Thanks for the responses everyone. It turned out the extra web config was the culprit. I somehow missed that when reading through the previous posts. Everything is now working correctly and my frustration is finally ended.

It did. But it's contents were different than Mike Tobisch. Mine contained:








The file also existed on the 2008 R2 server with the same value. I went back and retested with that server and found I was getting false results. With further testing I am getting the login prompt, so I must have logged in at some point on that machine and been remembered. Once I delete the file, or populate the impersonation tag, it auto logs in as it should. It makes more sense that this kind of tag is going to stop it from working, so I would wonder why I got a different file than Mike.

Does anyone know where I can find the documentation on setting up impersonation. All the links to the documetnation lead to a default dnn page with no information on impersonation or documentation. Google has been no help and I have searched all the auth ad documents.  I would really appreciate it.