Petraeus affair reveals risks of email

The scandal that caused the resignation of Gen. David Petraeus, one of the country's most decorated military professionals, has a lot of observers wondering: If the head of the CIA can't figure out how to keep his emails private, do the rest of us even stand a chance?

In a word, no -- or at least not without some real planning. "If you're just a normal person sending email, then it's pretty easy to trace," said Keith Jones, a computer forensic investigator. Every server an email hits en route to its destination "puts a little identifying line in there," Jones explains. "It's like a chain of custody, showing who had the email."

Petraeus had reportedly used a pseudonym to set up multiple email accounts that he used to send his mistress messages, including some on Gmail. One was a shared account that the two used to communicate via messages that they left in a drafts folder but never actually sent.

The idea was that if they left emails in the drafts folder -- known as an electronic drop box -- the messages wouldn't leave a trail and would be difficult for anyone to find.

There are ways to hide the e-bread-crumb trail, Jones said. For example, an anonymizer, also known as an anonymous proxy, can hide the sender's identifying information by accessing the Internet on the sender's behalf. It's akin to enlisting someone to deliver an envelope for you, Jones explained.

But most people -- whether they're sending memos about corporate marketing plans or messages to mistresses -- don't think about using such techniques.

"Most individuals and businesses don't think twice about sending private or confidential information over email," said Patrick Moorhead, an analyst at Moor Insights & Strategy. "For work email, assume someone is reading your email, as someone or something probably is."

This version of this story was originally published in Computerworld's print edition. It was adapted from an article that appeared earlier on

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