Has Outlook Become Inlook?

I don’t like Microsoft Exchange Server. I hate to say that, but I can’t get past it, even though I keep trying to like it. Years of helping people with Windows-based servers leads those people to assume that I’m an Exchange expert, so I periodically blow up my existing email-server software and install Exchange so that I can stay experienced enough to answer at least a few Exchange questions. But I’m soon reminded that Exchange is—in my opinion—a demanding hothouse flower that requires a full-time email administrator to run properly. And unfortunately, I’m the techiest person in my small company, and I can’t spend all my time on my email server. So I end up getting rid of Exchange and replacing it with something simpler, and all’s well until I get the Exchange itch again. (The early Exchange 12 stuff I’ve seen leads me to believe that I might return to the Exchange world in 2007, but we’ll see.)

Anyway, my Exchange 2003 server recently melted down, so I installed some inexpensive Windows-based server software that runs SMTP, POP3, IMAP4, HTTPMail and so on. That’s when I noticed how Microsoft-solipsistic Outlook has become. You see, installing Exchange 2003 led me to replace Outlook 2000 with Outlook 2003. Now, Outlook 2003 runs very well with Exchange 2003, but it doesn’t impress me all that much when acting as an SMTP, POP, IMAP or HTTPMail client.

Don’t get me wrong: Outlook 2003 works as one of those clients. It can receive and send email. But heck, Outlook Express can do that. No, I mean that Outlook 2003 lacks a number of Outlook 2000’s messaging capabilities, and I find that troubling. (I’ve never used Outlook XP, so I don’t know how long this has been true.) I used to run Outlook 2000 as a client for a basic SMTP, POP, and IMAP server in what Outlook called Internet Mail Only (IMO) mode, as opposed to Corporate Mode. Corporate Mode really means MAPI client, which means, “You’ve got an Exchange server.”

Although we IMO types were clearly the redheaded stepchildren of the Outlook world, Outlook 2000 was still pretty useful. Despite lacking an Exchange server, I could flag a message as important, something to return to and handle later. I’m not the world’s most organized person, so this was a pretty useful tool. I also liked the ability to filter incoming mail based on things like sender address or text in the subject or message body. It’s amazing how much junk you can automatically delete by just looking for “mortgage” or “Viagra” in the subject line. Outlook 2000 let you do that, but Outlook 2003 just turns up its nose and says, “Hey, buddy, those are server-based rules and there’s only one server I talk to.” Jeez, lighten up, okay?

It was also nice to look at a message in my Inbox and have Outlook tell me, “You replied to this message on this day.” Again, that functionality worked in Outlook 2000 without Exchange. Outlook 2003 seems to require Exchange; otherwise, the feature goes away. Makes you wonder why the software said that I was upgrading from Outlook 2000 to Outlook 2003, rather than downgrading.

Are any of these complaints showstoppers? No, not at all. But they’re blasted irritating, particularly when you look at the price of a copy of Outlook 2003. Are Exchange’s sales so moribund that Microsoft feels the need to convert Outlook 2003 from a fairly powerful email client with a nice calendaring feature—and, most important, the ability to sync with my Palm device—into a shill, a piece of glorified adware that reminds me constantly that I really, really should go back to Exchange if I want the full value for my Outlook buck? Given what I keep hearing about Exchange’s market share, that seems unlikely. And it’s sad that one of Outlook 2003’s most touted new features—the ability to cache messages when offline—doesn’t work in Outlook 2003 when it’s used as an HTTPmail client.

This a wrongheaded move. The fact is, despite all the talk about upcoming versions of Windows and Office, the pace of change in the Windows world has slowed tremendously. The days of new server releases every 12 to 18 months, accompanied by radical improvements, are over. And I know plenty of people who are still using Office 2000 without suffering any noticeable competitive disadvantages. That means it’s easier for those trying to copy Windows (and, of course, here I’m talking about the Linux community) to do so, resulting in competitive products that are feature-comparable without being nearly as restrictive. Basically, I’m saying that Windows just isn’t a fast-moving target anymore, so it’s more easily cloned, which means it’ll see more feature-level competitors. So, now seems like a terrible time for Microsoft to be hobbling Outlook in non-Exchange environments.

But then, I’m basically an optimist. Perhaps this is an aberration. Maybe Microsoft just really, really wants us to upgrade to Outlook 12 when it appears in late 2006 or early 2007. Maybe it’ll be a bit less Exchange-bigoted. I suppose I should go see if I can get on the list for the betas.