Remote Web Workplace in Essential Business Server 2008 Always Prompts for Password and Never Logs In

There is a published problem with EBS 2008 where Outlook prompts for a password all the time when connected over HTTP/RPC (Outlook Anywhere) – see the Microsoft EBS Team Blog. We have found that the same problem is also exposed in the Remote Web Workplace when trying to connect over Remote Desktop to your PC or to the servers.

The problem is that the authentication for the Remote Desktop is broken because Outlook has failed to connect based on the published issue mentioned above. The failure of Outlooks authentication breaks the DefaultAppPool is IIS. Recycling the application pool fixes the issue – but only for a short while. It breaks again at the next failed Outlook login. And because the breaks in authentication are due to Outlook it is difficult to see why Remote Desktop ceases to operate.

But apply the same fixes from the above blog and Remote Desktop begins to work and stays working.

To fix, run the following four commands from an elevated command prompt on the messaging server:

• %windir%\System32\inetsrv\appcmd.exe unlock config -section:system.webServer/security/authentication/windowsAuthentication
• %windir%\System32\inetsrv\appcmd.exe set config “Default Web Site/ews” -section:windowsAuthentication -useKernelMode:False /commit:apphost
• %windir%\System32\inetsrv\appcmd.exe set config “Default Web Site/AutoDiscover” -section:windowsAuthentication -useKernelMode:False /commit:apphost
• %windir%\System32\inetsrv\appcmd.exe set config “Default Web Site/OAB” -section:windowsAuthentication -useKernelMode:False /commit:apphost

The above commands are probably wrapped for reading on your screen – each bullet point is a single command to be entered as one line. Instructions for making changes via the GUI can be seen on the above blog post.