By Glen E. Howard
Dec 2, 2025
On Friday, November 28, several Ukrainian Sea Baby drones attacked two Russian shadow-fleet tankers, Kairos and Virat, in the Black Sea. Civilian crews from the two tankers were either evacuated or, in some cases, jumped overboard into the Black Sea to escape the burning vessels. Both tankers were en route to the Russian port of Novorossiysk without their energy cargo but are tied to the vast network of Russian shadow fleet tankers operating around the globe, helping Moscow to avoid Western energy sanctions.
While neither of the two vessels struck by Ukrainian drones sank during the attack, the strike is highly symbolic of what marks a new change in Ukrainian strategy aimed at severing a key economic lifeline for Russia that originates from its Black Sea port of Novorossiysk. Ukrainian USVs are now operationally capable of striking any Russian target in the Black Sea. As many as two Ukrainian Sea Baby naval drones, and possibly more, were used to attack the two oil tankers by operating in the form of a USV “Wolf Pack” pairing together to disable the vessels. By doing so, Kyiv has sent a powerful message to Moscow that its shadow fleet tankers are highly vulnerable at sea and at risk of being attacked when not loaded with their precious energy cargo.
Ukraine’s increasingly bold use of Uncrewed Surface Vehicles (USVs) in the Black Sea has opened a new chapter in maritime conflict—one that echoes the unrestricted warfare tactics of World Wars I and II. While those earlier eras saw submarines and naval blockades sever trade routes with near-total disregard for civilian economic traffic, today it is Ukraine’s precision autonomous platforms that are redefining sea denial strategy over who controls the sea—and at what cost.
The Strategic Importance of Novorossiysk
Ukrainian attacks on the two shadow fleet tankers are part of a Ukrainian strategy aimed at crippling the energy export capacity of Novorossiysk, one of Russia’s largest Black Sea ports. More than a naval base—Novorossiysk is the principal oil export hub for the Caspian Pipeline Consortium (CPC), through which 1 percent of the world’s oil supplies move each day (1.5 million barrels of oil per day) is exported to Western energy markets from Kazakhstan’s Tengiz oilfield.
Moscow earns between 30 to 35 percent of the revenue from the $2.5 billion in exports, which provides anywhere between $700-$750 million a year in oil revenue out of a total $2.5 billion earned by the CPC consortium (2024 data). While most of CPC’s oil exports originate from Kazakhstan, Novorossiysk is a vital energy hub in Russia’s energy strategy. Interrupting or threatening the CPC oil flow strikes at the core of Moscow’s oil revenues and undermines Russian power in the Black Sea.
For the past year, the tempo of Ukrainian drone and USV attacks on Russian warships has forced Moscow to relocate the bulk of its Black Sea Fleet (BSF) away from its naval bastion at Sevastopol to the more secure facilities of its secondary naval base at Novorossiysk. Protected by a layer of S400 air defense weaponry, the Kremlin thought until recently that its base was relatively secure. However, the port has become the focus of a combination of Ukrainian aerial and sea attacks that have forced the port to shut down on several occasions, and as recently as last week.
Novorossiysk has become increasingly vulnerable to attack due to Ukrainian advancements in its drone and missile production. In February 2025, Ukrainian drones intentionally targeted and disabled the Kropotkinskaya oil pumping station used to pump oil for the CPC at Novorossiysk. In September, the chief office of the CPC in Novorossiysk was damaged by a Ukrainian drone strike that was clearly designed to send a signal to the operators of CPC. More recently, a Ukrainian sea-drone attack shut down one of the Caspian Pipeline Consortium’s mooring berths near Novorossiysk, halting oil shipments and forcing tankers to load offshore.
Following the attack, Ukraine shifted its targeting strategy and began using its USVs to strike the remote offshore mooring devices known as Vapor Processing Units, or VPU-2s, which were seriously damaged in the attack, prompting an outcry from CPC officials. Two VPU berths are normally used for oil shipments, and a third is used only as a backup in case the other two are damaged. However, the third VPU-3 unit was damaged during a November 12 attack and is still undergoing repairs. Efforts to bring the unit back online reportedly can take up to two months, noted Interfax agency, citing a CPC representative. In short, the recent attacks have crippled the oil loading facilities at Novorossiysk, leaving the Kremlin in a major bind as it works with the CPC to bring its oil loading capabilities back online.
The CPC pipeline system is an international energy project, consisting of Russia, Kazakhstan, and international oil companies, and includes the American oil companies Exxon Mobil and Chevron. Chevron has a 50 percent stake in Kazakhstan’s Tengiz oil field while Exxon Mobil has a 25 percent share. In addition, CPC accounts for 80 percent of Kazakhstan’s oil exports. Hence, any reduction in activity in Novorossiysk causes significant damage to the economic interests of CPC and the government of Kazakhstan. Perhaps more any suspension in CPC exports from Novorossiysk could cause a geopolitical aftershock by forcing Kazakhstan to redirect its oil exports to alternative routes, such as through the South Caucasus via Azerbaijan and the Baku-Tbilisi-Ceyhan pipeline.
In addition to its sea-borne attacks on Novorossiysk, Ukraine has intensified its aerial and missile strikes on the Black Sea port by extending the range of its Neptune long-range missile to 1,000 kilometers. Last week alone, Ukraine reportedly destroyed as many as seven of Moscow’s prized S400s protecting the port of Novorossiysk during an attack. By reducing the array of S400s, Ukraine will find it much easier to attack the port, as Moscow is running short on the number of sophisticated air defense weapons it has to protect its valuable energy infrastructure. Moreover, Moscow’s strategic problems have worsened as Ukraine has ramped up its production lines, producing 40–50 Neptunes and as many as 90 Flamingos each month.
With this surge in missile production, Kyiv is inflicting greater damage on Novorossiysk and the CPC oil terminal. In military terms, Ukraine is now mounting a multi-complex campaign of deep-strike operations against a critical node of Russian infrastructure to cripple oil exports and overwhelm Russian air defenses.
USVs and Unrestricted Warfare
With the recent USV attacks on Friday, Ukraine is demonstrating Moscow is unable to protect its shadow fleet of oil tankers in the Black Sea—directly threatening the transportation infrastructure that underpins Novorossiysk’s export capacity. With the Russian Navy confined to its Black Sea bases due to the Ukrainian USV threat, Moscow will face a difficult choice: it must either deploy its remaining surface ships to escort the shadow-fleet tankers or allow them to sail to Novorossiysk unprotected. The first option would force the Russian navy out of its secure bases, exposing it to attacks by Ukrainian USV “wolfpacks.” The second would allow Ukraine to continue striking empty tankers shuttling between the Bosporus and Novorossiysk, exposing a major strategic vulnerability for the Kremlin as the tankers operating in the Shadow Fleet network become prime targets of attack.
Unlike traditional naval warfare, Ukraine’s naval campaign is utilizing inexpensive, expendable, unmanned systems to hunt large commercial vessels and attack vulnerable port facilities at long range. This inversion of scale—where low-cost drones challenge billion-dollar assets—resembles the historical shift introduced by the submarine in WWI, when cargo ships became targets in a contest of attrition at sea. But there is a crucial difference: Ukraine’s target selection is deliberate and bounded by sanctions regimes. The strikes have so far focused on Russian licensed shadow-fleet tankers, vessels tied to sanctions evasion, or oil infrastructure directly involved in sustaining Russia’s war against Ukraine.
What further compounds Moscow’s problem in the Black Sea is Turkiye’s invoking of the 1936 Montreux Convention under Article 19, which prevents another belligerent state, in this case Russia, from bringing additional naval assets into the Black Sea in wartime, creating, in effect, a closed sea. This effectively prevents Moscow from dispatching additional naval assets to the Black Sea from its bases in the Baltic to offset its naval losses, such as when the Russian heavy cruiser Moskva was sunk by a Ukrainian Neptune missile on April 14, 2022. To date, Ukraine has disabled or destroyed one-third of the Russian Black Sea Fleet since the outbreak of the war.
Ukraine can now add Russia’s fleet of shadow tankers to its disabled list as well. The recent Ukrainian USV attack on the two shadow fleet tankers is taking on the shape of a modern form of unrestricted warfare. Russia’s shadow fleet—opaque ownership, flags of convenience, insurers of dubious legitimacy—operates largely outside of conventional safety norms. Ukraine’s fleet of USVs now appears to be treating the Russian shadow fleet as legitimate prey in a battlespace where combatants and commercial actors are increasingly entangled.
The Black Sea, once controlled overwhelmingly by Moscow, is becoming a free-fire zone for unmanned interdiction, where the hunter is Ukraine, and the hunted is Russia’s shadow fleet, i.e., its wartime oil revenue used to fuel the Kremlin war machine.
If these attacks continue—and if Kyiv targets additional elements of Russia’s maritime economy in the Black Sea—this may herald a new phase of maritime warfare, one defined not by blockades or submarines but by remote, autonomous attrition warfare against the economic arteries of a belligerent state. Whether this becomes truly “unrestricted” will depend on how broadly Ukraine expands its target set and whether Russia retaliates in kind.
For now, the pattern is clear: the Black Sea is witnessing a 21st-century revival of strategies long forgotten since the two world wars—where the sea becomes a domain in which the lifeblood of an adversary’s economy can be struck without warning, where the smallest unmanned craft can reshape the strategic map of the Ukraine war, and where the Black Sea serves as a modern-day battlelab for the study of contemporary warfare.