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How to Send an Anonymous Email Message

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Heinz Tschabitscher
Do you want to send an email anonymously because, for example, you fear your views might not be appreciated by your boss? When avouching your opinion in public — critically important under more favorable circumstances — is unhealthy, anonymity becomes vital.

Hide Behind Remailers For Anonymity

To send an anonymous email message, you use a remailer, which sends it on to the final recipient and removes all traces to you, the original sender. Since the remailer does know where the message came from and the recipient (as well as the content of your message), too, the anonymity provided by employing one remailer is not airtight.

If you put two or more remailers in a chain and send the message in encrypted form, however, you can reach a very high degree of anonymity since no remailer knows both the sender and the recipient.

Send an Anonymous Email Message

To send an anonymous email message:

  • Choose at least two (currently reliable) remailers.
  • Make sure GnuPG is installed.
  • Make sure you have the remailers' PGP keys.
  • Open Notepad (or Vim, Emacs or any other plain text editor).
  • Type "::" on the first line.
  • Enter "Anon-To: " followed by the recipient's email address.
  • Leave one line blank.
  • Type your message.
  • Save the file to your Desktop as "mail.txt".
  • On Windows,
    • select Run... from the Start menu,
    • type "cmd" and
    • press Enter.
  • On any other platform,
    • open a command prompt.
  • Use "cd" to go to your Desktop directory.
    • On Windows, that's typically something like "cd c:\Documents and Settings\menon\Desktop".
  • Type "gpg -ea -r [last remailer address] mail.txt".
    • Replace [last remailer address] with the email address of the last remailer in your chain. If you chose two, that would be the second.
    • For example, I want to send an anonymous email through remailer@aarg.net and (then) anon@paranoici.org, so I type "gpg -ea -r anon@paranoici.org mail.txt".
  • Hit Enter.
  • If GnuPG asks you to verify that you want to encrypt to an unverified key, type "y" and hit Enter.
  • Open "mail.txt.asc" (the encrypted mail.txt file) in Notepad (or another plain text editor).
    • The file might also be called "mail.asc".
  • Type "::" in the first line.
  • Hit Enter.
  • Type "Anon-To: " followed by the email address of the last remailer in your chain.
    • The next to last remailer needs to send the message to the last remailer. This is also the email address you have just encrypted the message for.
    • To continue my example message, I'd type "Anon-To: anon@paranoici.org".
  • Leave one line blank.
  • Type "::" and hit Enter.
  • Type "Encrypted: PGP".
  • Make sure there is another empty line before the encrypted message starts.
  • Save the file as "mail.txt" again, overwriting the existing file.
  • Back on the command line, type "gpg -ea -r [next but last remailer address] mail.txt".
    • Replace [next but last remailer address] with the email address of the next but last remailer in your chain.
    • In my example, this is also the first remailer, remailer@aarg.net, so I type "gpg -ea -r remailer@aarg.net mail.txt".
  • If GnuPG asks you to verify that you want to encrypt to an unverified key, type "y" and hit Enter.
  • Type "y" and hit Enter to overwrite the exiting "mail.asc" file.
  • Open "mail.asc" in Notepad (or another plain text editor) again.
  • Add "::" at the top, followed by "Encrypted: PGP" on the next line.
  • Leave one line blank before the encrypted message starts.
  • Hit Ctrl-A (or Command-A or Alt-A, depending on your platform) to select the complete text.
  • Hit Ctrl-C (Command-C) to copy the selected text.
  • Create a new plain text message in your email program or email service.
  • Address it to the first remailer in your chain.
    • In my example, that would be "remailer@aarg.net".
  • Go to the message body and hit Ctrl-V (Command-V) to paste the text.
  • Send the message.
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