I have installed the Visual Studio 2010 Remote Debugger on a Windows Server 2003 (x86) server, and am attempting to connect to it results in the following error:
I had the same problems with the debugging service. The debugging service was starting automatically but I could never connect. I even turned off the firewall completely and that didn't help either.
Try running the debugging monitor (as opposed to the service) and connecting to that. You can find it in the start menu.
Confused about the difference between the monitor and the service? So was I. See http://social.msdn.microsoft.com/Forums/en/vsdebug/thread/afc80afc-c8eb-4831-915a-1edb8d188f98