Exchange Autodiscover

When Microsoft released Exchange Server 2007, one of the new features it included was Autodiscover. Autodiscover allows you to automatically configure Outlook 2007 clients, but, there is a lot more behind the Autodiscover functionality. When you have issues with the Out-of-Office or Free/Busy information in Outlook 2007 in combination with Exchange Server 2007 (or Outlook 2010 and Exchange Server 2010) it is likely that it is caused by a misconfiguration in the Autodiscover configuration. To make things more complex, the SSL certificates are involved here as well.

Note:
The Autodiscover process for Exchange 2007 and Outlook 2007 is practically the same as for Exchange 2010 and Outlook 2010. In this article I will use Exchange 2010 and Outlook 2010.

Autodiscover information is stored in a so called SCP or Service Connection Point. You can view this SCP using Active Directory Sites and Services after you have enabled the “View Services Node” option.

When installing the Client Access Server (Autodiscover is part of this Server Role) the SCP is automatically created in Active Directory and configured with the default values. If you have multiple CAS Servers there will be multiple SCP’s as well.

When Outlook 2007 is installed on a domain joined workstation then the Outlook client will query Active Directory for the Autodiscover information. Active Directory will return a list of SCP’s and the Outlook client will automatically select the first SCP in this list. Using the information found in the SCP the Outlook client will contact the Client Access Server for its configuration information and the Outlook client will be configured automatically.

Non-domain clients are a bit trickier to configure since they will not query the Active Directory. Because of this non-domain clients try to retrieve information using the Autodiscover website. The FQDN that the Outlook client will use is based on the SMTP address that is used when starting the Outlook 2010 client the first time. So, when an e-mail address Bob@blogger.com is entered, the Outlook client will start trying to connect to the Client Access Server using HTTPS. There are several URL’s that Oulook will use, but the most important is https://autodiscover.Blogger.com.

Please be aware that this is the (Internet facing) Client Access Server. So besides the normal Outlook Web Access URL like https://webmail.blogger.com the same Client Access Server is also contacted using https://autodiscover.blogger.com.  This is exactly the reason a Unified Communications (UC) or SAN certificate is needed. 

Note: You can actually use a single certificate for for both OWA and Outlook Anywhere.  Please see my other blog on SSL for both OWA and Outlook Anywhere

Besides the possibility to configure Outlook 2007 and higher clients using the Autodiscover process there’s more information, in this process.

• Out-of-Office information
• Availability Services
• Offline Address Book download information
• Unified Messaging information
• Exchange 2010 personal archive (for Outlook 2010 clients only)

In Exchange Server 2010 the properties related to these settings are configured during setup of the Client Access Server when entering the “this is an external facing Client Access Server” option. When you do not select this option, or in Exchange Server 2007 you have to configure these properties manually using the Exchange Management Shell:

Set-OWAVirtualDirectory –Identity 2K10HUBCAS02\OWA (default web site) 
-ExternalURL https://webmail.blogger.com/OWA

Set-OABVirtualDirectory –Identity 2K10HUBCAS02\OAB (default web site) 
-ExternalURL https://webmail.blogger.com/OAB

Set-WebServicesVirtualDirectory –Identity 2010CASUB02\EWS (default web site) -ExternalURL https://webmail.blogger.com/ews/exchange.asmx

Set-ActiveSyncVirtualDirectory –Identity 2K10HUBCAS02\Microsoft-Server-ActiveSync (default web site) 
-ExternalURL https://webmail.blogger.com/Microsoft-Server-ActiveSync

This setting is only valid for Exchange Server 2010:

Set-ECPVirtualDirectory –Identity 2K10HUBCAS02\ECP (default web site) 
-ExternalURL https://webmail.blogger.com/ECP

The last step is to configure the external DNS for both the webmail hostname as well as the Autodiscover hostname as they need to point to the external facing Client Access Server.

When you start up Outlook 2007/2010 you can automatically configure your profile, If all goes well you should be able to set your out-of-office settings and check other mailboxes free/busy information.

If you want to check that this is working correctly you can start Outlook and you will see the small Outlook icon in the system tray. Press the Control key together with a right mouse click, there you have two options:

• Connection Status
• Test E-mail AutoConfiguration

The connection status shows the various connections that are initiated between the Outlook client and the Exchange server. 
With the ‘Test E-mail AutoConfiguration’ there is the possibility to test the Autodiscover configuration.  Fill in your e-mail address and password, and to check the Autodiscover functionality only deselect the “Use Guessmart” and “Secure Guessmart Authentication”. When you click Test the Outlook client will check the full Autodiscover functionality and the results will be shown on the Results tab.


Another way, especially when troubleshooting your Autodiscover configuration, is the Remote Analyzer that is available on the Internet. Go on to www.testexchangeconnectivity.com. This site is developed by a few guys from the Microsoft Exchange Product Team. This site can help you troubleshoot all kinds of remote connectivity issues and gives detailed results after checking.