Entourage (Microsoft’s email app that comes with Office v.X for Mac OS X) has some great features. The seemingly unlimited criteria and actions for rules (filters) makes managing vast quantities of email a breeze. Other features I particularly appreciate are the ability to link messages to contacts automatically, and to filter messages based on categories in your address book (for example, I keep email addresses I accept direct mail to in a category called Direct Mail OK, and with one filter I can move them into a single mailbox. Much better than creating dozens of individual rules).

But Microsoft giveth and Microsoft taketh away: they sometimes do something so awfully stupid, you wonder if their software’s written by a schizoid programming team. For example, they have both “rules” to filter your incoming email, and “mailing list rules”… to filter your incoming email from a mailing list.

The difference? I’m not sure, really, but some mailing lists aren’t recognized as such, meaning you have to make a regular old rule if you want to filter it anyway!

So why bother with a separate “mailing list rule”?!

Another annoyance is Microsoft’s definition of “preference”. They offer you the “choice,” for example, of turning off the ability to view attached images in the body of your email.

But choosing that preference doesn’t work. How do I know? Because right now I’m looking at porn-spam, with attachments — pictures of naked women showing me how well-shaved they are — right in the body of my email.

Entourage also has an “option” to turn off “complex” html. What its definition of “complex” is I don’t know, because I’m constantly getting spam with color backgrounds, font changes and horizontal rules. I suppose “complex” includes only tables and CSS.

I dislike HTML email because it’s both a significant privacy and security hazard; by sending a “web tag” — an image hosted on a website — anyone can validate your email address: the minute you read the message they know you’re legit. They can also craft HTML that exposes your system to future attacks. Why would anyone want that feature turned on? And if you turn it off, why won’t it be honored?

But suppose I should feel secure that I’ve also turned off the “allow network access when displaying complex html” option, and rely on Microsoft’s stellar track record providing stable, well-designed and secure software.

Seriously though… Entourage has a slew of time-saving features (I haven’t even begun to delve into the calendaring system), but as glitzy as it is, the shortcomings, like the inability to completely turn off html email will probably be the number one reason I run back into the warm, comforting arms of Eudora 5.1b20 for OS x. I just value my privacy and security to0 much to be seduced by the pretty baubles.