ASP.NET Root Url Doesn't Resolve to Default.aspx

I have an asp.net web site that won't seem to resolve to Default.aspx when initially loading. When I debug on my local machine it loads Default no problem. Unless I try to navigate to "localhost:#####/". Then it gives a 404 error. When I deploy it to a staging server, give it a virtual path "mywebapp", and load it from "http://ift.tt/2iKvwl8" it gives a 404 as well. I have set Default.aspx to the top of the list for Default Document in IIS. If I navigate to "http://ift.tt/2zye6QD" the site loads just fine. Any suggestions? I would paste code but it is a large website and I quite honestly am not sure what I'm looking for anymore.