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CLOSING: I'm closing this question based on discussion in the comments and starting over from a fresh perspective.

On a Windows 2008 server with IIS-hosted websites, I've never been able to access those sites from within that machine. I never wound up solving the problem. Now I'm trying to set up Windows 2016 for the same websites, and I'm finding the same problem, using Internet Explorer 11. I can access those sites from other machines on my network, but not within the server hosting them.

What could be causing this?

  • you are using a browser other than IE/Edge right? are you entering the URL via Name or IP, and is the name or IP publically accessible, or only accessible from inside your LAN? are you using HTTP or HTTPS consistently from the server and the other systems (its easy to forget to specify HTTPS when using RClick -> Browse in inetmgr)? Do you have multiple sites, and are they all bound to individual IPs? – Frank Thomas May 1 '18 at 15:27
  • I just edited my question to show I'm using IE11. This happens with both http and https. The sites all share an IP address, but different host names. The sites are configured to accept all IP addresses as long as the host name matches. – Green Grasso Holm May 1 '18 at 15:29
  • Don't test with IE/Edge, as the Security configuration for server browsers breaks almost all sites. download chrome. also multiple names with the same IP + HTTPS can cause problems (SNI) with certificates. What is teh exact error the (non-IE) browser is displaying? – Frank Thomas May 1 '18 at 15:29
  • It seems strange that IE wouldn't work by default, given the IIS assumes you can view the site from within the server, as it provides links for doing exactly that! – Green Grasso Holm May 1 '18 at 15:31
  • The issue is that browsers on Servers are locked down with the Enhanced Security Configuration. see my answer here: superuser.com/questions/1008307/… – Frank Thomas May 1 '18 at 15:34

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