So this is an interesting turn of events.  Currently on a mission to replace every 2k3 R2 server with a shinny new 2k8 server.  So the big item to move right now is Terminal Services.  So we have our new TS server up and running but now we needed to license it.

So we build a license server and go to enter license information and what do we get - licenses are invalid.  After 4 hours with Microsoft Tech Support they mention that they have seen issues with TS Licensing and a virtual server.  I say, "no way - its an excuse".  Well, after we decommissioned the only physical box we had and discovered no joke.  So there are two big items I learned from Microsoft through this:

• Windows 2008 Licenses can only be served from a 2008 Licensing Server
• Windows 2008 License server cannot be run on virtual.

No word if the virtual problems are isolated to only VMware or to Hyper-V as well.

Installing the Terminal Services Gateway is a bit more difficult than installing Web Access.  Primarily because the services are wrapped with SSL, this causes TSGateway to take a more complex installation process.

• Step 1: Select Install Service Roles from the Terminal Services Role page.  Select TSGateway to add to your existing Terminal Server.
  
• Step 2: Accept the additional IIS components that need to be installed on your server.
  
• Step 3: Select the certificate you wish to wrap your Terminal Service connections with.  For more information on creating and installing your TS Gateway certificate my other blog posting here.
  
• Step 4: Choose to setup authentication roles now.
  
• Step 5: Choose the users/groups that will be able to authenticate through the TS Gateway
  
• Step 6: Choose the authentication methods you intend to support.  Also provide a name for your terminal services gateway CAP.
  
• Step 7: Provide a name for the RAP.  Also choose which workstation/servers this Gateway allows access to.  Or select all.
  
• Step 8: Choose the Network Access Protection items you need to install to your network.  You can leave the default selected and configure more options later.
  
• Step 9: Accept the additional IIS components that need to be installed.  No changes are required on this screen.
  
• Step 10: Hit next a few more times and your Terminal Services gateway is now installed on your server.  Go to the Terminal Services Gateway Manager tool in the Server Manager.  I found that although I selected a certificate during my installation process it did not actually install the certificate.  So select the Certificate Option and install your certificate.

NOTE: I found the problem with the certificate not holding.  It was due to the fact that in my IIS binding for TS Web Access I had selected to bind 443 to the IP Address and not to "Any Address".  As soon as I changed my IIS binding to "Any Address" all worked fine.  Didn't see that one coming that for sure!

Installing Microsoft Server 2008 Terminal Services Web Access is a fairly straight forward process but there are some gotcha's during the process.  So here is the steps to the setup and configuration.

• Step 1: Select Add Roles from Server Manager
• Step 2: Select Terminal Services from the Add Roles Wizard
  
•  Step 3: Choose Terminal Server and TS Web Access
  
• Step 4: Accept installation of additional IIS and ASP.NET options
  
• Step 5: Choose licensing mode for Terminal Services
  
• Step 6: Choose users and groups that can login to the terminal server
  
• Step 7: Accept the IIS options as presented.
  
• Step 8: Click install to accept the installation of Terminal Services 2008
  
• Step 9: Reboot.  After your reboot Terminal Services 2008 and Web Access will be installed onto your server.  It is now time to configure your server and your remote web apps.
• Step 10: Assign users who can use RemoteApp.  This is called Distribution Web Access.  You will notice that the description below the warning messages says that the TS Web Access Computers Group is empty.  Funny thing is, this group is horribly named as you of course cannot add computer/workstations to it.
  
  • Server Manager | Configuration | Local Users and Groups | Groups.  Select the TS Web Access Computers Group and add the users or groups who have access to the TS Web Access page.

• Step 11: Create your applications that will be available via TS Web Access.
  • Server Manager | Roles | Terminal Services | TS RemoteApp Manager.  Choose Add RemoteApp Programs and from the list select the application you wish to make available via TS Web Access.  If your application is not listed, choose the Browse button and find your application.
    
• To view your TS Web Access page visit http://servername/ts/.