On Tuesday, a New York federal judge told Apple that he is not happy with the company’s response regarding whether a law originally written in 1789 applies in a 21st century context. Put another way, can the American legal system compel Apple to hand the government the keys to unlock an iPhone?

In its filing one day earlier, Apple lawyers told a federal judge in New York that it is "impossible" for the company to help unlock an iOS 8 iPhone in a hypothetical criminal case. In this case, however, Apple noted that the phone in question is running iOS 7 (just 10 percent of current iOS devices are running that OS), which changes the calculus a bit.

"As a general matter, however, certain user-generated active files on an iOS device that are contained in Apple’s native apps can be extracted," Ken Dreifach, an attorney representing Apple, wrote in the company’s seven-page filing. "Apple cannot, however, extract e-mail, calendar entries, or any third-party app data."

Little is known about this case, which remains under seal, but federal authorities have obtained a search warrant to search the locked device.

This investigation is yet another example of the invocation of the All Writs Act, an 18th-century federal law that simply allows courts to issue a writ, or order, which compels a person or company to do something. For some time now, prosecutors have turned to courts to try to force companies to help in situations where it is otherwise stymied. But bringing Apple into a case like this is new.

"This case marks the first time a judge has questioned the authority of the All Writs Act to grant supplemental orders to accompany such warrants and asked Apple for its views on the feasibility and burden associated with such an order before issuing it," Dreifach added.

Federal prosecutors and Apple lawyers are scheduled to appear before the judge to discuss the matter on Thursday.

Dreifach seemed to indicate that the question of the All Writs Act was nearly moot, highlighting that on devices running iOS 8 or higher, there is "a feature that prevents anyone without the device’s passcode from accessing the device’s encrypted data. This includes Apple."

But in his Tuesday order, United States Magistrate Judge James Orenstein was not satisfied with Apple’s answer. He wrote:

In inviting Apple, Inc. ("Apple") to submit its views on the feasibility and burdensomeness of the government's request, I did not intend to limit its submission to those matters, but rather to focus its attention on particular factual questions. I therefore respectfully invite Apple to supplement its submission by addressing the legal question before the court; namely, whether the All Writs Act empowers the court to compel Apple to provide the technical assistance the government seeks.

Judge Orenstein’s order came the same day that Apple CEO Tim Cook forcefully rejected the notion that the company should create "backdoors" to its products that would allow the government access under certain conditions.

A looming tide

On Monday, attorneys from the American Civil Liberties Union and other affiliated groups filed an amicus brief , which the judge did not formally accept. That submission argues that the government’s attempt to force Apple into unlocking the phone is entirely unconstitutional.

"It would constitute a dramatic and unwarranted expansion of the government’s investigative authority, by permitting it to conscript into government service those who have done nothing wrong and who do not possess or control information to which the government is entitled," the attorneys wrote.

Outside legal scholars also noted that Apple has drawn the line between a locked iOS 7 device, which may technically be able to be opened, and fully encrypted iOS 8 devices—which will soon encompass all such iPhones and iPads."That is, I think, the correct distinction—as a matter of policy and as a matter of law. Pulling data from the former is an inconvenience," Jonathan Mayer, a law lecturer at Stanford University, told Ars by e-mail. "Pulling data from the latter requires a brute force attack or a backdoored software update (if either is even feasible)."

Brian Owsley, a former federal magistrate and current law professor at the University of North Texas, concurred—Apple is indeed highlighting to the court what is coming down the road. "Soon, it will be impossible for Apple to access encrypted cell phones because very few phones have operating software older than iOS 8," he told Ars. "In that sense, they are telling the government to buzz off. I thought it was candid in that [Apple] did not claim the request was unduly burdensome in isolation but set some parameters as to how it would become unduly burdensome."

“This Hail Mary play”

Dreifach concluded his filing by making a forceful argument about why Apple should not be compelled to help the government:

Public sensitivity to issues regarding digital privacy and security is at an unprecedented level. This is true not only with respect to illegal hacking by criminals but also in the area of government access—both disclosed and covert. Apple has taken a leadership role in the protection of its customers’ personal data against any form of improper access. Forcing Apple to extract data in this case, absent clear legal authority to do so, could threaten the trust between Apple and its customers and substantially tarnish the Apple brand. This reputational harm could have a longer term economic impact beyond the mere cost of performing the single extraction at issue.

Judge Orenstein has at least a decade-old history with the All Writs Act, having previously denied a similar government request to obtain real-time cell site data under the act.

He wrote in 2005:

Thus, as far as I can tell, the government proposes that I use the All Writs Act in an entirely unprecedented way. To appreciate just how unprecedented the argument is, it is necessary to recognize that the government need only run this Hail Mary play if its arguments under the electronic surveillance and disclosure statutes fail.

Judge Orenstein appears likely to side against the government, but he said he would wait to hear further from both parties to make a final ruling.