[PRIVACY] Guide: Encrypting Your Email Messages

Friday, August 16, 2013 @ 11:24 pm

This guide will show you how to securely encrypt and send messages to and from your friends/family with reasonable belief no one else would be able to intercept your messages. This tutorial uses Mailvelope and Gmail.

How It Works:

  1. You use one password to generate two keys: a public key and a private key
  2. You send/share your public key (NEVER private key) with contacts
  3. Vice-versa, contacts send you their public key to import (similar to adding them into your address book)
  4. You encrypt the message to your contact(s) with their public key
  5. They receive it
  6. They click on it and type in their passphrase
  7. The message is decrypted and they can read it

The above steps are made easy with an extension called Mailvelope. It works well in Chrome, and it is still in heavy development for Firefox.

Requirements:

  • An email account with Gmail, GMX, Yahoo, or Outlook
  • The Mailvelope extension (Chrome | Firefox: still under development and buggy)

Benefits:

  • No need to migrate to another email service
  • Email hosts cannot analyze the contents of your messages to generate relevant ads
  • Keep sensitive email messages secure while in transit and from the email host

Drawbacks:

  • Difficulty in searching for the specific message due to encryption (can be avoided by using descriptive but vague subject lines)
  • Low adoption/usage rates, translating into few people you are able to send/receive encrypted messages with (but we can change that today!)
  • You likely won’t be able to read encrypted messages easily when you’re on a different computer (e.g. cybercafe)

Installing and Setting Up Mailvelope:

  1. Install the Mailvelope extension (Chrome | Firefox: still under development and buggy)
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  2. Click on the Mailvelope icon in your toolbar and click on Options
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  3. You will see the below page:
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  4. Click on Generate Key
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  5. Fill out your name (recommended to abbreviate your name or use a nickname), email, click on Advanced and select 4096 for the Key size, and enter a secure passphrase (mix of letters, numbers, and symbols and at least 16 characters long)
  6. Click on Submit
  7. Click on General
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  8. Tick “Rich Text Editor” if you would like to be able to format your message, insert links and/or images
  9. For “Primary Private Key“, select the key you generated in step 6.
  10. Click Save
  11. Click on Security in the navigation menu
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  12. Change the three character Char Code to something of your choice
  13. Select a custom color
  14. Click Save
  15. Click on Display Keys to view your generated key:
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  16. To export your public key (to share with your family/friends to be able to send encrypted messages to you), click on your key and click on the Export button:
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  17. Select and copy everything inside the textbox to your clipboard. You could also save it as a file.8-16-2013 10-20-18 PM

Importing Public Keys:

In order to send encrypted messages to contacts, you have to import their public key. Here’s my public key!

  1. Copy and paste the entire public key to your clipboard:
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  2. Click on Submit

Sending Encrypted Email Messages:

Before you send encrypted email messages, make sure you have imported your contact’s public key in the steps above!

  1. Log into Gmail
  2. Compose a new message
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  3. Note that the notepad + pen icon will fade in. Click on it.
  4. Type in your message:
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  5. Click on the Lock icon when you’re done writing your message
  6. Click on the dropdown menu and #1, select which friend(s) you’d like to send the message to. Then #2, click on “Add“. Repeat for all the contacts you’d like to send the message to.
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  7. When you are done, click on “Ok“. The message will be encrypted:
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  8. Click on “Transfer” to transfer your encrypted message to the Gmail message box:
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  9. Type in the email addresses of the contact(s) you added in step #6 (To, Cc, or Bcc), with a subject line
  10. Send!

Reading Encrypted Messages:

  1. Open an encrypted message from a contact that was signed with your public key
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  2. An envelope with a lock icon will appear over the encrypted message. Click on it.
  3. Type in the password you generated your private and public keys in Installing and Setting Up Mailvelope step #5.
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  4. The message will be decrypted, with your three character code as a watermark to show its authenticity:
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And that’s it! You’re off to the races in terms of secure communication and regaining control over your privacy.

Don’t have anyone to communicate securely with? I’ve posted up my public key here.