Imagine sailing through the Black Sea with millions of dollars of crude oil in your hold, knowing that at any moment a silent, unmanned boat packed with explosives could come racing out of the dark. That’s no longer a hypothetical for the crews operating Russia’s so-called shadow fleet. It’s the new reality.
Just when everyone thought the energy war had settled into a grim but predictable rhythm, Ukraine reminded the world that it still holds some very sharp cards. In the early hours of Wednesday, another tanker – this time the Comoros-flagged Dashan – took a direct hit from a Ukrainian sea drone while heading toward the Russian port of Novorossiysk. Video footage released by Ukrainian sources shows the now-familiar sight: a fast-moving drone slamming into the stern, followed by a massive fireball that lights up the night.
This wasn’t a one-off. It was the third successful strike on a Russian-linked oil carrier in less than two weeks. And the message couldn’t be clearer: Kyiv is willing to take the fight straight to the heart of Moscow’s sanction-dodging oil trade.
A New Kind of Naval Warfare Is Here
For years we watched traditional naval battles fade into history books. Aircraft carriers, submarines, and anti-ship missiles still exist, of course, but the real action in 2025 seems to be happening at the waterline – and it’s being driven by drones that cost a fraction of what a single missile does.
Ukraine’s Security Service (SBU) didn’t even bother hiding their satisfaction. They openly claimed responsibility, calling the Dashan part of Russia’s “shadow fleet” – that murky collection of aging, often anonymously owned vessels that have kept Russian oil flowing to buyers in Asia and elsewhere despite Western sanctions.
“Another enemy oil tanker is out of service. This is systematic work to destroy the economic base that feeds Russian terrorism.”
– Statement attributed to Ukrainian security sources
What Exactly Is the Shadow Fleet?
Think of it as the maritime equivalent of dark-pool trading. After G7 price caps and EU import bans hammered official Russian oil exports, Moscow didn’t just shrug and walk away. Instead, it built an entirely parallel shipping ecosystem.
- Old tankers bought cheaply from Greek or other owners nearing the end of their working life
- Flags of convenience from countries like Comoros, Gabon, or Palau
- Complex ownership structures designed to hide the real beneficiary
- Often minimal or questionable insurance coverage
- Ship-to-ship transfers at sea to obscure cargo origin
By some estimates, this ghost armada now numbers close to 600 vessels – enough to move roughly 1.5 to 2 million barrels per day of Russian crude and products. That’s real money, even at discounted prices.
Why Target Tankers Instead of Refineries?
People keep asking this question, and honestly, it’s a fair one. Ukraine has spent months hammering Russian oil refineries with long-range drones. So why switch to hitting ships?
The answer is pretty straightforward when you look at the numbers. Refineries can be repaired – slowly, expensively, but they come back online. A tanker that takes a direct explosive hit to the engine room or cargo area? That’s usually a total loss. The Kairo, hit late last month, was towed to Bulgaria and immediately written off by surveyors.
Each destroyed or heavily damaged vessel represents not just the $20–40 million hull value but months of lost revenue while owners scramble to find replacements in an already tight shadow market. Multiply that by three (and potentially more) and you start eating seriously into Russia’s oil export capacity.
Insurance Markets Are Freaking Out
Shipping insurance was already a nightmare in the Black Sea. Now it’s turning into a full-blown crisis.
War-risk premiums have spiked again – some reports say daily rates for a single voyage have jumped to six figures. Underwriters are reviewing policies literally every day, and many traditional London-market insurers simply refuse to touch anything heading to Russian ports anymore.
That forces shadow fleet operators into even sketchier insurance arrangements – often state-backed Russian providers or small companies in Dubai or Asia that may not actually pay out when things go wrong. At some point, crews and shipowners start asking themselves whether the payday is worth the risk.
The Other Side of the Coin: Ukrainian Port Seizures
While the world focuses on exploding tankers, Ukraine is also playing offense closer to home. On the same day the Dashan burned, authorities in Odesa detained a cargo ship that had previously loaded grain in Crimea – territory Ukraine still considers illegally occupied.
The vessel flew an African flag and arrived to pick up steel pipes, but Ukrainian security services claim to have evidence it moved almost 7,000 tons of Crimean grain to North Africa back in 2021. The plan appears to be confiscating both ship and cargo.
It’s a reminder that this conflict isn’t just about drones and missiles. It’s also about squeezing every possible revenue stream Moscow relies on.
Where Does This Escalation End?
Russian officials are predictably furious. There’s talk – again – of retaliatory strikes on Ukrainian energy infrastructure as winter approaches. President Putin has made that threat before, and he’s followed through more than once.
But here’s the uncomfortable truth: both sides are now locked into a cycle that’s incredibly hard to break. Ukraine sees these attacks as legitimate self-defense against an economy funding the invasion. Russia sees them as economic terrorism. Neither side has shown much interest in de-escalation when it comes to hitting the other’s wallet.
In my view, the most worrying part isn’t even the immediate damage. It’s the precedent. Sea drones are cheap, effective, and getting better fast. If this becomes the new normal, every coastal state with a grievance suddenly has a playbook for waging low-cost, high-impact economic warfare.
We could be looking at a future where global shipping routes become as contested as airspace – and where the price of everything from gasoline to groceries reflects not just supply and demand, but whoever has the better drone swarm.
For now, the Black Sea remains the testing ground. And the tankers keep burning.
