The FBI and Apple have been at loggerheads for a few weeks now over an encrypted iPhone involved in a terrorist investigation. The iPhone belonged to a deceased terrorist who killed 14 people, and the FBI wants Apple to build a sort of digital skeleton key to allow them to access the material on that phone to aid in their investigations.

Apple objects that once the key has been created, nothing is preventing it from being requested for use against other encrypted phones—such as nearly 150 that New York would like to unlock if the FBI can get Apple to come through for that one.

It’s a tricky issue, but you don’t get a full sense of how tricky until you’ve watched John Oliver explain it. Oliver uses the occasional bit of salty language here and there, but he has a remarkable talent for getting to the heart of the issue and making it hilarious along the way. If you don’t feel like watching an 18-minute video segment, Ars Technica has a more detailed summary of the points he makes.

Meanwhile, NPR’s Morning Edition has interviewed Richard Clarke, former senior counterterrorism official for the Clinton and second Bush administrations, and found him highly sympathetic to Apple’s side. What’s more, he believes that the FBI is not really interested in cracking the terrorists’ iPhone so much as it wants to set a precedent that Apple has to cough up the code to let the FBI crack whatever phones it wants in the future.

If I were in the job now, I would have simply told the FBI to call Fort Meade, the headquarters of the National Security Agency, and NSA would have solved this problem for them. They’re not as interested in solving the problem as they are in getting a legal precedent.

Clarke adds that every expert he knows believes the NSA could easily crack the phone if it was given the task.

This is a tricky issue, because as a 2014 Supreme Court decision pointed out, smartphones aren’t just phones, but are effectively “an important feature of human anatomy,” and require a specific warrant to search. One of the original triggers of the Revolutionary War was the British habit of using general warrants to just go into a house and look for evidence of any crime.

“The fact that technology now allows an individual to carry such information in his hand,” the chief justice also wrote, “does not make the information any less worthy of the protection for which the founders fought.”

Among other things, our phones could contain a record of all the e-books we read on them. More than once, we’ve covered the possibility that the FBI could demand patron reading records from public libraries. Whatever e-books we keep on our phones would be the same in principle. Indeed, this piece from 2002 discussing suspected terrorists visiting a public library seems eerily prescient when it comes to demanding access to information because of a potential terrorist threat.

But another point that bears considering is that, if Apple were forced to come up with this skeleton key program, what guarantee is there that it wouldn’t ever leak? As John Oliver pointed out, there are already iPhone safecracker gizmos on eBay that can easily access phones running earlier versions of iOS. All it would take is a single leak to the wrong people, and the new iOS would become just as crackable.

And if there’s one thing e-book readers should have learned from the current state of DRM, it’s that weak protection measures can and will be circumvented. Just look at how trivially easy it is to crack Kindle or Adobe e-book DRM right now. While I’m just fine with it in that case, I would be strongly opposed to anything that might bring Apple’s so-secure-the-FBI-can’t-crack-it phone encryption down to that level.

And even if they do manage to circumvent it, what then? As John Oliver also points out, there are literally hundreds of apps and other solutions that provide end-to-end messaging encryption, many of them from outside the United States. And literally millions and millions of people use them—not because there are millions of criminals, but because people like their privacy. Even if the FBI manages to get Apple to knuckle under, what have they really won in the end?

As integral as phones have become to our daily life, to the point where even Disney movies reflect their ubiquity, this is an important issue that we shouldn’t simply let slide. A chain is only as strong as its weakest link, but letting Apple create a set of boltcutters could be a dangerous proposition.


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