Alright the set-up, ArcServer 10.2.1, Web Adaptor is on a Windows Server with IIS in our firewall's DMZ.
-security authentication process has been change to web-tier
-sharing settings have been changed, our AGOL accounts url (https://****.maps.arcgis.com) for our Portal URL
-sharing settings have been changed, our Web Adaptor url (hasen't been named yet so still using ip address) for our service url.
-The Server that our Web Adaptor resides on has been added as a "trusted server" that credentials can be sent to.
Server in the DMZ (I am going off of what our IT department has told me, I don't have access to this server but they are been really helpful in trying to figure this out)
-IIS has been configured for web-tier authentication
Here's the issue....
I will make a specific map service "private", however, the user roles present to make this service accessible to are still ArcServer factory roles.
I share the service with a group on our ArcGIS Online account, and try accessing the data in a web-map. Go to view it in Explorer after logging in with AGOL credentials. Open the map, Explorer prompts me to enter credentials in again as the layer is "secure", I put my credentials in, and it continues to tell me I have invalid credentials.
Does anyone know where my communication of credentials is being lost? What configuration setting have I missed? Any help would be appreciated. I feel like the set-up is very close, but I missing something very important.