Need some generic answers on remote debugging

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ASP.NET4

A little background in the past where I have worked the network admins always had remote debugging set up on our servers and everything worked without issue. Where I am now I had to install and set it up.

Here is where I am getting lost. I made a small console app to test with. Set it up the server and on on my local had no problem when executing on the server and stepping though the source on my local machine.

Now the real test , a web application code and pdb files loaded on the server. Remote debugger started. On my local I get a list of process on the server and see two instances of w3wp regardless of which one I attache to( and on the server I can see in the remote debugger window that I am attached) I never break on my brekpoints. I have missed something in getting set up but am at a loss as to what I have missed

What I have tried:

Searching in vaoin throu the tubes of the internet