dobropillya." Under this market's rules, infiltration shading inside the municipality is sufficient, even when the infiltrators never consolidate a position.

That is the template for every remaining contract. The question for each city is not "can Russia hold it?" but "can a small Russian group get inside the municipal boundary and stay long enough for ISW to map it?" Russian forces have used exactly that tactic in Kostiantynivka and Dobropillia: small groups infiltrating ahead of the main line rather than broad frontal advances. A Ukrainian brigade in the Pokrovsk direction reported that Russian forces try to infiltrate urban areas in its sector 70 to 80 times per day, according to ISW's October 4 assessment.

The Front-Runner: Druzhkivka at 38.5%

Druzhkivka is the natural front-runner. It sits directly north of Kostiantynivka, the city Russia has made its priority effort in Donetsk Oblast, and it is the last city before Kramatorsk on the main highway north. Of the four fortress-belt cities (Kostiantynivka, Druzhkivka, Kramatorsk and Sloviansk), it is the next in line from the south.

The price history follows the fighting in Kostiantynivka. Druzhkivka opened near 32% in May and traded between about 23% and 34% through June and most of July. It then jumped to about 51% on July 31, held in the 40s through early August and peaked near 54.5% in late August. That rise came with reports in late July of Russian pressure toward northern Kostiantynivka and toward Oleksiievo-Druzhkivka, a separate settlement on the road between the two cities. That road is the southern arm of any Russian pincer around Kramatorsk and Sloviansk. If Russia takes Oleksiievo-Druzhkivka, Druzhkivka itself, a few kilometers to the northwest, comes under direct threat.

The contract then fell from about 51.5% in mid-September to a low near 30.5% on October 4, and it has bounced back to 38.5% in the past week, including a jump of about four points on October 11. The bounce does not trace to a single confirmed advance toward Druzhkivka. The more likely drivers are steady reporting from Kostiantynivka itself: ISW's October 8 assessment cited footage published on October 4 showing Russian advances in northwestern Kostiantynivka, and its October 9 assessment found evidence that Russian forces had advanced into "less than 40 percent of Kostyantynivka" as of early October. Russia's Ministry of Defense has claimed the capture of Kostiantynivka, and ISW assesses that Russian forces have not seized the city. Meanwhile ISW lists "advance on Kostyantynivka and Druzhkivka from the south and southwest, east of the Kazenyi Torets River" as one of Russia's stated objectives in this sector.

There is a second route into Druzhkivka. Russia's offensive toward Dobropillia is aimed, according to ISW, at "a wide encirclement of the Fortress Belt from near Dobropillya and Pokrovsk west of the Kazenyi Torets River." ISW wrote on October 6 that Russian forces "have maintained the highest offensive tempo across the frontline in the Dobropillya direction." A Russian push from that area to the north and east would reach Druzhkivka's western approaches without going through Kostiantynivka. That is the scenario that most worries Ukrainian commanders, and it is the reason Druzhkivka trades well above the other cities.

The case against Druzhkivka is time and speed. Russia has fought inside Kostiantynivka for months and has still advanced into less than half of it by ISW's estimate. Druzhkivka is beyond it. An infiltration into Druzhkivka's southern districts would require Russian groups to move through or around a city where they have not yet consolidated control, under constant drone surveillance. At 38.5%, the market is pricing a little better than a one-in-three chance that this happens in the next 81 days, which is roughly fair given the infiltration-friendly rules, but the downward trend since August suggests the market sees the pace slowing, not accelerating.

The Biggest Mover: Kramatorsk and the Lyman Counteroffensive

The largest single move on the board over the past month belongs to Kramatorsk. The contract rose from about 20.5% in mid-August to about 33.5% in late August, held near 28-32% through mid-September, and then dropped to 20.5% on September 17 and 15% now. Over the past month alone the contract lost about 15.5 points, roughly halving its price. Sloviansk followed the same path, from about 23% in mid-September to 11.5%.

The catalyst was Ukraine's counteroffensive north of Lyman, which Ukrainian commanders call Operation Vivaldi. On September 15, 3rd Army Corps commander Andriy Biletsky confirmed the operation and said Ukrainian forces had cleared or liberated about 85 square kilometers in its first phase. A second phase liberated Shandryholove, Derylove and Drobysheve, and a third phase, publicized around September 28, took Nove, Ridkodub, Karpivka and other villages north of Lyman, for a total of 176 square kilometers across the three announced phases, according to ISW. ISW wrote on September 24 that Ukraine had eliminated the Russian salient north of Lyman.

That salient mattered because Russia's plan, as ISW describes it, was a two-pronged envelopment of the fortress belt: one arm from the northwest, seizing Lyman and crossing the Siversky Donets, and one from the southwest via Dobropillia and Pokrovsk. ISW assessed on September 15 that Vivaldi had achieved "the operationally-significant objective of disrupting the Russian effort to conduct a wide encirclement" of the fortress belt, and a pro-Kremlin milblogger agreed the Ukrainian gains would delay Russia's offensive on Sloviansk. Once the northern arm was gone, traders cut the odds of Russian groups reaching Sloviansk and Kramatorsk this year.

The pressure has continued into October. In its October 8 assessment, ISW reported that Russian milbloggers had acknowledged Ukrainian advances east of Sloviansk and Kramatorsk, including claims around Ozerne, Malynivka, Pyskunivka and Mykolaivka, though positions there likely remain intermixed. On October 9, ISW said evidence continued to emerge that Ukrainian forces had crossed the Siversky Donets River east of Sloviansk. ISW also noted Russian forces concentrated attacks near Kryva Luka and toward Mykolaivka on October 3 and 4 without advancing.

The move also shows how the price can swing on a contract that never resolved. Someone holding No on Kramatorsk from late August, when it traded near 66.5 cents, to today's 85 cents gained roughly 28% on the position, which at up to 4x leverage would be roughly 110% before fees, while a 4x Yes position opened at the August high would have hit its maintenance margin and been liquidated long before the bottom.

The war has still reached Kramatorsk in other ways. ISW reported a Russian glide bomb strike on two passenger buses in Kramatorsk on the morning of October 8 that killed at least 30 people and injured at least 18, citing President Zelenskyy. Strikes do not count for this market. Only ground presence on the ISW map does.

The Rest of the Field: Sloviansk, Sumy, Zaporizhzhia, Kherson and Kharkiv

Sloviansk, 11.5%. Sloviansk is the northernmost fortress-belt city and the one most directly affected by the Lyman fighting. Its contract opened near 26% in May, briefly touched 35.5%, then traded mostly between the high teens and the mid 20s through the summer before falling to 11% on September 18. It has been flat at 11.5% for the past week with almost no trading. The closest Russian pressure is east of the city around Kryva Luka and Mykolaivka, where ISW reports Ukrainian advances and a crossing of the Siversky Donets. A pro-Kremlin milblogger cited by ISW on October 9 suggested Russia could try to envelop the Sloviansk-Kramatorsk area from the west instead, but nothing on the map supports that before year-end. Sloviansk is the cheapest way on the board to bet on a reversal of the September trend: a return to its mid-September level would roughly double the contract, and that kind of move is where leverage of up to 4x adds the most per dollar of margin, with the matching risk if the price keeps sliding.

Sumy, 3.85%. Sumy has drawn Russian pressure along the northern border since 2025, but the city itself is not on the immediate line of contact. The contract peaked near 12.5% in late May and early June and has declined steadily since. ISW's October 9 assessment said Russian forces continued "limited offensive operations in northern Sumy Oblast" without advancing, and that Ukraine denied a Russian claim to have seized Kyianytsia, north of the city. ISW lists Russia's objective in Sumy Oblast as creating "defensible buffer zones" along the border, not an assault on the city. The contract carries some residual risk because infiltration groups can move far ahead of the line, but the trend is down.

Zaporizhzhia, 2.95%. The city sits well behind the front. ISW lists Russia's objective on the southern axis as advancing "within tube artillery range of Zaporizhzhia City," which by definition means Russian forces are not yet that close. The contract spiked to about 11.8% in late May and to about 8% in mid-August before settling near 3%. ISW reported Russian advances in western Zaporizhzhia Oblast on October 8 and a small Russian mechanized assault in the Huliaipole direction that produced at most a marginal advance. Those are real gains, but they are measured in villages, not distance to the city limits.

Kherson, 2.15%. Kherson is the one city on the board separated from Russian forces by the Dnipro River. The contract traded near 10% in late May and June and has fallen almost without interruption to just over 2%, the steadiest decline on the board. ISW reported no ground activity in the Kherson direction on October 7, 8 or 9. Kherson is also the thinnest market in the event, with under $10,000 traded, so its price is less informative than the others.

Kharkiv, 1.45%. Kharkiv is Ukraine's second-largest city and is currently the least likely entry on the board. The contract peaked near 11.3% in late May and fell to around 2-3% by September. ISW says Russia's objective in Kharkiv Oblast is to "approach Kharkiv City," and a Ukrainian drone company commander told ISW that Russian forces are trying to seize Kozacha Lopan, north of the city near the border, by the end of October. ISW also flagged a Russian Ministry of Defense claim to have seized Hannopillya, northeast of the city, as roughly 20 kilometers beyond the furthest assessed Russian advance. The gap between claims and the map is exactly why this market uses ISW's assessed layers rather than official statements.

The pattern across the five long shots is the same: every one of them peaked in late May or summer and has been grinding lower since. With the board this concentrated, the realistic Yes outcomes are Druzhkivka, then Kramatorsk, then Sloviansk, and all three depend on the same southern and western approaches. The contracts are correlated. If Russian infiltration groups reach Druzhkivka, the Kramatorsk price will move with it; if the Kostiantynivka front stalls, all three will drift lower together.

Catalysts: The Windows That Will Reprice the Board

ISW's daily map is the resolution source, so every update is a potential catalyst. Watch three layers in particular. An "Assessed Russian Infiltration Areas" polygon touching the southern edge of Druzhkivka would likely resolve that contract quickly, since the shading only has to survive one full update cycle. Movement around Oleksiievo-Druzhkivka is the early warning for that.

The Kostiantynivka battle. Russia's progress inside Kostiantynivka is the single best leading indicator for Druzhkivka and, indirectly, for Kramatorsk. ISW's finding that Russian forces have advanced into less than 40% of the city sets the baseline. A jump in that figure, or confirmed Russian presence in the northern districts of Kostiantynivka, would move Druzhkivka up. A stall would push it back toward its early-October low.

The Dobropillia flank. ISW's October 9 assessment said Russian forces may be increasing attacks around Dobropillia before the autumn mud season, and elements of the Russian 76th VDV Division are operating in that direction. The same assessment quoted a Kremlin-affiliated milblogger saying continued Ukrainian pressure on the northern flank would make attacks there "practically pointless." Any confirmed Russian move from the Dobropillia area toward the west and north of Druzhkivka would support the wide-encirclement scenario that ISW describes.

Operation Vivaldi's next phase. Biletsky has said the operation will continue beyond the phases announced so far. ISW reported Ukrainian advances toward the Zherebets River northeast of Lyman on October 9. Continued Ukrainian gains in the north would keep pressure on Sloviansk and Kramatorsk prices. A Russian recovery of lost ground north of Lyman would revive the two-pronged plan and lift both.

Weather. The autumn rasputitsa, the mud season, typically slows mechanized movement in October and November, though small infantry groups are less affected than armored columns. Frozen ground later in the winter can favor renewed assaults. With the deadline on December 31, the market has roughly one weather window left.

Diplomacy. The rules allow a Yes resolution if Russia gains actual control of a city through a negotiated settlement. Russia has long demanded that Ukraine withdraw from the remaining parts of Donetsk Oblast it controls, which include Druzhkivka, Kramatorsk and Sloviansk. In current reporting there is no agreement close to that. ISW's October 9 assessment noted that President Trump had announced a deal with Putin to waive sanctions on Russian diesel, but no deal on territory has been reported. Even a signed deal would need actual transfer of control before December 31 to count, which makes diplomacy a small factor for this market's timing.

Bottom Line

This market rewards precision about its rules. It does not ask whether Russia will capture these cities. It asks whether ISW will map any Russian presence, including infiltration, inside them before New Year's Eve. Dobropillia showed that bar can be met while a town remains under Ukrainian control, and that is the main reason Druzhkivka still trades near 38.5% despite Russia's slow progress in Kostiantynivka.

My read: Druzhkivka at 38.5% is close to fair and the most actively traded open contract on the board, with the risk skewed by the Dobropillia flank and the infiltration-friendly rules. Kramatorsk at 15% and Sloviansk at 11.5% look reasonable after the September repricing; the Lyman counteroffensive removed the northern arm of Russia's pincer, and October reporting has Ukraine pressing east of both cities rather than defending their outskirts. Sumy, Zaporizhzhia, Kherson and Kharkiv are priced as tail risks, and nothing in current ISW reporting justifies more than that before year-end. The most likely final board is one more Yes at most, with Druzhkivka the only contract where that is a live question. For anyone who disagrees with the September repricing or with Druzhkivka's level, each of these contracts can be traded with leverage on PredMart, as long as the position is sized for a market where one map update can move a price by ten points.

Trade with up to 4x leverage: predmart.com/event/which-cities-will-russia-enter-by-december-31