Hello Kyi Soe Thin,
Your understanding is correct, and the configuration you are attempting, separating the Remote Desktop Licensing role and the Session Host role onto two different servers in a Workgroup environment is technically unsupported and will not function correctly. While you can successfully ping the servers and even configure the Group Policy or Registry on Server #2 to point to the IP address of Server #1, the actual license issuance process will fail once the grace period expires.
The root cause is the authentication mechanism required by the Remote Desktop Licensing protocol (RPC). When a Session Host requests a CAL on behalf of a connecting device, the Session Host service (running as a local system account) must authenticate itself to the License Server. In an Active Directory environment, this is handled transparently via Kerberos and trusted computer accounts. In a Workgroup, Server #1 has no knowledge of Server #2's identity. Consequently, Server #1 will reject the RPC requests from Server #2, or Server #2 will simply report that no license server is available because it cannot establish a trusted channel to query the database.
To resolve this, you must install the Remote Desktop Licensing role directly on Server #2 (the Session Host). Since you are in a Workgroup, you are correctly limited to using Per Device CALs, as Per User CALs are strictly not supported without Active Directory. You will need to migrate or split your license pack to install the required number of Per Device CALs locally on Server #2. Once installed, open the RD Licensing Diagnoser on Server #2 and ensure it points to "localhost" or the local server name to validate that the licenses are available and the configuration is error-free.
I hope you've found something useful here. If it helps you get more insight into the issue, it's appreciated to accept the answer. Should you have more questions, feel free to leave a message. Have a nice day!
VP