Anonymous Email
Every data packet traveling through the Internet contains information about its sender and its recipient. This applies to email as well as any other network communication. There are several ways to reduce identifying information but no way to remove it completely.
Sending From Throw-away Email Accounts
One option is to use a throw-away email account. This is an account set up at a service like Gmail or Hotmail, used once or twice for anonymous exchange. When signing up for the account, you will need to provide fake information about your name and location. After using the account for a short amount of time, say 24 hours, you should never log in again. If you need to communicate further, then create a new account.
It is very important to keep in mind that these services keep logs of the IP addresses of those using them. If you are sending highly sensitive information, you will need to combine a throw away email account with Tor in order keep your IP address hidden.
If you are not expecting a reply, then an anonymous remailer like AnonEmail or Silentsender may be a useful solution. A remailer is a server that receives messages with instructions on where to send the data and acts as a relay, forwarding it from a generic address without revealing the identity of the original sender. This works best when combined with an email provider like Hushmail or RiseUp who are specially set up for secure email connections.
Both of these methods are useful, but only if you always remember that the intermediary himself knows where the original message came from and can read the messages as they come in. Despite their claims to protect your identity, these services often have user agreements that indicate their right “to disclose to third parties certain registration data about you” or they are suspected to be compromised by secret services. The only way to safely use this technique is to not trust these services at all, and apply extra security measures: send via Tor using a throw-away email address.
If you only need to receive email, services like Mailinator and MintEmail give you an email address that destroys itself after a few hours. When signing up for any account, you should provide fake information about your name and location and protect yourself by using Tor.
Be Careful about what you say!
The content of your message can give away your identity. If you mention details about your life, your geography, social relations or personal appearance, people may be able to determine who is sending the message. Even word choice and style of writing can be used to guess who might be behind anonymous emails.
You should not use the same user name for different accounts or use a name that you are already linked to like a childhood nickname or a favorite book character. You should never use your secret email for normal personal communication. If someone knows your secrets, do not communicate with that person using this email address. If your life depends on it, change your secret email address often as well as between providers.
Finally, once you have your whole email set up to protect your identity, vanity is your worst enemy. You need to avoid being distinct. Do not try to be clever, flamboyant or unique. Even the way you break your paragraphs is valuable data for identification, especially these days when every school essay and blog post you have written is available in the Internet. Powerful organizations can actually use these texts to build up a database that can “fingerprint” writing.