As the Russian threat grew, U.S. intelligence ties to Ukraine deepened

Intelligence-sharing between U.S. and Ukrainian spy agencies has greatly expanded since Russia's 2014 annexation of Crimea, with the two countries exchanging information obtained from eavesdropping on Russian military activities and cooperating on cybersecurity issues, according to more than half a dozen former U.S. intelligence and national security officials.

U.S. and Ukrainian intelligence have even participated in joint offensive cyber operations against Russian government targets, according to former officials.

CIA officials have also regularly traveled to Ukraine on intelligence exchanges, and Ukrainian intelligence officials have made reciprocal visits to the U.S. to swap information, according to former officials.

The exchanges are just a part of a growing, if informal, intelligence alliance between the U.S. and Ukraine. Yahoo News has previously reported that, since 2015, CIA paramilitaries have run a secret training program for Ukrainian special operations personnel and other Ukrainian intelligence officials at an undisclosed facility in the southern United States.

Although unique in character, in many ways the U.S.-Ukraine intelligence relationship “is about as robust ... as just about anybody else in Europe,” says a former senior CIA official.

American officials have considered the partnership critical enough to at least partially overcome longstanding security concerns within the U.S. intelligence community about Russia’s penetration of Ukraine’s spy services. Historically, CIA personnel have even been forbidden from any social relationships with Ukrainian nationals, and were required to formally report any contact with them, because of fears of pro-Russian elements, according to former officials.

For their part, before 2014, many Ukrainian security officials — aware of the immutable facts of geography, or ideologically pro-Russian, or merely opportunistic in nature — were skeptical of throwing their lot in with the United States.

But Russia’s annexation of Ukrainian territory, its support for separatists in two breakaway provinces, and its repeated saber-rattling on Ukraine’s borders has prompted a tilt toward Washington — hastening the very movement toward the West that Moscow’s actions have ostensibly attempted to forestall.

Now, with U.S. officials increasingly convinced that Russian President Vladimir Putin will order a new military incursion into Ukraine, and more than 100,000 Russian troops massing at that country’s border, the burgeoning U.S.-Ukraine intelligence relationship may be tested like never before.

So far the partnership has paid dividends for both sides. Particularly valuable for the NSA and CIA has been intelligence provided by the Ukrainians — often based on communications intercepts — regarding Russian military activities in eastern Ukraine and western Russia, according to former officials.

The CIA declined to comment. The NSA did not respond to a request for comment.

Because of the war on terror and the so-called pivot to Asia, the NSA’s coverage of Europe had shriveled by 2014, with American spy satellites also tied up in the Middle East, according to former officials. While U.S. agencies scrambled to redirect technical resources to Eastern Europe after Russia’s initial invasion of Ukraine, Ukraine’s own interception capabilities helped fill information gaps, and has remained an important intelligence stream for the U.S. since.

“The latency and granularity of their information was just better than what we had,” said a former NSA official. The Ukrainians have been reportedly adept at collecting Russian tactical battlefield communications, such as from unencrypted Russian military radios.

The NSA’s poor collection capabilities in the region — and need for Ukrainian or other outside intelligence support — was underlined by its lack of good on-the-ground intelligence after Russian-backed forces shot down a Malaysian civilian airliner flying over Ukraine in July 2014, killing all 298 people on board, recalled a former official.

Though the NSA eventually ramped up its spying in Eastern Europe, Ukraine, simply by dint of its location, continues to have a built-in advantage when it comes to technical spying on Russia, according to former officials. “In the end, a lot of it just comes down to proximity and line of sight and the Ukrainians, by virtue of where they are, are a massive SIGINT [signals intelligence] platform for the Russians,” said the former senior CIA official.

The U.S. and Ukraine have also increasingly cooperated on cybersecurity issues. What began as ad hoc sharing by the Ukrainians with the U.S. of samples of Russian malware — including from Russia’s 2015 cyberattack on the Ukrainian power grid and the catastrophic 2017 NotPetya attacks, which paralyzed Ukrainian banks, government agencies and the country’s energy grid before spreading globally — has become more formalized over time, according to former officials. U.S. intelligence officials have also traveled to Ukraine to examine the systems targeted by Russian cyberattacks to learn more about how to protect domestic U.S. critical infrastructure and help the Ukrainians defend themselves against future attacks.

Recently, the Ukrainians passed samples of the WhisperGate malware, which last month was used to destroy data on Ukrainian government websites, to contacts at the military’s U.S. Cyber Command for analysis, according to a former U.S. intelligence official. (Cyber Command did not return a request for comment.)

But cooperation on cyber issues has gone beyond information sharing. Looking to retaliate against the Russians for the 2016 election interference campaign, the CIA began working with the Ukrainians on joint offensive cyber operations to disrupt Russian government targets, according to former U.S. officials.

“The Ukrainians had a good understanding at the tactical level of Russian cyber operations,” says the former intelligence official. “I was surprised by what we were sharing with them, doing with them” on offensive cyber operations, recalled this former official.

Joint U.S.-Ukrainian cyber operations increased under the Trump administration, which devolved decision-making powers for such activities downward from the National Security Council to officials in the CIA and the NSA, according to a former national security official.

Ukraine has also been critical in providing U.S. spy agencies with financial intelligence, which was shared with Treasury Department investigators involved in sanctions designations, according to former officials. (Treasury did not return a request for comment.)

The intelligence that “was most useful was on stuff like financial flows in-country, and Russian or Ukrainian oligarchs who might be in Russia or have ties to the Russian government — there’s a wealth of information they had that otherwise we would have had a much harder time getting access to,” said the former national security official.

U.S. intelligence agencies have looked for ways to reciprocate, albeit carefully. Senior NSA officials directed their subordinates to find intelligence that could be shared with the Ukrainians without revealing sensitive U.S. spying techniques, according to former officials, sometimes with the idea that U.S. capabilities could help confirm prior Ukrainian reporting, bolstering Ukraine’s confidence in its own intelligence streams.

But while beneficial overall to U.S. spy agencies, the information provided by the Ukrainians can be uneven.

Their analysis was often “full of intrigue” and “wasn’t considered very authoritative,” said a former agency official.

Some CIA officials have suspected that the Ukrainians’ analysis or reporting was designed more to persuade U.S. policymakers about particular issues, recalled former agency officials.

How seriously to take the Ukrainians’ reporting has become a subject of debate within the CIA, according to the former senior agency official.

“There has definitely become some apologism for, ‘How dare you criticize or think twice about anything the Ukrainians are telling us,’ which has been frustrating for a lot of analysts,” says the former senior CIA official.

But overall, say former officials, the evolving U.S.-Ukraine intelligence relationship has been mutually advantageous — and even occasionally convivial. On one trip to the U.S., according to a former CIA official, Ukrainian intelligence officials brought a gift for their agency interlocutors: rolls of toilet paper with Putin’s face printed on them, and T-shirts with his face on it with text that read, in Russian, “Putin Is a Dickhead.”