When trying to set up Exchange on my new Surface Pro, it gets the internal hostname of the internal Client Access server instead of the hostname of the public-facing CAS, and therefore fails to connect. I recently made some changes to my Exchange 2010 environment with regard to hostnames in order to resolve an issue with internal clients connecting to the wrong Client Access Server, but I thought I got rid of all references to the internal hostname! And now it is back. The problem is even if I manually change the hostname to the correct one in Outlook's Repair Account wizard, when I run a Check Name, it sets it back to the internal one!
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My Outlook Anywhere works fine and sets the Internal CAS name when checking the name. That's fine.
What you need is More Settings -> Connection -> Exchange Proxy Settings to populate with the External URL. You probably need to run something like:
Enable-OutlookAnywhere -Server CAS01 -ExternalHostname "mail.contoso.com" -ExternalAuthenticationMethod "Basic" -SSLOffloading:$False
You can also set this through the GUI through the Configure External Client Access Domain wizard.
For more information, see this link.

Katherine Villyard
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Thanks for the help, but that gives me the following error: The virtual directory 'Rpc' already exists under 'ServerName.example.ca/Default Web Site'. Parameter name: VirtualDirectoryName + CategoryInfo : InvalidArgument: (ServerName\Rpc (Default Web Site):ADObjectId) [Enable-OutlookAnywhere], ArgumentException + FullyQualifiedErrorId : 78712C6B,Microsoft.Exchange.Management.SystemConfigurationTasks.EnableRpcHttp – Erik Johnson Dec 27 '14 at 18:17
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1Interesting... After a reboot of the Exchange server, everything started working as it should. Thanks! – Erik Johnson Dec 30 '14 at 20:24