Sanctioned, Stateless, and Still Sailing: Expert Insights from the Frontlines of Maritime Sanctions

At a Glance:

• The EU’s 19th sanctions package and the U.S. actions on Rosneft and Lukoil mark a turning point in global energy enforcement.
• False-flag vessels now account for 29% of the dark fleet, with new fraudulent registries emerging from Tonga, Maldives, Mozambique, Angola, Botswana, Zambia, and Gambia.
• Fragmented enforcement between the U.S., EU, and UK is leaving regulatory gaps that enable evasion.
• GPS jamming, spoofing, and weakly flagged vessels are creating rising safety and environmental risks.
• Experts agree: compliance now depends on real-time visibility and proactive intelligence as shipping goes darker.

A Turning Point for Sanctions, Security, and Shipping

In Q4 2025, maritime sanctions enforcement took another leap forward. With the EU’s 19th sanctions package and OFAC’s designation of Rosneft and Lukoil, regulators made it clear that energy flows, not just vessels, are now at the center of enforcement strategies.

While sanctions designations continue to expand, deceptive shipping practices (DSPs) are evolving even faster. Ships are switching flags mid-voyage, masking false port calls as legitimate operations, and hiding behind entities that thrive in regulatory gray zones. Static tools can no longer keep pace with this level of sophistication.

In Windward’s Sanctions on Rosneft & Lukoil and a New Era of Maritime Evasion webinar, leading experts from government, industry, and compliance unpacked what this new era means. 

The discussion brought together Claire Grunewald, Independent Sanctions Consultant and former OFAC officer, Ian Bolton, Founder and CEO of Sanctions SOS, Erik Hånell, President and CEO of Stena Bulk AB, and Michelle Wiese Bockmann, Senior Maritime Intelligence Analyst at Windward.

Each brought a distinct perspective but reached the same conclusion: the industry is entering a period of deep uncertainty where visibility, coordination, and speed of response define resilience.

The New Sanctions Reality

Sanctions enforcement has entered a new phase. The designations of Rosneft and Lukoil, alongside the EU’s 19th package, targeted the lifeblood of Russia’s economy – its energy exports. This time, enforcement is not about isolated vessels but about cutting into the core flows that sustain the country’s export network.

These measures reach far beyond the companies named. Any entity they control is now subject to restrictions, drawing financial institutions, insurers, and traders into deeper compliance exposure. The threat of secondary sanctions has created a chilling effect across global markets, pushing even non-U.S. players to adopt stricter practices to avoid being cut off from international trade.

Price spikes were limited by timing, but disruption is already altering behavior at sea. Legitimate fleets are shrinking as compliant tankers become harder to source, while the gray fleet grows to fill the gap. Freight rates have soared, and operators face a narrowing margin between commercial opportunity and regulatory risk.

Energy markets can adjust to supply shocks. But when sanctions target the arteries of global trade itself, the adjustment is slower, costlier, and far more complex. What began as a policy tool is now redefining how the maritime sector functions day to day.

False Flags, Real Risks

As enforcement intensifies, evasion is evolving in parallel. A growing share of the dark fleet is now sailing under false or fraudulent flags, masking identity and ownership through fabricated or unrecognized registries. What began as a fringe tactic has become a defining feature of maritime deception.

In the past quarter alone, multiple new registries have surfaced within the last month and a half – from Tonga, Maldives, Mozambique, Angola, Botswana, and Zambia – with Gambia entering the top ten for the first time as operators search for jurisdictions willing to look the other way. These stateless or falsely registered ships now represent nearly 29% of the global dark fleet and an even higher 62% of all sanctioned tonnage.

False-flagging obscures sanctions risk and creates a parallel maritime system operating without regulation or liability. Many of these vessels are old, poorly maintained, and uninsured, compounding the safety and environmental threats for every legitimate ship sharing the same routes.

Flag switching, falsified ownership trails, and fabricated certificates now enable sanctioned cargo to move under the appearance of legitimacy. For compliance teams, this evolution renders traditional screening methods insufficient. Without behavioral visibility and vessel-level intelligence, sanctioned cargo can slip through even the most diligent controls.

The Enforcement Gap

Despite a unified message on Russia, enforcement has diverged sharply between jurisdictions. The United States continues to lead with the most restrictive and far-reaching measures, effectively setting the tone for global compliance. Its vessel designations leave little room for interpretation – once listed, a ship is blocked from trade, financing, and insurance.

By contrast, the EU and UK have mirrored Washington’s actions but without the same extraterritorial force. Services to sanctioned vessels are prohibited, and port bans apply, yet enforcement depends on how stringently each member state acts. Some have been swift to implement rules, while others, often large shipowning nations, apply them with less urgency.

This uneven implementation has created space for uncertainty and opportunity. When enforcement varies, compliance becomes a matter of geography, and operators adept at exploiting gaps can continue trading under different flags or jurisdictions. For legitimate players, the result is an uneven playing field and a growing risk of inadvertent exposure.

Fragmented regulation also challenges insurers and financial institutions. With differing definitions, thresholds, and risk appetites across regions, even well-intentioned actors struggle to know which standards apply. Until enforcement becomes consistent, the sanctions framework will remain both a deterrent and an invitation, depending on which side of the compliance line a company operates.

Security Meets Sanctions

The risks surrounding the dark fleet are no longer limited to compliance. As the number of sanctioned and stateless vessels grows, maritime safety and environmental stability are becoming collateral damage.

Many of these ships are old, poorly maintained, and operate under weak or fraudulent flags. With limited oversight and minimal insurance coverage, even minor incidents can escalate into large-scale hazards. Each additional sanctioned vessel increases the probability of accidents and disruption across congested shipping lanes.

As legitimate fleets shrink and shadow fleet activity rises, navigational deception – from GPS jamming to falsified AIS signals – threatens every compliant ship sharing the same routes. Coastal states are stepping up patrols and challenging suspicious tankers, but the operational risk is already systemic.

Security and compliance can no longer be separated. Where weak governance and fraudulent flags intersect, enforcement gaps turn quickly into safety incidents, and every stakeholder, from shipowners to insurers, bears the cost.

Seeing Through the Dark

As deceptive shipping practices expand, visibility has become the defining factor in maritime risk management. Static tools can flag what has already happened. Modern intelligence must reveal what’s happening now, and what’s likely to happen next.

Layered technologies are beginning to illuminate blind spots across global trade. Early detection workflows now combine multiple data sources, from remote sensing and RF tasking to SAR and optical imagery, to identify dark activity in near real time. When an anomaly appears, tasking satellite and radar data can confirm which vessels are operating without transmitting, and optical imagery or object detection completes the operational picture.

This approach is already being applied in high-risk regions such as the Mediterranean and off Malta, where semi-dark ship-to-ship transfers are common. By connecting event detection with context – who the vessels are, where they operate, and who they interact with – organizations can move from awareness to action.

In an environment defined by opacity, layered intelligence is becoming the new compliance standard. Clear visibility is now the difference between reacting to risk and anticipating it.

What 2026 Requires

The next year will demand agility above all else. After a year defined by sanctions expansion, false-flag proliferation, and deepening enforcement divides, 2026 will test how quickly organizations can adapt.

The dark fleet will not disappear overnight, but its composition will evolve. Older vessels will gradually phase out as market and safety pressures mount, creating opportunities for a safer, more transparent fleet. Yet uncertainty will remain a constant. Policy priorities can shift without warning, and every stakeholder, from traders to regulators, will need the flexibility to adjust in real time.

For the maritime community, resilience now depends on two things: speed and clarity. Rapid assessment of emerging sanctions, dynamic screening, and regular risk evaluations will separate those who can navigate change from those caught off guard.

Turning Visibility into Action

The ability to fuse behavioral data, remote sensing, and real-time detections is what turns awareness into action. This approach reflects how Windward’s Maritime AI™ enables organizations to bridge detection and decision, creating shared intelligence, faster responses, and greater operational certainty.

2025 proved how complex the maritime domain has become. The path forward lies in technology that brings clarity to that complexity. Years of volatility have made the industry more adaptable, and with platforms designed to deliver visibility, context, and speed, the maritime ecosystem is better positioned to respond to whatever comes next.

2026 will reward those who can see first, understand fast, and act with confidence.

Watch the full webinar recording to explore these insights in depth.