Usability. Despite my comments above about configurability, I have to admit that Outlook’s functionality is superb. As much as I like Thunderbird and others, their user interfaces pale in comparison. I’ve tried dozens of different mailers on Windows, Linux, and OS X, and I’ve yet to find a user interface like Outlook. While some people don’t like the “kitchen sink” approach to having so many things embedded in one application, I always found the interface to be intuitive and easy to get along with—at least, when things worked properly.

Related Articles
Mozilla Firefox vs. Internet Explorer: Which is Safer?

Is the Mac Really More Secure than Windows?

Mac vs. Linux: Which is More Secure?

The Emerging Dell-Linux-Apple War

FREE IT Management Newsletters

But wait, you say, you thought this was a security comparison. It (still) is. I’m a firm believer that software should be easy to use to include configuration of security features and such.

Having said that, it’s been my observation that Outlook’s user interface has been the victim of “creeping featurism” over the years, and some configuration attributes and such can be obfuscated in layers of menus. Still, kudos are due.

Qualitative score: Outlook gets an A- while Thunderbird gets a C.

The other guys. Ok, I said that I’m comparing Outlook against its competition, but that I’d stick primarily with Thunderbird. What about the security of the other guys? Well, if you’re serious about email security, you’ll use a simple textual mailer that doesn’t know HTML from its ASCII. Elm, Mutt, and Berkeley Mail come to mind. Of course, they all fail the usability test miserably in my view, but in terms of security, they’re unbeatable.

The vast majority of email borne security woes stem from “rich” context like HTML, embedded scripts, and attachments. Since many of these “dumb” mailers don’t know how to interpret these things, they’re quite immune to such poxes.

Qualitative score: Outlook gets an F while the other guys get an A+.

So, it’s not so easy to compare security of emailers. Note that I’ve completely ignored the ability to plug into proprietary mail servers such as Microsoft’s Exchange. I’ve kept my comparisons principally to the user end and have assumed open standards on the back end. I’ve also not talked about integration with security products and capabilities like PGP and S/MIME. Most enterprise grade emailers can handle both of these admirably these days. We’ll address these things in more detail in a future column.

For me, I’m going to stick with anything but Outlook for email for the reasons I’ve cited above. I’m a big believer in Apple’s Mail.app mailer, coupled with Apple’s other Outlook-like apps like iCal and Address Book. I’d still like to see more security features there, however. Let’s hope Leopard brings us Mac users some of this.