Starting next week, the nation's top court will see three significant tech cases. Digital era confounds the courts

The Founding Fathers weren’t big on texting.

Courts have long struggled to deal with key questions at the intersection of individual privacy and ever-advancing technology with little guidance from the Constitution or from prior cases – now judges and experts are hoping that’s about to change.


The sense of urgency from the bench was shown recently when the First Circuit Court of Appeals declined to rehear a key privacy case and Chief Judge Sandra Lynch took the unusual step of issuing a statement calling on the Supreme Court to get involved: “Only the Supreme Court can finally resolve these issues, and I hope it will.”

( PHOTOS: Who’s who on the Supreme Court)

Starting next week, the nation’s top court is set to consider whether to take up three key related cases, including the one Lynch encouraged them to take. Here are the big tech issues that could finally get decided:

Cigarette anyone?

Is searching a cellphone like looking in a pack of smokes? That’s the question that some courts are facing, relying on a 40-year-old case for precedent that experts say has been overtaken by modern technology.

Lower courts have been split on the authority of police to search your technology. Currently, court rulings have required warrants to search a cellphone in six states, while they are not required in 20 other states, according to a map put together by Forbes and the Electronic Frontier Foundation.

One of the reasons the courts are divided, experts say, is that an important case on the subject was decided in 1973 and involved drugs found in a pack of cigarettes.

( Also on POLITICO: Supreme Court agrees to hear cases on contraceptive mandate)

“The question becomes, when the Supreme Court was talking about searching a container, it was talking about a cigarette pack. With the amount of information a cellphone can store, is that different from a cigarette pack?” said Hanni Fakhoury, a staff attorney with the Electronic Frontier Foundation.

And the questions only get tougher from there.

“Let’s say,” Fakhoury continued, “that the court says police can search the cellphone incident to an arrest: How far does that extend? …Massachusetts says it extends to a call log. Well what about an app? What if you have Dropbox? Does it extend to stuff stored only on the phone? Does it extend to the cloud?”

One of the cases the Supreme Court will decide soon whether to hear, U.S. v. Cotterman, deals with the border search of a man with a prior sex offense in which child pornography was found on his laptop. While officers are allowed to search individuals and their belongings at the border without a warrant, the suspect challenged whether that extends to files on devices they carry with them.

( Also on POLITICO: SCOTUS to weigh presidential visit protests)

“The present case illustrates this unique aspect of electronic data. … It is as if a search of a person’s suitcase could reveal not only what the bag contained on the current trip, but everything it had ever carried,” wrote 9th Circuit Justice M. Margaret McKeown , who authored the opinion in Cotterman. “With the ubiquity of cloud computing, the government’s reach into private data becomes even more problematic.”

On Dec. 6, the Supreme Court will also announce whether to grant a case, Wurie v. U.S.. involving police searching a suspect’s call logs after an arrest, while another case that could come before the top court, Riley v. California, concerns a suspect’s pictures and videos. The court could hear those two cases together.

What’s your password?

In the age of encryption and passwords, law enforcement officials can obtain a warrant for a hard drive, but they may not be able to access the material on it. So can police compel someone to provide a password or to unlock an account or decrypt a file?

Courts have in some cases ruled that individuals can refuse to provide a password under their Fifth Amendment right not to incriminate themselves. In 2012, the 11th Circuit Court of Appeals said that a suspect could essentially plead the Fifth to avoid providing a password to police, because providing the password would be the same as testifying that the material on the hard drives belonged to him.

( Also on POLITICO: Justices turn down surveillance case)

In some cases, however, police get around that issue by showing they can prove in other ways that the individual had control and possession over the device in question, and in 2009 a U.S. district judge in Vermont ordered a suspect provide his password to decrypt files for police, which he eventually did, leading to his conviction on child porn charges.

The topic is currently before the Massachusetts Supreme Court. In that case, a lawyer was charged with mortgage fraud and police confiscated computer and devices from his home, but couldn’t get into them because of his encryption. The government alleges there is evidence of his crime on the computers, but the defense argues there is no proof as to what the computers were used for, only that the lawyer had bought them.

Fakhoury said resolution of the issue is becoming even more important as device-locking technologies advance.

“We’re getting new permutations of this issue because the iPhone came out, what, two months ago, and everyone’s using fingerprints to lock their phone,” he said. “The new technology is going to be unlocking the phone with your eyes, or who knows what. And again the courts are moving slow on this.”

Follow @politico

Where have you been?

Another nettlesome issue brought up in part by the ubiquity of cellphones and smartphones is the ability of police to track a person’s movements.

While the Supreme Court ruled last year that police cannot affix a GPS tracking device to a car without a warrant, it decided U.S. v. Jones based on a question of trespassing, which doesn’t apply when police get location information from a suspect’s devices or service provider.

The courts are also split on this issue. In July alone, two courts made opposite rulings: The 5th Circuit Court of Appeals in Texas found that law enforcement may get cell location data from service providers without a warrant. In a New Jersey case, a very different result - the state supreme court held that the state’s constitution requires a warrant.

The key question centers around what’s called “third-party doctrine.” The Supreme Court in the 1970s ruled that when a consumer trusts information with a third party, like a bank or phone company, they give up the right to keep that private from the government.

The problem, experts say, is that the cases that established that rule were decided decades before smartphones and the Internet, in cases about pen registers — devices that are installed on landlines to record the numbers a phone dials — and paper bank records, a far cry from the wealth of data consumers today send to a range of service providers in their day-to-day lives.

“Judicial opinions rely heavily on analogy and tying old cases to new cases, and that becomes very difficult when technology is evolving rapidly,” said Alan Butler, the appellate advocacy counsel for the Electronic Privacy Information Center.

Can anyone take on the NSA?

The rules about personal information trusted with major companies loom large over perhaps the most public debate about privacy: Widespread surveillance by the National Security Agency revealed last summer by leaker Edward Snowden.

Under the 1970s cases, the metadata associated with phone calls and Internet use that the NSA tracks would be fair game for the government to obtain without a court-issued warrant.

“As of right now, the Fourth Amendment has nothing to say about the metadata program run by the NSA,” Vanderbilt law professor Christopher Slobogin said, “because all that metadata is . . information given to a [company], and the Supreme Court has held that you assume the risk that when you make a phone call.”

But the unique and complicating factor with NSA surveillance is that it is secret, leaving experts scratching their heads as to how an individual can even challenge the surveillance in court.

Last year, before Snowden’s leak, the Supreme Court ruled in a surveillance case that the individual couldn’t prove they had been the subject of surveillance, and thus had no ability to challenge the government’s programs.

“It’s a Catch-22,” Slobogin said. “In order to challenge NSA surveillance, you have to prove you’re under surveillance, but you can’t find out from the NSA whether your calls are being monitored.”

In a speech in September, Justice Antonin Scalia told an audience he believes the courts will ultimately have to decide on government surveillance, although he said he believes they are not the ideal body to make the call. Scalia didn’t address who should decide, but called the courts the branch of government “that knows the least” about the high-tech and security issues at stake.

With technological change not slowing down any time soon, pressure for the law to keep up is high. While most agree a legislative solution would be ideal, privacy experts are pessimistic about Congress getting its act together. Lawmakers for years have been discussing updating the Electronic Communications Privacy Act, but progress has been limited.

“We’ve had essentially the same law on the books since 1986 and it’s horribly out of date, and everyone agrees it’s horribly out of date, but we’re reliant on Congress,” said Butler, of Electronic Privacy Information Center.

Some of the frustrations for advocates are built into the judiciary: Often, federal judges are selected for their esteemed and lengthy careers and while those decades of experience mean judges of a certain age know the law, they may not know about the most modern technologies.

“Justice [Elena] Kagan a couple weeks ago was talking about how the Supreme Court struggles to use email, which is kind of funny but kind of scary at the same time,” Fakhoury said. “We had a case involving a guy charged with cyberstalking on Twitter, and we had to explain to the judge in his 60s what Twitter was.”