Deputy Attorney General Rod Rosenstein has spent months hinting that the Trump administration will take a harder line against the tech industry’s trend toward unbreakable encryption. | Carlos Osorio/AP Photo Texas killings may aid Rosenstein’s crusade on encryption

The investigation into last weekend’s mass shooting in a Texas church may launch a new round in the decades-old fight between the FBI and Silicon Valley over law enforcement’s access to encrypted data.

And this time, the government player leading the charge will be Deputy Attorney General Rod Rosenstein, who has spent months hinting that the Trump administration will take a harder line against the tech industry’s trend toward unbreakable encryption.


It’s a cause Rosenstein has quietly pursued for years, including two cases in 2014 and 2015 when, as the U.S. attorney in Maryland, he sought to take companies to court to make them unscramble their data, a DOJ official told POLITICO. But higher-ups in President Barack Obama’s Justice Department decided against it, said the official, who isn’t authorized to speak to the news media about the cases.

Now Rosenstein may get another chance as the FBI tries to gain access to the iPhone used by Devin Patrick Kelley, the gunman who killed 26 people Sunday at the First Baptist Church in Sutherland Springs, Texas. So far, encryption on the devices has thwarted their efforts, a U.S. official disclosed this week.

Encryption that blocks law enforcement “costs a great deal of time and money. In some cases, it surely costs lives,” Rosenstein told a breakfast audience Thursday in Maryland, citing the stymied investigation. “That is a very high price to pay.”

Rosenstein is perhaps best known for hiring special prosecutor Robert Mueller to investigate possible collusion between President Donald Trump’s campaign and Russia. Rosenstein also played an instrumental role in Trump’s firing of former FBI Director James Comey — who had previously been the Justice Department’s most outspoken encryption critic. Comey repeatedly warned that the increasingly ubiquitous technology allows terrorists, drug dealers and other wrongdoers to “go dark.”

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Digital security specialists and civil libertarians strongly disagree with Rosenstein and Comey, insisting that guaranteeing law enforcement’s access to people’s secure chats and emails would inherently weaken the protections that keep the world safe from hackers and oppressive regimes.

But Rosenstein believes the government's inability to pry open that digital chatter is hamstringing lawful investigations into terrorism, child pornography and all manner of crime.

“I want our prosecutors to know that, if there’s a case where they believe they have an appropriate need for information, and there is a legal avenue to get it, they should not be reluctant to pursue it,” Rosenstein told POLITICO in an interview last week in his Justice Department office, days before the Texas massacre.

Rosenstein’s remarks followed months of speeches on a topic that has entangled the tech and law enforcement communities for decades — including an inconclusive court battle between the FBI and Apple in 2016. If a similar fight erupts this time, many on both sides of the debate expect Trump and Attorney General Jeff Sessions to be much more aggressive in going after the industry.

So far, there’s no indication that prosecutors will pursue that path in the Texas case— for one thing, the FBI may be able to recover Kelley’s data from a computer or his iCloud backup. But before the shooting, the other Justice Department official told POLITICO that “interest” exists inside DOJ “in exploring the use” of existing laws to force a court battle to set a precedent on the issue. (The official spoke on the condition of anonymity to discuss internal deliberations.)

The Obama administration spent years trying to persuade tech firms to voluntarily redesign their encryption to enable access by law enforcement. But after former government contractor Edward Snowden exposed the massive underbelly of the government’s surveillance apparatus in 2013, the companies rushed to introduce new privacy and security features — both to avoid looking like government stooges and to meet the needs of newly anxious customers.

For some tech products, such as Apple’s iPhone and Facebook’s WhatsApp messaging app, the trend has included encryption that even the companies themselves cannot break.

Tensions between the government and Silicon Valley came to a head in February 2016, when the Justice Department sued Apple over its refusal to help the FBI access the locked iPhone of one of the shooters who killed 14 people in an ISIS-inspired attack in San Bernardino, Calif. The government eventually dropped the case after saying it had found another way to gain access to the phone, and the debate has essentially been at a standstill since then.

But in an October speech at the U.S. Naval Academy, Rosenstein indicated that the Trump administration was tired of waiting for the tech industry’s cooperation.

“The approach taken in the recent past — negotiating with technology companies and hoping that they eventually will assist law enforcement out of a sense of civic duty — is unlikely to work,” he said.

Participants on both sides of the encryption debate took notice.

“It’s basically the gloves coming off,” said Riana Pfefferkorn, a cryptography fellow at Stanford University’s Center for Internet and Society.

“His comments telegraph the concern that is clear across government — that we are not getting the traction,” said Ron Hosko, a former head of the FBI’s Criminal Investigative Division who now leads the Law Enforcement Legal Defense Fund.

Rosenstein and his allies have one thing in their favor: Silicon Valley has lost sway with the public since the Apple-FBI dispute, with Americans becoming increasingly suspicious of the behemoth industry’s priorities and motivations. The companies are struggling to respond to extremists who use their technologies for propaganda and recruitment, as well as the Russian government’s use of social media to spread divisive content before the 2016 election.

“If there was going to be a legislative fix or oversight, this is the time that it would happen,” said Robert Anderson, who headed the FBI’s criminal and cyber branch from 2014 to 2016.

Indeed, Pfefferkorn said she was “somewhat worried about the [government’s] ability to capitalize on that public sentiment.”

Few expected that Rosenstein would become the driving force behind the government’s attempts to get visibility into encrypted chatter. In fact, tech specialists wondered whether the government might become rudderless on the subject after the sudden ouster of Comey, who built a reputation as the government’s top encryption warrior and led the fight with Apple.

But Rosenstein has taken the encryption mantle from Comey — months after writing the scathing rebuke of the former FBI director’s conduct that the White House offered as the official explanation for firing him.

The deputy attorney general has been interested in encryption for years, in part because of several vexing experiences during his 12 years as U.S. attorney in Maryland.

The first case, in 2014, involved a wiretap of “a violent organization” that Rosenstein declined to identify. “Our attorneys realized that they were not capturing all the text communications” because some members of the group used Apple’s encrypted iMessage platform, he said.

The second case, in 2015, involved data stored on a phone. Rosenstein said the phone maker, which he would not name, “was uncooperative with us.”

“My experience in those cases made it clear to me just how serious this issue was for traditional law enforcement,” he told POLITICO. “Increasingly it’s impacting our attorneys in their routine criminal cases.”

Rosenstein supported taking the tech companies to court in both instances, but higher-ups in Washington ruled against it.

“There was hope that we could resolve encryption-related issues amicably with the providers,” said the other DOJ official.

But that hope is eroding, and behind the scenes, officials are considering other possible solutions. In recent months, the National Security Council's cyber team has “convened to form options” for Trump and his team, according to a U.S. official who requested anonymity to discuss internal deliberations. Rosenstein would not comment on discussions among agencies, but he said that “senior officials in the department and the administration recognize that this is a problem.”

And the DOJ’s No. 2 has received backing from Christopher Wray, Trump’s new FBI director, who said last month that encryption prevented federal agents from gaining access to more than 6,900 devices in the first 11 months of the 2017 fiscal year. Sessions has also occasionally referenced encryption. But mostly, it has been Rosenstein making the public case.

The deputy AG said his frequent engagement on the encryption issue was “a conscious decision on my part … because I think it’s one of the most important law enforcement challenges we face.”

His arguments have enraged civil liberties advocates, with many tech experts taking issue with Rosenstein’s characterizations of their community, as well as his technical assertions.

Pfefferkorn accused Rosenstein of essentially calling tech companies “un-American,” a charge he denies.

“It’s not un-American to try to make a profit,” Rosenstein told POLITICO. But “when you see somebody advertising a device … and part of their marketing is, ‘The government can’t get into this,’ you have to think about what it is they’re trying to achieve there.”

On the technical front, Rosenstein has suggested that companies could design strong, warrant-friendly encryption because some already scan emails to generate ads. But Dan Boneh, a Stanford University computer science professor, told POLITICO that Rosenstein’s remarks mischaracterized how email scanning worked, saying it is “not done on encrypted data.”

Rosenstein believes his point stands: “The question is, can you build in enough security so that the ability to comply with the court order doesn’t defeat the encryption? … And I think that there are experts who acknowledge that it can be done.”

