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Anatomy of a dead-drop: email spycraft gone bad (continued)

This is a test. What's wrong with this picture? Go ahead. Re-read the paragraphs and see if you can figure out where Buff went wrong.

OK. Time's up.

Let's deal with the basics here. When you send an email message, generally, from one Internet account to another, you're uploading a message to a server (usually using the POP3 protocol), then your server sends a message to the recipient server, usually using SMTP (Simple Mail Transport Protocol). At that point, the message is stored on the recipient server until it's downloaded to an email client like Outlook.

If you eliminate the email client, for example, if you're sending from a Gmail account to a Hotmail account, you're eliminating the POP3 phase of message transmission. But because you're sending a message between servers, your message is still sent over SMTP from server to server.

If one person accesses a draft email box on a Web-based email service like Hotmail or Gmail, and another person accesses the same draft email box, there is no message sent between servers via SMTP. In this, Joe Buff and Felix-the-SEAL are correct.

Uh, but duh. See, Felix is supposedly accessing his Web-based email account from some cyber-cafe or other Internet access point. All his Web access is being transmitted up and down from the Web-based email server to his browser window and back. Yes, Felix might have a secured browser with the little key lock icon, but he's still transmitting the messages.

It's just that rather than transmitting them between servers, he's transmitting them from the server to his browser and back. It's tough to say which is less secure, but no matter what, Buff's statements "They couldn't be intercepted in transit by covert adversaries either" and "The messages are never in transit" are both dead wrong.

If he did this in real life, Felix would have been caught or killed, the secretary would have disavowed any knowledge of his actions, and Tom Cruise would have ruined the whole franchise by disrespecting Mr. Phelps. Well, that did happen. I've never forgiven Cruise for ruining Mr. Phelps' reputation and Oprah has never forgiven Cruise for trying to dislocate her shoulder. We're just not big on Tom Cruise here at OutlookPower.

Seriously, if you happen to be a spy (and, yes, we actually have some of them reading OutlookPower, believe it or not), don't do what Felix did. You'll get caught.

We do actually have a lot of government folks reading OutlookPower, DominoPower, and the other ZATZ magazines. We know this because every so often we get a call from the CIA ordering some of our Solutions Guides.

Nothing makes your day more surreal than when your wife calls out, "Honey, the CIA's on the phone. And on your way home from coffee, could you pick up some milk?"

Tonight, it got just a bit more surreal. As I was typing this, my keyboa

For more information on Joe Buff's great books, visit http://www.joebuff.com.
For more than 20 years, David Gewirtz, the author of Where Have All The Emails Gone? and The Flexible Enterprise has analyzed current, historical, and emerging issues relating to technology, competitiveness, and policy. David is the Editor-in-Chief of the ZATZ magazines, is the Cyberterrorism Advisor for the International Association for Counterterrorism and Security Professionals, and can be reached via email at david@zatz.com.




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