Here's the scenario (please read this and not just the title, this is not an application setup issue):

  • The application works fine over 80 (http) and 443 (https) from the public-facing IP address.
  • From the internal IP address, we can only access the port 80 (http) side and the 443 (https) side gives a 'page not found' error.
  • In IIS Manager, under Actions > Browse Web Site, it links to the public IP address over 443, not to the internal.

Why is this? Is this by design? We have confirmed that it is not an internal network setting prohibiting access over 443 (remember that it works fine on the public IP address, which is the one that counts anyways - but trying to figure out why this is).

  • 2
    My guess is that it's an internal DNS issue. You probably have site.external.com configured somewhere on a DNS server in a zone and you probably have an SSL binding on this site for port 443 that is something like site.external.com so when you try to browse to it, it uses the DNS on your network and tries to externally hit it. Can you try just manually typing in h t t p s : / / IPOFWEBSITEINTERNALLY in your web browser? What happens then? – Brad Bouchard May 14 '14 at 19:29
  • How do you access the https site on the internal IP? If you access it by IP like https://[fda7::1]/ there won't be a matching certificate. I'd ensure the domain name used by the client matches the certificate to rule out that possible source of errors. – kasperd May 14 '14 at 19:37
  • Of course it's an application setup issue - what else do you think it is? If you're using host headers, IIS presents the host header to you as part of the binding. If you add a binding sans host header, you can use that. – TristanK May 14 '14 at 23:19

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