Outlook on the Mac: And they lived happily ever after?

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As everyone in the Mac universe learned after Thursday’s Microsoft MacBU conference call, Entourage is going away, Outlook is coming to the Mac, and everything will now be perfect for all users of Exchange on the Mac. Well, that last part is completely silly, but I’ve seen some reactions that make me think that people honestly think that Outlook on the Mac means Mac users are going to get a 100-percent feature-compatible version of Outlook.

No. You most certainly are not—nor, in fact, were you ever—going to get that. For one, Outlook on Windows still supports versions of Exchange Server going back to at least Exchange 2003 if not earlier. This is because in addition to using Web Services to connect to Exchange 2007 and the upcoming Exchange 2010, Outlook on Windows supports MAPI, or the Messaging API. MAPI support is certainly not the magic spell that all too many people in the Mac world think it is, but it does allow Outlook to connect to a wide range of Exchange versions. This is important as, contrary to what the Exchange team would like, you don’t just upgrade your Exchange version because a new one exists.

While there’s nothing in Thursday’s Microsoft announcement about specific protocol support in Outlook Mac, I would be highly surprised if it will support connecting to Exchange via MAPI. Given how even the Exchange team is deprecating MAPI starting with Exchange 2010, the idea that it would show up in what is essentially a new product to be released in late 2010 makes almost no sense. So it’s safe to assume that Outlook on the Mac will be a Web Services-only client. Not running Exchange 2007 or later? Outlook Mac will be just a big e-mail client that opens .ics files too. Maybe there will be some LDAP access, maybe not. (I’d like to think the Mac BU won’t dump LDAP as a separate protocol, but it’s not out of the question.)

So right there, you’re not matching up with Outlook. Before you pooh-pooh this as not being important, there are a lot of companies that are still on Exchange 2003. It works well for them, so why upgrade?

As for Visual Basic for Applications support in the upcoming version of Outlook, that’s a coin toss at the moment. However, even if Outlook includes VBA, it’s not going to have the OS-level hooks that VBA on Windows gets. It would be an Office-only tool. If you want to interact with the rest of the OS, you’re using AppleScript. If Outlook doesn’t have VBA, then there’s a whole mess ‘o stuff in the Windows version that won’t work on the Mac version. The situation is a bit of a Morton’s Fork—either way, it’s another place where Mac users wind up on the short end.

This isn’t necessarily bad. There are features that the Mac version of Office has right now that don’t exist on the Windows version because it would make no sense whatsoever. The same thing goes for the other direction—you’re not going to see the Windows version of Office build an AppleScript engine just to match the Mac version of Office. The Mac BU isn’t going to code a feature and associated its infrastructure just to fill in a checkbox. In fact, you might prefer certain things like oh, type, to be based on the Mac OS model. (Were I to be a cynical IT admin, I’d lay decent odds that the proposed feature set for the version of Entourage that was going to be in the next version of Office for the Mac and this “brand new exciting version of Outlook” would probably map out pretty close to identical. Would a company change a product name solely to change perception? Oh. Heck. Yeah. But I’d have to be pretty cynical to think that.) I find it fascinating that the same group of users that will scream about how bloated Word is, will insist on bloating Outlook just to match a feature list. But that’s life in the computing world.

However, there’s another side to this: What about people using Entourage with non-Exchange groupware servers? For example, there are two groupware servers that support Entourage directly that run on the Mac—Kerio Mail Server and XC Connect. I don’t know the details of XC Connect’s support, but I know that Kerio supports HTTP-DAV for Entourage, which lets Entourage talk to Kerio like it was an Exchange server. With Outlook on the Mac, (or the just-released Entourage Web Services edition), that won’t work. Kerio will have to support Exchange Web Services to talk to Outlook as anything but a POP/IMAP server. Calendaring will be using .ics files. Joy. Unless Outlook Mac supports MAPI, and those server manufacturers write a Mac-based Web Services connector for a single product. That isn’t released yet.

True, there is CalDAV, which is supported by most groupware servers on the Mac. Apple, Kerio, Zimbra, and Communigate Pro all support CalDAV, and it’s a useful protocol for calendaring. However, we don’t know if Outlook on the Mac will support it, although given Microsoft’s attitude towards CalDAV since its inception—CalDAV? But we have Exchange!—I’m not holding my breath.

So for a certain subset of Mac users in the enterprise, who only talk to Exchange 2007 and up, and need more than what Apple may provide in Snow Leopard or for people who want a unified e-mail/contact/calendar/task client and have no need of group calendaring and only need POP/IMAP/SMTP for e-mail, then Outlook on the Mac will be a good fit. For everyone else… who knows?

I think the answer might be “either use Exchange 2007 or later, get your server vendor to support yet another MS-only connection protocol, or use another groupware client.” I hope not, because in my experience, the vast majority of Mac users fall somewhere in between those two groups I described above, and they’re starting to look like the group that will make do with either whatever version of Office they’re using now, or they’ll find something else. Face it, most of the SMB market doesn’t need Exchange. Something like Apple’s offerings, or Kerio works fine for them.

It affects me directly, because my company uses Kerio, and it’s a solid groupware server. It affects me personally, even more so, because I really like Entourage. I like the fact that it has better rules, mailing list management, scheduling, and (ironically) a better and more reliable AppleScript implementation than Mail, iCal, and Address Book combined. I like the strong integration that I get with Entourage as opposed to the “sorta” integration I get with three apps. I like having it all right there in one place. I’ve been using Entourage since it first came out—before if you count betas. I live in that app.

But I need to get work done more. If Outlook won’t let me do that on my terms in accordance with my needs, then the fact that it’s new, made from Cocoa—heck made from gold—won’t matter. If it won’t do what I need it to do, it’ll never get used. Which is a shame, because these days, “Office” for me is iWork plus Entourage. But if Outlook is an Exchange-only groupware client? It’ll only be on my hard drive if I have to support people using the next version of Office.

[John C. Welch is a frequent Macworld contributor. By day, he runs the network for The Zimmerman Agency of Tallahassee, Fla. His other (mostly profane) musings can be found at Bynkii.com.]

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