The Liberal Gun Club Forum

On Dec. 29, 2016, the Obama administration announced that it was giving nearly three dozen Russian diplomats just 72 hours to leave the United States and was seizing two rural East Coast estates owned by the Russian government. As the Russians burned papers and scrambled to pack their bags, the Kremlin protested the treatment of its diplomats, and denied that those compounds — sometimes known as the “dachas” — were anything more than vacation spots for their personnel.

The Obama administration’s public rationale for the expulsions and closures — the harshest U.S. diplomatic reprisals taken against Russia in several decades — was to retaliate for Russian meddling in the 2016 presidential election. But there was another critical, and secret, reason why those locations and diplomats were targeted.

Both compounds, and at least some of the expelled diplomats, played key roles in a brazen Russian counterintelligence operation that stretched from the Bay Area to the heart of the nation’s capital, according to former U.S. officials. The operation, which targeted FBI communications, hampered the bureau’s ability to track Russian spies on U.S. soil at a time of increasing tension with Moscow, forced the FBI and CIA to cease contact with some of their Russian assets, and prompted tighter security procedures at key U.S. national security facilities in the Washington area and elsewhere, according to former U.S. officials. It even raised concerns among some U.S. officials about a Russian mole within the U.S. intelligence community.

“It was a very broad effort to try and penetrate our most sensitive operations,” said a former senior CIA official.

American officials discovered that the Russians had dramatically improved their ability to decrypt certain types of secure communications and had successfully tracked devices used by elite FBI surveillance teams. Officials also feared that the Russians may have devised other ways to monitor U.S. intelligence communications, including hacking into computers not connected to the internet. Senior FBI and CIA officials briefed congressional leaders on these issues as part of a wide-ranging examination on Capitol Hill of U.S. counterintelligence vulnerabilities.

These compromises, the full gravity of which became clear to U.S. officials in 2012, gave Russian spies in American cities including Washington, New York and San Francisco key insights into the location of undercover FBI surveillance teams, and likely the actual substance of FBI communications, according to former officials. They provided the Russians opportunities to potentially shake off FBI surveillance and communicate with sensitive human sources, check on remote recording devices and even gather intelligence on their FBI pursuers, the former officials said.

“When we found out about this, the light bulb went on — that this could be why we haven’t seen [certain types of] activity” from known Russian spies in the United States, said a former senior intelligence official.

The compromise of FBI systems occurred not long after the White House’s 2010 decision to arrest and expose a group of “illegals” – Russian operatives embedded in American society under deep non-official cover – and reflected a resurgence of Russian espionage. Just a few months after the illegals pleaded guilty in July 2010, the FBI opened a new investigation into a group of New York-based undercover Russian intelligence officers. These Russian spies, the FBI discovered, were attempting to recruit a ring of U.S. assets — including Carter Page, an American businessman who would later act as an unpaid foreign policy adviser to Donald Trump’s 2016 presidential campaign.

The breaches also spoke to larger challenges faced by U.S. intelligence agencies in guarding the nation’s secrets, an issue highlighted by recent revelations, first published by CNN, that the CIA was forced to extract a key Russian asset and bring him to the U.S. in 2017. The asset was reportedly critical to the U.S. intelligence community’s conclusion that Russian President Vladimir Putin had personally directed the interference in the 2016 presidential election in support of Donald Trump.

Yahoo spoke about these previously unreported technical breaches and the larger government debates surrounding U.S. policies toward Russia with more than 50 current and former intelligence and national security officials, most of whom requested anonymity to discuss sensitive operations and internal discussions. While the officials expressed a variety of views on what went wrong with U.S.-Russian relations, some said the United States at times neglected to appreciate the espionage challenge from Moscow, and paid a significant price for a failure to prioritize technical threats.

“When I was in office, the counterintelligence business was … focused entirely on its core concern, which is insider threats, and in particular mole hunting,” said Joel Brenner, the head of U.S. counterintelligence and strategy from 2006 to 2009. “This is, in fact, the core risk and it’s right that it should be the focus. But we were neither organized nor resourced to deal with counterintelligence in networks, technical networks, electronic networks.”

The discovery of Russia’s newfound capacity to crack certain types of encryption was particularly unnerving, according to former U.S. officials.

“Anytime you find out that an adversary has these capabilities, it sets off a ripple effect,” said a former senior national security official. “The Russians are able to extract every capability from any given technology. ... They are singularly dangerous in this area.”

The FBI’s discovery of these compromises took place on the heels of what many hoped would be a breakthrough between Washington and Moscow — the Obama administration’s 2009 “reset” initiative, which sought to improve U.S.-Russia relations. Despite what seemed to be some initial progress, the reset soon went awry.

In September 2011, Vladimir Putin announced the launch of his third presidential campaign, only to be confronted during the following months by tens of thousands of protesters accusing him of electoral fraud. Putin, a former intelligence officer, publicly accused then-Secretary of State Hillary Clinton of fomenting the unrest.

It was around this time that Putin’s spies in the United States, operating under diplomatic cover, achieved what a former senior intelligence official called a “stunning” technical breakthrough, demonstrating their relentless focus on the country they’ve long considered their primary adversary.