Authentication issues with Outlook Anywhere and Terminal Services Gateway (TS Gateway)

by Juan Carlos · June 24, 2008

I had plenty of issues with this, but then I found this website: http://technet.microsoft.com/en-us/library/cc546071.aspx and here is the re-cap of the steps you need to take to make it work! yay!

Use the procedure that follows to fix these authentication issues:

Microsoft Outlook® repeatedly prompts you for credentials through Outlook Anywhere (previously known as RPC over HTTP)
Login on remote computers fails if you are using the Connect to Computer feature in Remote Web Workplace

To fix the authentication issues with Outlook Anywhere and TS Gateway

Open the Registry Editor: Click Start, in the search field type regedit, and then press ENTER.
In the User Account Control window, click Continue.
Browse to HKEY_LOCAL_MACHINESystemCurrentControlSetServicesMSExchangeServiceHost. RpcHTttpConfigurator.
Click RpcHttpConfigurator, and then double-click PeriodicPollingMinutes.
In the Edit DWORD (32-bit) Value dialog box, change Value data: to 0, and then click OK.
Click Start, in the search field, type services.msc, and then press ENTER.
In the User Account Control window, click Continue.
Right-click Microsoft Exchange Service Host, and then click Restart.
Click Start, click Administrative Tools, and then click Internet Information Service (IIS) Manager.
In the User Account Control window, click Continue.
In the Connections pane, expand <your server name>.
Expand Sites, and then expand SBS Web Applications.
Click Rpc, and then in the /Rpc Home pane, in the IIS section, double-click Authentication.
Verify that Basic Authentication and Windows Authentication are enabled. If either authentication is disabled, click it, and then in the actions pane, click Enable.