One minute David Petraeus was a storied General and the elite head of the world’s most extensive spy network, and the next he was the poster child for how not to communicate online. It turns out that the General used a trick that is allegedly also used by Al Qaeda: Not hitting Send and leaving the email in the Drafts folder of an account where both parties have login access. Unfortunately for the General, the FBI is wise to these tricks and they opened up that Gmail account and located the relevant emails faster than the General could say “whoops, there goes my career.” His “how the mighty have fallen” story can be a lesson to anyone who would much rather not have the contents of their confidential emails plastered all over the internets.

Online Marketers Need to Keep Emailed NDA Info Private

Truly anonymous emailing should not be construed to be the sole terrain of criminals, smugglers, inside traders, terrorists and cheaters. There are countless reasons why online marketers may want to keep their electronic communications permanently private. Many companies operate under a swath of Non Disclosure Agreements that carry considerable legal penalties should any of the confidential information be revealed to parties not authorized under the terms of the agreement. So if you’re communicating via email any aspect of that information to a colleague who is also fully authorized to be made aware of it, you certainly don’t want it to be intercepted and posted publicly… as that would get your company in a world of hurt in court.

Tor Is the Private Emailer’s Best Friend

Even though the name has become synonymous with bit-torrent pirates who want to download copyrighted content such as movies and music without leaving tracks, Tor is actually the private emailer’s best friend. Tor is a system that “almost totally” ensures online anonymity by encrypting through SSL multiple times and redirecting your traffic through a network of servers designed to conceal your actual IP. The “almost totally” refers to the fact that the NSA can decrypt SSL as easily as the FBI can access Petraeus’ Gmail, so if you’re a terrorist you have no hope of escaping their surveillance. However, the NSA doesn’t really care if you email a colleague to tell them you’re about to launch a new iWidget, so online marketers can use Tor without fearing the arrival of a SWAT team at their front door.

Free Services Have No Payment Bread Crumb Trail

Keeping your IP out of your email flow is not the only security precaution. Your email system itself should be as secure as possible. To that end, Hushmail is recommended as their HTTPS servers are set up to anonymize users, but there are other very valid options. There is a vast number of fully anonymous email services available and it’s recommended that you only use the free ones. That’s not to save your hard earned money but if you have to pay for a service you are creating a paper trail to your credit card or PayPal account and that’s leaving clearly visible bread crumbs along the trail all the way back to you.

Disposable email accounts are also quite popular among the private communications options. These accounts can be used once and then disposed of, and can serve a valid purpose in keeping private data private. It must be noted that even these disposable accounts are recoverable to some degree as once any byte is placed on a server anywhere a truly dedicated party can figure out how to get at it, even if it’s been deleted. In the server world there is no such thing as deletion as some data can be recovered after four, five or even six memory rewrites, not to mention that many servers back up continually so that even the most immediately deleted data still lives on in the backup medium for all eternity.

Do you want a communications medium that is effectively untrackable and truly private? May I suggest a carrier pigeon? Unless there is someone in the flightpath with a really big net on their roof…