Can I use a single TS Licensing Server to issue TS CALs to Terminal Servers in multiple untrusted domains and workgroups?
Terminal Server Licensing Servers can only issue TS CALs to Terminal Servers which are located in the same domain or in trusted domains. This is documented in this KB article: 279561 – How to Override the License Server Discovery Process in Windows Server 2003 Terminal Services If you want a single TS Licensing Server to issue TS CALs to Terminal Servers in multiple, untrusted domains and workgroups, you will have to place the TS Licencing server in a workgroup, not a domain. Then any Terminal Server in any domain or workgroup will be able to receive TS CALs from the TS License server. The License Server Auto Discovery process will not work with this setup, but adding the Preferred Licensing Server registry key in the Terminal Servers will fix that. Be sure to add the correct registry key, follow KB 279561 for 2003 Terminal Servers and 239107 for W2K Terminal Servers. To give anonymous connections access to the Licensing Server, you also have to make sure that the access token for anon
