Entourage Is the Big Pothole on the Road to the Mac

I locked it in a drawer. I left it in the lab. I tried to give it back to IT. But at the end of the day, I resurrected my old Windows laptop so I could run Outlook to get my e-mail and wouldn't have to use Entourage

In my ongoing quest to “go Mac,” e-mail has been a real sticking point. I have found Entourage unusable for day-to-day work, and so have had to come up with some ways around it.

Using Parallels on my Mac mini worked OK, but if I were in a real enterprise setting, that would be a fair amount of licensing.

I tried using Outlook Web Access. When accessing OWA from the Safari 4 public beta (which I like a lot) or Firefox 3.0.10 from Mac OS X running on my mini, I get the crippled Outlook Web interface. No search, no rule creation, no drag and drop to create a new contact (also not available in IE). Basically, OWA in a non-IE browser is a read and write experience that is not sufficiently capable for daily work use.

OWA really works well only from an Internet Explorer 8 browser instance. And that means back to Parallels or VMware Fusion and running a Windows guest on my Mac. After looking around, my only real hope is Snow Leopard and its promised integration with Microsoft Exchange.

I know users who redirect their Exchange mail to Gmail. In an unregulated business with minimal IT resources, that seems to work. It would probably even work for me if I wasn't so old-fashioned. I still use my Ziff Davis e-mail address to get quick access to the sources I use on a daily basis. 

Since I don't want to change my work e-mail address and I use a Mac for my daily work, I really felt up against the wall. And that's why I brought my trusty Lenovo ThinkPad X31 out of retirement to serve as my e-mail terminal. The Windows licenses are already paid for. The device has enough horsepower (really pony power, at this point in its life) to run Outlook. And even though I have an Apple Cinema Display, I do like using the laptop for my e-mail, leaving more room for applications on my Mac desktop system.

Why am I going to all this trouble?

Entourage is a second-class e-mail client. Since I've already griped about it, I'll leave well enough alone except to say this: I get a lot of e-mail. Some e-mail is more important to me than other e-mail. In fact, some e-mail is so important that I want to see it before any other e-mail in my in-box.

For example, e-mail from my eWEEK colleagues is routed, via an Exchange rule, to a folder called "00 EWEEK," so that the folder is always at the top of my list. I also create rules on a temporary basis so that e-mail messages pertaining to a product that I'm actively testing get shunted into "0000 Active Test," and e-mail messages from the sources that I've developed over the years get put into "0000 Active Priority."

E-mail destined for Active Test changes all the time. The Active Priority list changes more slowly, but it does change. These rules have worked well for me over the years, and Entourage’s inability to play by these rules is what pushed me back to the PC for e-mail.

All of this is why I am so anxious to see Snow Leopard in action. I'm hoping that the next major release of the Mac OS X operating system will yield the full-fledged e-mail integration experience that I must have to get my work done on a Mac.

Now, I'm new enough to the Mac-Windows war zone that I don't fully know whether it’s Apple or Microsoft that has the power to make my dream come true.

I'm starting to care at this point because I really like not worrying (too) much about the security of my Mac mini. While I was working on this story, my Windows system kicked off a virus scan (as it does every Wednesday at 2 p.m.). While the scan was grinding away—chewing up CPU bandwidth and tripping up disk performance—my Mac was placidly letting me do all the productive work I could desire, except easily use my e-mail.

During the "dark time," as I call my weekly anti-virus check, I use OWA. I'd like to see that experience significantly improved for non-IE browsers—again, so I can use it from Safari or Firefox with all the features I'm used to getting if I use IE. For full-fledged enterprise adoption of the Mac, the e-mail hurdle is a very real barrier.