Connecting Entourage with Exchange 2007

*UPDATED 6/28/2010*

The typical installation of Exchange 2007 includes the CAS, MBX and HUB roles.  Entourage requires little if any server configuration to connect in this topology.


However, once these roles are separated, there’s a few additional steps to take.


One thing to note – you do not need to install the latest WebDAV component from the IIS team in order to get Entourage to work with Exchange 2007 on Windows 2008 server.  If you’ve already installed the component:  I've included steps below to uninstall it.  However, with the new Entourage 2008 Web Services Edition free upgrade, I would highly recommend upgrading your Entourage clients than continue to support WebDAV.


If you still require WebDAV version of Entourage in your environment though, here's what you'll need to do to get things right.  On the Exchange 2007 server the IIS WebDAV component is installed:



1)       Stop the W3svc service [this usually prevents the need to reboot]   net stop w3svc

2)       Uninstall the WebDAV component from Control Panel, Programs and Features

3)       Start the W3svc service  net start w3svc

4)       run the following commands from the Exchange Management Shell

Remove-OwaVirtualDirectory "exchange (default web site)"

-Refresh IIS manager to ensure the exchange virtual directory has been removed

New-OwaVirtualDirectory "exchange" -OwaVersion Exchange2003or2000 -VirtualDirectoryType Mailboxes -WebSiteName "Default Web Site"

5)       Ensure the proper permissions are configured on the Exchange virtual directory:

CAS role == Basic

MBX role == Windows Auth [as well as SSL settings with Require SSL unchecked]

6)       Run iisreset /noforce


The steps above show the basic setup requirements for Entourage:

On the CAS, the /Exchange virtual directory needs to have Basic authentication,

On the MBX, the /Exchange virtual directory needs to have Windows Auth enabled and the SSL requirement unchecked.


A great troubleshooting step from here is to enable Forms Based Authentication on the CAS for the OWA virtual directory in Exchange Management Console.  Once that is enabled, if you see redirection working properly for OWA through your browser, then most likely your server is configured correctly.


For example, for Entourage to work, you need to be able to access https://CAS/exchange from the Apple client you want to run Entourage from [which after getting redirected to the OWA FBA page you should be able to log in].  From the CAS, you should also be able to access http://MBX/exchange - If these two tests work, then you most likely need to visit

931350  You cannot connect to your mailbox on Exchange Server when you use Entourage for Mac


It’s better to work from https://CAS/exchange to http://MBX/exchange - if connecting to the CAS won’t work, then connecting the MBX over the Exchange virtual directory won’t work either.





Comments (3)

  1. Anonymous says:

    I have got an Essential Business Server 2008, which has CAS, MBX and HUB roles in one Messaging server and Edge Transport in the Security server.

    Does your article still applys to an Essential Business Server 2008 in order to get Entourage 2008 WSE get email from Outside of office?

    Outlook Anywhere works great, but I can’t make Entourage 2008 WSE work without a VPN connection.

    Please advise me.

  2. Austin McCollum says:

    kucheong – Entourage EWS [Exchange Web Services] edition is entirely different – so I should probably create a new blog entry!  However, EWS works on a subset of URLs needed for Outlook Anywhere.  One way to test…

    While using Outlook Anywhere, hold the CTRL key down and right click on the Outlook icon in the lower right hand icon tray.  In that context menu, select "Test E-mail Autoconfiguration".  Unselect the guessmart checkboxes, then press enter.  This will return the EWS URLs that Outlook Anywhere is using.  Essentially if Outlook Anywhere Out of Office and Availability features work, then check to make sure Entourage EWS has the same server EWS URLs configured in Account settings.

    I will create a new post regarding some tips and tools to troubleshoot this great new version of Entourage in a week or so!


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