Russian forces have conducted sustained offensive operations around Kupiansk in Kharkiv Oblast since late 2024, establishing limited bridgeheads east of the Oskil River and attempting infiltrations into the city itself. Russian claims of full control in November 2025 were followed by Ukrainian counterattacks that recaptured northern and southern districts, encircled small Russian groups, and restored control over most of the municipality by December 2025. Through May 2026, Ukrainian units have continued clearing remaining infiltrators via drone strikes and ground operations, while Russian assaults near Novoosynove, Petropavlivka, and other outskirts have produced no confirmed territorial gains. These dynamics, including Ukrainian interdiction of logistics and incremental Russian manpower commitments without decisive breakthroughs, shape trader assessments of the low likelihood of complete Russian capture by the June 30, 2026 resolution date.
基于Polymarket数据的AI实验性摘要。这不是交易建议，也不影响该市场的结算方式。 · 更新于Ukrainian forces maintain full control over Kupiansk despite Russian infiltration attempts
Ukrainian forces confirmed full control of Kupiansk, repelling Russian infiltration attempts in small groups. This confirmation of Ukrainian control further reduced market confidence in Russia capturing all of Kupiansk by the end of 2026.
Ukrainian forces maintain control of Kupiansk amid Russian infiltration attempts
December 31 dips to 17%4%
Reports confirmed that Ukrainian forces fully control Kupiansk despite Russian infiltration attempts. Ukrainian counteroffensives and strikes on Russian logistics have reduced Russian offensive capabilities, further diminishing the likelihood of Russian capture of Kupiansk by the end of 2026, reflected in the market's low price for the December 31 outcome.
Ukrainian forces strike Russian positions in northern Kupiansk, Russian control remains limited
December 31 drops to 18%9%
Geolocated footage showed Ukrainian strikes on Russian positions in northern Kupiansk, with reports that Russian forces only hold isolated groups without stable control. This confirmed ongoing Ukrainian dominance and contributed to further price decline.
Ukrainian forces maintain full control over Kupiansk despite Russian infiltration attempts
December 31 drops to 18%5%
Ukrainian forces confirmed full control of Kupiansk, with Russian troops only attempting small infiltration groups that were largely unsuccessful. This confirmation solidified market expectations that Russia would not capture all of Kupiansk by the end of 2025.
Russian military claims capture of Kindrashivka near Kupiansk
June 30 drops to 2%5%
On May 30, Russian military claimed that the 121st Motor Rifle Regiment captured Kindrashivka, a village near Kupiansk, indicating localized Russian gains but not full control of Kupiansk municipality. This claim did not translate into full capture of Kupiansk, influencing market prices downward.
Leaked Russian map falsely claims control of towns including Kupiansk
December 31 dips to 23%4%
A leaked Russian Ministry of Defense map was found to falsely claim control of Kupiansk and other towns, with no Russian presence detected in key areas. This further discredited Russian claims and reinforced market skepticism about Russia capturing Kupiansk.
ISW reports Russian generals feeding Kremlin false maps exaggerating territorial gains
December 31 dips to 26%2%
ISW reported that Russian generals have been providing the Kremlin with false maps claiming towns, including Kupiansk, that were never captured. This misreporting likely leads to unrealistic Kremlin demands and reflects a steep slowdown in Russian advances, reinforcing market doubts about Russian capture of Kupiansk by year-end.
ISW exposes Russian false claims about Kupiansk capture
December 31 plunges to 18%33%
Euromaidan Press reported that Russian Defense Minister Andrei Belousov ordered accelerated advances to match inflated maps, revealing Russia had falsely claimed to hold half the city while Ukrainian forces had largely cleared Kupiansk by late December.
Russian Defense Minister orders acceleration of advances in Kupiansk direction amid false claims
December 31 drops to 19%9%
Russian Defense Minister Andrei Belousov ordered increased pace of advances in Kupiansk and nearby directions, likely to align ground realities with exaggerated maps. Russian military command continued false claims about Kupiansk control, while ISW confirmed Ukrainian control and elimination of Russian infiltrators, causing further market decline.
Russian military command continues exaggerated claims about Kupiansk
December 31 plunges to 27%29%
Despite evidence of Ukrainian control, Russian military command persisted in overstating territorial gains in Kupiansk, undermining credibility and contributing to market price decline for Russian capture by year-end.
ISW reports Russian military exaggerations about Kupiansk control
December 31 plunges to 27%17%
ISW reported that Russian military command has exaggerated their control over Kupiansk, with Ukrainian forces having largely liberated the town by late 2025 and continuing to eliminate remaining Russian infiltrators. This undermined confidence in Russian claims and contributed to the market price decline.
Putin expresses belief in capturing Donetsk and Luhansk by Fall 2026, but Kupiansk remains contested
December 31 drops to 18%9%
Despite Putin's confidence in capturing Donetsk and Luhansk oblasts by Fall 2026, ISW assessments and battlefield realities showed slow Russian advances and continued Ukrainian control in Kupiansk. Russian military command's exaggerated claims about Kupiansk contrasted with evidence of Ukrainian control, leading to further market price declines for full Russian capture by December 31.
Russian military command exaggerates advances in Kupiansk area amid Ukrainian control
December 31 dips to 26%1%
Despite Russian claims of advances and orders to increase offensive pace near Kupiansk, ISW reports confirm Ukrainian control with only limited Russian infiltrators remaining. Russian military command's misinformation likely misleads strategic expectations, reducing market confidence in Russian capture by year-end.
Leaked Russian Defense Ministry map reveals exaggerated Russian control near Kupiansk
December 31 plunges to 26%30%
A leaked Russian Ministry of Defense map dated April 9 was published, showing frontline positions that ISW assessed as exaggerated, with Russian forces not having fully captured Kupiansk. Russian military command was criticized for misreporting the Kupiansk sector, contributing to market skepticism about Russian advances and causing a sharp drop in the December 31 outcome price.
ISW: Russian order to accelerate Kupiansk advances unaccompanied by ground gains
June 30 dips to 2%4%
ISW’s May 28 assessment noted that Russian Defense Minister Andrei Belousov ordered faster advances, but there was no evidence of actual territorial gains around Kupiansk. The disconnect between command promises and field reality caused a brief price dip from 6 % to 2 % as traders discounted the likelihood of a full capture.
ISW reports Russian military command exaggerates Kupiansk battlefield claims
December 31 drops to 21%7%
The Institute for the Study of War highlighted that Russian military leadership repeatedly misrepresented the situation in Kupiansk, with evidence showing Ukrainian forces largely liberated the town and only small Russian infiltrators remain. This undermined Russian credibility and lowered market expectations for Russian capture by year-end.
ISW reports Russian generals feeding Kremlin false maps exaggerating Kupiansk gains
December 31 plunges to 28%28%
On May 28, ISW revealed that Russian military command exaggerated territorial gains in Kupiansk, feeding false maps to Kremlin leadership. This exposed the gap between reported and actual control, causing a sharp drop in market prices for the December 31 outcome.
Leaked Russian map exaggerates Russian control in Kupiansk, ISW highlights false reporting
December 31 plunges to 28%22%
A leaked Russian Ministry of Defense map falsely claimed control of towns including Kupiansk, while ISW confirmed Russian forces had not entered or held significant parts of Kupiansk. This exposed Russian command misinformation and further reduced market confidence in Russian capture by year-end.
ISW reports only limited Russian infiltration in Kupiansk, Ukrainian forces maintain control
December 31 dips to 27%1%
Geolocated footage showed only a very limited number of Russian infiltrators in Kupiansk, with Ukrainian forces maintaining positions and having cut off infiltration routes. Ukrainian military intelligence confirmed elimination or capture of Russian soldiers who briefly infiltrated the area.
Russian strikes target Kupiansk amid ongoing contested control
December 31 dips to 27%1%
Russian forces conducted strikes on Kupiansk and surrounding areas, indicating continued attempts to pressure Ukrainian positions. However, these strikes did not translate into territorial gains, reflecting the stalemate and Ukrainian defensive resilience.
Ukrainian forces eliminate remaining Russian infiltrators in Kupiansk
December 31 dips to 26%1%
Geolocated footage and Ukrainian statements confirmed that only a very limited number of Russian infiltrators remained in Kupiansk, with Ukrainian forces maintaining control and eliminating infiltration routes. This solidified the market's negative outlook on Russian capture chances.
Report on brutal fighting and Russian infiltration attempts through pipelines near Kupiansk
December 31 plunges to 28%22%
Ukrainian forces described intense combat against Russian troops using underground pipelines to infiltrate Kupiansk, with Russian soldiers having very short survival times. This highlights ongoing contested control and challenges for Russian forces to establish firm presence in Kupiansk.
Russian forces redeploy from Kupiansk area, indicating abandonment of capture efforts
December 31 plunges to 28%28%
On May 25, ISW reported indicators that elements of the Russian 272th Tank Division were redeploying away from the Kupiansk area to other fronts, suggesting that Russia may have abandoned efforts to seize Kupiansk. This contributed to a sharp decline in market prices for Russian capture by December 31.
Russian infantry geolocated in northeast Kupiansk amid ongoing attacks
December 31 dips to 27%1%
Geolocated video footage confirmed Russian infantry presence in northeast Kupiansk and ongoing attacks east of the Oskil River, indicating continued Russian pressure but no decisive control. The tense situation and lack of Russian territorial consolidation contributed to market skepticism about Russian capture.
Russian infantry geolocated in northeast Kupiansk amid ongoing attacks
June 30 dips to 2%4%
On May 24, reports indicated Russian infantry presence in the northeast of Kupiansk itself, showing Russian attempts to infiltrate the city. However, the situation remained tense without decisive Russian control, reflecting continued contestation of the area.
Russian forces continue limited infiltration missions near Kupiansk
December 31 dips to 27%1%
Russian forces conducted infiltration missions near Kupiansk but failed to make significant territorial gains, with Ukrainian forces striking back effectively. This ongoing stalemate contributed to declining market confidence in Russian capture.
Russian military command reallocates forces away from Kupiansk area
December 31 dips to 26%2%
Reports indicated that Russian military command planned to move over 1,000 servicemembers from near Kupiansk to the Slovyansk direction, suggesting abandonment of efforts to seize Kupiansk at this time. This strategic shift signaled reduced Russian focus on capturing Kupiansk, reinforcing market skepticism about full capture by year-end.
Ukrainian forces seize tactical initiative across frontline
June 30 dips to 2%3%
General Oleksandr Syrskyi announced Ukrainian offensive actions exceeded Russian assaults, marking a decisive shift in battlefield momentum.
ISW notes Russian forces largely absent in Kupiansk, area contested by Ukrainian counterattacks
December 31 plunges to 27%24%
On May 20, ISW highlighted that Russian forces had minimal presence in Kupiansk compared to earlier in the year, describing the area as a contested zone with ongoing Ukrainian clearing operations. This assessment contributed to a sharp decline in market prices for Russian capture by December 31.
Ukrainian forces maintain full control over Kupiansk despite Russian infiltration attempts
December 31 plunges to 27%24%
Ukrainian commanders confirmed full control of Kupiansk, describing Russian forces as limited to small infiltration groups using underground pipelines. This contradicted Russian claims of control and led to a significant drop in market confidence for Russian capture by December 31.
Ukrainian commander states Kupiansk is a contested 'gray zone'
June 30 dips to 2%1%
On May 20, a Ukrainian commander described Kupiansk as largely contested with neither side holding firm positions, and ISW adjusted its assessment to depict Ukrainian counterattacks and absence of firm Russian control. This further decreased market confidence in Russian capture by June 30.
ISW describes Kupiansk as contested gray zone with reduced Russian presence
December 31 drops to 44%7%
ISW reported that Russian forces no longer held firm positions in Kupiansk, describing it as a contested gray zone with significant Ukrainian clearing operations. This diminished the likelihood of Russia fully capturing Kupiansk by the resolution date, reflected in declining market prices for the December 31 outcome.
ISW maps Kupiansk as contested ‘gray zone’ after Ukrainian clearing operations
June 30 dips to 2%1%
The May 20 ISW update described Kupiansk as a “contested gray zone” with Russian presence far weaker than in January and highlighted Ukrainian clearing operations. This reinforced market sentiment that Russian capture was unlikely, pushing the Yes price down to 2 % by the end of May.
ISW reports Kupiansk largely contested with Ukrainian counterattacks ongoing
December 31 dips to 44%2%
On May 20, ISW assessed Kupiansk as a contested "gray zone" with neither Russian nor Ukrainian forces holding firm positions, reflecting ongoing Ukrainian clearing operations and reduced Russian presence. This assessment further decreased market confidence in Russian full capture by December 31.
Ukrainian commander describes Kupiansk as contested gray zone with limited Russian presence
December 31 plunges to 28%23%
A Ukrainian commander stated that Russian forces had significantly reduced presence in Kupiansk compared to January 2026, describing the area as a contested gray zone with neither side holding firm positions. ISW adjusted its control assessment to depict Ukrainian counterattacks and clearing operations in Kupiansk, signaling diminished Russian control and impacting market confidence in Russian capture.
Ukrainian counterattacks recapture much of Kupiansk since November 2025
December 31 plunges to 28%17%
Ukrainian forces have conducted a series of counterattacks since November 2025, recapturing much of Kupiansk and liberating significant territory in southern Ukraine. This sustained Ukrainian offensive further diminished the likelihood of full Russian control of Kupiansk by the end of 2026, contributing to market price declines.
ISW assesses Kupiansk as contested 'gray zone' with no firm Russian control
June 30 dips to 2%3%
By May 20, ISW reported Kupiansk as a contested area with neither Russian nor Ukrainian forces holding firm positions, reflecting ongoing Ukrainian counterattacks and clearing operations. This assessment contributed to the market's decline in probability for full Russian capture by June 30 and December 31.
Ukrainian commander confirms Kupiansk largely contested, Russian presence minimal
December 31 plunges to 33%18%
A Ukrainian commander described Kupiansk as a contested "gray zone" with neither side holding firm positions, and noted Russian forces do not have nearly the presence they had earlier in 2026. This assessment led to market doubts about Russia capturing all of Kupiansk by year-end.
Ukrainian drones inflict 19,203 Russian casualties in May
June 30 dips to 2%3%
Ukrainian drones struck 19,203 Russian personnel in the first 19 days of May, exceeding Russia's recruitment rate and demonstrating Ukraine's growing tactical advantage.
Ukrainian forces eliminate remaining Russian sabotage elements in Kupiansk
A Ukrainian company commander reported on May 19 that Ukrainian forces killed or captured the last Russian sabotage and reconnaissance elements in Kupiansk, describing the area as a contested 'gray zone' with no firm Russian control. This further reduced market confidence in full Russian capture by June 30.
Ukrainian commander reports elimination of remaining Russian sabotage elements in Kupiansk
December 31 drops to 42%9%
A Ukrainian company commander reported that as of May 18, Ukrainian forces had killed or captured the remaining Russian sabotage and reconnaissance elements in Kupiansk, describing the area as a contested gray zone with no firm Russian control. This reinforced market skepticism about Russian capture prospects by year-end.
Ukrainian forces advance in Kostyantynivka area near Kupiansk
Geolocated footage and reports indicate Ukrainian forces advanced and hold positions in areas near Kupiansk, including Illinivka and Kostyantynivka outskirts, demonstrating continued Ukrainian operational presence and contesting Russian control in the region.
Russian General Gerasimov falsely claims advances west of Kupiansk
December 31 drops to 46%5%
Russian Chief of General Staff Valery Gerasimov claimed Russian forces were advancing west of Kupiansk, implying full capture, but this was contradicted by Ukrainian and independent sources showing no such control. This false claim contributed to market skepticism about Russian capture prospects.
ISW reports Russian forces hold only limited infiltration in Kupiansk, no consolidated control
December 31 drops to 46%5%
ISW assessed that Russian forces do not hold consolidated positions within Kupiansk and only a few infiltrators remain, indicating that full capture is unlikely in the near term. This assessment contributed to declining market confidence in a December 31 capture.
Russian forces claim limited gains near Kupiansk but fail to secure city
December 31 drops to 45%6%
Russian Ministry of Defense claimed seizure of Kutkivka north of Kupiansk, but ISW and other sources found no evidence of significant Russian control within Kupiansk, estimating only about 14% infiltration. Ukrainian forces actively repelled Russian infiltration attempts, maintaining control of the city. This undermined market confidence in a full Russian capture by year-end.
Russian military falsely claims advances west of Kupiansk
December 31 drops to 46%5%
Russian Chief of the General Staff Gerasimov claimed advances west of Kupiansk, implying control of the city, but ISW and independent analysts assessed these claims as false. Russian forces have not seized Kupiansk and lack the capacity to make significant advances there.
Russian forces conduct no assaults near Kupiansk amid ongoing Ukrainian control
On May 12, Ukrainian General Staff reported no Russian assault operations in the Kupiansk direction, with continued Ukrainian control and Russian forces limited to attacks on infrastructure rather than territorial advances.
ISW highlights Ukrainian gains and Russian offensive stall in spring 2026
June 30 dips to 3%2%
ISW reported that Ukrainian forces made their most significant gains since August 2024, including liberating large parts of Kupiansk, while Russian forces failed to make operationally significant advances and suffered heavy casualties. This reinforced market skepticism about Russia capturing all of Kupiansk by the end of 2025.
Kremlin holds truncated Victory Day parade with no tanks
June 30 dips to 2%3%
Russia's truncated Victory Day parade with no tanks and only 10 foreign leaders signaled deteriorating military morale and a shift in strategic posture.
ISW says Ukrainian counter‑attacks have pushed Russian forces into isolated pockets in Kupiansk
June 30 dips to 2%4%
The ISW assessment published on May 8 reported that Ukrainian forces were conducting counter‑attacks in Kupiansk and that Russian troops were largely confined to a few isolated pockets, such as a hospital that had been destroyed. The assessment signaled a clear setback for Russian control of the municipality, prompting market participants to lower the probability of a full Russian capture.
Russian MoD claims Ukrainian drones and artillery continue after ceasefire
June 30 dips to 3%2%
Despite a unilateral Russian ceasefire, the MoD reported continued Ukrainian drone and artillery attacks, indicating ongoing combat intensity and challenging Russia's ability to achieve territorial consolidation.
Ukraine, Russia agree on three-day ceasefire and prisoner exchange amid ongoing conflict
On May 8, Ukraine and Russia announced a three-day ceasefire and prisoner exchange, reflecting a temporary pause in hostilities but no change in control of Kupiansk. This maintained the contested status and contributed to market uncertainty.
ISW reports Russian forces likely do not maintain positions in Kupiansk
June 30 dips to 2%1%
On May 8, ISW assessed that Russian forces likely do not maintain positions in Kupiansk after months of struggling to support isolated servicemembers infiltrated into the city. Ukrainian forces continued to impose high costs on Russian operations, indicating Russia had not captured all of Kupiansk municipality.
ISW confirms Kupiansk remains contested with no firm Russian control
June 30 dips to 5%1%
ISW's May 8 assessment confirmed that Russian forces had not secured full control of Kupiansk, with Ukrainian counterattacks ongoing and the city largely a contested zone. This reinforced market skepticism about a full Russian capture by June 30.
ISW reports intensified Ukrainian counterattacks and limited Russian gains in Kupiansk area
June 30 dips to 4%2%
The Institute for the Study of War noted that Ukrainian forces had liberated large portions of Kupiansk starting November 2025 and continued to conduct intensified strikes against Russian lines, while Russian advances stalled and suffered high casualties. This assessment reduced confidence in Russia fully capturing Kupiansk by the end of 2025, impacting the market price for the June 30 outcome.
ISW confirms no evidence of Russian control beyond Kupiansk hospital area
June 30 dips to 2%3%
ISW stated on May 8 that they had not observed evidence of Russian control beyond the Kupiansk Central District Hospital area, indicating Russian forces likely do not maintain positions in central Kupiansk. This contributed to the market price declining to 2% Yes.
ISW reports no significant Russian control gains in central Kupiansk as ceasefire begins
June 30 dips to 2%1%
ISW noted no granular evidence of Russian control beyond the Central District Hospital in Kupiansk as of May 8. A three-day ceasefire from May 9 to 11 was agreed, limiting offensive operations and indicating stalled Russian advances.
Ukraine and Russia agree to three-day ceasefire including Kupiansk area
On May 8, Ukraine and Russia agreed to a three-day ceasefire from May 9 to 11 for Victory Day celebrations and a prisoner exchange, halting offensive operations near Kupiansk and preventing any immediate territorial changes. This maintained low market prices for Russian capture.
Ukraine and Russia agree on three-day ceasefire and prisoner exchange
June 30 dips to 2%1%
On May 8, Ukraine and Russia announced a three-day ceasefire and exchange of 1,000 prisoners each, temporarily halting hostilities including around Kupiansk. This reduced immediate chances of Russian capture and contributed to market decline in probability.
ISW confirms no Russian control beyond Kupiansk Central District Hospital
December 31 dips to 50%1%
ISW reported on May 8 that there was no granular evidence of Russian control in central Kupiansk beyond the Central District Hospital, reinforcing the assessment that Russian forces had not captured the municipality. This likely suppressed market optimism for Russian capture by December 31.
Russian soldiers encircled in Kupiansk hospital fight last battle after Ukrainian airstrike
December 31 drops to 46%5%
A Russian milblogger reported on May 7 that about 20 Russian soldiers encircled in Kupiansk City Hospital fought until the end after a Ukrainian airstrike destroyed the hospital, implying loss of Russian control in central Kupiansk. This event reinforced perceptions of weakening Russian hold, impacting the December 31 market option.
Ukrainian airstrike destroys Russian-held Kupiansk City Hospital, killing encircled Russian soldiers
December 31 plunges to 28%28%
A Ukrainian airstrike on May 7 destroyed the Kupiansk City Hospital where about 20 Russian soldiers had been encircled since December 2025, implying Russian forces no longer hold central Kupiansk. This event significantly reduced market confidence in a full Russian capture by December 31.
Russian soldiers encircled in Kupiansk hospital reportedly killed in Ukrainian airstrike
June 30 dips to 4%2%
On May 7, a Russian milblogger reported that about 20 Russian soldiers encircled in Kupiansk City Hospital fought their last battle after a Ukrainian airstrike destroyed the hospital, implying Russia no longer holds central Kupiansk positions. This reinforced market skepticism about full Russian capture.
Ukrainian airstrike destroys Kupiansk hospital, killing remaining Russian troops
June 30 dips to 2%4%
A Ukrainian milblogger reported that a group of about 20 Russian soldiers trapped in Kupiansk City Hospital fought their “last battle” after a Ukrainian airstrike destroyed the building, confirming that Russian forces had lost their last foothold inside the city. The news reinforced the perception that Russia could not yet capture the whole municipality and pushed prices sharply lower.
Russian troops advance near Pishchane on Kupiansk axis, OSINT reports
June 30 rises to 7%4%
On May 6, Russian forces reportedly advanced near Pishchane on the Kupiansk axis, indicating ongoing Russian offensive efforts to capture territory near Kupiansk. Despite these advances, full control of Kupiansk was not achieved, contributing to market uncertainty.
ISW reports Russian forces suffered net territorial losses in April 2026
June 30 plunges to 6%20%
The Institute for the Study of War reported on May 2 that Russian forces suffered a net loss of territory in April 2026, including around Kupiansk, indicating stalled Russian advances and strengthening Ukrainian control. This caused a sharp drop in market price from 26% to 6%.
Ukrainian commander says Russian foothold in Kupiansk remains a contested gray zone
June 30 dips to 2%4%
The May 2 ISW assessment quoted a Ukrainian brigade commander describing Russian attempts to expand a foothold on the left bank of the Oskil River while Russian servicemen remained hidden in basements in Kupiansk. The description of a “gray zone” and limited Russian presence added to market doubts about a full capture, supporting the price decline.
Russian forces suffer net territorial losses in April, including near Kupiansk
June 30 plunges to 6%20%
ISW reported Russian forces suffered net territorial losses in April 2026, including around Kupiansk, with advances stalling and Ukrainian forces regaining ground. This contributed to a sharp market price drop from 26% to 6% Yes.
Pravda Germany: Russian forces see gradual improvement near Kupiansk in early May
June 30 rises to 6%1%
A May 1 article from Pravda Germany highlighted “gradual improvement” for Russian forces near Kupiansk. The optimistic tone briefly lifted the Yes price to 6 % on May 1, but subsequent contradictory reports quickly erased the gain.
Russian forces gradually improve control near Kupiansk but fail to capture city
June 30 rises to 6%3%
By early May, Russian forces expanded their zone of control in settlements near Kupiansk, such as Kurylivka-1, but Ukrainian forces maintained positions on the bridgehead east of Kupiansk and repelled assaults, preventing full capture of the city.
ISW reports Russian advances in Kupiansk area minimal, Ukrainian forces hold contested positions
ISW's April 30 assessment indicated that Russian forces had not made significant advances in Kupiansk, with Ukrainian forces conducting clearing operations and holding firm positions, leading to a contested 'gray zone' status rather than full Russian control. This contributed to low market confidence in a full Russian capture by June 30.
Russian military claims control over Doroshivka near Kupiansk
On April 29, Russian military claimed to have taken control over Doroshivka, a village near Kupiansk, signaling incremental Russian advances in the area but not full control of Kupiansk itself. This maintained some market optimism for Russian gains but not full capture.
Ukraine uses unmanned systems to clear Russian positions near Kupiansk
June 30 dips to 3%3%
Ukraine's 'Lava' unit conducted fully robotized operations destroying Russian fortified positions near Kupiansk without deploying infantry, demonstrating Ukrainian technological and tactical advantages. This reduced Russian footholds and lowered market confidence in full Russian capture.
Russian forces renew assaults on both banks of Oskil river near Kupiansk
June 30 dips to 5%1%
On April 27, Russian troops renewed attempts to infiltrate Kupiansk through Holubivka village north of the city, including using gas pipelines. Ukrainian forces were managing to stop these attempts, indicating contested control and ongoing fighting.
Gwara Media: Russians renew Kupiansk north‑infiltration attempts with limited success
June 30 dips to 3%2%
Gwara Media reported that Russian troops were still attempting infiltrations north of Kupiansk, but the article emphasized “more complicated” fighting and no decisive breakthroughs. The lack of progress reinforced the downtrend in the market’s Yes probability.
Russian forces attempt infiltration into Kupiansk via disused gas pipelines
June 30 rises to 6%1%
Russian troops renewed infiltration attempts into Kupiansk through disused gas pipelines and small infantry groups, reflecting ongoing efforts to regain foothold but without decisive territorial gains.
ISW reports no significant Russian battlefield gains over past year
June 30 drops to 5%5%
The Institute for the Study of War confirmed that Russian forces had failed to achieve any significant operational breakthrough, while Ukrainian forces expanded their battlefield gains during winter and spring 2026, undermining Russian territorial ambitions.
Russian troops get slightly closer to northern Kupiansk, Ukrainian military reports
June 30 rises to 6%1%
On April 23, Ukrainian military spokesperson Viktor Trehubov reported Russian troops moved slightly closer to Kupiansk from the north, attempting infiltration despite Ukrainian control. This maintained market uncertainty about full Russian capture.
Russian troops advance slightly closer to Kupiansk, attempt infiltration via Holubivka
June 30 rises to 6%1%
On April 23, Ukrainian sources reported slight Russian advances near Kupiansk and renewed infiltration attempts through Holubivka village, including underground gas pipelines. This indicated ongoing Russian pressure but no decisive control, causing a minor market uptick reflecting potential for future gains.
Gwara Media: Russian advances near Kupiansk remain minimal, claims of control dismissed
June 30 dips to 3%2%
Gwara Media reported that Russian troops had only moved “slightly” closer to Kupiansk and that Russian claims of full control were dismissed as “drug‑fed delirium.” The article highlighted continued Russian pressure but no decisive breakthrough, which helped keep market sentiment low throughout the April‑May window.
Russian troops move slightly closer to Kupiansk from the north
On April 23, Ukrainian military spokesperson Viktor Trehubov reported Russian troops had moved slightly closer to Kupiansk from the north, attempting infiltration using tree cover. This indicated ongoing Russian pressure but no full capture of the city.
Reports of Russian advances west of Kupiansk amid Ukrainian troop redeployments
June 30 rises to 6%1%
On April 18, frontline reports indicated Russian forces advanced west of Kupiansk, causing Ukrainian troops to redeploy to other sectors. This suggested increased Russian pressure near Kupiansk but no full capture of the city, leading to a slight market price increase.
Russian forces advance west of Kupiansk amid Ukrainian troop redeployments
On April 18, reports indicated Russian troops made recent advances west of Kupiansk, causing Ukraine to shift units from the Kupiansk sector to the Vovchansk area. This suggested increased Russian pressure but no full capture of Kupiansk, leading to a slight market price fluctuation.
ISW says Russian attacks near Kupiansk make no progress, Ukrainian counter‑attacks noted
June 30 dips to 3%2%
ISW’s April 13 assessment reported Russian attacks near Kupiansk but no confirmed advances and noted Ukrainian counter‑attacks in nearby villages, signalling a stall in Russian momentum. The market dropped from 5 % to 3 % shortly after, reflecting lower confidence that Russia would capture the municipality.
Russian forces intensify assaults on Kupiansk outskirts but fail to capture city
June 30 dips to 7%2%
Russian troops launched multiple attacks on the outskirts of Kupiansk, attempting to regain foothold, but Ukrainian forces maintained control of the city itself. The ongoing fighting without full Russian capture reinforced market skepticism about a complete Russian takeover by June 30.
Ukrainian counterattacks continue to erode Russian control in Kupiansk
June 30 dips to 3%2%
Ukrainian forces intensified strikes and counterattacks since late 2025, liberating large parts of Kupiansk and maintaining contested control into spring 2026, undermining Russian hold on the city and reducing market confidence in full Russian capture by June 30.
Russian forces launch multiple attacks near Kupiansk outskirts
On April 12, Russian forces carried out three attacks in the Kupiansk sector targeting Petropavlivka, Podoly, and Zahryzove, indicating ongoing Russian efforts to regain foothold near Kupiansk. This sustained pressure kept the market cautious about a full Russian capture by June 30.
Kremlin declares short-term ceasefire over Orthodox Easter amid ongoing Kupiansk clashes
On April 11, a Kremlin unilateral ceasefire came into effect, but both sides accused each other of violations. Fighting near Kupiansk continued with Russian infiltration attempts, indicating ongoing contested control and limiting Russian advances.
ISW reports Russian infiltration overestimates in central Kupiansk
June 30 dips to 7%2%
On April 1, ISW noted that Russian presence in central Kupiansk was likely overestimated and Ukrainian forces had eliminated enduring Russian positions in the city center, indicating no full Russian control. This assessment contributed to a decline in market confidence for the June 30 outcome.
Russian ministry claims new gains in Kupiansk amid fresh fighting
A Russian defence briefing claimed fresh territorial gains in Kupiansk, and geolocated video footage suggested renewed fighting. This brief optimism caused the modest price uptick in late March (around 9–10 %).
Russian Ministry of Defense claims gains near Kupiansk amid unclear situation
June 30 dips to 8%2%
Russian Defense Ministry reported capturing nearby Kivasharivka and claimed territorial gains in Kupiansk, but the situation remained unclear with ongoing fighting, reflecting continued contested control and low market confidence in full Russian capture.
Ukrainian forces identify minimal Russian presence in Kupiansk
June 30 dips to 7%2%
On March 28, Ukrainian Joint Forces Task Force reported only six active Russian call signs in Kupiansk, indicating a very limited Russian presence and suggesting Ukrainian control of the area. This news likely contributed to low market confidence in Russian capture of Kupiansk by June 30.
Ukrainian forces report minimal Russian presence in Kupiansk
June 30 dips to 5%1%
On March 28, Ukrainian officials identified only six active Russian call signs in Kupiansk, indicating a significantly reduced Russian presence and suggesting Ukrainian advances in the area. This news likely contributed to a decrease in market confidence for Russian full control by June 30.
ISW reports ongoing fighting east of Kupiansk with Russian forces attempting to regain ground
June 30 dips to 9%1%
Russian forces were reported attempting to seize areas near Kupiansk but only controlled small remaining areas east of the Oskil River, with fighting ongoing. This indicated Russia had not captured all of Kupiansk and was unlikely to do so soon.
ISW assessment confirms Ukrainian control and Russian setbacks near Kupiansk
On March 25, ISW reiterated that Ukrainian forces had maintained control over Kupiansk since mid-December 2025 and that Russian forces had failed to regain significant territory, solidifying market consensus against Russian capture by June 30.
ISW: Ukrainian counterattacks in Kupiansk direction stabilize Ukrainian control
June 30 dips to 9%4%
The Russian Offensive Campaign Assessment reported that Ukrainian forces had launched successful counterattacks in the Kupiansk direction in November 2025, which stabilized Ukrainian control over the town and pushed Russian forces out of several settlements.
ISW confirms ongoing Ukrainian control and Russian failure to capture Kupiansk fully
June 30 dips to 8%2%
ISW's March 25 assessment reiterated that Ukrainian forces held Kupiansk and that Russian forces were unlikely to make rapid breakthroughs, confirming the market's low probability pricing for Russian capture by June 30.
Ukrainian forces intensify mid-range strike campaign against Russian military assets
Ukrainian forces significantly increased drone and artillery strikes on Russian logistics, military equipment, and manpower, degrading Russia's offensive capabilities and contributing to market skepticism about Russian territorial gains.
ISW reports continued Russian infiltration near Kupiansk without territorial gains
June 30 dips to 9%1%
Geolocated footage showed Russian forces operating in Kivsharivka near Kupiansk in infiltration missions that did not change control of terrain. Ukrainian forces continued to impose tactical challenges on Russia, reinforcing the market's low probability of full Russian capture by June 30.
Russian forces conduct mechanized assaults near Kupiansk as part of spring offensive preparations
June 30 rises to 10%4%
Russian forces increased mechanized assaults near Kupiansk in mid-March 2026, signaling preparations for a spring-summer offensive. However, these assaults were limited in scale and did not result in significant territorial gains, maintaining uncertainty about full capture prospects.
ISW reports Russian claims of Kupiansk advances
June 30 dips to 3%3%
The ISW reported that Russian Defense Minister Sergei Gerasimov claimed Russian forces had seized 12 settlements in Ukraine in March 2026, but ISW only observed evidence of two settlements seized.
Gerasimov inflates Russian gains near Kupiansk; ISW says no change
June 30 dips to 7%2%
Gen. Gerasimov claimed on 17 Mar that Russian forces had pushed the front 12 km west of Siversk and controlled 85 % of Novoosynove, but ISW reported no such territorial gains. The contradiction sowed doubt about Russian propaganda, nudging the market further toward a ‘No’ outcome.
Ukrainian President Zelenskyy reports more territory retaken than lost in prior 30 days
June 30 dips to 5%1%
On March 17, Ukrainian President Volodymyr Zelenskyy stated that Ukrainian forces had retaken more territory than Russia had captured in the previous month, signaling Ukrainian resilience and counteroffensive success near Kupiansk. This news likely reduced market confidence in Russia capturing all of Kupiansk by June 30, 2026.
Russian forces in Kupiansk reduced to about 20 troops confined to small area
June 30 drops to 5%6%
Ukrainian spokesperson Viktor Trehubov reported that only about 20 Russian troops remain inside Kupiansk, confined to a limited area and unable to reach outskirts. This indicated Russian failure to capture the city fully, contributing to the market's low price for a Russian capture by June 30.
Russian infiltrations near Kupiansk do not change control of terrain
June 30 dips to 9%3%
On March 12, reports indicated Russian infiltrations in northeastern and eastern Kupiansk but ISW assessed these did not change control of terrain, confirming Ukrainian hold and diminishing prospects of Russian capture by June 30.
Ukrainian forces advance on Kupiansk axis, ISW reports
June 30 dips to 12%2%
Geolocated footage showed Ukrainian advances north of Kivsharivka, a settlement south of Kupiansk, indicating continued Ukrainian momentum in the Kharkiv region.
Russian forces infiltrate Kupiansk outskirts but fail to change control
June 30 dips to 9%3%
Reports indicated Russian infiltrations in northeastern and eastern Kupiansk and toward eastern Kivsharivka, but ISW assessed these did not change control of terrain or the forward edge of the battle area. This maintained the status quo and supported market skepticism about full Russian capture.
Ukrainian forces encircle about 20 Russian soldiers in Kupiansk
June 30 rises to 10%4%
On March 12, 2026, Ukrainian forces reportedly encircled roughly two dozen Russian troops in Kupiansk who were unable to conduct active operations. Ukrainian forces avoided engaging them to reduce risk, demonstrating Ukrainian dominance in the area and further lowering the probability of Russian full control by June 30.
ISW: Ukraine advances near Kupiansk, counter Russian offensive in Zaporizhzhia
June 30 dips to 13%1%
ISW assessed that Ukrainian forces had pressed simultaneous counterattacks across multiple sectors, including near Kupiansk, forcing the Russian command to make strategic-level decisions and likely requiring abandonment of previous Spring-Summer 2026 offensive plans.
Ukrainian forces advance north of Kivsharivka near Kupiansk
Geolocated footage published on March 10 showed Ukrainian advances north of Kivsharivka, a settlement south of Kupiansk, indicating continued Ukrainian pressure and control in the Kupiansk area. This sustained Ukrainian momentum contributed to the market's low valuation of Russian capture by June 30.
Ukrainian advances north of Kivsharivka near Kupiansk reported by ISW
June 30 dips to 9%3%
Geolocated footage and ISW reports showed Ukrainian forces advancing near Kupiansk, indicating continued Ukrainian pressure and contestation of the area, reinforcing doubts about Russian full capture and pushing market prices lower.
ISW: Ukraine advances near Kupyansk, counter Russian offensive in Zaporizhzhia Oblast
June 30 dips to 12%3%
Ukrainian forces confirmed advances near Kupiansk and halted Russian progress across western Zaporizhzhia Oblast, forcing Russian command to redeploy elite units from multiple oblasts.
Ukrainian forces advance near Kupiansk, halting Russian progress
June 30 dips to 12%2%
ISW assessed that Ukrainian forces confirmed advances near Kupiansk and halted Russian progress in nearby regions, forcing Russian command to redeploy elite units. This demonstrated Ukrainian resilience and limited Russian territorial gains, further reducing market expectations for a full Russian capture by June 30.
ISW reports Ukrainian advances near Kupiansk, countering Russian offensive
June 30 dips to 9%1%
By March 10, 2026, the Institute for the Study of War reported Ukrainian advances near Kupiansk and that Russian forces were forced to redeploy elite units due to Ukrainian counterattacks, further diminishing Russian prospects of capturing Kupiansk fully by the resolution date.
ISW reports Ukrainian advances near Kupiansk, Russian forces redeploy elite units
June 30 drops to 9%5%
By March 9, ISW reported Ukrainian advances near Kupiansk and that Russian command was forced to redeploy elite units to sustain combat, indicating Russian difficulties in regaining territory and lowering chances of capturing Kupiansk by June 30.
ISW map shows full Ukrainian control of Kupiansk on March 9
June 30 dips to 9%3%
ISW released a terrain‑control map for March 9 showing the entire Kupiansk municipality shaded blue (Ukrainian‑held). The visual confirmation that no part of the city was red on the ISW map caused a further collapse of the ‘Yes’ price, as the market interpreted the map as decisive evidence against a Russian capture.
Ukraine eliminates Russian sabotage group attempting to mine near Kupiansk
June 30 dips to 15%3%
Ukrainian paratroopers detected and eliminated a Russian sabotage group attempting to mine territory near Zahryzove in the Kupiansk direction, preventing Russian forces from gaining tactical advantage. This reinforced Ukrainian control and contributed to the market's decline.
Ukraine regains more territory than Russia captured in February 2026
June 30 dips to 12%1%
Ukrainian forces were reported to have regained more territory than Russia captured in February, with explicit mention of strengthening control around Kupiansk. The continued Ukrainian gains pushed the market down to the low‑teens.
Ukrainian forces strengthen control around Kupiansk amid ongoing operations
June 30 dips to 7%2%
In early March, Ukrainian commanders reported strengthening control around Kupiansk, continuing to contain Russian forces and preventing breakthroughs. This sustained Ukrainian dominance contributed to the market price remaining low for Russian capture prospects.
Besieged Russians in Kupiansk high‑rises dwindling, Ukrainian military says
Euromaidan Press noted that the remaining Russian troops in Kupiansk high‑rises were “dwindling,” reinforcing the view that Russia would not capture the municipality. This helped keep the Yes price low, hovering around 13 % through late February.
Ukrainian military reports besieged Russians in Kupiansk high-rises dwindling
June 30 dips to 12%2%
Ukrainian forces reported that the remaining Russian garrison in Kupiansk was shrinking and trapped in apartment blocks, unable to leave, signaling continued Ukrainian control and diminishing Russian prospects for full capture.
Ukrainian military reports dwindling besieged Russian troops in Kupiansk high-rises
June 30 dips to 9%3%
On February 27, Ukrainian military sources reported that the remaining Russian soldiers trapped in Kupiansk high-rise buildings were dwindling, indicating the collapse of Russian efforts to regain control. This further diminished market confidence in a Russian capture by the deadline.
Ukrainian military says besieged Russians in Kupiansk high-rises dwindling
June 30 rises to 14%1%
On February 27, 2026, Ukrainian military reported that remaining Russian troops in Kupiansk were besieged in high-rise buildings and dwindling in number, indicating Russia's failure to capture the city fully and supporting the market's decline.
Ukrainian military reports besieged Russian troops in Kupiansk high-rises dwindling
June 30 dips to 12%3%
The Ukrainian military reported that the remaining Russian troops in Kupiansk were besieged in apartment blocks with dwindling supplies and only about 20 active radios detected, indicating the collapse of Russian control efforts. This news reinforced the market's bearish outlook on Russian capture by June 30.
Ukrainian intelligence reveals Russian troops hidden in Kupiansk since late 2025
June 30 dips to 14%1%
A report detailed how Russian troops infiltrated Kupiansk covertly and that Ukrainian forces have been actively contesting the city since late 2025, indicating ongoing Ukrainian resistance and contestation rather than full Russian control, contributing to market price decline.
Kupiansk operation ongoing but slowing, Russians never fully controlled city
June 30 dips to 13%1%
By February 25, 2026, reports confirmed the Kupiansk operation was still ongoing but at a slower pace, with Russian forces never having full control of the city. This prolonged stalemate and Ukrainian infiltration efforts contributed to the market's continued decline in Russian capture probability.
Ukrainska Pravda reveals Russian claims of Kupiansk capture were false
June 30 dips to 9%4%
A detailed report exposed that Russian forces never fully controlled Kupiansk despite Kremlin claims, with Ukrainian intelligence and forces actively contesting the city. This further undermined market confidence in Russian capture.
ISW Report Shows Ukraine Gains Territory in February 2026
June 30 drops to 14%6%
ISW confirmed Ukrainian forces liberated more territory than they lost in February 2026, marking their first net territorial gain since the summer 2023 counteroffensive.
Kupiansk operation ongoing but at slower pace; Russians never had full control
June 30 dips to 9%3%
Reports confirmed that Russian forces never fully controlled Kupiansk, with Ukrainian forces holding positions adjacent to Russian troops. The ongoing operation at a slower pace indicated continued Ukrainian control and resistance to Russian capture, further depressing market confidence.
ISW reports Ukrainian counterattacks stabilize Kupiansk, pushing back Russian forces
June 30 plunges to 15%35%
ISW assessment highlighted Ukrainian successful counterattacks in the Kupiansk direction since November 2025, stabilizing control over the town and retaking territory, undermining Russian claims of full capture and reducing market confidence in a Russian capture by June 30.
ISW reports Ukrainian forces hold Kupiansk after December counteroffensive
June 30 plunges to 15%35%
The Institute for the Study of War reported that Ukrainian forces stabilized control over Kupiansk following counterattacks in mid-December 2025, pushing Russian forces out of nearby settlements. This indicated that Russia had not captured the entire municipality, negatively impacting market confidence in a full Russian capture by June 30.
ISW reports Ukrainian advances near Kupiansk and counter Russian offensive
June 30 drops to 14%6%
The Institute for the Study of War reported that Ukrainian forces had confirmed advances near Kupiansk and were halting Russian progress, forcing the Russian command to redeploy elite units in response.
ISW reports Ukrainian forces stabilized control over Kupiansk after mid-December counterattacks
June 30 dips to 12%2%
The Institute for the Study of War reported on February 24 that Ukrainian forces had stabilized control over Kupiansk following counterattacks starting mid-December 2025, pushing Russian forces out of nearby settlements. This confirmed ongoing Ukrainian dominance and limited Russian presence, reinforcing market skepticism about Russian capture.
ISW: Battlefield realities disprove Russia's claim that Ukrainian defeat is inevitable
June 30 jumps to 20%5%
The Institute for the Study of War reported Ukrainian forces had liberated 183 km² near Kupiansk between December 11-25 and a net gain of 165 km² in February, showing significant Ukrainian territorial advances.
ISW reports Ukrainian counterattacks stabilized control over Kupiansk area
June 30 dips to 13%2%
The Institute for the Study of War reported that Ukrainian forces launched counterattacks in mid-December 2025 that stabilized control over Kupiansk and retook territory, pushing Russian forces out of several settlements. This assessment reinforced doubts about Russian capture of the city.
ISW assessment: Russian attacks around Kupiansk stall, Ukrainian control holds
December 31 dips to 12%3%
The ISW’s February 24 assessment highlighted that Russian forces were still attacking around Kupiansk but were unable to advance, while Ukrainian forces continued to hold the city and push back Russian infiltrations. The assessment reinforced the view that a Russian seizure was unlikely, driving the market further down.
Ukraine holds off Russian yearlong campaign for Kupiansk with December counteroffensive
June 30 dips to 18%4%
Ukraine successfully repelled Russian attempts to capture Kupiansk during a surprise counteroffensive in December 2025, maintaining control of the city into early 2026. This demonstrated Ukrainian resilience and limited Russian territorial gains, contributing to the market price decline.
Russian soldiers surrender to Ukrainian forces in Kupiansk via “I Want to Live” program
June 30 jumps to 20%5%
Several Russian servicemen surrendered to Ukrainian forces in Kupiansk through a state-run surrender program, indicating weakening Russian hold and morale in the city, reinforcing market skepticism about Russian full capture.
Russian soldiers surrender in Kupiansk amid ongoing Ukrainian operations
June 30 plunges to 22%28%
Russian servicemen in Kupiansk surrendered through the Ukrainian "I Want to Live" program, indicating Ukrainian control and ongoing operations within the city. This event underscored that Russian forces had not secured full control of Kupiansk, negatively impacting market confidence in a complete Russian capture by June 30.
Russian soldiers surrender near Kupiansk after contacting Ukrainian chatbot
June 30 dips to 13%2%
A group of Russian soldiers surrendered to Ukrainian forces via the “I Want to Live” chatbot in Kupiansk, showing the city’s continued Ukrainian dominance and further eroding the chance of a full Russian capture. The market slipped another few points after the story.
Ukrainian forces repel Russian infiltration attempts near Kupiansk
June 30 plunges to 22%28%
Ukrainian defense forces successfully thwarted Russian infiltration and breakthrough attempts near Kupiansk, maintaining control over the city and capturing prisoners. This demonstrated Ukraine's strong defensive posture and reduced market confidence in Russian capture by June 30.
Ukraine claims confident control of Kupiansk, few Russian troops remain
December 31 plunges to 15%35%
Euromaidan Press reported that Ukrainian Joint Forces spokesperson Viktor Trehubov said Ukraine had ‘confident control’ over Kupiansk with only a few dozen Russian troops left in a single city block. The report signaled that the Russian effort to retake the city had stalled, prompting traders to sharply downgrade the probability of a Russian capture.
Ukraine reports confident control of Kupiansk, few Russian troops left
June 30 plunges to 15%35%
Euromaidan Press reported that Ukraine had “confident control” over Kupiansk with only a few dozen Russian troops remaining, indicating that Russia was unlikely to capture the whole municipality. This optimism drove the market sharply lower, dropping the Yes probability from 50 % to about 15 % the next day.
Ukraine reports confident control over Kupiansk with only dozens of Russian troops left
June 30 plunges to 15%35%
On February 16, Ukrainian sources reported confident control over Kupiansk, with Russian forces reduced to a few dozen troops cornered in one quarter. This news indicated the failure of Russian attempts to retake the city by their February deadline, causing a sharp market price drop.
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