At a Glance 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...
At a Glance What Is the Dark Fleet? The dark fleet is a loose but increasingly well-defined group of oil tankers and cargo vessels that engage in deceptive shipping practices to transport sanctioned oil and other restricted commodities. These vessels continue trading globally while deliberately complicating detection, attribution, and enforcement under international maritime regulation. Unlike...
From Brexit, to refugees, to spillovers from the Syrian and Libyan civil wars – there’s plenty to keep Europeans up at night. And these are just the things we can see. What about the stuff we can’t?
The second edition of our European Threat Map reveals some of the anomalies found when applying AI-driven, behavioral analysis to vessels, enabling organizations – such as Frontex and Italy’s Guardia di Finanza – to anticipate threats, and stay ahead of their adversaries.
Amid the drug smuggling, human trafficking and sanctions evasion detected, there are a number of key findings, including:
The Black Sea is significantly riskier than the Mediterranean; there are about three times as many “risky” vessels visiting the Black Sea vs the Med.
Despite EU sanctions on Syria and Crimea, commercial shipping activities continue to take place in the waters around these territories, indicating probable sanction evasions.
In Europe, Guernsey and Romania have the highest proportion of incorporated companies whose vessels display “risky” behavioral patterns.
Over the previous year, 42 vessels displayed patterns of behavior similar to ships caught with drugs on board.
Stay tuned for threat maps for other parts of the world. For now, stay safe!
Download a PDF of the map
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Border Security & Intelligence
Russian Dark Fleet Tankers Seek Shelter Along Turkish Coast from Ukrainian Drone Strikes
At a Glance 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…
What Is the Dark Fleet? How Shadow Tankers Fund Sanctioned Regimes
At a Glance What Is the Dark Fleet? The dark fleet is a loose but increasingly well-defined group of oil tankers and cargo vessels that engage in deceptive shipping practices to transport sanctioned oil and other restricted commodities. These vessels continue trading globally while deliberately complicating detection, attribution, and enforcement under international maritime regulation. Unlike…
The Week in Focus Western Hemisphere: Venezuela Enforcement Escalates A Non-Sanctioned Tanker Is Seized When the U.S. Coast Guard boarded the tanker Centuries (IMO 9206310) in international waters off Venezuela, its AIS signal placed it near Aruba and Curaçao. Windward data confirms the vessel was operating far closer to the Venezuelan coast, a familiar pattern…
Venezuela on Notice: What Comes Next for Dark Fleet Enforcement
At a Glance From Seizure to Sustained Pressure The seizure of the VLCC Skipper off Venezuela was not an isolated enforcement action. It marked the opening move in a broader escalation of pressure against sanctions-evading tanker networks. Within days of the seizure, the United States announced a blockade on sanctioned oil tankers entering and leaving…
Maritime Defense Weekly: Venezuela Blockade, Dark Fleet Under Fire
The Week in Focus Three developments this week carry direct implications for maritime operations worldwide: the U.S. announcing a blockade on sanctioned Venezuelan tankers as Caribbean dark fleet activity surges 95% year-on-year; Ukraine expanding drone strikes against Russia’s sanctions-evasion tankers in the Black Sea; and escalating air-sea confrontations in the East China Sea prompting a…
The Dark Fleet Is No Longer Invisible: What the Venezuela Tanker Seizure Signals
At a Glance From Monitoring to Intervention The dark fleet – tankers engaging in dark activities while moving sanctioned oil, cycling through false flags, and obscuring ownership – has continued to expand, reaching more than 1,900 vessels by the end of Q3. Governments had visibility into this activity. What was less consistent was how that…
Windward Launches WhatsApp Integration for Instant Risk Insights
At a Glance Redefining Vessel Screening for a Real-Time World In global trade and shipping, decisions are rarely made from behind a desk. A call from port control, a sudden request from a counterpart, or a time-sensitive deal can trigger the need for immediate screening. Whether it’s a compliance check to prevent sanctions breaches or...
Navigate 2025’s Maritime Risk Landscape with Maritime AI™ at London International Shipping Week
As the global shipping community gathers for London International Shipping Week (LISW) 2025, one reality stands out: disruption is the operating environment, not the exception. The maritime ecosystem is under sustained pressure, and adapting to this high risk era is now a prerequisite for business continuity. From sanctions and signal interference to fraudulent documents and...
AI-Automated Document Validation: Streamlining Trade Against Real Maritime Activity
Global trade still runs on paper. Bills of Lading, certificates of origin, price attestations, and other documents remain the backbone of maritime trade, yet also its most persistent Achilles’ heel. Forged paperwork fuels fraud, delays compliance, and stalls cargo worth millions. Windward’s new AI-Automated Document Validation changes that, by cross-checking every document against what actually...
From Risk Platform to Collaborative Ecosystem: Reducing Friction in Chartering
By Ami Daniel, Co-Founder & CEO, Windward When we founded Windward.ai in 2010, we were a small startup of engineers and maritime experts using AI to bring order to chaotic oceans. Today, with nearly 300 customers — including governments, shipowners, energy firms, insurers, and traders — our Maritime AI™ platform influences billions in daily trade....
From AI Products to an AI Company: Windward’s Internal Gen AI Journey
By Ami Daniel, Co-Founder & CEO, Windward At Windward, we’ve always believed in staying ahead of the curve. But with Gen AI, the curve isn’t just shifting—it’s exploding. This isn’t just another tech wave. It’s a fundamental rewiring of how we operate, build, and scale. So we made a clear decision: AI isn’t a feature....
