Brad Heath

USA TODAY

The U.S. Justice Department’s demand that Apple help it break into a locked iPhone is the latest in a series of legal disputes with tech companies over users’ privacy that have been going on for more than a decade.

So far, nearly all of those contests ended the same way.

“Historically the judiciary has been very deferential to law enforcement,” University of California, Hastings law professor Ahmed Ghappour said. “And history could be very indicative of how this will play out.”

The latest episode began this week, when a federal magistrate judge in California ordered Apple to help FBI agents break into the locked iPhone used by one of the gunmen in the December massacre in San Bernardino, Syed Rizwan Farook. Apple CEO Tim Cook said the company would fight the order, and Apple has refused to help unlock at least one other locked phone in the past.

For tech companies, such battles have often not gone well.

In 2007, for example, tech giant Yahoo balked at a secret order from the Foreign Intelligence Surveillance Court requiring it to turn over customer records to the National Security Agency. But the company relented when a judge on the surveillance court threatened to impose a fine of $250,000 a day – and double it every week. A federal appeals court upheld the surveillance court’s order.

In 2013, a federal judge held the founder of Lavabit – an email service that had been used by former NSA contractor Edward Snowden – in contempt for not turning over the electronic key the company used to encrypt users’ communications. Lavabit founder Ladar Levison eventually gave the key to the FBI, but did so by printing it out in very small type.

Most such disputes have involved federal agents seeking access to troves of information tech companies now keep about their users – everything from contents of emails to records that can precisely track the location of someone’s cellphone. Its fight with Apple comes with one important difference.

Instead of asking the computer maker to turn over information, a federal magistrate ordered the company to create new software for the FBI that would bypass some security features on newer versions of its iOS operating system. The order also requires Apple to add an electronic signature to the new software so that Farouk’s phone will recognize it.

“The fight here is that the software the government wants does not exist. They’re trying to force engineers to write a special version of iOS, then sign it,” said Christopher Soghoian, the American Civil Liberties Union’s principal technologist. He said such an order raises the prospect that the FBI could ultimately force software makers to push compromised versions of their software directly to users’ phones and computers in a way that would be difficult to detect.

But Apple has also rebuffed efforts to help agents unlock older versions of the iPhone, using tools that it had already created for the job.

Last year in Brooklyn, federal prosecutors asked a magistrate to force Apple to unlock a phone running iOS 7 so that they could use the phone’s contents in a drug case. The company declined, even though in the past it had “repeatedly assisted law enforcement officers in federal criminal cases by extracting data from passcode-locked iPhones pursuant to court orders,” prosecutors said in a court filing.

Apple has argued that complying with the request would be burdensome. A judge has yet to decide whether to force Apple to comply.

Still, Justice Department lawyers told a different federal judge in Brooklyn last year that the government has the ability to crack newer versions of the iPhone on its own. “The lack of a passcode is not fatal to the government’s ability to obtain the records,” Assistant U.S. Attorney Karen Koniuszy wrote in a court filing.

Immigration and Customs Enforcement Special Agent David Bauer testified in September that the government could use a device known as an IP-Box to crack four-digit passcodes while preventing the phone from wiping out its contents.

Bauer said the IP-Box is made “by a single individual” in China. It is not, he said, a traditional law enforcement device. “My best description of it, honestly, would be that it’s a hacking tool,” he said.