Encrypting your Email Communications using
PGP
If you are watching this tutorial as part of the conference
materials, the software is on a separate CD.
Alternately, you can obtain the software at the following URLs:
www.gpgtools.org (Mac)
www.gpg4win.org (Windows)
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There are many technologies, techniques and tools. Each is intended to address a different problem.
We will address the challenge of communicating privately via email using Public Key Encryption.
If you grasp the concept of how Public Key Encryption works, developing additional security practices become much simpler.
“Encryption works. Properly implemented strong crypto systems are
one of the few things that you can rely on.”
- Edward Snowden
VERY BRIEF primer on encryption as it applies to email
Configure your laptop and email software to send and receive encrypted email
Windows Mac
Outlook (2010) Apple Mail
Confidentiality – Preventing unwanted disclosure of
information
Integrity – Ensuring that content as well as identity
can be trusted.
Availability – Ensuring that data and systems are
available when expected.
Encryption is the process of encoding information so that only authorized parties can read it.
Shared Secret / Symmetric Key
Both the sender and the receiver use the same encryption key. Works very well, but it requires the sender and receiver to be able securely share the key ahead of time. That is a problem in the world of email.
Public Key / Private Key
A different key is used to decode than to encode a message. (Wait ... I’ll explain). This is what is used to encrypt email.
The enabling technology is commonly known as PGP or GPG
During setup, two keys are generated, a public key and a private key. The keys are mathematically related, but one cannot be
used to derive the other.
What is encrypted with one key can be decrypted with the other. What is encrypted with one key CANNOT be decrypted by itself.
So here is how it works ... The public key is distributed far and wide to any and all. The
private key is a closely guarded secret.
Public Keys are used to encrypt. Private Keys are used to decrypt
Make sure your recipient has PGP / GPG ... and knows how to use it! Make sure you have the recipient’s public key.
Type your message in your mail program and click encrypt.
Select the recipients Public Key to use for encryption and click Send
Assume you have my pubic key and that you know it belongs to me Assume that you know with a high degree of confidence that I have closely guarded my private key
I can “fingerprint” my message with my private key. Using my public key in your possession, you can verify the fingerprint.
Since the fingerprint is unique to my private key, you know the message came from me
What is Signing ?
Signing is the act of digitally certifying that an email you have sent did in fact come from you. It is comparable to the use of a signet and a seal.
Mac
PC
Run gpg4win on thumb drive
Under Choose Components, check all except
GpgOL
Claws-Mail
Complete Installation (May require reboot) Under Programs, confirm new folder
Ggp4Win and launch program Kleopatra
Run GPG Suite from directory Accept all default settings and install Close to finish installation
In Spotlight type and run GPG Keychain Access
Next - Create Keys ...
Mac
PC
In Kleopatra click File | New Certificate
Select Create a personal OpenPGP key pair
Enter name and email address. Under Comment, enter “private” or “work” Click Advanced Settings. Review and change as necessary (expiration date). Click Next and Create Key.
Enter passphrase and repeat. DO NOT FORGET. (I recommend a sentence). Click Finish
Launch GPG Keychain Access Click New
Enter name and email address. Open
Advanced Options in the Comment field, enter “private” or “work”
Set Expiration if desired. Leave other default settings. Click Generate Key Enter passphrase and repeat. DO NOT FORGET. (I recommend a sentence). Click Finish
Next - Configure Email ...
Outlook
Install Outlook GPG Plug-in - gpg40_setup.exe Accept default settings
Thunderbird
Install Thunderbird plug-in nameed Enigmail by clicking Tools | Add-ons and search for add-in Enigmail
Apple Mail
No configuration necessary
(Note This is trial software)
Next - Distribute Public Keys
Mac
PC
Open GPG Keychain AccessRight-click your key and hit Export
CLEAR THE BOX THAT SAYS Allow Secret Key Export (IMPORTANT)
Save the file to your desktop and email as an attachment to:
Open Kleopatra
Select your certificate and click Export Certificates
Save the file to your desktop and email as an attachment to:
You will receive an automatic response from
[email protected] with our Public Key attached. Save that file to your desktop immediately.
Distribute Public Keys
Remember: You need “my” public key to send me an encrypted email. My public key (that you received from my automatic response) is my “lock” that I send you. I have the key to unlock it. You need to put my public key in your “keychain”
Mac
PC
Open GPG Keychain Access Click Import and select the file saved on your desktop named caseyconfpublickey
Click Open
Open Kleopatra
Click Import Certificates and select the file saved on your
desktop named
caseyconfpublickey Click Open
Mac Apple Mail
PC Outlook
Launch Apple Mail
Click Compose New Message compose a test email to
caseyconference. [email protected]
Click the “lock” icon to make sure it is locked. Make sure there is a
checkmark in the “seal” icon.
Click Send. Enter your PGP pass phrase from earlier.
Launch Outlook. If asked for gpg4o settings, accept default.
compose a test email to caseyconference. [email protected]
Ensure there is a checkbox in both Encrypt and Sign.
Click Send. Enter your PGP pass phrase from earlier
We will respond with an encrypted and signed email from [email protected]
You encrypt a message with another party’s public key You decrypt a message with your own private key You sign a message with your own private key
You verify a signature with another party’s public key
Does the whole email get encrypted? NO What if I want to encrypt to many recipients? How about GMail via a browser?
What if I lose my key or my computer crashes? iPad / iPhone: openGP and iPGMail