We're in the process of migrating our Terminal Services infrastructure from 2003 to 2008. During testing we found printing easy, including with Star TSP800 printers. Then one day everything changed. We built a new workstation image and discovered the drawer kick from the Star to the cash drawer wasn't working. All options were grayed out on the server and the driver settings weren't transferred from the host machine to the Terminal Services session.
Star support reported they experienced the same problem. And after a bit of messing around we managed to get it working. The key? Easy Print.
I won't explain Easy Print here, this is a pretty good explanation, but I will say it saved my hide. By using the Windows XP driver that didn't support 2008, we managed to get the printer working in 2008.
Here's what we needed:
1. A legacy driver on the host machine that 2008 didn't like so terminal services would use Easy Print.
2. A locally mapped printer on the host (TCP/IP and LPT both tested.)
3. A terminal services client that supports RDP 6.1 (appears as 6.0.6001)
4. Windows updates up to recently. We didn't manage to pin the exact update down.
And voila, we have legacy thermal printers.
I didn't find any documentation on this when doing research. Hopefully this helps someone else!