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During oral arguments today in the case City of Ontario v. Quon, which considers whether police officers had an expectation of privacy in personal (and sexually explicit) text messages sent on pagers issued to them by the city, the justices of the Supreme Court at times seemed to struggle with the technology involved.

The first sign was about midway through the argument, when Chief Justice John G. Roberts, Jr. - who is known to write out his opinions in long hand with pen and paper instead of a computer - asked what the difference was “between email and a pager?”

Other justices’ questions showed that they probably don’t spend a lot of time texting and tweeting away from their iPhones either.

JUSTICE GINSBURG: But my question is, an employee reads this policy and says, oh, my e-mails are going to be subject to being monitored –

MR.DAMMEIER: Sure.

JUSTICE GINSBURG: Wouldn’t that employee expect that the policy would carry over to pagers? When you think of what’s the reason why they want to look at the e-mails, wouldn’t the same reason apply?

At one point, Justice Anthony Kennedy asked what would happen if a text message was sent to an officer at the same time he was sending one to someone else.

“Does it say: ‘Your call is important to us, and we will get back to you?’” Kennedy asked.

Justice Antonin Scalia wrangled a bit with the idea of a service provider: “You mean (the text) doesn’t go right to me?” he asked.

The Chief Justice admitted he believed that once “you push a button; it goes right to the other thing” without passing through a service provider. When Attorney Dammeir pointed out that in today’s society it is reasonable to assume texts travel through a service provider, rather than directly from one device to another, Justice Scalia admitted, “Yeah, I didn’t know.”

Then he asked whether they can be printed out in hard copy: “Could Quon print these spicy little conversations and send them to his buddies?” Scalia asked.

CHIEF JUSTICE ROBERTS: Maybe — maybe everybody else knows this, but what is the difference between the pager and the e-mail?

MR. DAMMEIER: Sure. The e-mail, looking at the computer policy, that goes through the city’s computer, it goes through the city’s server, it goes through all the equipment that — that has — that the city can easily monitor. Here the pagers are a separate device that goes home with you, that travels with you, that you can use on duty, off-duty.

CHIEF JUSTICE ROBERTS: You can do that with e-mails.

The Chief Justice went on to ask “if you punched in in [sic] your search station, you know, give me all the bakers in Washington, that would make it patentable?” Typewriters? Search stations?

It wasn’t just the justices who had technical difficulties. When Justice Samual Alito asked Quon’s attorney Dieter Dammeier if officers could delete text messages from their pagers in a way that would prevent the city from retrieving them from the wireless carrier later, Dammeier said that they could.

A few minutes later, Alito gave Dammeier another shot at that question.

“Are you sure about your answer on deletion?” Alito asked.

Dammeier admitted that he didn’t know. “I couldn’t be certain,” he said.

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None of the Supreme Court Justices in the case appeared to possess a familiarity with the workings of modern technology.

Laws governing technology are expanding at an ever-increasing rate. As soon as a new technology arises, governing legislation follows closely behind. It is up to the courts to interpret these laws in a fair and predictable manner. Predictability of the laws governing the creation, protection, transfer and use of technology are critical to the smooth flow of business in our society. Failure to accurately and fairly administer laws relating to technology costs industries billions of dollars and paves the way for the unscrupulous to capitalize on perceived weaknesses in the law.

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