Outlook Anywhere doesn’t work

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Outlook Anywhere doesn’t work

Case 1: The user setup Outlook Anywhere on his Outlook 2003. The Outlook keep promoting for the password. The problem is the Outlook Anywhere in Exchange 2010 is setup to use Basic Authentication, but the Outlook is set to use NTLM Authentication.

Case 2: The outlook 2007 prompts for the password when running Outlook Anywhere. Even you enter the correct password, it prompts for the password again. We found both Exchange server and Outlook were setup to using NTLM Authentication. Changing to Basic Authentication works. Someone stated: Some Corporate Firewall solutions do not allow NTLM authentication to pass through them (e.g. some of the Cisco Pix, Nortel Connectivity) & as a result Outlook Anywhere works Internally but not Externally due to Authentication problems.
Case 3: OWA worked without any issues but Outlook Anywhere kept prompting me for credentials and no matter which credentials I used it would not work. The issue was that the certificate that I had created was issued to the FQDN of the server which is not what I was using for my OWA/CAS site. I was using "owa.domainname."

After opening a ticket with MS they advised me to redo the certificate so that the issued to was "owa.domainname" and also move the "owa.domainname" to be the first subject name.

I applied the new certificate and the credentials were taken right away.

Case 4: incorrect Server Name Specified in the RPC/HTTPS Configuration in Outlook.

Case 5: incorrect External host name in Exchange 2010 Management Console/Server Configuration/Client Access/Server Properties/Outlook Anywhere.

Case 6: you need to ensure AutoDiscover is working properly. Her is the info: http://technet.microsoft.com/en-us/library/bb232838%28EXCHG.80%29.aspx.

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