Exchange and Small Business Server

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We recently switched over a client’s small infrastructure to Small Business Server 2008.  SBS 2008  has SQL 2008 and Exchange 2007 imbedded.  The customer wanted to keep the same internal and external FQDN names used previously with Exchange 2003.

I had them purchase a SAN certificate with all the standard names in an Exchange 2007 or 2010 environment.  We installed the certificate, made sure everything was set in both internal and external DNS, and started setting up clients.

Webmail and Active-Sync were fine after I went through and defined all the URLs in the CAS area under server configuration, however all the Outlook clients constantly popped certificate errors.  This caught me off guard at first considering the server had a SAN certificate installed that contained the server NetBIOS name and internal FQDN in the certificate.  Then I remembered the Autodiscover internal URL.

2007 and 2010 use the Autodiscover web services for many functions including client auto-configuration, free-busy data, and offline address book downloads. SBS by default uses remote.domain.com for a good bit of its “remote” functionally.   Sure enough, when looking at the attributes of the CAS, the autodiscover service uri was set to remote.domain.com as well.  The Exchange Web Service was set this way also.  Both can only be changed through the Exchange Management Shell.

To Change the Autodiscover service URLs:

To Change the Autodiscover virtual directory URLs:

To Change the Exchange Web Services virtual directory URLs:

The rest of the Web Directory URLs can be changed from inside the Exchange Management Console.