The Black Sea has become increasingly treacherous for Russia’s shadow fleet of oil tankers. Following a wave of Ukrainian maritime drone strikes in late November and December, vessels transporting Russian crude have abandoned their traditional direct routes across open water. Instead, they’re taking a dramatically longer path — hugging the coastlines of Georgia and Türkiye, and in some cases entering Turkish territorial waters.

New data from Windward has identified six dark fleet tankers recently observed operating unusually close to Türkiye’s coastline. This finding corroborates earlier reporting by The Insider which documented at least two tankers — Torx and Jumbo — altering their routes after the drone attacks began.

The Vessels Seeking Shelter
Windward Maritime AI™ identified the following tankers exhibiting coastal-hugging behavior near Türkiye:
Vessel IMO Flag Status
BELOMOR 9384435 Russia Last seen near Greece, bound for Port Said
JUMBO 9290335 Sierra Leone Positioned off Turkish coast, “For Orders”
VIREL 9299874 Vanuatu Near Turkish waters, bound for Port Said
TENDUA 9299862 Sierra Leone Near Russian port, “For Orders”
VAYU 1 9290517 Benin Near Russian port, “For Orders”
TORX 9311610 Panama Last seen near Egypt

All six vessels have been flagged as “High” smuggling risk by Windward’s Maritime AI™ platform. Several share connections to shell companies registered in the Seychelles, Mauritius, and the Marshall Islands — jurisdictions commonly used to obscure beneficial ownership in shadow fleet operations.

Why the Route Change Matters
The traditional shipping lane from Novorossiysk to the Bosphorus runs directly across the center of the Black Sea. The new coastal route adds approximately 350 miles (roughly 70% more distance) to each voyage. That’s additional fuel costs, longer transit times, and increased operational complexity for every barrel of Russian crude.

But for shadow fleet operators, the calculus is simple: the open sea has become a hunting ground.

Since late November, Ukrainian naval drones have struck multiple tankers with increasing precision:

November 28: Tankers Kairos and Virat attacked simultaneously off Türkiye’s coast.
November 29: Virat struck again; the vessel later changed its flag to Russian and limped to the port of Tuzla.
December 2: Midvolga 2 attacked approximately 80 nautical miles off the Turkish coast.
December 10: Dashan targeted south of Feodosia while transiting at maximum speed with its transponder switched off.
The Kairos ran aground off Bulgaria after the attack. The Dashan strike was conducted jointly by Ukraine’s Security Service (SBU) and the Ukrainian Navy, demonstrating increasing coordination in maritime operations.

The Turkish Territorial Gambit
By sailing within or near Türkiye’s 12-nautical-mile territorial waters, shadow fleet operators may be calculating that Ukraine will be more hesitant to strike—an attack in Turkish waters could be construed as a violation of Turkish sovereignty.

The Kremlin has already characterized previous attacks as “encroaching on the sovereignty of the Republic of Türkiye.” Turkish authorities, for their part, have stated the incidents pose a “serious threat to navigation, human life, property, and the environmental safety of the region.”

This creates a delicate diplomatic situation. Türkiye has not sanctioned Russia and remains an important transit point for Russian oil exports. Yet the presence of aging, poorly maintained tankers hugging its coastline—vessels with questionable insurance and opaque ownership structures—poses genuine risks to Turkish waters and beaches.

The Bigger Picture
The shadow fleet now comprises over 1,900 vessels globally, according to Windward’s Q3 2025 risk report — an estimated 10% of all tankers worldwide. The EU has sanctioned nearly 600 vessels, with 41 additional designations announced in the most recent tranche.

These vessels share common characteristics: advanced age (most are 15-25 years old), flags of convenience from jurisdictions with minimal oversight, shell company ownership structures, and inadequate or nonexistent insurance. The environmental risks are real, as demonstrated by a December 2024 oil spill in the Black Sea caused by two Russian shadow fleet vessels, the worst such incident in the region this century.

The route changes observed in the Black Sea represent a tactical adaptation, not a strategic solution. Ukrainian drone capabilities continue to improve, and the SBU has signaled it will continue targeting vessels that transport Russian commodities in violation of international sanctions.

For the aging tankers of Russia’s dark fleet, the waters are getting warmer. And not in a good way.
Source: Windward