Russian forces conducted drone strikes against Ukraine on the night of May 20 to 21 and a missile strike against Ukraine during the day on May 21.
Ukrainian Air Force Commander Lieutenant General Mykola Oleshchuk reported that Russian forces launched 29 Shahed-136/131 drones from Primorsko-Akhtarsk, Krasnodar Krai, Kursk Oblast, and occupied Cape Chauda, Crimea and that Ukrainian forces shot 28 Shaheds down over Odesa, Mykolaiv, Dnipropetrovsk, Kharkiv, Cherkasy, Kherson, and Kirovohrad oblasts on the night of May 20 to 21.[84] Kharkiv Oblast Military Administration Head Oleh Synehubov stated that falling Shahed debris damaged four civilian objects in Kharkiv City, and Kharkiv City Mayor Ihor Terekhov reported that there was an explosion at a transportation infrastructure facility in the city.[85] The Sumy Oblast Military Administration reported that Russian forces conducted a strike against production infrastructure in Konotop with an unspecified missile.[86]
Ukrainian President Volodymyr Zelensky stated in an interview with Reuters published on May 20 that Russian forces are using 300 aircraft in Ukrainian territory and reiterated that Ukrainian forces need about 120 to 130 F-16s or other advanced fighter aircraft to achieve air parity with Russia.[87]
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The Russian military command reportedly initially planned that Russian forces would quickly make significant advances in northern Kharkiv Oblast, but the limited force grouping deployed to the area suggests that the Russian military command likely changed these plans in the lead up to offensive operations in Kharkiv Oblast.
Ukrainian President Volodymyr Zelensky indicated that the limited Russian offensive in northern Ukraine is achieving its goal of drawing attention away from intense Russian offensive operations in eastern Ukraine. Zelensky stated in an interview with Reuters published on May 20 that the situation in northern Kharkiv Oblast is now stable but that “no one” is paying attention to the wave of Russian offensive operations in Donbas in the Chasiv Yar (Bakhmut), Pokrovsk (Avdiivka), and Kurakhove (west of Donetsk City) directions.[7] Zelensky stated that the situation in northern Kharkiv Oblast has been stable for about a week, which is consistent with the slowing pace of Russian advances in the Lyptsi (north of Kharkiv City) and Vovchansk directions following the initial few days of relatively rapid tactical advances.[8] Russian forces recently intensified their efforts to seize the operationally-significant town of Chasiv Yar west of Bakhmut as the tempo of operations in northern Kharkiv Oblast decreased, highlighting how the northern Kharkiv Oblast effort aims to draw and fix Ukrainian forces and create opportunities for Russian forces elsewhere in the theater.[9] As ISW has consistently reported, Russian forces' most immediate prospect for operationally-significant gains remains the Chasiv Yar direction, as seizing Chasiv Yar would enable Russian forces to set conditions to attack part of a "fortress belt" of cities forming the backbone of Ukraine's Donetsk Oblast defenses, and Russian forces likely seek to exploit unfavorable situations for Ukrainian forces defending near Chasiv Yar and Avdiivka before US military assistance arrives at the frontlines at scale.[10] The Ukrainian General Staff has reported for the past week that Russian forces maintain a higher tempo of offensive operations in the Avdiivka direction even as the situation in northern Kharkiv Oblast has stabilized.[11]
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- The Kremlin continues to time its nuclear saber-rattling to coincide with major policy discussions in the West as part of a Kremlin reflexive control campaign to influence Western decision-makers.
- Ukrainian President Volodymyr Zelensky indicated that the limited Russian offensive in northern Ukraine is achieving its goal of drawing attention away from intense Russian offensive operations in eastern Ukraine.
- The Russian military command reportedly initially planned that Russian forces would quickly make significant advances in northern Kharkiv Oblast, but the limited force grouping deployed to the area suggests that the Russian military command likely changed these plans in the lead up to offensive operations in Kharkiv Oblast.
- Russian authorities recently arrested the former commander of the 58th Combined Arms Army (CAA), Major General Ivan Popov, on fraud charges.
- The Kremlin is likely using the pattern of recent arrests of high-ranking officials on corruption charges in the Russian MoD to conceal the real reasons for Popov's punishment almost 10 months after his conflict with the Russian military command and subsequent dismissal from his command position.
- Satellite imagery indicates that Ukrainian forces likely damaged the Russian Black Sea Fleet's (BSF) Tsyklon small missile ship in occupied Sevastopol, Crimea on May 19.
- Russian forces recently made confirmed advances near Vovchansk, Kreminna, Chasiv Yar, and Donetsk City.
- A Russian milblogger claimed that frequent Ukrainian drone strikes against Russian vehicles that lack electronic warfare (EW) systems along the frontline have created an "urgent" shortage of off-road vehicles.
- Russian authorities continue to illegally and forcibly deport Ukrainian citizens, including children, to Russia and to forcibly remove Ukrainian citizens deeper into occupied Ukraine.
Satellite imagery indicates that Ukrainian forces likely damaged the Russian Black Sea Fleet's (BSF) Tsyklon small missile ship in occupied Sevastopol, Crimea on May 19. Satellite imagery dated May 20 shows a damaged building, a rescue ship, and a floating crane near the port where the Tsyklon was docked on May 17.[27] Ukrainian and Russian sources reported on May 20 that Ukrainian forces struck the Russian Tsyklon Karakhut-class (project 22800) small missile ship in Sevastopol Bay with three US-provided ATACMS missiles on May 19.[28] Ukraine's Southern Operational Command and Navy Spokesperson Captain Third Rank Dmytro Pletenchuk stated on May 21 that that there are no more Russian Karakurt-class ships in the Black Sea following the Ukrainian strike against the Tsyklon on May 19.[29] Pletenchuk stated that the Tsyklon was the "last missile carrier" in occupied Crimea and that Russian forces have likely moved all remaining BSF missile carriers to basing in Novorossiysk.[30] Pletenchuk stated that the Tsyklon had only been in service for a year and had not yet launched a cruise missile strike. Pletenchuk stated that Russia planned to deploy five Karakurt-class ships in the Black Sea, but that Ukrainian forces previously destroyed the Askold in November 2023, that Russian forces moved the Amur and Tucha from the Black Sea to the Caspian Sea, and that the fifth unnamed ship is still under construction in Taganrog, Krasnodar Krai.[31]
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