Here is my problem, I have two XP PC's (SP2) with VS2005 installed on them. (One is a VMware PC is that makes any difference)

On the non-VMware PC I can open a web project located on a remote web server via file share and run Debug and it works as expected.

On the VMware PC, doing the same thing (pointing to the same app) I run debug and I get the message box "Unable to Start Debugging on the Web Server. The microsoft visual studio remote debugging monitor (msvsmon.exe) does not appear to be running on the remote computer."

 Firewall settings are the same between the two.

 Any ideas why it works on one PC and not the other.

This error means that the web server do not have the service running.  I do not recommend running debugging on a remote server because its quite slow. 

Anyway, if you wish to know how to set this up, this may help

http://blogs.msdn.com/greggm/archive/2004/10/04/237519.aspx

Bruce L, the thing is I am sure that the service is running on the web server, how do I know this? Because on one machine remote bugging works against the web server while on the other machine I get this message. So if it works on one, then that tells you that the service is running on the web server.

I am logged on to both machines with the same Domain ID...
Currently I have firewalls turned off on both machines.

Do you think that issue may lay with the fact that the machine that is not working is hosted on a VMware instance?

I don't think hosting it on VMWare makes a difference but it is remotely possible.

Sorry can't be of much help.