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Do you think of e-mail as a digital postcard or a signed and sealed letter? If you're not using an encryption tool to send your e-mail, regardless of how you answered that question, your e-mail is essentially a postcard transmitted in plain text and available for anyone on the internet to read.
If you'd like to keep your e-mail, or at least some of your e-mail, from prying eyes, you need to use some sort of encryption. There is a protocol for sending messages in secure format, but since almost no e-mail hosts support it, it isn't yet a very good solution.
At the moment the best solution is to use either PGP (Pretty Good Privacy) or GPG (Gnu Privacy Guard) a similar, but free and open source, encryption scheme.
PGP and GPG both rely on shared keys which means that once you send an encrypted e-mail only those recipients with your shared key can read it.
What you'll need:
<a href="http://www.pgp.com/index.html">PGP</a> or <a href="http://www.gnupg.org/">GPG</a>. Both will work, but PGP is not free or open source.
A plug-in for your e-mail client.
Solutions by client
Apple Mail (OS X 10.4, earlier versions require additional steps)
There's a <a href="http://www.sente.ch/software/GPGMail/English.lproj/GPGMail.html#Download">plug-in available</a> for Apple Mail that utilizes Mail's unofficial plug-in architecture to add GPG/PGP features.
You'll need three components installed: <a href="http://macgpg.sourceforge.net/">GPG</a>, <a href="http://macgpg.sourceforge.net/">GPG KeyChain Access</a>, and the <a href="http://www.sente.ch/software/GPGMail/English.lproj/GPGMail.html#Download">GPG Mail.app plugin</a>. GPG and the Mail plug-in are available as package installers with instructions GPG KeyChain Access is pre-compiled and can be easily dragged to your application folder.
Open GPG Keychain Access and create a private key. This is yours alone, don't share it or your GPG messages will be compromised.
In creating the private key, keychain Assistant also sets up your public key which you can export and share with your friends and associates so they can decrypt your messages.
Now that your Keys are set up, it's time to open Mail.app. Create a new message and you should see a small toolbar just above the message body with options to encrypt and what key to use.
Congratulations, no more postcards for you.
Thunderbird
Thunderbird on all platforms has a plug-in very similar to that of Mail.app. <a href="http://enigmail.mozdev.org/download.html">Enigmail</a> requires Thunderbird 2.0 and GPG 1.4.7 or later.
For Mac users the installation and GPG set mirrors that of Mail.app. For Windows users the process is roughly the same and <a href="http://enigmail.mozdev.org/gpgconf.html">Mozilla has a step-by-step guide</a> that walks you through the process.
Outlook
There is a <a href="http://www3.gdata.de/gpg/">plug-in for Outlook</a> that supports GPG, but unfortunately it's currently limited to a German version. The developers claim an english version is in the works.
Network Associates, the corporation behind PGP, offers a <a href="http://na.pgpstore.com/product.aspx?sku=3118545&section_id=58&culture=en-US">plug-in package solution</a>, but it will set you back a hefty $200.
GMail
If you aren't concerned about encrypting your e-mail messages, consider that most web providers like Yahoo and Google don't just send plain text messages, they actively scan your messages to deliver targeted ads — paranoid yet?
Unfortunately, due to the limitations of web-based interfaces, encrypting messages in GMail is no easy task.
But don't dispair, an industrious Greasemonkey hacker has done the hard work for you. The Greasemonkey script <a href="http://www.langenhoven.com/code/emailencrypt/gmailencrypt.php">GMail Encrypt</a> will work with any browser that supports Greasemonkey to encrypt all your outgoing GMail messages, though as the author admits:
<blockquote>
Due to the fact that Javascript can not handle stupendously large numbers in a timely fashion, even with the BigInt functionality, this encryption is not bulletproof. This routine will conveniently encrypt your emails well enough to prevent your coworker and probably your employer from reading your emails. However, if you decide to annoy somebody working for the NSA then DO NOT be surprised if some bulky guys pull up at your front door in a black SUV.
</blockquote>
The rest
There are a lot more e-mail clients out there than these three and many offer GPG solutions. OpenPGP maintains a <a href="http://openpgp.vie-privee.org/courrier_en.html">list of clients that support GPG</a>.
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