I noticed when I got a Windows 7 that when I connect to different servers with Remote Desktop (RDP) that my clipboard was not working. I also noticed that it only happened on particular servers. As it turned out the servers that I was having trouble getting the clipboard to map were servers I had not accessed yet. I typically save the settings for each of the servers I connect to. In the case of these new servers I was just opening the Remote Desktop client and connecting.
So what was going on? There were a couple of things that caused seemingly random behavior.
1. When I got my new Windows 7 laptop I did not open the remote desktop client and gone to the Local Resources tab and checked the Clipboard checkbox and most importantly, I had not clicked the Save button on the General tab. If you don’t click the save button your preference will not be saved. Thus every time you use RDP client you will need to click the Clipboard checkbox, which I was not doing.
2. The other thing that made this seem random was that in most cases I use my saved settings that are specific to each server.
While researching this, I did find an excellent article that talks about how to fix what sounds like the same symptoms, but is actually a server configuration issue (RDP Clipboard mapping not enabled on terminal services) or bug (have to kill and re-launch rdpclip)