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How to keep your e-mail communications concealed by learning from the Petraeus affair

Gen David Petraeus

The e-mail exchange between David Petraeus and his biographer Paula Broadwell got him busted and had he been more careful, he could have saved himself. I am not suggesting that people like him shouldn’t be caught, but considering the fact that he was heading one of the most reputed intelligence and espionage agencies in the world, he should have known better. This also shows that he wasn’t as smart as he should have been.

First, a quick primer, as explained in this ReadWrite blog post, on how actually they were exchanging messages with each other.

In order to avoid e-mail chains from being generated on the Gmail servers, the general had created a dummy account with a pseudonym. Both the general and his paramour used to create messages and then save them as drafts. Both had access to this account. After one had created a draft, the other would log in and read the draft. Consequently, no e-mail was sent and no e-mail chain was created in Gmail. Once deleted, drafts are also very difficult to retrieve. Whereas it is not clear whether Petraeus and Broadwell deleted the drafts after reading them or not, this is basically how they were using the e-mail communication.

Then how were they caught?

Paula Broadwell was sending threatening e-mails to one Jill Kelley from another Gmail account. So when Jill Kelley approached the FBI it was kids stuff to find out that the anonymous account being used by the general and her lover had the same IP address that was being sent by the person threatening Kelley.

According to the blog post mentioned above, the general could have done the following in order to keep his messages concealed (although the methods are not foolproof, they can work in most of the cases):

  • Hide your IP address: This is the simplest way of keeping your communication anonymous. Tools like Tor can help you conceal your real IP address when you are browsing the Internet and using your e-mail. You can also create an alternative and encrypted Virtual Private Network by using an application called Hamachi.
  • Use disposable e-mail: Do you know you can create e-mail messages that are automatically deleted after they have been read? Disposable e-mail services such as Spamex and Mailinator can help you achieve exactly that.
  • Use encryption: There are many e-mail encryption tools available that you can use to encrypt your messages so that they are not intercepted midway. Although they are not a viable solution for intelligence and law agencies such as the CIA or the FBI, the common folks can make good use of these.
  • Delete your drafts: Even if you’re not sending each other e-mails and are simply saving drafts, make sure that you delete the draft after reading it. As already mentioned above, once deleted, it is always very difficult to get a draft back.