Using Non-Windows Systems to Access Exchange Server 2010 : Configuring and Implementing Entourage for the Mac

2/19/2011 5:18:14 PM
Understanding the need for a more comprehensive functional solution for Mac, Microsoft provides a powerful Exchange Server client for the Macintosh as part of their Office 2008 package called Entourage 2008. This option is very effective for Mac users’ internal and external connectivity needs because it provides the same look and feel that Mac users are familiar with and many of the enhanced functions of the latest Windows-based Outlook client.

The most compatible platform with the Mac operating system, Entourage 2008 provides support for email, calendaring, contact management, junk email filtering, synchronization, and even support for handheld devices when combined with Exchange Server 2010. Exchange Server administrators can now leverage the Entourage client to provide Mac users with a familiar look and feel while delivering full integration with added features and access to Exchange Server 2010 data.

Features and Functionality

The Entourage 2008 client software combined with the Exchange Server 2010 platform and latest service packs can provide enhanced functionality for the Mac user in many areas not before available. The Entourage 2008 for Mac Web Services edition update provides Entourage users access to synchronize tasks, store attachments in calendar appointments, and other features that were not supported in the original release of the Entourage 2008 application. To download the latest Entourage updates, go to www.microsoft.com/mac/downloads.mspx.

When combined with the Exchange Server update, Entourage provides extensive support and enhanced functionality in the following areas:

  • Enhanced Autodiscover capability— Autodiscover is a feature added to Exchange Server 2007 (and continued in Exchange Server 2010) that provides automatically failover intelligence for client systems to connect to a surviving Exchange server node if a server failure occurs. With Autodiscover enabled, when an Exchange Server 2010 server fails over to another server, the client will reconnect to Exchange Server automatically.

  • Full synchronization support— With the Web Services edition, an Entourage client will synchronize tasks, notes, and categories, features that weren’t synchronized with the original release of Entourage 2008.

  • Attachment support— The Web Services edition also supports the synchronization of calendar appointments that have attachments.

Deploying Entourage 2008

Requirements for installing Entourage 2008 vary slightly from the requirements of Outlook and other Exchange Server solutions. Before installing and configuring Entourage 2008 clients, administrators must ensure that minimum hardware requirements at the Mac desktop are met and the Exchange Server 2010 prerequisites have been configured. In addition, the client must be updated and installed with the required updates and software to ensure proper functionality and connectivity when accessing Exchange Server mail data.

Before installing Entourage, ensure that the following requirements and configurations have been enabled on the Exchange server:

  • Microsoft Exchange Server 2010 with the latest updates


  • Outlook Web App

Though most of these settings are already enabled to support Windows-based client connectivity to Exchange Server, review and address any of the hardware and software requirements for installing Entourage by reviewing Table 1 and the software prerequisites for Exchange Server 2010.

Table 1. Entourage 2008’s Mac Hardware Requirements
ProcessorMemoryHard Disk Space
Intel or PowerPC G4 or G5 (500MHz or faster)512MB1.5GB available disk space
Other Requirements  
Mac OS X installed

Mac OS X 10.4.9 or later

Version of Entourage installed

Office for Mac 2008 Standard or Special Media Edition

Verify that the Mac client desktop hardware you are installing meets the minimum hardware requirements to install Entourage 2008, as listed in Table 29.2. If you do not know what hardware is installed on the Mac client, use the Mac System Profiler available on the Tools menu of the Mac desktop to display and evaluate the hardware installed on the Mac desktop.

After the Exchange server has been prepared and the hardware requirement for Entourage has been addressed, the next components to support Entourage are the updates and software requirements for the Mac client. Before the installation of Entourage 2008 can be completed, the following components must be installed or updated in the Mac client:

  • Office 2008 for Mac— To install Entourage 2008, the Microsoft Office 2008 for Mac suite must be installed.

  • Install Updates— Because upgrades can be completed after the installation of Office 2008 for Mac, administrators can install any available updates before running the Upgrade Wizard or configuring any identities.

  • Microsoft Exchange Update— When connecting Entourage 2008 to Exchange Server 2010, be sure to install the latest Office 2008 Service Pack on the client computer that includes the Web Services edition for Entourage 2008.


To address Office 2008 updates, Microsoft provides an autoupdate feature for the Office for Mac suite. Download and install the latest update version from Microsoft at www.microsoft.com/mac/downloads.aspx.

To provide functionality for junk email filtering with the latest definition files, install the junk email filter update from Microsoft at http://www.microsoft.com/mac/downloads.aspx.

After all updates have been completed and requirements met, the installation of Entourage 2008 can be completed, and the Entourage client can be connected to Exchange Server. To configure the Entourage client for Exchange Server support, follow these steps:

Enhancing Authentication with NTLM V2

To further leverage the available features of Windows and Exchange Server, administrators can enable NTLM version 2 for authentication of Mac users when connecting with Entourage clients.

To encrypt a password using NTLM V2, select the properties of the Exchange Server mail account and select the Advanced Features tab. Enable password encryption by selecting the Always Use Secure Passwords option.

Entourage 2008 does not support NTLM version 1; ensure that the default domain policy is configured to support NTLM version 2 before connecting Entourage 2008 clients.

Launch the Entourage 2008 client, and select Tools, Accounts.

Select the Mail tab, select New from the New drop-down box, and enter the account type for connecting to Exchange Server.

Enter the user information for the account connecting to Exchange Server with the client:

  • Account Name— Enter the name of the account created in Active Directory for the Mac user to connect to Exchange Server.

  • Password— Provide the password for the Active Directory account or leave this entry blank to prompt the user to log on when connecting to Exchange Server.

  • Domain Name— Enter the name of the Active Directory domain where the account is a member.

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