The Supreme Court is an openly — even proudly — technophobic institution. Cameras are forbidden, which means there are no images or videos from high-profile cases, and briefs and other legal filings only recently became available at the court’s website. Chief Justice John Roberts argued in 2014 that these Luddite tendencies are just part of the legal system: “The courts will always be prudent whenever it comes to embracing the ‘next big thing.’” The justices — who communicate mostly on paper, rather than via email — can sometimes seem as analog as the institution they serve. There was the moment when in a 2014 case about cell phone privacy, Justice Samuel Alito asked what would happen if a suspect were carrying personal information on a “compact disc.” That same year, Justice Stephen Breyer was ribbed for spinning out an extended hypothetical about a “phonograph record store.”

There are systemic reasons for the court’s reluctant approach to technology — American law is a backward-looking enterprise even outside the highest court. But regardless of why it’s happening, legal scholars say the consequences are clear: When Supreme Court justices lack an understanding of what technology means for the lives of the people affected by their decisions, they will struggle to respond effectively to technological change.

Any day now, that risk will be confronted anew. The court will issue a ruling in Carpenter v. United States, a case that revolves around the government’s use of cell phone records, obtained without a warrant, to re-create the movements of a robbery suspect, Timothy Carpenter. During the oral argument in November, the government contended that its actions were in line with a past Supreme Court decision, which ruled that people can’t have an expectation of privacy for information that they voluntarily turn over to a third party, like a phone company. But Carpenter’s lawyers said his Fourth Amendment right to privacy was violated. They argued that technological advancements like smartphones, which can give investigators access to a defendant’s every movement, makes the Supreme Court’s precedent dangerously out of date.

Even if the Supreme Court were to rule in Carpenter’s favor, as seems likely based on the oral argument, some digital privacy advocates wonder whether it would be too little too late. After all, the Supreme Court is settling this question more than 10 years after the release of the iPhone and nearly 20 years after cell phone location records began to be used in courtrooms. Requests for cell phone data are common in law enforcement and have been for a while. Should the Supreme Court have stepped in sooner? Or are delays necessary to ensure that the law is consistently applied in the face of rapid technological change?

In the past, the justices’ failure to understand the implications of new technologies has led to situations in which an initial decision was reversed but only after a significant period of time. In 1928, for example, the Supreme Court was faced with a potential privacy violation: The FBI had wiretapped a bootlegger, Roy Olmstead, without receiving court approval. Chief Justice William Taft wrote that the action wasn’t unconstitutional, since the Fourth Amendment protects “the right of the people to be secure in their persons, houses, papers, and effects” and nobody had physically entered Olmstead’s home to obtain the incriminating information. In an influential dissent, Justice Louis Brandeis argued that Taft was ignoring the obvious similarities between a sealed letter — which was protected from warrantless searches — and a phone call. Modern technology (in this case, the phone), he wrote, gave the government “subtler and more far-reaching means of invading privacy.” Nearly 40 years later, in 1967, seven Supreme Court justices echoed Brandeis’s thinking in a decision that overturned the ruling in the Olmstead case. But in the intervening years, Taft’s interpretation was the law of the land, which meant that wiretapping without a warrant was legal.

It’s this kind of lag that worries Ryan Calo, a law professor at the University of Washington. In the Carpenter case, the justices are responding to a precedent from 1979, when the court ruled that law enforcement didn’t need a warrant to use a pen register — a device that records the numbers dialed from a telephone — to track a defendant’s calls. This, Calo said, is a far cry from today’s detailed cell phone records, but the law treats them as though they’re the same. “How far do civil liberties have to be eroded before the courts say it’s a problem?” he said. “Technology moves quickly, and if the courts aren’t responsive, we can get into situations where law enforcement has to be doing these Orwellian things before the courts act.”

Some legal experts argue that judges shouldn’t be responsible for extensively researching every new technology that comes before them. Other countries have specialty courts, but American judges are generalists, which means that they’re constantly facing disputes in areas that are outside their expertise. Paul Ohm, a professor at Georgetown Law, said that in these situations, it’s up to the lawyers to explain what the justices need to know.

But the challenge is that regardless of how cutting edge an innovation seems, our legal system operates by slotting new things into older categories, which means that judges evaluate a new technology based on its similarity to something that has been ruled on in the past. The result is that the justices are often presented with different metaphors for how to think about a certain kind of tech. Recently, the court has contemplated whether a cell phone is equivalent to something like a wallet or a diary, whether the internet is similar to a space like a street or a park, and whether a streaming television company is more like a cable provider or an equipment company like RadioShack. “Tech cases quickly turn into battles of analogies,” said Rebecca Crootof, a lecturer in law and a research scholar at Yale. Often, the winning analogy will determine how the court rules — which means there’s a lot at stake in getting it right.

Sometimes these comparisons are downright bizarre — and they may not fully capture what a technology is doing. In 2012, for example, Justice Antonin Scalia noted in his majority opinion that a GPS tracker attached to a car was plausibly akin to a colonial-era constable who might have climbed into the back of a stagecoach to track a suspect. Some, including Alito, criticized the metaphor as emblematic of Scalia’s tendency to look to the past for legal solutions, saying that the majority opinion focused too much on the fact that the GPS was affixed to the car — therefore constituting a kind of physical “trespass” — rather than the broader question of whether warrantless 24-hour surveillance was legal.

If trying to analogize every new technology to an older technology poses one kind of risk, there’s another danger in overemphasizing the newness of a particular innovation or the speed of technological change. Daniel Hemel, a professor at the University of Chicago’s law school, pointed to a majority opinion last year in which Justice Anthony Kennedy declared that “the forces and directions of the Internet are so new, so protean, and so far reaching that courts must be conscious that what they say today might be obsolete tomorrow.” A perspective like Kennedy’s, Hemel said, is a “disconcerting” way to think about the law. Lawyers need to be able to construct arguments based on how the court ruled in the past, so even if technologies are shifting quickly, the court’s rules and standards shouldn’t become obsolete.

But even if caution is a virtue, basic knowledge is also necessary to be able to respond to technological change in a timely and responsive way — even if it’s just assessing which metaphor is more accurate. “The Supreme Court is faced with competing analogies for new technology all the time,” Calo said. “So a certain amount of sophistication is necessary to be able to evaluate which one is right. And it’s not always clear that the justices have that.”

Additional reporting by Oliver Roeder.