When accessing a remoteapp site such as http://hostname/rdweb a credentials prompt appears, after entering credentials and clicking on a published application, a second credentials prompt appears.
The first prompt is coming from IIS at the second prompt is coming from the actual terminal server that the published application is coming from. I wanted to get rid of the IIS prompt since the website is only accessible internally. To remove the IIS prompt edit the RDWebAccess.Config file located at c:\Windows\Web\RDWeb\App_Data\ and ensure that the section <ServerName> value is set to “localhost” as in the below example. If you have the actual host name, remove it.
<webFeedSettings ServerType="rdserver"> <ServerName>localhost</ServerName> </webFeedSettings>
The second thing to check is your IIS settings. The authentication mode should be for Anonymous and Windows on the top level site as well as the RDWeb site.