I haven't touched much about debugging but I admit that sometimes you have no other chance than analyzing a post-mortem dump or live dump to troubleshoot a problem. Our "Debugging Tools for Windows" package comes with a very hand VBScript : "adplus.vbs". It simplifies lots of things for us.

I was working on a customer scenario. The environment was x64 and I was trying to take a hang dump of a process. I issued the "adplus -hang -p 1234" command. Script started to do all the works for me but it failed with "Error 76 - Path not found". It was surprising to me as I haven't specified a path.

Then I needed to check the script and noticed that the problem was a variable named "strPackageName". This was the string storing the name of the file to be created. Thinking that a process is get mad at a really long path and a long name. I put an if statement like below right before "Wscript.Echo "Attaching the debugger to: " & strPackageName" line in the script : 

     if LEN(strPackageName)>30 then
        strPackageName=LEFT(strPackageName,30)
    end If

and it started working again. All I was lose is some part of the dump file name but It wasn't so much important thing to me as I had the dump :)

Wanted to share with you thinking that you may hit the same thing.

Happy debugging :)