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Old 06-04-2008, 03:51 PM
iastaff iastaff is offline
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Default Sending Anonymous Email via SSH2

Date: Tuesday June 3, 2008
Author: Jared T.
Organization: International Alliance Privacy Services
Contact: Please use this form

The most commonly asked question that I get asked is "How can I send completely untraceable email?" To answer that question, I usually explain the following:

As we all know, I highly promote the usage of SSH2 Technology for surfing the web as it allows completely anonymity behind a layered wall of 768 bit encryption and a new ip address. But what if we wanted to send email in the same manner? Can we send it under SSH2 Technology? You bet we can!

Since we will be sending email out under esmpts, this article will focus on client based email instead of web based http email. Our SSH2 server will be the one actually sending your messages. For those of you familiar with the Putty program, you will understand what I am talking about in the next few paragraphs. For those of you not familiar and those of you that have never used SSH2, this will be a learning experience for you.

As we created a specific surfing port on our local computer for normal web surfing, port 1500 for those of you that are clients of mine, we can create a new port in Putty for email. Under the same profile name, where you previously entered the other ports, all we have to do is create a new port now. We will use our local port 26 and the remote port 25 for this example. You can actually use any port not in use already by your operating system but I will keep it simple for this article and try not to get too technical.

For this article, I will use Mozilla's Thunderbird as our client based email program. This is the program I use every day and I could not think of a better or highly scalable email client that supports everything I want it to. Thunderbird is absolutely free and has no cost associated with it. It is produced by the same makers as Fire Fox is. If you have trust in your heart for Fire Fox, then you'll love Thunderbird just as much. When downloading Thunderbird, its a good idea to grad the add-on "Enigmail" as this will provide our email encryption. (I will explain this in more detail in another article.)

Now that we have Thunderbird with the "Enigmail" add-on, we set up our email accounts as normal. Once in the configuration settings, we need to take a good look at "Outgoing Server SMTP" as this is where we set up the specific port as defined in the Putty program. In Putty, we added port 26 as our outgoing smtp port. Now, we must tell Thunderbird to use this port. Our server name is "localhost" and our port is 26. When these settings are put in, be sure to select TLS or SSL as the secure connection method. There is no need to use the other boxes that ask for authentication because server authentication is provided by the Putty program itself.

Now we are ready. When you have written and addressed your email and are ready to send it, go ahead. The Thunderbird client will transfer your email to the Putty specified port and request the remote server to pick it up. A connection is made and a security certificate from the remote server is presented to you. You must select "Accept This Certificate" so the server can create a secure connection to you. Once the certificate has been accepted, the secure connection is established and the email is accepted and sent. Since you used the localhost protocol, your real ip address is not included in the outgoing email. What is added in place of your real ip address is the localhost ip address of 192.168.1.2 which makes it impossible to trace the real senders ip address. The servers ip address is included in the headers though. This has to be there in case the email bounces back or the email cannot be delivered to the recipient. In that case, it bounces back to the sender's account saying "Undeliverable Email" or something to that effect and it tells you why it could not be delivered.

How's that for anonymity? I will write an article on using Enigmail and encryption within Thunderbird shortly.
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