Hi BitShift
i also tried to do the same thing and end up working like this (some one else told me these steps to follow) and it works, but with little hassle of turning on/off as in step 1.
1. In the IIS admin console, set your application to _not_ require client
certificates.
2. Load your solution/project in VS.NET.
3. Start debugging the project by running it from VS.NET.
4. While it's already debugging (started in step 3), use the the IIS admin
console to set your application to require client certificates.
5. Continue your debugging run. You should be able to see the client
certificate in the requests for the remainder of the debugging session.
hope it helps
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Ch. Zeeshan Nasir