Operational Intelligence Briefing: Ukraine Focus (Updated as of Sun Jun 01 18:46:26 2025)

Major Updates

• Ukrainian Deep Strike Operations - "Web" Operation (New Details from Zelenskyy):
  • Zelenskyy Reveals Scope and Intent: President Zelenskyy provided significant new details on "Operation Web," stating that 117 drones were used, operated by personnel across three time zones, and that the "office" for the operation was located "on the territory of Russia, directly next to the Russian FSB administration in one of their regions." He further claimed that 34% of Russia's strategic cruise missile carriers on airfields have been hit. This underscores the audacity, planning, and successful execution of the deep strike campaign. (Zelenskiy / Official, РБК-Україна, STERNENKO, ЦАПЛІЄНКО_UKRAINE FIGHTS, Оперативний ЗСУ, ASTRA)
  • Preemptive Strike Claim: Zelenskyy also stated that Ukraine had intelligence about Russia's preparation for "another massive strike" before launching "Operation Web," framing the deep strikes as a preemptive defensive measure. (РБК-Україна)
  • Russian Internal Discontent Amplified: Russian milblogger Alex Parker Returns expresses profound frustration and anger, explicitly questioning accountability within the Russian leadership for the "disgrace" of the airfield attacks and alleging systemic "irresponsibility" and "betrayal." This further deepens the observed internal Russian disillusionment. (Alex Parker Returns)
  • Russian Spin on Aircraft Vulnerability: Alex Parker Returns attempts to rationalize the vulnerability of strategic aircraft on open airfields by citing the 2010 START-3 treaty, claiming aircraft are displayed openly for inspection and transparency. This indicates an emerging Russian narrative attempting to deflect blame from internal security failures. (Alex Parker Returns)
  • US Knowledge of Attack Denied: CBS (reported by TASS) claims the US administration was not aware of Ukraine's preparations for the airfield attack, contradicting earlier Ukrainian reports that the Trump administration was pre-notified. This divergence requires further verification. (ТАСС)
• Renewed Dialogue between Ukraine and Russia: Russian Statements Pending:
  • Medinsky Confirms Tomorrow's Statements: Russia's chief negotiator, Vladimir Medinsky, confirmed upon arrival in Istanbul that "detailed statements" on Russia's position regarding Ukraine would be made tomorrow. This confirms Russia's intent to use the platform for a public declaration. (ТАСС, Alex Parker Returns, Colonelcassad)
  • Russian Maximalist Sentiment: Russian milblogger "Два майора" expressed a provocative sentiment, wishing for "something terrible and loud" to hit the Ukrainian government quarter in Kyiv at the moment negotiations begin in Istanbul. This reflects extremist views within Russia that reject diplomacy and advocate for continued escalation. (Два майора)
• Air Raid Sirens: Continued Ballistic Threat from Kursk and New Drone Threat in Russia:
  • Kyiv and Sumy regions are under continued ballistic missile threat from Kursk Oblast, with warnings extending to Poltava region (specifically Hrebinka). (КМВА, Повітряні Сили ЗС України, Оперативний ЗСУ, STERNENKO, Николаевский Ванёк)
  • A new UAV threat warning has been issued for Yelets and Yelets district in Russia. (Игорь Артамонов)

Ground Operations and Frontline Dynamics

• Donetsk Oblast: Continued Pressure on Pokrovsk and Drone Activity:
  • Resource Appeal for Pokrovsk Direction: The Ukrainian 4th National Guard Brigade "Rubizh" has appealed for donations of EcoFlow Delta 2 Max charging stations (2 units), inverter generators (2 units), and Starlink 3rd generation (2 units) for forces defending the Pokrovsk direction, indicating critical equipment needs in this active area. (БУТУСОВ ПЛЮС)
  • Drone Strike Footage: "БУТУСОВ ПЛЮС" released video footage of a drone strike on a residential area, showing a damaged house and another structure on fire, indicating continued use of drones in populated areas, likely in frontline zones. (БУТУСОВ ПЛЮС)
  • Konstantinovka Maps: "Z комитет + карта СВО" shared multiple military maps labeled "#Константиновка" (Konstantinovka), providing visual context for ongoing Russian pressure in that direction. (Z комитет + карта СВО)
• Sumy Oblast: Russian Claims of Further Advances:
  • New Territorial Claims: Colonelcassad claims Russian forces are "successfully advancing" in Sumy Oblast, stating "Kondratovka entered the Sumy People's Republic" and Yablonovka is likely next. He also reports ongoing fighting for Yunakovka. This indicates continued Russian efforts to expand territorial control in the region. (Colonelcassad)
  • Russian Drone Strike Footage: "Операция Z" shared video footage claiming Russian marine drone strikes on Ukrainian targets in Sumy Oblast, showing destruction of fortifications, M777, and other equipment. (Операция Z)
  • Sumy Direction Maps: "Z комитет + карта СВО" shared military maps depicting the "Sumy Direction" as of June 1, 2025, with areas marked as "Territory that has come under control of the Russian Armed Forces," visually corroborating Russian claims of advances. (Z комитет + карта СВО)
• Kharkiv Oblast: Training Ground Strike Confirmed by MoD Russia:
  • Russia's MoD released video footage claiming an Iskander missile strike on a "tent camp of the 158th Separate Mechanised Brigade and the 33rd Separate Mechanised Brigade of the AFU at the Novomoskovsk training ground." This aligns with previous Ukrainian confirmations of a strike on a training unit with fatalities. (MoD Russia)
  • Oleg Syniehubov, head of Kharkiv Oblast administration, re-shared Zelenskyy's video, implying solidarity and direct communication regarding the situation. (Олег Синєгубов, голова Харківської ОДА)
• Dnipropetrovsk Oblast: Serhiy Lysak, head of Dnipropetrovsk Oblast administration, re-shared Zelenskyy's video, indicating the impact of the ongoing conflict and possibly the training ground strike on the region. (🇺🇦Сергій Лисак / Дніпропетровська ОДА (ОВА))
• Zaporizhzhia Oblast: The Zaporizhzhia Oblast Military Administration re-shared Zelenskyy's video, underscoring the relevance of central Ukrainian leadership messages to regional administrations. (🇺🇦 Запорізька обласна військова адміністрація 🇺🇦)

Aerial & Naval Activity

• Ukrainian Deep Operations (Expanded Scope and Impact): President Zelenskyy's detailed accounting of 117 drones used across three time zones and the strategic placement of the operation's "office" near an FSB administration office significantly expands the understanding of "Operation Web's" complexity and brazenness. The claim of hitting 34% of strategic cruise missile carriers, if verifiable, represents a substantial strategic blow. The revelation of intelligence indicating a planned Russian massive strike adds a layer of preemptive justification to the operation.
• Russian Air Activity (Persistent Ballistic Threat): The continuing ballistic missile threat from Kursk Oblast towards Kyiv, Sumy, and Poltava confirms an ongoing, immediate aerial threat, directly linked to potential Russian retaliation for Ukrainian deep strikes. The new UAV threat in Yelets, Russia, suggests ongoing cross-border activity or perceived threats.

Strategic Projections

This update significantly deepens the understanding of Ukraine's strategic intent and capability in "Operation Web." President Zelenskyy's detailed disclosure of 117 drones, multi-time zone operations, and the audacious placement of the "office" near FSB headquarters underscores the unprecedented scale and sophistication of Ukraine's deep strike campaign. The claim of hitting 34% of Russia's strategic cruise missile carriers, if validated, represents a critical degradation of Russia's long-range strike capabilities and a substantial shift in the strategic balance. Framing the operation as a preemptive strike against an impending Russian "massive attack" further legitimizes Ukraine's actions on the international stage.

The internal Russian discontent is visibly escalating, with milbloggers directly criticizing the "irresponsibility" of the leadership and the "disgrace" of the airfield attacks. This internal pressure could compel Moscow to demonstrate a more decisive response in the near term, or alternatively, further highlight a lack of unified strategy. The attempt by some Russian sources to rationalize the vulnerability of strategic aircraft via treaty obligations indicates a struggle within Russia to control the narrative and deflect blame from their own security failures.

The imminent start of negotiations in Istanbul, combined with Russia's declared intent to make "detailed statements" on its position, sets the stage for a critical diplomatic moment. However, the provocative sentiment from a Russian milblogger wishing for a missile strike on Kyiv during talks underscores the fragility of this diplomatic track and the deep-seated maximalist views that still influence Russian decision-making.

On the ground, Russia continues its incremental advances in Sumy and Donetsk Oblasts, pushing to solidify its territorial gains and pressure Ukrainian logistics. The confirmed Iskander strike on a Ukrainian training unit in Kharkiv highlights Russia's continued targeting of Ukrainian force generation, a critical vulnerability. The Ukrainian appeal for equipment in Pokrovsk indicates ongoing heavy fighting and a need for sustained support for frontline units.

Overall, the conflict is characterized by Ukraine's escalating and highly effective deep strike capabilities forcing Russia onto the defensive strategically, while Russia simultaneously pursues ground attrition tactics and seeks to inflict punishment through mass aerial attacks. The diplomatic discussions will unfold against this backdrop of intense military pressure and internal Russian turmoil.

Risk Assessment

• Intensified Russian Retaliation (Extreme): Zelenskyy's detailed revelations about "Operation Web" (117 drones, 34% hit on carriers, FSB proximity) significantly increase the likelihood of extreme Russian retaliation. The ongoing ballistic threat from Kursk is an immediate manifestation.
• Escalated Information Warfare (High): Russia will likely intensify its "terrorism" narrative and attempts to discredit Ukraine, while trying to manage internal discontent. The differing reports on US notification of the attack also highlight the contested information space.
• Continued Civilian and Military Casualties (High): Persistent ballistic threats, drone strikes on residential areas, and direct targeting of Ukrainian training units confirm an ongoing high risk of casualties.
• Ukrainian Logistics and Force Generation Pressure (High): Continued Russian ground advances and targeting of training facilities pose a significant threat to Ukraine's ability to sustain operations and generate new forces. The equipment appeal from Pokrovsk further highlights this.
• Internal Russian Instability (Medium): The public criticisms from milbloggers regarding Russian leadership's "irresponsibility" could indicate growing internal fractures or discontent, which, while potentially destabilizing for Russia, could also lead to unpredictable or harsher actions.
• Diplomatic Stalemate (High): The maximalist rhetoric from some Russian figures and the potential for Russia to use the Istanbul talks for propaganda rather than substantive negotiation suggest a high risk of diplomatic deadlock.

Resource Allocation Considerations

• Prioritize Advanced Air Defense Systems: Immediately deploy and integrate all available air defense assets, particularly for Kyiv, Sumy, Poltava, and other regions under ballistic threat. Expedite requests for Western air defense and munitions.
• Secure Training and Force Generation Facilities: Enhance physical and aerial defense for all Ukrainian military training grounds and troop concentration areas. Implement dynamic dispersal and concealment strategies.
• Sustain and Evolve Deep Strike Capabilities: Continue to invest in and innovate drone technology, launch methods, and operational security for deep strike missions. Focus on intelligence-led targeting of critical Russian military infrastructure.
• Strategic Communications on Deep Strikes: Proactively communicate the military legitimacy and strategic necessity of "Operation Web," emphasizing its role in countering Russian aggression and protecting Ukrainian civilians. Counter Russian "terrorism" narratives with verified evidence of Russian war crimes.
• Support Frontline Units in High-Pressure Zones: Prioritize rapid fulfillment of equipment requests (e.g., charging stations, Starlinks) for units in active combat zones like Pokrovsk.
• Monitor and Exploit Russian Internal Dynamics: Continue to analyze Russian milblogger sentiment and internal critiques for potential opportunities in information warfare or to anticipate shifts in Russian strategy.
• Strategic Approach to Istanbul Negotiations: Maintain a principled, realistic stance in Istanbul, prepared for Russian attempts to use the platform for propaganda. Leverage recent military successes to strengthen the negotiating position.
• Enhance Civilian Preparedness: Reinforce public awareness of air raid alerts and expand evacuation support where needed, especially in newly threatened areas.