Turns out that Windows 2008 Terminal Server Easy Print technology is not as easy after all. It is a great technology, but there are some things to watch out for.
Requires Windows 2008 with TS Role (Duh!)
Also requires RDP v6.1 (which comes with Vista and XP Service Pack 3).
Also Requires .NET Framework v3.0 SP1 or later.
The technology states that it will automatically redirect print jobs via RDP to the local printers. Most of the time, it works great. However, I found out that it definitely does not work across Remote Web Workplace on SBS2003. It requires a direct connection via RDP. Normally, this is done through port 3389.
For more information – http://technet.microsoft.com/en-us/library/cc753853.aspx
*** UPDATE ***
Just found out that RDC v6.1 is available for Windows XP SP2.