Ok so I finally figured out the problem and it had nothing to do with the pass through proxy. I decieded to start from scratch, so I deleted the bookmark link, web acl's and pass through proxy settings for the password managment server that we were using on the IVE for that particular external user Role. I added the bookmark back in the role and created a web resource policy for the password server to allow access to all resources. In the Web Application Resource Profile, I noticed that the "auto single sign-on" options were enabled for NTLM so out of curiosity, I changed the option to allow auto policy to auth through kerberos and retested. Bamm it worked! Apparently NTLM auth allowed users to log in but somewhere in the backend they were using Kerberos to auth back to the front end. That explained why users could log in to the password mangement ui but when they were trying to go to other places on the server they were presented with the 404 message. Also it explained why the server was so slow when it was being queried. thank you guys for replying to my thread and at least giving me options to look at I appreciate it.
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