Russia launched multiple winged missiles and drones targeting several Ukrainian regions between 11:05 PM and 11:35 PM UTC on October 2nd, 2025. Attacks were reported in Poltava, Sumy, and Chernihiv regions, with specific mention of "Iskander-K" cruise missiles and "ShahED-136" type UAVs. The "monitorwar" feed confirmed winged missiles passing Hadyach towards Sumy/Chernihiv region, and the Air Force of Ukraine reported cruise missiles past Gadyach heading west, and in Kharkiv and Sumy regions. The "monitor 1654 | Kharkiv" channel reported 28 "Shah" type UAVs in the Kharkiv area. During this 30-minute reporting window, "monitorwar" also noted winged missiles (identified as "Iskander-K") from the Kharkiv region flying towards Sumy region, specifically the Okhtyrsky district. The "monitor" feed reported a group of winged missiles (Im. Iskander-K) passing Hadyach in the direction of Sumy/Chernihiv region. The Air Force of Ukraine confirmed cruise missiles in Kharkiv and Sumy regions, with vectors indicated as "birch" and "Okhtyrka" respectively. Additionally, the Air Force of Ukraine reported cruise missiles passing Pavlograd with a course to the north. Earlier reports from the period of 10:35 PM to 11:05 PM UTC on October 2nd, 2025, indicated Ukrainian drone attacks on Russia's Krasnodar Krai, including Novorossiysk and Sochi, where the "Carpet" plan was implemented at Sochi's airport. This follows previous reports from October 2nd, 2025, where Ukrainian intelligence stated that drone attacks across Russia had forced airport closures in Sochi and Gelendzhik as of 11:55 PM UTC. The "monitor" feed reported explosions in Poltava between 10:30 PM and 10:35 PM UTC on October 2nd, 2025, identifying projectiles as likely "Iskander-K" missiles. A source shared on X.com, @kimhvik2, suggested on October 2nd, 2025, that Russia is likely planning a combined drone and ballistic missile strike in the coming days, not excluding "Iskander-K" cruise missiles. The same source noted little movement by TU-95MS aircraft used in recent strikes and indicated "Iskander-m" locations in Bryansk, Voronezh, and other regions were receiving new loads of "Iskander-m/KN-23" ballistic missiles.