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I am trying to secure a few application pages with role base authorizations can't seem to get it working , if I set a deny rule for all users the rule works, but anything with a specific group or username doesn't work I am using claims based authentication.

and direction is appreciated

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Maybe you can try different approach. You can secure application in page code rather to alter/add web.config file(s).

This link is bit old but for general info will be ok:

I still have few scars left from my last fight with Sharepoint web.config.

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