KYIV — The cluttered car carrying a mother and her 12-year-old daughter seemed barely worth the attention of Russian security officials as it approached a border checkpoint. But the least conspicuous piece of luggage — a crate for a cat — was part of an elaborate, lethal plot. Ukrainian operatives had installed a hidden compartment in the pet carrier, according to security officials with knowledge of the operation, and used it to conceal components of a bomb.

Four weeks later, the device detonated just outside Moscow in an SUV being driven by the daughter of a Russian nationalist who had urged his country to “kill, kill, kill” Ukrainians, an explosion signaling that the heart of Russia would not be spared the carnage of war.

The operation was orchestrated by Ukraine’s domestic security service, the SBU, according to officials who provided details, including the use of the pet crate, that have not been previously disclosed. The August 2022 attack is part of a raging shadow war in which Ukraine’s spy services have also twice bombed the bridge connecting Russia to occupied Crimea, piloted drones into the roof of the Kremlin and blown holes in the hulls of Russian naval vessels in the Black Sea.

These operations have been cast as extreme measures Ukraine was forced to adopt in response to Russia’s invasion last year. In reality, they represent capabilities that Ukraine’s spy agencies have developed over nearly a decade — since Russia first seized Ukrainian territory in 2014 — a period during which the services also forged deep new bonds with the CIA.

The missions have involved elite teams of Ukrainian operatives drawn from directorates that were formed, trained and equipped in close partnership with the CIA, according to current and former Ukrainian and U.S. officials. Since 2015, the CIA has spent tens of millions of dollars to transform Ukraine’s Soviet-formed services into potent allies against Moscow, officials said.

The agency has provided Ukraine with advanced surveillance systems, trained recruits at sites in Ukraine as well as the United States, built new headquarters for departments in Ukraine’s military intelligence agency, and shared intelligence on a scale that would have been unimaginable before Russia illegally annexed Crimea and fomented a separatist war in eastern Ukraine. The CIA maintains a significant presence in Kyiv, officials said.

The extent of the CIA’s involvement with Ukraine’s security services has not previously been disclosed. U.S. intelligence officials stressed that the agency has had no involvement in targeted killing operations by Ukrainian agencies, and that its work has focused on bolstering those services’ abilities to gather intelligence on a dangerous adversary. A senior intelligence official said that “any potential operational concerns have been conveyed clearly to the Ukrainian services.”

Many of Ukraine’s clandestine operations have had clear military objectives and contributed to the country’s defense. The car bombing that killed Daria Dugina, however, underscored Ukraine’s embrace of what officials in Kyiv refer to as “liquidations” as a weapon of war.

Over the past 20 months, the SBU and its military counterpart, the GUR, have carried out dozens of assassinations against Russian officials in occupied territories, alleged Ukrainian collaborators, military officers behind the front lines and prominent war supporters deep inside Russia. Those killed include a former Russian submarine commander jogging in a park in the southern Russian city of Krasnodar and a militant blogger at a cafe in St. Petersburg, according to Ukrainian and Western officials.

Ukraine’s affinity for lethal operations has complicated its collaboration with the CIA, raising concerns about agency complicity and creating unease among some officials in Kyiv and Washington.

Even those who see such lethal missions as defensible in wartime question the utility of certain strikes and decisions that led to the targeting of civilians including Dugina or her father, Alexander Dugin — who officials acknowledge was the intended mark — rather than Russians more directly linked to the war.

“We have too many enemies who are more important to neutralize,” said a high-ranking Ukraine security official. “People who launch missiles. People who committed atrocities in Bucha.” Killing the daughter of a pro-war firebrand is “very cynical,” the official said.

Others cited broader concerns about Ukraine’s cutthroat tactics that may seem justified now — especially against a country accused of widespread war atrocities — but could later prove difficult to rein in.

“We are seeing the birth of a set of intelligence services that are like Mossad in the 1970s,” said a former senior CIA official, referring to the Israeli spy service long accused of carrying out assassinations in other countries. Ukraine’s proficiency at such operations “has risks for Russia,” the official said, “but it carries broader risks as well.”

“If Ukraine’s intelligence operations become even bolder — targeting Russians in third countries, for example — you could imagine how that might cause rifts with partners and come into serious tension with Ukraine’s broader strategic goals,” the official said. Among those goals is membership in NATO and the European Union.

This article is based on interviews with more than two dozen current and former Ukrainian, U.S. and Western intelligence and security officials who spoke on the condition of anonymity citing security concerns as well as the sensitivity of the subject. The pressure on Kyiv to score victories against Russia and find ways to deter further aggression create incentives to exaggerate the record and capabilities of Ukraine’s services. The Post vetted key details with multiple sources including Western officials with access to independent streams of intelligence.

The CIA declined to comment.

CIA-Ukraine partnership

SBU and GUR officials describe their expanding operational roles as the result of extraordinary circumstances.

“All targets hit by the SBU are completely legal,” the agency’s director, Vasyl Malyuk, said in a statement provided to The Post. The statement did not specifically address targeted killings but Malyuk, who met with top CIA and other U.S. officials in Washington last month, said Ukraine “does everything to ensure that fair punishment will ‘catch up’ with all traitors, war criminals and collaborators.”

Current and former U.S. and Ukrainian officials said both sides have sought to maintain a careful distance between the CIA and the lethal operations carried out by its partners in Kyiv. CIA officials have voiced objections after some operations, officials said, but the agency has not withdrawn support.

“We never involved our international partners in covert operations, especially behind the front lines,” a former senior Ukrainian security official said. SBU and GUR operatives were not accompanied by CIA counterparts. Ukraine avoided using weapons or equipment that could be traced to U.S. sources, and even covert funding streams were segregated.

“We had a lot of restrictions about working with the Ukrainians operationally,” said a former U.S. intelligence official. The emphasis was “more on secure communications and tradecraft,” and pursuing new streams of intelligence inside Russia “rather than ‘here’s how you blow up a mayor.’ I never got the sense that we were that involved in designing their ops.”

Even so, officials acknowledged that boundaries were occasionally blurred. CIA officers in Kyiv were made aware of some of Ukraine’s more ambitious plans for strikes. In some cases, including the bombing of the Kerch Bridge, U.S. officials registered concerns.

Ukraine’s spies developed their own lines about which operations to discuss and which to keep under wraps. “There were some things that maybe we wouldn’t talk about” with CIA counterparts, said a second Ukraine security official involved in such missions. He said crossing those boundaries would lead to a terse reply from Americans: “We don’t want any part of that.”

The CIA’s deep partnership with Ukraine, which persisted even when the country became embroiled in the impeachment scandal surrounding President Donald Trump, represents a dramatic turn for agencies that spent decades on opposing sides of the Cold War. In part because of that legacy, officials said, it was only last year that the CIA removed Ukraine from the agency’s “non-fraternization” list of countries regarded as such security risks that contact with their nationals for agency employees is forbidden without advance permission.

The CIA-Ukraine collaboration took root in the aftermath of 2014 political protests that prompted Ukraine’s pro-Russian President Viktor Yanukovych to flee the country, followed by Russia’s annexation of Crimea and its arming of separatists in the eastern regions of Donetsk and Luhansk.

The initial phases of cooperation were tentative, officials said, given concerns on both sides that Ukraine’s services were still heavily penetrated by the FSB — the Russian agency that is the main successor to the KGB. To manage that security risk, the CIA worked with the SBU to create an entirely new directorate, officials said, one that would focus on so-called “active measures” operations against Russia and be insulated from other SBU departments.

The new unit was prosaically dubbed the “Fifth Directorate” to distinguish it from the four long-standing units of the SBU. A sixth directorate has since been added, officials said, to work with Britain’s MI6 spy agency.

Training sites were located outside Kyiv where handpicked recruits were instructed by CIA personnel, officials said. The plan was to form units “capable of operating behind front lines and working as covert groups,” said a Ukrainian official involved in the effort.

The agency provided secure communications gear, eavesdropping equipment that allowed Ukraine to intercept Russian phone calls and emails, and even furnished disguises and separatist uniforms enabling operatives to more easily slip into occupied towns.

The early missions focused on recruiting informants among Russia’s proxy forces as well as cyber and electronic eavesdropping measures, officials said. The SBU also began mounting sabotage operations and missions to capture separatist leaders and Ukrainian collaborators, some of whom were taken to secret detention sites.

But the operations soon took a lethal turn. Over one three-year stretch, at least half a dozen Russian operatives, high-ranking separatist commanders or collaborators were killed in violence that was often attributed to internal score-settling but in reality was the work of the SBU, Ukraine officials said.

Among those killed was Yevgeny Zhilin, the leader of a pro-Russian militant group in eastern Ukraine, who was gunned down in 2016 in a Moscow restaurant. A year later, a rebel commander known as “Givi” was killed in Donetsk as part of an operation in which a woman who accused him of rape was enlisted to plant a bomb at his side, according to a former official involved in the mission.

Ukrainian officials said the country’s turn to more lethal methods was driven by Russian aggression, atrocities attributed to its proxies and desperation to find ways to weaken a more powerful adversary. Many also cited Russia’s own alleged history of conducting assassinations in Kyiv.

“Because of this hybrid war we faced an absolutely new reality,” said Valentyn Nalyvaichenko, a member of Ukraine’s parliament who served as SBU director in 2015, when the Fifth Directorate was created. “We were forced to train our people in a different way.”

He declined to elaborate.

Transforming Ukrainian military intelligence

Even while helping to build the SBU’s new directorate, the CIA embarked on a far more ambitious project with Ukraine’s military intelligence service.

With fewer than 5,000 employees, the GUR was a fraction of the size of the SBU and had a narrower focus on espionage and active measures operations against Russia. It also had a younger workforce with fewer holdovers from Soviet times, while the SBU was still perceived as penetrated by Russian intelligence.

“We calculated that GUR was a smaller and more nimble organization where we could have more impact,” said a former U.S. intelligence official who worked in Ukraine. “GUR was our little baby. We gave them all new equipment and training.” GUR officers “were young guys not Soviet-era KGB generals,” the official said, “while the SBU was too big to reform.”

Even recent developments have seemed to validate such concerns. Former SBU director Ivan Bakanov was forced out of the job last year amid criticism that the agency wasn’t moving aggressively enough against internal traitors. The SBU also discovered last year that Russian-made modems were still being used in the agency’s networks, prompting a scramble to unplug them.

From 2015 on, the CIA embarked on such an extensive transformation of the GUR that within several years “we had kind of rebuilt it from scratch,” the former U.S. intelligence official said. One of the main architects of the effort, who served as CIA station chief in Kyiv, now runs the Ukraine Task Force at CIA headquarters.

The GUR began recruiting operatives for its own new active measures department, officials said. At sites in Ukraine and, later, the United States, GUR operatives were trained on skills ranging from clandestine maneuvers behind enemy lines to weapons platforms and explosives. U.S. officials said the training was aimed at helping Ukrainian operatives protect themselves in dangerous Russian-controlled environments rather than inflicting harm on Russian targets.

Some of the GUR’s newest recruits were transfers from the SBU, officials said, drawn to a rival service flush with new authorities and resources. Among them was Vasyl Burba, who had managed SBU Fifth Directorate operations before joining the GUR and serving as agency director from 2016 to 2020. Burba became such a close ally of the CIA — and perceived Moscow target — that when he was forced from his job after President Volodymyr Zelenskyy’s election the agency provided him an armored vehicle, officials said. Burba declined to comment for this article.

The CIA helped the GUR acquire state-of-the-art surveillance and electronic eavesdropping systems, officials said. They included mobile equipment that could be placed along Russian-controlled lines in eastern Ukraine, but also software tools used to exploit the cellphones of Kremlin officials visiting occupied territory from Moscow. Ukrainian officers operated the systems, officials said, but everything gleaned was shared with the Americans.

Concerned that the GUR’s aging facilities were likely compromised by Russian intelligence, the CIA paid for new headquarters buildings for the GUR’s “spetsnaz” paramilitary division and a separate directorate responsible for electronic espionage.

The new capabilities were transformative, officials said.

“In one day we could intercept 250,000 to 300,000 separate communications” from Russian military and FSB units, said a former senior GUR official. “There was so much information that we couldn’t manage it ourselves.”

Troves of data were relayed through the new CIA-built facility back to Washington, where they were scrutinized by CIA and NSA analysts, officials said.

“We were giving them the ability — through us — to collect on” Russian targets, the former GUR official said. Asked about the magnitude of the CIA investments, the official said: “It was millions of dollars.”

In time, the GUR had also developed networks of sources in Russia’s security apparatus, including the FSB unit responsible for operations in Ukraine. In a measure of U.S.-Ukraine trust, officials said, the CIA was permitted to have direct contact with agents recruited and run by Ukrainian intelligence.

The resulting intelligence windfall was largely hidden from public view, with intermittent exceptions. The SBU began posting incriminating or embarrassing communications intercepts, including one in which Russian commanders were captured discussing their country’s culpability in the 2014 shoot-down of a Malaysian Airlines passenger jet.

Even so, officials said the intelligence obtained through the U.S.-Ukraine cooperation had its limits. The Biden administration’s prescient warnings about Russian President Vladimir Putin’s determination to topple the Kyiv government, for example, were based primarily on separate streams of intelligence Ukraine wasn’t privy to initially.

In some ways, officials said, Ukraine’s own collection efforts fed the skepticism that Zelenskyy and others had about Putin’s plans because they were eavesdropping on military and FSB units that themselves were not informed until the eve of the war. “They were getting an accurate picture from people who were also in the dark,” one U.S. official said. Targeting Moscow with drones

Russian forces never succeeded in taking Kyiv. But both GUR structures that the CIA funded were among dozens of key installations targeted in Russian strikes in the war’s first days, according to officials who said the facilities survived and continue to function.

Ukraine’s new intelligence capabilities proved valuable from the start of the war. The SBU, for example, obtained intelligence on high-value Russian targets, enabling strikes that killed several commanders and narrowly missed Russia’s top-ranked officer, Valery Gerasimov.

Over the past year, the security services’ missions have increasingly centered on targets not only behind enemy lines but well into Russia.

For the SBU, no target has been a higher priority than the Kerch Bridge that connects the Russian mainland to the annexed Crimean Peninsula. The bridge is a key military corridor and also carries such symbolic significance to Putin that he presided over its inauguration in 2018.

The SBU has hit the bridge twice over the past year, including an October 2022 bombing that killed five people and put a gaping hole in westbound traffic lanes.

Zelenskyy initially denied Ukrainian responsibility. But SBU director Malyuk described the operation in extraordinary detail in an interview earlier this year, acknowledging that his service had placed a powerful explosive inside a truck hauling industrial-size rolls of cellophane.

Like other SBU plots, the operation involved unwitting accomplices, including the truck driver killed in the explosion. “We went through seven circles of hell keeping so many people in the dark,” Malyuk said in an interview about the operation, which he said hinged on the susceptibility of “ordinary Russian smugglers.”

U.S. officials who had been notified in advance raised concerns about the attack, officials said, fearing Russian escalation. Those misgivings had presumably dissipated by the time the SBU launched a second strike on the bridge nine months later using naval drones that were developed as part of a top secret operation involving the CIA and other Western intelligence services.

Malyuk’s highly public account of the operation defies typical intelligence tradecraft but serves Kyiv’s need to claim successes and reflects an emerging rivalry with the GUR. Kyrylo Budanov, Ukraine’s military intelligence chief, has made a habit of touting his agency’s achievements and taunting Moscow.

The two services overlap operationally to some degree, though officials said the SBU tends to pursue more complex missions with longer lead-times while the GUR tends to work at a faster tempo. Ukraine officials denied that either agency was directly involved in the September 2022 attack on the Nord Stream 2 pipeline in the Baltic Sea, though U.S. and other Western intelligence agencies have concluded that Ukraine was linked to the plot.

The GUR has used its own fleet of drones to launch dozens of attacks on Russian soil, including strikes that have penetrated Russian air defenses to hit buildings in Moscow. Among them was a May 2023 operation that briefly set fire to a section of roof in the Kremlin.

Those strikes have involved both long-range drones launched from Ukrainian territory, as well as teams of operatives and partisans working inside Russia, officials said. Motors for some drones were purchased from Chinese suppliers with private funding that couldn’t be traced to Ukrainian sources, according to an official who said he was involved in the transactions.

Assassinations in Russia

GUR has also ventured into assassinations, officials said.

In July, a former Russian submarine commander, Stanislav Rzhitsky, was shot four times in the chest and back in Krasnodar where he reportedly worked as a military recruiting officer. Rzhitsky, 42, was known to use the fitness app Strava to record his daily running routes, a practice that may have exposed his location.

The GUR issued a coy statement deflecting responsibility but citing precise details about the circumstances of Rzhitsky’s death, noting that “due to heavy rain the park was deserted” and there were no witnesses. Officials in Kyiv confirmed the GUR was responsible.

Even while acknowledging responsibility for such actions, Ukrainian officials claim the moral high ground against Russia. The SBU and GUR have sought to avoid harm to innocent bystanders even in lethal operations, officials said, while Russia’s scorched-earth raids and indiscriminate strikes have killed or injured thousands of civilians.

Security officials said that no major operation by the SBU or GUR proceeds without clearance — tacit or otherwise — from Zelenskyy. A spokesperson for Zelenskyy did not respond to requests for comment.

Skeptics nevertheless worry Ukraine’s use of targeted killings and drone strikes on Moscow high-rises help neither its cause against Russia nor its longer-term aspirations to join NATO and the E.U.

A senior Ukrainian official who worked closely with Western governments coordinating support for Ukraine said that attacks on noncombatants and bombings of Moscow buildings feed Putin’s false narrative that Ukraine posed a growing danger to ordinary Russians. “It plays into his lies that Ukrainians are coming for them,” the official said.

That view appears to be in the minority. Others see the attacks as boosting morale among besieged Ukrainians and achieving a degree of vigilante accountability for alleged Russian war crimes that many Ukrainians are skeptical will ever lead to adequate sanctions from the United Nations and international courts.

The car bombing that killed Dugina last year continues to stand out as one of the more extreme cases of lethal revenge one that not only targeted noncombatants but involved a Ukrainian woman and a presumably unwitting pre-teenage girl.

Russian authorities had barely finished clearing the debris when the FSB identified Natalia Vovk, 42, as the principal suspect. She had entered Russia from Estonia in July, according to the FSB, took an apartment in the same complex as Dugina, and spent weeks conducting surveillance before slipping back into Estonia with her daughter after the explosion occurred.

The FSB also identified an alleged accomplice who Russia alleged had provided Kazakh license plates for Vovk to use on her vehicle, a Mini Cooper, while traveling in Russia; helped assemble the explosive; and fled to Estonia before the attack.

Ukraine authorities said Vovk was motivated in part by Russia’s siege of her home city, Mariupol. They declined to comment on the nature of her relationship to the SBU or her current whereabouts.

The attack was intended to kill Dugin as he and his daughter departed a cultural festival where the pro-war ideologue, sometimes branded as “Putin’s brain,” had delivered a lecture. The two were expected to travel together, but Dugin stepped into a different vehicle. Vovk also attended the festival, according to the FSB.

At the time, Ukraine vigorously denounced involvement in the attack. “Ukraine has absolutely nothing to do with this, because we are not a criminal state like Russia, or a terrorist one at that,” said Mykhailo Podolyak, an adviser to Zelenskyy.

Officials acknowledged in recent interviews in Kyiv, however, that those denials were false. They confirmed that the SBU planned and executed the operation, and said that while Dugin may have been the principal target, his daughter — also a vocal supporter of the invasion — was no innocent victim.

“She is the daughter of the father of Russian propaganda,” a security official said. The car bombing and other operations inside Russia are “about narrative,” showing enemies of Ukraine that “punishment is imminent even for those who think they are untouchable.”

Shane Harris in Washington and Mary Ilyushina in Riga, Latvia, contributed to this report.

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