How to Send an Anonymous Email Message

A remailer is one way to send anonymous emails

A woman holding up a blank sheet of paper.
  Jiraporn Gurle / EyeEm / Getty Images

You might send anonymous emails for any number of reasons, like to express an opinion to an unreceptive recipient, to avoid embarrassment, or to maintain distance from the topic at hand.

One way to write an email anonymously is to use a remailer. After you send the message, the email is ultimately sent to the final recipient and removes all traces to you, the original sender.

Because the remailer does know where the message came from, as well as the recipient (plus the content of your message, if it is not encrypted), the anonymity provided by employing only 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, because no remailer knows both the sender and the recipient.

There are lots of ways to browse the web anonymously, like with proxy servers and VPNs, but those methods don't necessarily hide your email identity, but instead just your originating IP address.

How to Send an Email Without Revealing Your Identity

We'll be using the GnuPG program in Windows to send an anonymous email. The program works in macOS and Linux, too.

  1. Choose at least two reliable remailers.
    1. Visit this list of Type-I (Cypherpunk) remailers and look for a consistent and recent history of replies by the remailers, preferably sent within four hours.
  2. Install GnuPG on your computer.
  3. Get the remailers' PGP keys.
  4. Send an empty email to the remailer's address with remailer-key in the subject line.
  5. Import into GnuPG the PGP key you receive back from the remailer.
  6. Create a new document in a plain text editor and type :: on the first line.
  7. Type Anon-To: on the next line, followed by the recipient's email address.
  8. Leave one line blank.
  9. Type your message.
  10. Save the file to your Desktop as mail.txt.
  11. Open Command Prompt.
    1. The quickest way to get to Command Prompt in Windows is to use the Run dialog box. Use the WIN+R keys to open the Run dialog box, and enter cmd.
  12. Use the cd command to navigate to your Desktop folder.
    1. Here's an example: cd C:\Users\Jon\Desktop.
  13. Enter gpg -ea -r [last remailer address] mail.txt.
    1. 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, if you want to send an anonymous email through remailer@aarg.net and anon@paranoici.org, you'd type gpg -ea -r anon@paranoici.org mail.txt.
  1. If GnuPG asks you to verify that you want to encrypt to an unverified key, type y and hit Enter.
  2. Open mail.txt.asc (the encrypted mail.txt file) in Notepad (or another plain text editor). The file might also be called mail.asc.
  3. Type :: in the first line.
  4. Hit Enter.
  5. Type Anon-To: followed by the email address of the last remailer in your chain.
    1. 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.
    2. To continue our example message, type Anon-To: anon@paranoici.org.
  6. Leave one line blank.
  7. Type :: and hit Enter.
  8. Type Encrypted: PGP.
  9. Make sure there is another empty line before the encrypted message starts.
  10. Save the file as mail.txt again, overwriting the existing file.
  11. Back on the command line, type gpg -ea -r [next but last remailer address] mail.txt.
    1. Replace [next but last remailer address] with the email address of the next but last remailer in your chain.
    2. In our example, this is also the first remailer, remailer@aarg.net, so we type gpg -ea -r remailer@aarg.net mail.txt.
  1. If GnuPG asks you to verify that you want to encrypt to an unverified key, type y and hit Enter.
  2. Type y and press Enter to overwrite the existing mail.asc file.
  3. Open mail.asc in Notepad (or another plain text editor) again.
  4. Add :: at the top, followed by Encrypted: PGP on the next line.
  5. Leave one line blank before the encrypted message starts.
  6. Press Ctrl+A (or Command+A or Alt+A, depending on your OS) to select the complete text.
  7. Use Ctrl+C (or Command+C) to copy the selected text.
  8. Create a new plain text message in your email program or email service.
  9. Address the email to the first remailer in your chain. In our example, that would be remailer@aarg.net.
  10. Go to the message body and hit Ctrl+V (or Command+V) to paste the text.
  11. Send the message.