Melvin Rivera has written a nice tutorial for Mail users explaining how to get a digital certificate from Thawte and how to use Mail.app’s digital signature and encryption features.

He outlines the process for creating an account at Thawte and requesting a certificate and then installing it.

Further sections follow on the difference between a digitally signed and an encrypted message, and how to use them.

It’s interesting to compare Melvin’s take on secure email in Mail.app with Matt Haughey’s experience , which wasn’t so positive.

Melvin thinks it works well and is a good tool to have in your email armoury:

Other than the process of going though an external website for obtaining a certificate, Mail’s integration of signed and encrypted messages is seamless. It’s a great feature that is just hidden until needed. Making the user experience simple and clean. And there’s nothing like discovering a great new feature on an App you’ve been using for a long time now.

Joar Winfor has also produced a more detailed walkthrough for secure email in Mail.app, but more detail is not always good for everyone.thawte, certificate, X.509, digital signatures, encryption, secure email, security, mail.app, apple mail

Matt Haughey (his wikipedia entry kewl!) has written a great piece on the frustrations of trying to set up and use encryption in Mail.app.

He suggests that,

Encryption seems to lie somewhere between privacy, security, and a mountain of engineering acronyms and standards. Unfortunately for regular people, most of these systems are overbuilt and the process is so painful that I would argue it barely even functions.

He describes his experience of following Joar Winfor’s excellent tutorial on setting up encryption in Apple Mail, drawing attention to the frustrations of the whole process.

He also makes a few suggestions on how some usability could be introduced. A great read.encryption, mail.app, Apple Mail, usability, user friendly, certificates, Thawte, just too bloody difficult

As part of my steep learning curve about encrypted mail in Apple Mail I came across a howto on the O’Reilly mac devcenter, that explains the proccess for requesting a certificate from Thawte.

It says that you can’t use Safari to get your certificate. Probably you couldn’t when this howto was written in January 2004.

But you can now. I just did. There’s no option to select Safari from the browser options in Thawte’s request process, but selecting “Netspace Communicator or Messenger” works.

Then click on the URL in the email from Thawte announcing that your certificate has been issued. Safari will happily download it and automatically add it to your Keychain.

So spare yourself the hassle of mucking around with another browser.

You might also like to follow the guide recommended by Andreas Amann in the comments: http://www.joar.com/certificates/.