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Do Macs love Exchange?

Snow Leopard finally promises native Exchange connectivity for Mac users; here’s how to make it manageable.

One of the most interesting new features for small business in Apple’s recent OS X 10.6 Snow Leopard release is support for Exchange Server in the native Mail, calendaring, and Address Book applications. In the recent past, the only way to work with Exchange Server on a Mac was to either rely on Entourage or to use the native OS X applications’ standards-based support – such as IMAP - to access email, without getting all the features of Exchange.

OS X doesn’t come with an all-in-one Outlook-style application that includes mail, calendaring, and contacts. Instead, much like Windows Vista, OS X includes separate applications for each task, although the applications generally integrate well with one another. Now, given the applications’ ability to natively connect to Exchange Server, Mac users can have a more robust set of experiences.
 

Requirements and setup

Snow Leopard itself is available only on Intel-based Macs, so older PowerPC-based hardware doesn't get the new Exchange functionality. In addition, Snow Leopard relies on Exchange Server 2007 and later, so older versions of Exchange Server will need to be upgraded. OS X utilizes Exchange Web Services (EWS), which makes it easier to pass Exchange traffic through firewalls; you’re probably already using EWS for Outlook Web Access and Exchange ActiveSync to mobile devices.

Creating a new Exchange Server 2007 account in Mail.app.
Creating a new Exchange Server 2007 account in Mail.app.

Setting up a connection between a Mac and the Exchange Server computer is straightforward: in the Mail application, open Preferences and select the Accounts tab. Add a new account, and select the Exchange 2007 account type. You’ll be prompted to provide the email address and password for your Exchange Server account and Mail should auto-discover everything else it needs to know. You’ll also be prompted to include Address Book and calendar sync; enabling these options automatically creates Exchange-connected accounts in the Address Book and iCal applications. Note that Address Book sync is required if you want the user to be able to select names from the Exchange Global Address List when sending email.
 

Features and capabilities

Because OS X relies on EWS, it is in some ways similar to IMAP. The Mac will contain a local copy of all Exchange data – enabling offline use if the customer desires – and keep that content synchronized with what’s on the Exchange Server computer. This is pretty much how modern versions of Outlook work, too.

Although the three native applications don’t provide the same feature set as Outlook, they do provide the core capabilities an average user expects. They can work with Exchange events, meetings, and appointments in iCal, and invite other users to attend them. Free and busy information is published by iCal to Exchange Server, and you can view other users’ free and busy schedule in iCal.

Viewing free and busy information in iCal makes it easier for Mac users to schedule meetings.
Viewing free and busy information in iCal makes it easier for Mac users to schedule meetings.

Not everything in Exchange is synchronized: Notes, for example, don’t sync into the Mail application and OS X doesn’t include a dedicated ‘notes’ application (apart from Dashboard widgets, which also don’t sync to Exchange). The Exchange support in OS X focuses on contacts, calendars, and messages only.
 

Troubleshooting

We’ve run into problems downloading the contents of large Exchange mailboxes when the Exchange Server computer has certificate authentication enabled; Apple refers to a Microsoft recommendation that you keep fewer than 5,000 messages in Exchange mailboxes, and acknowledges that this issue can occur when a mailbox contains more than 11,000 messages. The only solution is to clean up the mailbox and try again.

Most other problems are down to connectivity. Keep in mind that both HTTP and HTTPS are used, so the relevant ports must be clear between the server and client.
 

Central configuration needs Extra tools

With most small businesses having at most a handful of Macs, individual setup isn’t too large a task. Unfortunately, Macs don’t provide native central configuration similar to Windows’ Group Policy features. Apple does provide Group Policy-like central configuration via the Workgroup Manager software, but that requires the use of an OS X Server on the customer network, which all of the Mac clients must authenticate to. If you need centralized configuration for a customer – including centralized Mail configuration – you'll have to invest in one of the third-party products that extend Windows Group Policy to non-Windows clients such as Macs. Quest Software (quest.com) and Centrify (centrify.com) are the two major players in the space.


Snow Leopard and Microsoft Exchange
First impressions of and discussions of the Exchange features shortly after Snow Leopard’s release:
tuaw.com/2009/08/30/snow-leopard-and-microsoft-exchange-first-impressions

Mac OS X v10.6: Using Microsoft Exchange 2007 (EWS) accounts in Mail
Official Apple information on Exchange accounts in Mail:
http://support.apple.com/kb/HT3748



Extra

Outlook and Entourage

While most Mac users needing Exchange connectivity have had it through Microsoft Entourage for years, this new core support can – for some users – eliminate the need for the more-expensive Office Mac license that includes Entourage.

Microsoft recently announced that Microsoft Office 2010 for the Mac would include an all-new Outlook application designed specifically for Macs. Once upon a time, Office for the Mac included Outlook, but Mac users felt the application looked and felt too much like a Windows application; in Office X for the Mac (introduced in 2002), Microsoft abandoned Outlook on Macs in favour of Entourage, an Outlook-like application. Entourage received generally lukewarm reviews; users felt it lacked the full functionality of Outlook, didn’t integrate as well with Exchange Server as Outlook does, and missed having the same features as their Windows-using colleagues. The return of Outlook to the Mac will bring those features, and the Office Mac development team promises a truly Mac experience – not just a Windows port.
 


 
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