How To Encrypt Your Email & Other Communications

Across the globe, over 2 billion people are sending over 144 billion emails a day, and nearly every single one of those messages can easily be intercepted by someone other than the recipient. Even without the NSA spying on us, the insecurity of the protocol that makes up for so much human communication today, should be of concern to all of us.

Even if you encrypt your own internet connection, if you use Tor, or a VPN for example, once you send an email, the server usually passes that on in plain text, through several routers, eventually finding its way to the server hosting the recipients email account, and then the recipient usually will download or read that message through an unencrypted connection, that also has to pass through numerous routers across the internet. At any point along that path, someone with access to the equipment passing that traffic, can intercept the messages they are passing, and read them. Especially considering that 25% of all email communication is business related, it’s nothing short of insanity that security in this protocol is something that almost nobody stops to think about.

So I was really happy when Barry Hayes posted in the request forum, asking for a How To Anarchist guide to PGP.

First off, good job on the HDD encryption and anonymous browsing articles.

I discovered PGP email encryption a few months ago, and I think it would be good to have a how-to article for those non-techies out there who feel a need to send secure emails.

Thanks,

Buckwheat

Lucky for you, it is possible to encrypt not only your emails, but other communications as well, using PGP. Pretty Good Privacy (PGP) is a data encryption and decryption computer program that provides cryptographic privacy and authentication for data communication. It was created by Phil Zimmermann in 1991, and was later introduced as an internet standard known as OpenPGP, which now makes it available to you, for free, in a variety of ways. There is no known way to decrypt PGP, even the United States Federal Government has not cracked it, or at least, has not acknowledged the ability to do so. Zimmerman was actually investigated for exporting munitions after creating the program, because the United States Government considers encryption this strong, to be a weapon.

There are many ways to use PGP, this guide will be discussing GPG4Win, Microsoft Outlook, and a Chrome plugin called Mailvelope. Like all “How To Anarchist” guides, this guide assumes you have a basic understanding of how to browse the web and handle files. This guide also assumes you are using Windows, but PGP is available for Mac, Linux, Android, and other platforms.

Step 1. Download and Install GPG4Win. The installation is a “Next Next Next” sort of process, so I won’t describe that in detail.

Step 2. Find GPG4Win in your Programs Menu, and open Kleopatra
gpg2

gpg1

Step 3. In Kleopatra, click File, then click New Certificate
gpg3

Step 4. Create a Personal OpenPGP Key Pair
gpg4

Step 5. Enter details for the certificate, and click Next
gpg5

Step 6. Review the details, and click “Create Key”
gpg6

Step 7. Create, and Confirm, a strong passphrase.
gpg7

gpg7a

 

Step 8. Now that your key has been created, let’s create a backup, click “Make a Backup of Your Key Pair”
gpg8

Step 9. Choose a path to store the backup in, and click OK (Maybe you want to put it in the hidden volume of your TrueCrypt file) You don’t want anybody getting their hands on this file, this file in combination with your passphrase, will allow an attacker to decrypt your messages.
gpg9

Step 10. Click File, then click “Export Certificates”
gpg10

Step 11. Choose a location to save the certificate, and click save.

Step 12. The file you just saved is your “Public Key” send this file to people who you want to communicate securely with. When they send you a message, they will need this to encrypt the message for your eyes only. You can give anybody this key, you can even post it publicly on your website for all to see.

Step 13. Get certificates from other people who you want to send secure messages to, and import them into Kleopatra by Import Certificates.

Now that you have your certificates, you have a number of options available to you.

You can encrypt any message for anything, gmail, instant messenger, even facebook. For this example, I’m going to send my Facebook alter ego an encrypted message, then decrypt it.

Step 1. Open Notepad, it should be in your programs menu under accessories. Any text editor will do, and theoretically you could even begin typing your message on facebook, but, facebook, gmail, and other web applications read your text as you type it, sometimes because they are just nosey, in other cases because they are saving drafts.
gpg17

Step 2. Type your message into notepad
gpg18

Step 3. Press CTRL+A to Select All, Then CTRL+C To copy the message to the clipboard
gpg19

 

Step 4. Find the Kleopatra icon in the system tray, right click on it, and in the resulting menu, go to clipboard, and click encrypt
gpg20

Step 5. Click Add Recipient, Choose one from your list of certificates, click OK, then click Next
gpg21

Step 6. You will be shown a message informing you that the encryption has been completed, click OK.
gpg22

Step 7. Open a messaging dialog with your friend on facebook, and press CTRL+V To paste the encrypted message to your friend
gpg23

Step 8. When you receive the encrypted message, drag your mouse to highlight it, and press CTRL+C to copy it to the clipboard.
gpg24

Step 9. Right click Kleopatra in the system tray again, go to clipboard, and click Decrypt/Verify
gpg25

Step 10. Enter your passphrase.
gpg26

Step 11. Kleopatra will inform you that the message has been copied to your clipboard, click finish, then go back to notepad and press CTRL+V to paste the decrypted message and read it.
gpg27

gpg18

 

You can use this method for any communications method you desire, facebook, webmail, instant messenger, anything that transfers text, that allows you to use a clipboard to copy and paste, can be encrypted and decrypted with Kleopatra.

 

If you have Microsoft Outlook installed, an extension for Outlook was included in your GPG4Win installation.

Using GPG4Win with Microsoft Outlook.

Step 1. Create a new email in Microsoft Outlook.

Step 2. Enter the address of the person you wish to send the message to (In this instance, I’m going to send myself an email for testing purposes, you should do the same), enter the subject (Subject will be readable by anyone who might intercept the message, nothing sensitive in the subject line), and enter your message.

Step 3. You should see a tab near the top of your new message window that says “GpgOL” Click on it.

Step 4. Click Encrypt
gpg11

Step 5. Select the certificate of your recipient, if the recipient is in your contacts, it may already be selected, in which case, click OK.
gpg12

Step 6. Your message is now encrypted, click send. It should look something like this.
gpg13

Step 7. When you receive the encrypted message, double click it to open it, Click on the GpgOL tab in the window, and click Decrypt
gpg14

Step 8. Enter your passphrase, and click OK.
gpg15

Step 9. Read your decrypted message.
gpg16

 

While writing this article, I found a really neat browser plugin for Google Chrome, called Mailvelope. There is a version in development for firefox as well, but I will just cover chrome for now.

Mailvelope is a browser plugin that makes using PGP in your webmail applications like GMail, Hotmail, and Yahoo! very simple.

Step 1. Install Mailvelope from the Chrome Web Store.

Step 2. In Chrome, find the icon for Mailvelope and click on it.
gpg28

Step 3. Click Options
gpg29

Step 4. Click “Import Keys”
gpg30

Step 5. In Kleopatra, click File, and click Export Secret Keys
gpg31

Step 6. Select a location, and name for the file ending in .asc, check “ASCII Armor” and click OK
gpg34

gpg33

Step 7. Back in Mailvelope options, click Choose File, find the key you just exported, and click submit
gpg35

Step 8. Sign into gmail, and create a new message addressed to yourself, you will notice a new icon in the message body, click on it.
gpg36

Step 9. A new compose window pops up, enter your message into it, and then click the lock icon to the right.
gpg37

Step 10. Select your recipients certificate, then click Add, then click OK
gpg39

Step 11. Click Transfer, and the encrypted message will be pasted into the body of the message, click OK to send.

Step 12. When you receive the encrypted message, the Mailvelope icon will appear on top of it, click on it
gpg40

Step 13. Enter your passphrase, and click OK
gpg41

Step 14. Read your decrypted message.
gpg42

 

That’s pretty much it for this article. PGP is powerful encryption that is open source and available to anybody. If this guide confused you at all, let me know in the comments below, or in the forum, and I’ll try to clarify the confusion. Once you’ve done this a couple of times, it’s very easy to do, and it will make your communications impossible to intercept. That not only makes your life more secure, it makes the world a better place.

Feel free to add my public key to your address books, and send me encrypted messages anywhere, and be sure to share this article with your friends and on social networks. The more widely used this technology is, the less incriminating it looks, and of course, you can only exchange encrypted messages with someone who has set this up already and given you their public key.

—–BEGIN PGP PUBLIC KEY BLOCK—–
Version: OpenPGP.js v.1.20130820
Comment: http://openpgpjs.org
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=HJAf
—–END PGP PUBLIC KEY BLOCK—–

 You may also be interested in encrypting your files.