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.

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.

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.

It wasn’t just the justices who had technical difficulties. When Justice Samuel 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.

More on oral arguments in the case here on Lawyers USA Online.

* UPDATE: As several commentators have noted, the Court’s official transcript quotes Justice Roberts as asking, “what is the difference between the pager and the e-mail?” – suggesting he may have been inquiring in this context, and not more generally.