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I have moved from Windows 2003 server to Windows 2008 and have some issues related to IIS or networking I would rather say.

I have two NIC's in the server. One is with a fast IP address given by the ISP XX.XX.XXX.XXX which is connected to the internet and the other one is a local one with and address looking like

In the RRAS the first NIC is configured as the public interface going on the internet and the services provided by the server such as Web server and mail server are added as offered services on that interface meaning that the RRAS sees that as a Proxy.

The other one, the internal one, is meant to be the router for the local network to access the internet.

Everything works fine meaning that I can get on the internet without any problems from the internal network and my websites on the server are accessible from the Internet. THE HUGE problem is when I try to access my websites from within the local network - nothing happens. I don't get a 404 page, it just hangs on there and nothing happens. The web server is configured correctly and is accessible from internet.

Any idea why or what kind of configuration problems I might have?

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As an aside I would HIGHLY recommend you use a stand alone router for all of this. While Windows can act as a router I have never seen the point, especially since a small Linksys or NetGear can easily do the job of Windows. Any particular reason you are using the server as a router? – Brent Pabst Oct 1 '12 at 20:22
I second the notion. Also I'd just as strongly recommend to separate publicly accessible services from your LAN. A public-facing web server should be placed in a DMZ. – Ansgar Wiechers Oct 1 '12 at 20:58
Thank you for your answers. The strange thing is that while from the local network I can navigate on the Internet and from the server itself I can see my sites, I can not do that from any machine on the network. Why I use the Windows as a router is quite simple.. I don't know how to do something different. The server have two NIC one facing the internet and one facing the internal network. So how should I proceed as I have no clue on this? Thank you! – Julian Oct 3 '12 at 12:10

I think you may be running into a hairpin issue, where you are sending traffic into your local lan segments interface, it should then be hair pined on the outbound interface but isnt.

The easiest solution would be to connect to the webserver on its internal IP (192.x) address. You may need to have IIS set to bind against both the external and internal IP.

That would be the easiest, (read not the best) way of fixing it.

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Adding on to Steve's answer...

Manually entering the web server's address into your local hosts file for the internal IP should do the trick as well.

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