First off, you need to use the remote debugging monitor that ships with VS2008, although they look identical the VS2005 monitor won’t work with VS2008. Next problem is where to find the monitor. In VS2005 it was a separate install on the VS2005 setup disks, in VS2008 it’s installed into the common IDE folder under VS2008 (…Program Files\Microsoft Visual Studio 9.0\Common7\IDE\Remote Debugger\x86). You simply copy the files from there to the machine you want to monitor. As for getting it to use breakpoints and the like then it’s back to the old tricks of remote debugging. Basically to make life easy it’s much better to just rebuild the DLLs you’re interested in and ship them to the target…saves a lot of hassle.
A quick post about a couple of potential gotcha’s with remote debugging in VS2008.