Hi,

In terminal server 2008 R2, I'm trying to setup outlook account (Exchange 2013).

The account is setup automatically but when it searches for my email account it prompts for user and password and after filling the details it's working fine.

in other terminal server in my organization it doesn't do it and the configuration is working smooth without any user and password prompt.
Attached screen shot:

Any suggestions how to solve it so it won't prompt for user and password ?
Than

After further investigation i saw that the proxy authentication settings are configured to BASIC AUTHENTICATION instead of NTLM.

After changing it to NTLM and reopening outlook it got back to BASIC.

In other servers it's setup to NTLM.

Any suggestions ?

Hi Liran,

Based on my research, this problem is likely a misconfiguration on the autodiscover service on the server. The ClientAuthenticationMethod parameter is used by the autodiscover service to tell the client what authentication method to use. If you change the authetication method manualy, the next time the client contacts he autodiscover service it will be changed to the value set by the ClientAuthenticationMethod parameter. You need to set the ClientauthenticationMethod to NTLM.

Disabled the Outlook-Anywhere on 2 of the non-production CAS servers
Verified that the production servers are having just NTLM-Authentication on the servers

Reference: http://technet.microsoft.com/en-us/library/dd439374(EXCHG.80).aspx

Since this issue is more likely caused by Exchange site, If you need further assistance on it, I'd recommend you post your question to the Exchange server forum:

https://social.technet.microsoft.com/Forums/office/en-US/home?category=exchangeserver

The reason why we recommend posting appropriately is you will get the most qualified pool of respondents, and other partners who read the forums regularly can either share their knowledge or learn from your interaction with us. Thank you for your understanding.

Steve Fan
TechNet Community Support