WASHINGTON, DC – Ukraine’s recent Sea Baby drone strike didn’t just torch two shadow-fleet tankers in the Black Sea. According to seasoned Russia strategist Glen Howard, it signals a shift: Kyiv is no longer simply degrading Russia’s navy – it is targeting the financial infrastructure sustaining Moscow’s war effort.
In an analysis for the Saratoga Foundation, Howard, the foundation’s president, argues last week’s unmanned surface vehicle (USV) attack provides the clearest evidence yet that Kyiv has shifted its maritime campaign from striking Russian warships to directly targeting Moscow’s economic lifelines.
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Those lifelines converge at Novorossiysk, Russia’s crucial Black Sea oil hub and the beating heart of the Kremlin’s sanctions-evading shadow fleet.
Strategic shift at sea
In an interview with Kyiv Post, Howard argued that Ukraine has transitioned from simply containing the Russian Black Sea Fleet to deliberately targeting the commercial infrastructure that supports Russia’s war.
“For the past year, Ukrainian USVs have confined the Russian Black Sea Fleet to its bastion at Sevastopol,” he said, noting that fear of Magura V and Sea Baby drones pushed much of the fleet to Novorossiysk and even into the Sea of Azov.
The result, he added, is overcrowding, a lack of maneuver space, and an increasingly defensive Russian posture.
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Turning Novorossiysk into a bottleneck
Howard said the latest strike is part of a broader, sustained effort to make Novorossiysk unreliable as an export hub for the Caspian Pipeline Consortium (CPC), which moves roughly one percent of global oil.
“This is the beginning of a sustained effort to make Novorossiysk inoperable as an oil export hub,” he said.
He noted that Ukraine has spent the past six months hitting the port and its associated infrastructure: processing sites near Port Kavkaz, CPC offices, and now the offshore Vapor Processing Units (VPUs) that allow tankers to load crude.
Several VPUs, he said, have been rendered inoperable by USV strikes – “a first in naval warfare” – with Moscow scrambling to repair at least one while others remain offline.
Howard emphasized the strategic logic: By disabling offshore loading infrastructure and striking empty tankers en route to Novorossiysk, Ukraine is severing the links that move sanctioned Russian oil from the pier to market. And that forces the Kremlin into a corner.
“Moscow has two choices,” he said: “sit back and watch Ukraine attack its shadow fleet network, or come out of its protective harbors and provide an escort for the tankers – thereby putting the warships at risk of being attacked by the USVs.”
He underscored that Ukraine is avoiding environmental catastrophe by focusing on unloaded tankers; the goal, he said, is to disable vessels at sea and disrupt the illicit trade that keeps them profitable.
How vulnerable is Novorossiysk?
Howard warned that the combined pressure on the port’s air defenses, offshore terminals, and tanker routes is already having a cumulative effect.
“It effectively shuts down the shadow fleet operations in the Black Sea in one stroke,” he said, while also “simultaneously shutting down Novorossiysk as an oil terminal providing one percent of total global oil supplies.”
Like Ukraine’s drone attacks on Russian refineries, these strikes may have temporary physical effects, he said, but they carry significant psychological weight – enough that Russian President Vladimir Putin has already accused Ukraine of “modern-day piracy.”
But the broader implications will depend on how quickly Russia can repair its offshore systems and whether sustained pressure forces geopolitical recalculations. One potential outcome, Howard said, is pushing Kazakhstan to reroute oil via Azerbaijan and the Baku–Tbilisi–Ceyhan pipeline.
The evolution of Ukraine’s “wolfpacks”
Howard told the Kyiv Post that Ukraine’s USV tactics are becoming more sophisticated with every attack. Effective strikes require planning, intelligence cooperation from allies, and favorable sea conditions – a growing challenge as winter sets in.
But he said Kyiv’s confidence is rising, even as Russia withdraws ships to distant ports and shelters more of its fleet behind the Kerch Strait.
The economics of the tactic are irresistible, Howard argued: a $200,000 sea drone disabling a $14 million warship – or, increasingly, a shadow-fleet tanker.
Wolfpacks typically operate in pairs, often aiming to strike rudders to disable a vessel and force it back to port, as seen in last Friday’s attack.
Ukraine’s ability to penetrate Russian port defenses with USVs, he said, demonstrates how quickly both the technology and tactics are evolving.
And as Moscow concentrates its limited defenses around warships, a new vulnerability has emerged: “Who or what is going to protect the tankers loading up with oil offshore?” Howard asked. “The Russians are overstretched. They can’t protect everything and be everywhere, which allows the wolfpacks to pick their prey.”
“It’s why I called my article The Hunter and the Prey,” he emphasized.
New phase of the conflict
Howard’s assessment lands at a moment when Washington and European capitals are debating the long-term sustainability of Ukraine’s defense strategy.
His core argument – that Kyiv is shaping a new maritime battlespace where unmanned systems can disrupt Russia’s war economy – is likely to provoke discussion among policymakers watching for signs of escalation.
Whether the pressure on Novorossiysk becomes decisive, or whether Russia adapts, remains an open question.
But Howard says one reality is already clear: Ukraine, a country with no conventional navy, has turned the Black Sea into a zone where the Kremlin can no longer operate with impunity.
For now, Kyiv’s drones are rewriting the rules of naval power – and forcing Moscow to confront a new kind of maritime war, one in which the hunter and the hunted have traded places.