Issues connecting when client request is from server to itself?

Can anyone help me understand why when the client that is making the request (to a virtual server) is the pool member that traffic is being passed to it will fail?

 

I have an application server that can be accessed by going to https://app1.test.org/rest/services. https://app1.test.org is a virtual server call it 192.168.10.50. All requests are then passed on to server1 10.10.100.1

 

Virtual Server details: standard, http profile, Client and server ssl profile, and source address set to automap.

 

When I go to https://app1.test.org/rest/services from any machine other then server1 the page comes up without any issues. Note this page has AD integration so will recognize who I am and bring up the page.

 

When I try to access https://app1.test.org/rest/services from server1 I am prompted to login but doing so will not work and not sure why.

 

I have taken a packet capture of both requests and tried to compare them the one from the server starts out like this which I think is the issue but not sure how to solve?

 

 

Any ideas would be much appreciated. Thanks