Petraeus Mission Impossible: Cloaking Email, Online Identities

Is there any way to keep online identities and the content of email communications hidden?

Clearly, covering one's tracks is tough to do, as demonstrated by David Petraeus, the highly decorated general who last year became director of the CIA. Notably, his affair with Paula Broadwell -- hardly a national security matter -- came to light this week after the FBI found that the couple was using a Gmail account to communicate.

Still, for the director of a U.S. intelligence agency to have been caught in this manner is, frankly, a security embarrassment. Rather than using a VPN to mask their IP addresses or encryption to scramble the contents of their messages, or simply avoiding email altogether, Petraeus and Broadwell communicated using saved Gmail drafts. Having gone to the trouble to hide what they were doing, why didn't they find a more secure communications mechanism?

Then again, no amount of hiding their online tracks may have helped foil determined investigators. Even supposedly master hackers have been identified after just one small misstep.

[ Seems it's getting harder to maintain your privacy. See Google Says Government Surveillance Growing. ]

Consider the example of LulzSec leader Sabu -- real name, Hector Xavier Monsegur. He reportedly failed to mask his IP address just once or twice before logging into an IRC chat room, which ultimately allowed the FBI to pinpoint his real IP address and then identity. Meanwhile, Backtrace Security also found, hidden in a LulzSec chat file, a domain name that led to a subdomain that mirrored a page where Monsegur had posted a picture of his beloved Toyota AE86.

Seeing so-called security experts commit basic information security errors isn't a new occurrence. Arguably, it even led to the rise of the Anonymous hacktivist collective. According to journalist Parmy Olson's book We Are Anonymous, the collective had lost steam after its Church of Scientology and PayPal exploits. Then HBGary Federal CEO Aaron Barr launched a PR stunt meant to drum up business, publicly boasting that he would soon unveil the identities of key Anonymous players. That led the key players, including Sabu, to see just what Barr knew -- he turned out to not have identified them at all -- as well as make a lesson of him to any other would-be Anonymous enemies.

As Olson recounts, Sabu scanned the HBGary Federal website and found -- ironically, for an information security firm -- that it was built using a commercial content management system that contained a known vulnerability. Using a SQL injection attack, the hacktivists retrieved a list of HBGary employees' usernames and passwords, although the latter had been hashed using MD5. While that temporarily stymied Sabu -- the group was still sharpening its technical skills -- he uploaded three of the passwords to the hashkiller.com forum. Its members quickly cracked the hashes and shared the plaintext passwords, including Barr's work password, which was "kibafo33."

The hackers then tested whether Barr's password worked for any of his other website accounts. Remarkably, Barr, a self-described information security expert, had reused his work password on numerous sites -- including Facebook, Flickr, Twitter, Yahoo as well as World of Warcraft. On Super Bowl Sunday 2011, Anonymous owned those accounts and began issuing vulgar tweets in Barr's name and providing links to a torrent file containing over 70,000 HBGary emails that it had surreptitiously copied and deleted from the company's servers.

Compared to the HBGary episode, Petraeus' Gmail missteps -- still surprising for the head of an intelligence agency -- appear less galling. In the end, however, his story isn't just about the startling ease with which one's supposedly hidden communications or identity can be uncloaked, our country's poor privacy protections or an investigation that should never have begun. Rather, it's also about human errors.

Namely, Broadwell was jealous of Jill Kelley, a married Tampa socialite who volunteers with wounded veterans and military families, and her friendship with Petraeus, which she saw as a threat. So Broadwell sent threatening emails to Kelley, who passed them to FBI agent Frederick W. Humphries II, which triggered the investigation. Given that Broadwell, who was married, was having an affair with the director of the CIA, shouldn't more discretion have been the order of the day?

With information security--as in life--the biggest wildcard remains the human factor.