On the morning of October 23, the cargo ship Khoryv sent a distress call 13 nautical miles off Constanța, Romania. Territorial waters end at twelve. Whoever flew the drone that sank her knew where the line was, and chose to stand one mile outside it.
That mile is the story. It is the difference between an attack on a NATO member and an incident in a NATO member's exclusive economic zone. It is the difference between Article 5 and a press release. The London insurance market understood this before most capitals did. When the Joint War Committee extended its Black Sea listed area on September 16, it covered the entire sea except the territorial waters of Bulgaria, Georgia, Romania and Turkey. The underwriters drew the same line the drone operators did. Nobody should find that comforting.
This is what gray zone conflict looks like. Freighters burning off the coasts of two NATO allies, sailors lost in cold water, and attacks clustered around the Sulina Channel, which became the main outlet for Ukrainian grain after Russia hammered Ukraine's own ports. It is war at a time and place of the attacker's choosing, priced just below the point where anyone is obliged to do anything about it.
"The problem is that we cannot prove it"
Bulgaria's prime minister, Rumen Radev, is nobody's idea of a Russia hawk. He told his parliament the logic of the attacks points to Moscow, and then said the quiet part out loud: "The problem is that we cannot prove it."
NATO's response has been built to solve Radev's problem. After the North Atlantic Council met on October 20, the Alliance announced it would send maritime patrol aircraft, radar, drones, intelligence personnel and forensic teams to examine the explosives. A U.S. Navy P-8 Poseidon is already flying the Black Sea. These are sensible deployments. They are also answers to the wrong question.
Play the scenario out. Grant NATO perfect attribution. The forensic teams recover a guidance board with Russian markings. The P-8 tracks a launch back to a known site. The Alliance announces, with high confidence, that the Russian Federation sank the ship. Now make it worse: the next drone hits a tanker alongside the pier at Constanța, the fire spreads, and thousands of civilians are dead.
The Kremlin denies it. Within the hour, Russian state media points at Kyiv, and it doesn't have to work hard to sell the story. Ukraine has been running its own maritime drone campaign since July, so the Black Sea is full of Ukrainian drones, and everyone knows it. A few Western commentators find the denial "plausible enough to warrant caution." Allies invoke Article 4 and consult. Statements are issued. Sanctions, already near their ceiling, are tightened at the margins. Then nothing happens, because every capital in the room is doing the same arithmetic: Russia has nuclear weapons, the Black Sea is not worth a war, and the dead are already dead.
You don't have to imagine that sequence. We ran it on July 17, 2014, when a Buk missile destroyed Malaysia Airlines Flight 17 over eastern Ukraine and killed everyone aboard. A Dutch-led investigation established in 2016 that the launcher had been delivered from Russia, and by 2018 that it came from a Russian army unit. The ICAO Council found Russia responsible in May 2025. The European Court of Human Rights did the same that July. Moscow denied all of it, spent years promoting theories that blamed Ukraine, and in 2022 invaded the country the missile had been fired over. Attribution was as good as attribution gets. The consequence, eleven years later, was an order to enter into good-faith negotiations on reparations.
That is the lesson Moscow took from MH17, and it is the one we refuse to learn. Deniability is not a shield for the attacker. It is a gift to the defender who would rather not act. Russia doesn't need us to believe its denials. It only needs us to want to.
Operational freedom is the target
The point of these strikes isn't the ships. It's the water around them. Every hull that burns off Sulina raises the premium on the next one, pushes a charterer toward a different route, and teaches a shipowner that a NATO coastline offers no protection. The attacker never has to declare a blockade. The market imposes it for him. Freedom of action shrinks by increments, each too small to justify a response, until the defender wakes up to find that the sea he was sure he controlled has a new landlord.
This is how Russia and China will impose costs on the West for the foreseeable future. Not with the decisive battle our doctrine, our budgets, and our military exercises are built around, but with a steady accumulation of incidents chosen for their deniability, timed to our distractions, and calibrated to our fear of escalation. Salami slicing is not a new idea; Beijing has practiced it in the South China Sea for more than a decade. What's new is the drone, which makes the slicing cheap, precise and anonymous.
The Black Sea gray zone is not one-sided, and pretending otherwise hands Moscow its talking points. Ukraine's Operation Molochka, launched in July, claims to have disabled 300 Russian-linked vessels in the Black and Azov Seas. Turkey's foreign minister says both sides are mounting heavy attacks to establish superiority before winter.
The distinction holds. Ukraine is striking the logistics of the country that invaded it, mostly sanctioned tankers serving Russian ports and occupied Crimea. Russia is striking grain ships in the economic zones of two NATO members that are not party to the war, with the apparent aim of making Ukraine's last reliable export route uninsurable. One is a belligerent waging war at sea. The other is exporting that war to the Alliance's doorstep and daring it to notice.
Taiwan won't look like Hellscape
If you want to know what a Taiwan conflict will look like, watch the Black Sea.
In 2024, Adm. Samuel Paparo said he wanted to "turn the Taiwan Strait into an unmanned hellscape" to defeat what he described as Beijing's likely plan: a massive attack with little warning. It's a sound concept, and the CNAS work that fleshed it out this year is serious. Hellscape is built to break an amphibious assault at the water's edge.
Beijing is rehearsing something else. The PLA's Justice Mission 2025 drills in December, run alongside the China Coast Guard, simulated a blockade of Taiwan's main ports and control of the waterways that carry its energy imports. This year the China Coast Guard and Maritime Safety Administration have run what the Jamestown Foundation calls a "quasi-quarantine" east of the island, creating the appearance of administrative control without declaring a blockade. Taiwan has already prosecuted a Chinese captain for severing an undersea cable. Each step is a law enforcement action, an inspection, an accident. None of them is an invasion.
A drone swarm waiting in the Strait for a landing force has nothing to shoot at when the adversary is a coast guard cutter boarding a container ship for a "safety inspection." The first Taiwanese or American drone to fire makes Taipei the aggressor. So Beijing won't cross the Strait. It will tighten the noose: a quarantine, a severed cable, an insurance listing, a shipping line that quietly decides Kaohsiung isn't worth the premium. It will bank on the world's risk aversion. It’s already working. After the May summit in Beijing, Washington paused a record $14 billion arms package for Taiwan, and the President described those sales as a "very good negotiating chip". Taiwan will not be conquered. It will be persuaded, one closed option at a time, that there is nothing left to defend.
You cannot deter gray zone coercion with a capability designed for the war the adversary is careful never to start. The answer has to live in the same band the attacker does: below the threshold of general war, above the threshold of pain. Three steps would help in the Black Sea, and each has a Pacific twin.
Presence that denies, not presence that watches. Turkey, Romania and Bulgaria already run a Mine Countermeasures Task Group whose mandate was widened in July to cover undersea infrastructure. Montreux restricts warships of non-Black Sea states, not the littoral navies. Widen the mandate once more, to counter-drone escort of merchant traffic through allied economic zones, and buy the equipment from the Ukrainians who have kept their own grain corridor open under fire. In the Pacific, the equivalent is a convoy and escort plan for a quarantine, not only a kill chain for an invasion.
Decide the response before the incident. The moment of decision is where risk aversion wins, because it is always easier to wait for one more forensic report. Allies should agree in advance, and say publicly, what a verified strike on shipping in their waters will cost Moscow: a pre-approved tranche of capability released to Ukraine, a pre-agreed number of shadow fleet hulls detained. Attribution should trigger an equivalent consequence, not another discussion. Taipei and Washington need the same menu for a quarantine, written now, while no one is under pressure.
Take the market off the adversary's side. When insurers and charterers do the attacker's work, governments need a sovereign war-risk backstop for vessels trading to allied ports, so the next listed-area extension doesn't function as a blockade by spreadsheet. Taiwan will need that backstop on the first day of a quarantine, not the ninetieth.
None of this is escalation. It is the minimum required to make the gray zone cost something.
The Khoryv went down one mile outside a line we drew. The adversary picked the mile. Next time it will pick the hour, the cargo, the flag and the ocean. The question for the Alliance isn't whether we can prove who did it. It's whether, once we prove it, we will do anything.———
The Cipher Brief is committed to publishing a range of perspectives on national security issues submitted by deeply experienced national security professionals. Opinions expressed are those of the author and do not represent the views or opinions of The Cipher Brief.
Have a perspective to share based on your experience in the national security field? Send it to Editor@thecipherbrief.com for publication consideration.
Read more expert-driven national security insights, perspective and analysis in The Cipher Brief
