How to Encrypt Microsoft Outlook 2003 Using TrueCrypt
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E-mail is one of those bogeymen, especially for those who desire true security in their communications. The problem is that 90% of users don’t use any sort of protection on their e-mails. It’s — to use the old example — as if we were sending each other messages using postcards rather than letters sealed in an envelope. Imagine your bank or, even worse, your mother sending you a letter that everyone who cared to could read! Well, that’s e-mail. And that doesn’t confine itself to your e-mail server or the connection between it and your computer. If anyone knows how and where to look, your computer’s e-mail is just as visible to the world.
Those who really need to protect themselves will have gotten themselves secure e-mail accounts like Hush Mail or some other corporate encrypted e-mail. But for those of us who need an extra level of protection or are simply paranoiacs (like me), the data is sitting on your machine for all the world to see.
So, what will release me, poor soul, from this scourge of e-mail that is open to anyone who sits down at my computer screen or hacks through my oh-so-inadequate security? The answer is encryption! And the beauty of this is that good encryption is available for free via TrueCrypt.
I use Microsoft Outlook 2003 for my e-mail communications and so figured out a way to make it work with TrueCrypt to allow for a simple way of keeping my data safe. Yes, Outlook will password-encrypt your PST files, but if you have them stored in your keychain (like I do) anyone sitting down at your machine and starting up Outlook will be able to read them. This will make it much more difficult for them, provided you dismount your TrueCrypt drive when you’re done e-mailing!
Please be advised that this procedure will not work with Outlook Express. You must be running the full version of Microsoft Outlook! Thunderbird can be made to do similar things, if you prefer that, but that is beyond the scope of this article.
I am going to assume that you have some level of experience in working with Windows XP, especially when it comes to copying files or looking at hidden folders. For those of you who are beginners, I will recommend not doing this without the help of a more experienced friend, as you could conceivably break something in the process.
In order to do this we will have to go through five steps:
- We’ll download and install the necessary software.
- We’ll create a TrueCrypt volume to place your Outlook.pst file in.
- We’ll mount the TrueCrypt volume and move your Outlook.pst file to it.
- We’ll reconfigure Outlook to look for the Outlook.pst file in the encrypted volume.
- We’ll use my script to create icons to quickly mount and dismount the encrypted volume and start Outlook at the appropriate time.
Now, let us begin.
Step 1: Download and Install the Necessary Software
As you should already have Microsoft Outlook installed and in use at this time, all you will need to get yourself is TrueCrypt. Download the latest version from http://www.truecrypt.org . I will go through this process using TrueCrypt 4.3. The newer versions may look slightly different that what I will use, but the idea is the same.
I am going to assume you know how to open a ZIP file and that you will be able to run the installer contained in it and so will skip down to the other program, or more precisely, script that I will recommend you download. This is a little VBScript script that I wrote which will generate two other VBScript scripts that will automatically mount and dismount your encrypted e-mail drive. It is available from the link below.
 Download the VBScript to Generate TrueCrypt/Microsoft Outlook 2003 Mount
Format: ZIP Archive | File Name: gtcscript.zip | Size: 5 KB
URL: http://www.hawke-ai.com/dl/dlcontrol.php?f=gtcscript
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