Two State Department staff members leading a delegation of Silicon Valley executives to Syria have learned that social media and diplomacy don’t always go together. Syria, a closed society that blocks its citizens’ access to sites like Google, Facebook, and YouTube, but apparently not Twitter, could have told them that.

The two young staff members, Josh Cohen, 28, and Alec J. Ross, 38, described in today’s New York Times as “…the most visible of a small band of new-media evangelists who are trying to push a pinstriped bureaucracy into the digital age …” sent a series of tone-deaf Twitter dispatches while on their trip (first flagged here by Foreign Policy’s Josh Rogin), challenging a Syrian communications minister to a cake-eating contest in what they called an act of “creative diplomacy” and this one from Cohen that read, “I’m not kidding when I say I just had the greatest frappacino (sic) ever at Kalamoun University north of Damascus.”

According to the Times:

The two staff members…were rapped on the knuckles for generating what the State Department officials called “stray voltage.”

Ross, a technology advisor to the Obama presidential campaign, and Cohen, who has written two books about jihad and genocide, had previously been lauded by their boss, secretary of state Hillary Clinton, for ther “21st-century statecraft.” Some of their previous projects include a network they developed in Mexico to enable people to report drug-related crimes on their cellphones, which sounds strangely like the product of some kind of State Department-sponsored version of the Knight News Challenge.

Cohen is known for asking Twitter not to take its site down for routine maintenance during last summer’s election protests in Iran for fear that it would disrupt the spread of information promoted through the social network. (As it turns out, the Twitter Revolution meme was wildly overhyped.)

Ross and Cohen’s mission in Syria, officially classified as a state sponsor of terrorism, seems to have been centered around using the potential investment power of the companies in tow (Microsoft, Dell, Cisco Systems and others) as a cudgel to encourage the country to ease its tight control of the Internet. (A 2004 sanctions waiver allows American technology companies to export software and hardware as long as they are not used by the government against Syrian citizens.) According to the New York Times:

The delegation told (Syrian President Bashar al-Assad) that companies would invest more in Syria if it stopped blocking social media Web sites like Facebook and YouTube, and did a better job of protecting intellectual property.

The San Francisco Chronicle reported that the Syrian state news agency, Sana, said, “the American executives discussed setting up authorized centers for (their) companies in Syria.”

In other words, if Syria eases restrictions on free speech, it could get a nice Dell customer service center in Damascus!

The takeaway from the whole ordeal, as indicated by the Times’ kicker quote from State Department spokesman, Philip J. Crowley, who uses Twitter to report on Clinton’s daily activities, is to stay on-message.

…Crowley said he was careful to get the tone right. “I’m not going to tell everyone what I had for lunch,” he said. “Ever.”

But if the State Department and its tech-exec delegation were trying to woo its Syrian hosts toward a more open society, they seem to have done the exact opposite in presenting an object lesson in the very off-message-messiness that social media facilitates and that undemocratic governments like Syria’s like to avoid. If the Syrians should learn any lesson from their guests’ “stray voltage,” it is this: when you open channels of communication, stuff you don’t want the world to see will inevitably leak out. Stuff like anti-government sentiment, or your glee at finding American-style iced coffee in the middle of a hostile nation.

For diplomats themselves, Twitter, that very personal megaphone often used to promote very corporate brands and their official company lines, seems perfectly crafted for the sort of undiplomatic, off-the-cuff, foot-in-mouth moments that can easily go off-message (Note that Joe Biden’s Twitter feed went dark right around the time he was nominated for the vice presidency.) Can you imagine if Gen. Stanley McChrystal had had a Twitter feed?

So if the U.S. government actually wants closed societies to unblock the channels of communication enjoyed in the rest of the world, perhaps social media and diplomacy are best not mixed within the very government circles that espouse those principles of free speech. Or perhaps they should own their gaffes and use them to embrace the beautiful, messy, cacophony of voices that we like to call the First Amendment.

Meanwhile, Cohen continues to tweet the sort of information that blurs the line between professional and personal, (Anyone else sooo excited for the season premiere of Entourage?) in the sort of dispatches that the Times called “youthful indiscretions.” Or that you could also call “the sometimes messy but always glorious result of free speech.” Whichever.

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Alexandra Fenwick is an assistant editor at CJR.