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Snow Leopard’s Exchange support won’t deliver Outlook parity

By John Rizzo
July 14, 2008

Snow Leopard's "out-of-the-box support" for Microsoft Exchange 2007 is the only new user-level feature listed at Apple’s Snow Leopard preview page. The rest are under-the-hood enhancements. But for those longing for Entourage alternatives, Snow Leopard’s Exchange client won’t be the Mac equivalent of Outlook in terms of functionality. It might not even be an Entourage.

That's because with Snow Leopard's Exchange clients, Apple isn’t aiming to create Mac parity with Outlook for Windows. Apple’s aim is to create Mac parity with iPhone 2.0.

Connecting iPhone 2.0 with Exchange is a major part of Apple’s push to get iPhones in the enterprise, where Blackberries have been the hand-held device of choice. iPhone 2.0 users not only get “push email” from Exchange Server, but can now accept meeting invitations and locate contacts in Exchange's global address list (GAL). The situation now is that iPhones have these built-in capabilities, but Macs do not—unless you add software from Microsoft.

Having these features in Mail, iCal, and Address Book will provide the out-of-box functionality that iPhone 2.0 has, with a user interface experience presumably superior to that of Entourage. But these are features that Entourage 2008 already has. An improved user interface isn’t going to satisfy those who are frustrated with Entourage’s lack of feature-compatibility with Outlook. But there is no reason for Apple to put the development resources into creating Exchange features that go beyond what is in iPhone. Which means Snow Leopard won’t include important Outlook features that are not in Entourage. For instance:

No Notes and Tasks. iPhone 2.0 doesn’t support Notes and Tasks content on Exchange servers, and Apple hasn’t mentioned it anywhere in connection with Snow Leopard. Mac users could also use the ability to configure Notes and Tasks sharing permissions. These are abilities that Windows users have, but Entourage has never had them. Neither will Snow Leopard.

No support for PST files. There doesn’t seem any reason to believe that Apple will support the reading and writing of Outlook’s PST files, another feature glaringly absent from Entourage. Mac users want to import and export data between machines without having to go through Exchange Server or use a converter, which can take a long time. This was a feature supported by the old Outlook 2001 for Mac OS 9.

No support for Public folders. This is an Outlook feature that Microsoft has "deemphasized" in Exchange 2007, so Apple is not likely to add it. Microsoft does refer to Public folders as a legacy feature, so it will be around for a while.

It won’t be MAPI. Apple says that Snow Leopard “uses the Exchange Web Services protocol to provide access to Exchange Server 2007.” This is a clear statement that MAPI is not part of the picture. MacWindows readers have complained for years that Entourage does not use MAPI, the native protocol of Outlook. Microsoft’s old Outlook 2001 for Mac OS 9 was a MAPI client, making the switch to Entourage was a bitter pill for many.

Network administrators say they want MAPI so they don’t have to configure Exchange differently for Mac users. Entourage requires administrators to enable WebDAV (also used in Outlook Web Access) and LDAP on Exchange Server. Entourage uses LDAP to do directory lookups in the Global Address List. While Outlook uses MAPI to directly query the GAL, Entourage uses LDAP to communicate with an LDAP service, which, in turn, communicates with the GAL. The LDAP service middleman can sometimes show up as slower responses from the GAL for Entourage users.

No offline mode for syncing the GAL. But an even bigger deficit to Entourage’s LDAP-to-GAL approach is that Entourage doesn't provide offline access to the Global Address List. When offline, Entourage users only have access to their personal contacts as well as GAL addresses that the client recently use in email messages. Since Microsoft hasn’t figured out a way to do this without MAPI, Apple isn’t likely to bother. It’s more than a client-side issue.

And, the reason Apple isn’t using MAPI is that it is following the direction of Microsoft, which says "MAPI is de-emphasized in Exchange 2007" and that it “has been replaced by Exchange Web Services.” Microsoft further advises developers (including Apple) that "new applications should use Exchange Web Services, and developers should migrate applications to Exchange Web Services whenever feasible."

But there is another problem with an Exchange-Web-Services-only approach:

Snow Leopard’s Exchange compatibility may not work with Exchange 2000 and 2003. Although Exchange Web Services protocol is used in Exchange Server 2007, Exchange 2000 and 2003 do not support it. Entourage 2008 supports both Exchange Web Servers and WebDAV, which enables it to work with Exchange Server 2000 and 2003 as well as 2007. So here’s a case where Entourage could have more functionality than Snow Leopard.

Snow Leopard’s Exchange clients won’t stop the glitches that Entourage users see. MacWindows has been continuously report bugs and glitches with Entourage since it first became an Exchange client. Last year, we reported instances of Exchange Server slowing down when large numbers of Entourage clients were connected. The problem appears to have been that Entourage implemented WebDAV in a way that didn’t quite sit right with Exchange 2003. Microsoft’s Mac Business Unit, the group that creates Office, presumably has good access to the technology of Exchange Server and the Microsoft engineers who build it. Could Apple have done better?

There’s no reason to believe that Snow Leopard’s Exchange compatibility/stability would be any better than Entourage’s. Mac OS X’s built in SMB file sharing has been plagued with problems in Leopard, and before that, when Tiger first shipped. Not to mention Leopard’s problems with Active Directory and issues with virtual private networking.

Snow Leopard’s Exchange clients are like to be easier to learn and use than Entourage, requiring fewer mouse clicks to accomplish tasks, and will most likely give iPhone users a consistent experience. But if the announcement raised the hope of Mac users and administrators frustrated with Entourage’s lack of functionality and bugginess, they are likely to be disappointed with Snow Leopard’s Exchange clients. Mac users will remain second-class Exchange clients. Comment below

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Copyright 2008 John Rizzo. All rights reserved.