Title            Securing Thunderbird email with OpenPGP
Date            2005.01.10 7:00
Author            Daniel Rubio
Topic            
http://software.newsforge.com/article.pl?sid=05/01/06/1557216

Email is commonly used in business today, yet only a small percentage of
users take the time to guarantee their email is sent in a secure and
confidential manner. If you're not part of that elite group, read on to
learn how to setup OpenPGP with the Mozilla Thunderbird mail component.

OpenPGP is a patent-free encryption scheme based on the same security
architecture as the commercial version of PGP, which has been available
since the early 90's. Thunderbird uses OpenPGP through the GnuPG
implementation -- developed by the Free Software Foundation -- for
interpreting and sending digitally signed and encrypted messages.

The first step in setting up Thunderbird with OpenPGP is to have GnuPG
installed on your system. The majority of Linux distros include this package
in their official release. Query for it on your system be entering the
following command: which gpg. If it's not found, or if you are using a
different operating system like Windows or MAC, then you will need to
download and install it.

The cornerstone to GnuPG's security -- and hence OpenPGP -- are key pairs.
Made up of a private and a public key, they are used throughout the security
loop by both sender and receiver, as we will observe in the rest of this
article.

To create a key pair using GnuPG, enter gpg --gen-key at the command line.
You will be prompted with a series of questions, such as the encryption
algorithm, key size -- which will reflect the encryption strength -- your
name, email address and a passphrase. Using the default answers is generally
sufficient. Just keep in mind that your passphrase will be your means to
access the key pair and confirm your identity locally. The actual key pairs
you generate will be stored in your user home directory under .gnupg if you
are using Linux, or under another specific GnuPG directory if you are using
Windows or MAC.

Once you have created your key pair, it's time to configure Thunderbird to
use them. In order to simplify the deployment of OpenPGP within Thunderbird,
a special plug-in named Enigmail can be used. Download this plug-in and
install it using the Tools--Extensions menu in Thunderbird. Then exit
Thunderbird and restart it. You will then be prompted for the initial
configuration settings.

The first task is setting the path in which GnuPG is installed. By default
this is /usr/bin/pgp on Linux. You will also be able to indicate special
flags to be used when invoking GnuPG, and to allow Thunderbird to recall
your passphrase for a certain length of time each session. This to avoid
re-typing the security credential every time you send an encrypted -- or a
digitally signed -- message. The other tabs provided on this initial windows
setup offer more advanced features, which we will not explore now. You can
modify them later from the Enigmail--Preferences menu.

We are now ready to send an email using OpenPGP. Compose a message and
select the OpenPGP icon atop the composer, a pop-up window will offer you
three choices: Sign Message, Encrypt Message & Use PGP/MIME. We will explore
the first two in the following paragraphs.

The simplest and most non-intrusive manner of assuring security is signing
your messages. This process guarantees that even if some users are
ill-equipped to fulfill their part of the security chain -- as we will
further outline -- you can guarantee integrity to others.

Signing a message places a fingerprint onto the body of your message -- an
actual text fragment -- which is generated from your private key. This
fingerprint can later be correlated by the recipient of the message, using
the public key of your key pair. This is why you make the public key readily
available. In the event someone tries to forge a signed message pretending
to be you, or tampers with your mail enroute, your recipient need to perform
a check against your public key to detect such activity.

Enigmail checks signed messages automatically upon receipt, and informs you
if the signature doesn't match the public key. The reason signing a message
is so non-intrusive, is that you don't force all your recipients to verify
the signature. If the recipients wish to do so, they can obtain your public
key and verify that the message is authentic. If they don't wish to do so,
the message can still be read.

The actual publication of your public key can be done several ways. The
simplest being to send it -- the public key -- to your contacts. You can
also publish your public key information on a centralized database, like
Keyserver.net . This allows your contacts to obtain the key themselves,
without having to send it to each of them individually. You can use GnuPG or
Enigmail to create a text version of your public key. In Enigmail, select
the OpenPGP Key Management option for exporting it to a text file. In GnuPG
you can use the following command line sequence : gpg --armor --export
[EMAIL PROTECTED], where [EMAIL PROTECTED] is the email used for creating the 
key
pair.

Since being able to correlate signed messages with public OpenPGP keys is
part of receiving secure messages, Enigmail also offers the possibility to
import all the public keys of your contacts. You'll need to have the public
key of anyone you wish to send encrypted messages.

If you opt to encrypt a message with OpenPGP, you will be prompted through a
pop-up window to select the public key of your intended recipient. Once it
has been encrypted with a public key, only the holder of the complementary
private key can read it. Contrary to signing a message, encrypting an email
requires that both parties be involved in the security process.

Once you are comfortable using these OpenPGP alternatives with Thunderbird,
you can set default behaviours from the Enigmail-Preferences menu. If you
administer multiple email accounts, each will require its own key pair,
since the email address is a part of the basis for the generation of your
keys.

If you use Thunderbird as your email client, hopefully you will now begin
using OpenPGP as described here to ensure yourself a more secure email
environment.

Daniel Rubio is the principal consultant at Osmosis Latina, a firm
specializing in Enterprise Software development, training and consulting
based in Mexico.

Links

   1. "OpenPGP" - http://www.openpgp.org/
   2. "Mozilla Thunderbird" - http://www.mozilla.org/projects/thunderbird/
   3. " GnuPG " - http://www.gnupg.org/
   4. " Enigmail " - http://enigmail.mozdev.org/
   5. " Keyserver.net " - http://www.keyserver.net/en/



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