I finally upgraded to Microsoft Office 2004. My favorite new feature that is totally overdue is the implementation of S/MIME in Entourage. Here’s some Instructions on setting up Entourage for S/MIME, but it’s really pretty easy to figure out. Using the Safari browser, which now supports key generation in Panther, I went to the Thawte website and requested a new certificate for my email address. Once the certificate was approved and retrieved, I simply selected the new key in the Security tab within the Edit Account dialog for both signing and encrypting messages. To sign or encrypt a message, choose the desired function from Message > Security, or from the Security menu on the Options button. Or just choose to sign and/or encrypt all messages by default, although to encrypt you need to have the recipient’s key on your machine.
Secure email via S/MIME is also available in Apple Mail and Mozilla-based email clients such as the Mozilla suite, Netscape, and Thunderbird. So Mac OS X users have options out there for the choice of email client. And on Windows, S/MIME is widely interoperable with Outlook and Outlook Express, and just about all platforms are supported by one or more Mozilla-based products. For years, Mac users were stuck with Netscape 4, and Mac OS X users had to wait until S/MIME finally appeared in Mozilla, which in it’s early iterations was pretty sketchy. All this has been a long time coming – it’s nice to finally see a well-rounded suite of S/MIME-compatible email clients out there finally.
Update: Just saw Microsoft’s article on message security for Entourage 2004. Good overview of how to sign and encrypt messages with Entourage.