We have a TSLS (2008 SP2, not R2) issuing both 2003 and 2008 Per Device CALs. I have no Issues with the 2008 CALs. It has 5 or so batches of 2003 CALs, and hands out some (group A), but not others (group B). When CALs run out on group A, it doesn't grab CALs from Group B, and throws error 22. Of note, this for a Citrix xenapp implementation.
This is what the event log says:
Log Name: System Source: Microsoft-Windows-TerminalServices-Licensing Date: Event ID: 22 Task Category: None Level: Warning Keywords: Classic User: N/A Computer: Description: The Terminal Services license server "TS licensing server name" does not have any Terminal Services client access licenses (TS CALs) installed and registered with the Microsoft Clearinghouse for product "Windows Server 2003 - Terminal Server Per Device CAL Token". Therefore, the Terminal Services license server cannot issue TS CALs of the type "Windows Server 2003 - Terminal Server Per Device CAL Token" to the terminal server "IP of a TS". To resolve this problem, install additional TS CALs as required.