A Phase of Parallel Negotiation and Pressure in the Russia-Ukraine War: Implications of the Drone Threat to Zelenskyy and the Deep Strike on Novorossiysk

Executive Summary

Russia suspended airstrikes on Kyiv for three days to coincide with the visit of the Witkoff-Kushner special envoy delegation but resumed them immediately after, reaffirming its established pattern of operating separate channels for negotiation and military pressure. To offset its disadvantages in ground warfare, Ukraine is attempting to strengthen its negotiating position by expanding deep strikes into Russian territory, targeting sites such as the Black Sea Fleet base in Novorossiysk and gas facilities in Yamalo-Nenets. The drone threat incident involving President Zelenskyy's plane, which triggered alerts in Romanian and Moldovan airspace and across NATO's warning network, demonstrates that gray-zone risks are spreading beyond Ukraine's borders into the airspace of NATO member states. The phase of parallel negotiation and pressure is assessed as the most likely scenario for the next 3-6 months (55% probability), which would entail a high likelihood of sporadic risks to Black Sea shipping lanes and recurring incidents in European airspace. Businesses and governments need to distinguish between diplomatic announcements and physical indicators in their assessments and establish a framework for weekly reassessments of risks to logistics transiting through Novorossiysk and to assets with European exposure.

I. Situational Analysis

Russia-Ukraine War Situational Analysis: The Drone Threat to Zelenskyy's Plane and the Deep Strike on Novorossiysk

1. Background and Developments

President Putin ordered a three-day suspension of airstrikes on Kyiv, effective midnight on September 5 [4]. This measure was timed to coincide with the visit of the U.S. special envoy delegation of Witkoff and Kushner to Moscow [4]. Kremlin spokesperson Peskov explained that the decision was related to the U.S. delegation's preparatory schedule [4]. Ukraine had also previously announced its corresponding position of refraining from airstrikes during the negotiation period [4].

Prior to that, on September 4, a Russian drone conducted a precision strike on the headquarters of the SBU (Security Service of Ukraine) in central Kyiv [11][14][17]. The drone crashed directly into the building upon detonation, injuring at least 12 people [14][17]. President Zelenskyy described the attack as a "significant escalation" and vowed retaliation [14]. This attack occurred on the same day that President Trump stated at the White House that "Putin has no intention of attacking NATO" [6]. This incident already revealed the Kremlin's pattern of operating separate channels for negotiation and physical pressure.

On August 12, Ukrainian forces struck the Black Sea Fleet base in Novorossiysk, Krasnodar Krai, using rockets, fighter jets, and maritime drones [2]. Four Russian warships were damaged in what is considered Ukraine's most successful operation in the Black Sea [2]. During the same period, Ukraine proposed a mutual cessation of attacks on civilian targets in the Black Sea, but Russia delayed its response and maintained its missile offensive [2].

2. Current Situation

At midnight on September 8, the three-day truce ended [4]. In the early hours of September 9, immediately after the truce expired, Russia resumed drone strikes on Kyiv [1][12]. The attack, which involved jet-propelled drones, killed at least one person and injured 17 [1][12]. Two of the injured were children [12]. Several residential buildings were also damaged [1][12]. The Swiss newspaper Le Temps reported three deaths and 19 injuries, indicating that local tallies were fluctuating [7].

On the same day, September 9, Ukraine struck a gas facility in the Yamalo-Nenets Autonomous Okrug on Russian territory. Located more than 3,000 km from the border, this was recorded as the longest-range deep strike since the start of the war [1]. Simultaneously, the General Staff of the Armed Forces of Ukraine announced that it had again struck the Novorossiysk naval base and an oil terminal with drones [3][15]. The governor of Russia's Krasnodar Krai, Veniamin Kondratyev, stated that the attack killed at least four people (including a child) and injured 29 [9]. Novorossiysk is a key gateway for Russian crude oil and grain exports and has been a recurring target for Ukraine [9].

On September 9, while traveling from Moldova to Oslo to attend the funeral of King Harald V of Norway, President Zelenskyy's plane was nearly shot down by a drone shortly after takeoff [5][13][16]. Norwegian Prime Minister Jonas Gahr Støre disclosed this fact to the broadcaster NRK [16]. Støre did not specify the drone's origin [13]. However, the newspaper Aftenposten reported that the drone was presumed to be a Russian-made Shahed-type and that alerts were issued on the same day in Romanian and Moldovan airspace and across NATO's warning network [16]. The Italian news agency ANSA, citing a source in the Ukrainian presidential office, reported the position that "it was an alert situation issued from Moldova" [8]. Prime Minister Støre commented, "This is the reality we must face" [10].

3. Key Actors and Positions

The Russian Kremlinis maintaining its policy of operating separate channels for negotiation and military pressure [4]. The three-day truce timed with the special envoys' visit was not a comprehensive peace agreement but a localized measure to manage the negotiation period [4]. The resumption of airstrikes almost immediately after the truce ended is seen as having been a planned procedure [4]. Despite Ukraine's strikes on symbolic targets like Novorossiysk and the SBU headquarters, Russia has not altered its pattern of combining conciliatory messages at the negotiating table with military pressure on the ground.

The Ukrainian governmentseeks to maintain military deterrence by continuously demonstrating its deep-strike capabilities. The strike on the Yamalo-Nenets gas facility is highly symbolic, as it targeted a location more than 3,000 km from the border [1]. The repeated strikes on Novorossiysk are an extension of its economic pressure strategy targeting Russia's energy and grain export infrastructure [2][9]. At the same time, President Zelenskyy has leveraged the incident where his plane was nearly targeted to achieve the diplomatic effect of reaffirming the reality of the security threat from Russia to European nations.

The Norwegian government, through Prime Minister Støre, publicized the incident to raise alarm within Europe [16]. By highlighting that the event occurred during a neutral occasion—the funeral of King Harald V—Norway emphasized the message that Russia's gray-zone threats are not confined to specific military fronts.

The U.S. Trump administrationattempted to restart negotiations through the Witkoff-Kushner special envoy delegation [4][6]. However, the reality of the SBU headquarters strike just before the visit and the end of the truce followed by renewed airstrikes immediately after revealed the weak grounds for optimism. President Trump's statement that "Putin has no intention of attacking NATO" was contradicted by the drone attacks occurring at the same time, exposing internal divisions in the White House's messaging on Russia [6].

Moldova, Romania, and NATOare now in a position of re-evaluating their airspace alert systems following the incident with Zelenskyy's plane [16]. Moldovan President Sandu condemned the incident [1]. With even countries that do not border Russia now exposed to drone threats, NATO's ability to mount a unified response is once again being tested.

4. Key Issues

First is the issue of the truce's effectiveness. The three-day suspension of airstrikes on Kyiv was a procedural measure subordinate to the special envoys' schedule [4]. The fact that this truce, announced without any legal or institutional foundation, was immediately reversed upon its expiration undermines the credibility of any similar localized truce proposals in the future.

Second is the spread of gray-zone threats. The incident involving Zelenskyy's plane was reported without the drone's origin being clearly identified [13][16]. This overlaps with recent cases, such as the drone attack on a cargo plane at Germany's Leipzig/Halle Airport and airspace incursions in Estonia and Latvia [6], supporting the evidence that gray-zone pressure from Russia is expanding beyond Ukraine's borders across Europe.

Third is the mutual escalation of deep strikes. Ukraine's strikes on Yamalo-Nenets and Novorossiysk and Russia's renewed airstrikes on Kyiv show that neither side is lowering the level of physical pressure, even during a negotiation phase [1][3][9][12]. This suggests that progress in the negotiation channel should be assessed not by diplomatic announcements like presidential calls or envoy visits, but by physical indicators such as strikes on energy facilities and actual frontline developments [4].

Fourth is the discrepancy in civilian casualty statistics. The death toll from the Kyiv airstrikes has been reported differently by various media outlets, ranging from one to three people [1][7][12]. This indicates the fluidity of on-the-ground tallies and highlights the need to interpret initial reports with an awareness of their inherent uncertainty.

II. In-Depth Analysis

In-Depth Analysis of the Russia-Ukraine War: Structural Sources of Gray-Zone Pressure and the Mechanism for Decoupling Negotiation from the Battlefield

1. Analysis of Root Causes

The immediate trigger for the recent events was the end of the three-day localized truce that lasted from September 5 to 8. However, this truce was never a product of peace negotiations. It was a temporary measure ordered by Putin to coincide with the Moscow visit of the Witkoff-Kushner special envoy delegation [4]. Kremlin spokesperson Peskov described it as a "decision related to the preparation and conduct of the U.S. delegation's visit" [4]. This means it was not a result of progress in negotiations but an ancillary condition for them to proceed. Its legal basis was, in effect, subordinate to the envoys' schedule. The resumption of airstrikes after the delegation departed and the three days had passed was thus more akin to a planned procedure.

A more fundamental cause is that Russia has operated separate channels for negotiation and military pressure from the outset. On September 4, the very day President Trump stated at the White House that "Putin has no intention of attacking NATO," a Russian drone conducted a precision strike on the SBU headquarters in Kyiv [6][14][17]. This shows a high-level diplomatic message and an actual military action moving in opposite directions on the same day. The positive assessments from the Putin-Trump phone call, which occurred almost simultaneously with the resumption of airstrikes on September 9, should be seen as a repetition of this same pattern. From the Kremlin's perspective, diplomatic announcements are a tool for managing relations with the United States, while strikes on the battlefield are a tool for applying tangible pressure on Ukraine. The two channels serve different objectives and do not constrain each other.

Ukraine's expansion of strikes on Novorossiysk and Yamalo-Nenets stems from a separate logic. Facing a significant disadvantage in troops and firepower in ground warfare, Ukraine seeks to balance the military situation by paralyzing Russia's energy export infrastructure and military supply lines from a distance. The successful August 12 strike on the Novorossiysk Black Sea Fleet base, which damaged four Russian warships, demonstrated the effectiveness of this strategy [2]. The September 9 strike on the Yamalo-Nenets gas facility, targeting a location more than 3,000 km from the border, can be read as an attempt by Ukraine to send the message that no part of Russian territory is a safe zone [1].

2. Structural Context

Political Structure: The Kremlin's participation in negotiations is proceeding on a separate track aimed at normalizing relations with the United States. This track is not directly linked to actual progress on the battlefield in Ukraine. The visit of the Witkoff-Kushner delegation, presidential calls, and conciliatory signals sent via Hungary all function as tools to manage hardline public opinion against Russia within the U.S. and to maintain channels for dialogue. On the other hand, Hungary's expulsion of Russian diplomats shows that there is significant distrust of the Kremlin's conciliatory messages within Europe [6]. The gap in threat perception between Germany and the Baltic states on one side, and Romania on the other, is also a factor that structurally delays a unified NATO response [6]. Within this fractured structure, Russia secures room to pursue both negotiation signals and military pressure concurrently.

Economic Structure: Novorossiysk is a key gateway for Russian crude oil and grain exports [9]. The fact that this port is repeatedly targeted exposes the vulnerability of the Russian economy's foreign trade structure, which is overly concentrated on Black Sea routes. During the August attack, two large grain export terminals were also damaged, which has ripple effects not only for Russia but for the entire international grain market that relies on the Black Sea. The strike on the Yamalo-Nenets gas facility suggests a restructuring of the economic security landscape, as it demonstrates that Russia's energy export capacity, even 3,000 km behind the European front, is now within Ukraine's strike range [1].

Security Structure: The incident involving Zelenskyy's plane is the first case since the war began where the Ukrainian head of state's personal safety was directly threatened while traveling outside the country's borders. Although Norwegian Prime Minister Støre did not specify the drone's origin [13], Aftenposten presumed it to be a Russian-made Shahed-type [16]. The fact that alerts were simultaneously triggered in Romanian and Moldovan airspace and across NATO's warning network on the same day [16] shows that this threat is not confined to Ukrainian territory but has a gray-zone character, encroaching upon the airspace of NATO members and neighboring countries. This follows the same pattern as the late August drone incursion into Estonian and Latvian airspace and the drone attack on a cargo plane at Germany's Leipzig/Halle Airport [6]. A structural problem is that while various European countries point to Russia as the perpetrator of such incidents, they have failed to reach a consensus on clear attribution of responsibility or a coordinated response.

3. Historical Precedents and Comparison with Similar Cases

The pattern of a localized truce followed by an immediate resumption of hostilities is consistent with Russia's approach to negotiations since 2022. In past cases, such as the Istanbul negotiations (March-April 2022) and the Black Sea Grain Initiative (July 2022-July 2023), Russia combined flexibility at the negotiating table with sustained pressure on the battlefield. In the case of the grain deal, Russia continued to attack Ukrainian port facilities in Odesa and elsewhere even while the agreement was in effect, and ultimately terminated the deal unilaterally. The recent three-day Kyiv truce was likewise not a formal agreement but a temporary measure ancillary to the envoy visit, meaning its sustainability was low from the start [4].

The recurring nature of the Novorossiysk strikes is also noteworthy. The attacks on August 12 and September 9 occurred just over three weeks apart [2][3][15]. This suggests that these are not one-off symbolic operations but that Ukraine has designated Novorossiysk as a constant target. A similar pattern of repeated strikes has been observed with the Crimean Bridge (October 2022, July 2023) and the Sevastopol Black Sea Fleet base (continuously since 2023). The assessment that Novorossiysk has emerged as the Russian Navy's last major stronghold after Sevastopol was rendered largely non-functional [2] suggests that Ukraine's deep strikes are part of a process that has progressively reduced the operational radius of Russia's Black Sea Fleet.

It is difficult to find a clear precedent for a drone threat against a head of state in transit. However, the May 2023 drone incident over the Kremlin and the repeated incidents since 2024 of debris from Russian drones and missiles falling in the airspace of the Baltic states and Poland show that cross-border unmanned aerial threats had already become commonplace. What is new about the recent incident is that the target of the threat was elevated to a national leader's official aircraft, and that it was widespread enough to simultaneously trigger alerts in Moldovan and Romanian airspace and across NATO's warning network [16].

4. Key Variables Shaping Future Developments

The first variable is whether the U.S.-mediated channel makes tangible progress. The visit by the Witkoff-Kushner delegation and the presidential calls have not yet led to physical results. The future benchmark for assessment will not be joint statements between leaders, but whether trilateral negotiations are actually convened and whether the scope of any truce is expanded [4].

The second variable is whether Ukraine's deep strikes have a tangible impact on Russia's negotiating posture. If the strikes on Novorossiysk and Yamalo-Nenets inflict cumulative damage on Russian energy exports, this could become a pressure point that forces the Kremlin to reconsider its incentives for negotiation. Conversely, if Russia deems the damage tolerable, the deep strikes will likely only lead to a cycle of attritional responses, independent of the negotiation process.

The third variable is the unity of Europe's response to gray-zone threats. The gap in threat perception between Germany and the Baltic states versus Romania, along with internal European distrust surrounding Hungary's stance on Russia [6], are structural factors delaying a common NATO response. If incidents involving the airspace of NATO members, like the one with Zelenskyy's plane, recur, a key point to watch in the coming months will be whether this gap narrows or instead deepens disagreements among member states.

The fourth variable is Russia's internal capacity to sustain the war. Reports that Russian military casualties have surpassed 1.5 million [15] indicate that troop losses are accumulating. Whether this figure has reached a critical threshold that would tangibly affect the Kremlin's negotiating posture will be verifiable through trends in frontline troop movements over the next few months.