How to setup Outlook Autodiscover and Outlook Anywhere from LAN and Internet (with two certificates) on Exchange 2010 in a single server scenario

 

Ever wondered how will you configure outlook autodiscover and outlook anywhere in the simplest scenario. I am assuming that you are running a single server hosting all roles and CAS is also published on the Internet for access to emails from Internet.

Setup:

You need two certificates, one each for autodiscover and the other for mail. You also need two external IP address pointing to two internal IP addresses. The external IP addresses should point to mail.mydomain.com and autodiscover.mydomain.com

Configuration

• Remove the auto discover Virtual Directory (VD) from the default site.
  

Remove-AutodiscoverVirtualDirectory -Identity "SERVERNAME\autodiscover (Default Web Site)"

• Create a new website in IIS. You can name the website as autodiscover
  
• Create the autodiscover VD in this new website
  

New-AutodiscoverVirtualDirectory -Websitename Autodiscover -BasicAuthentication:$true -WindowsAuthentication:$true

• Enable outlook anywhere on the server
  

Enable-OutlookAnywhere -Server SERVERNAME -ExternalHostname "mail.mydomain.com" -DefaultAuthenticationMethod "Basic" -SSLOffloading:$False

• Set the autodiscover location on the CAS server
  

Set-ClientAccessServer -Identity SERVERNAME -AutoDiscoverServiceInternalUri "https://autodiscover.mydomain.com/autodiscover/autodiscover.xml"

• Run the below commands to setup the other VDs properly
  

Set-OABVirtualDirectory –Identity SERVERNAME\OAB (default web site) -InternalURL https://mail.mydomain.com/OAB ExternalURL https://mail.mydomain.com/OAB -RequireSSL:$true

Set-WebServicesVirtualDirectory –Identity SERVERNAME\EWS (default web site) -ExternalURL     https://mail.emydomain.com/ews/exchange.asmx -InternalURL https://mail.mydomain.com/ews/exchange.asmx -BasicAuthentication:$True

Set-OWAVirtualDirectory –Identity SERVERNAME\OWA (default web site) -InternalURL https://mail.mydomain.com/OWA -ExternalURL https://mail.mydomain.com/OWA

Set-ECPVirtualDirectory –Identity SERVERNAME\ECP (default web site) -InternalURL https://mail.mydomain.com/ECP -ExternalURL https://mail.mydomain.com/ECP

Set-ActiveSyncVirtualDirectory –Identity SERVERNAME\Microsoft-Server-ActiveSync (default web site) -ExternalURL https://mail.mydomain.com/Microsoft-Server-ActiveSync -InternalURL https://mail.mydomain.com/Microsoft-Server-ActiveSync

 

You can then use https://www.testexchangeconnectivity.com to test Auto discover and Outlook Anywhere you just configured.

I was able to do this setup by referring to this link (although it is a Wxchange 2007 link) http://technet.microsoft.com/en-us/library/bb332063(EXCHG.80).aspx

 

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Tags: Exchange Server, Autodiscover, Outlook Anywhere
Published Date: 20110326