OS: Windows 2003 x64 R2
I spent the best part of my morning yesterday trying to figure out why my terminal licensing server isn’t issuing license. At first I thought there was an issue with the license server so I reactivated it with Microsoft. Still not issuing licenses?!!?
Well, here’s an interesting fact! Windows 2003 licensing server doesn’t monitor or decrement per user licenses. This means you have to guess how many licenses you need, but as its unmonitored terminal services won’t prevent you accessing the server if you go over your purchased amount.
If you configure Per Machine licensing mode the server will issue those license and time stamp them for 3 months.
In Windows 2008 Microsoft monitor per user licenses!
Also see Microsoft article http://technet.microsoft.com/en-us/library/cc738962%28WS.10%29.aspx