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Windows 8 fails to load HTTPS site for Windows 2012 RD Gateway when redirected with local Host file

I have a Windows 2012 server which we are testing with RD Gateway and 2 Windows 8 workstations.  To test the RD Gateway I change the entry in the Host file to redirect my TSGateway from the production system to the Test system.  Now the strange part is that I can open and view the RD Gateway default web page from a Windows 8 system that was upgraded from Windows 7, but a Fresh install of Windows 8 fails to view the default web page.  The fresh load can ping the TSGateway by name and replies with the correct address, so I know that part works.  If I change to my production Windows 2008 TS Gateway server, both the upgraded and fresh install system connect without a problem.

Is there something new in Windows 8/IE 10 that causes problems when trying to use the Host file for HTTPS sites?  

Thanks
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YeoLyle
Asked:
YeoLyle
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1 Solution
 
becraigCommented:
What is the error you get when trying to view the page from the windows 8 (freshly built) system.
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YeoLyleAuthor Commented:
The error is pretty generic "This page can't be displayed".  When I run the IE 10 capture the packets I see under the Initiator Frame URL "res:ieframe.dll/dnserror.htm".  I receive this error when the Windows 8 system is outside our network.  Now here is the kicker, when the Windows 8 system is connected internally the "Host" edit allows the connection to the TSGateway and displays the web page.  So it appears that only when I want to test using a Host file through the public Internet does it not want to work.

Thanks.
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becraigCommented:
Run the following command to determine if your dns is resolving via the dns server the win8 system is using

nslookup hostname.com  (Where hostname is the name for the gateway you are connecting to)

This should be able to tell you if that name is resolving publicly, you can also try doing an nslookup at http://centralops.net.


It sounds like it might just be dns where the dns server handling NS for your domain might not be responding or does not have an A record for that domain name / host.
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becraigCommented:
Also in the browser click on the more information button to see what error is displayed there might be more information there.
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YeoLyleAuthor Commented:
NSLookup is working as designed where it does return the Internet DNS record.  I am using a HOSTS file with a custom record for the RDGateway to point to my Test system.  The HOSTS file is checked before DNS and so IE should not be looking for the DNS record.  
On the Windows 7 upgraded to Windows 8 both command prompt and IE return the Test system when the HOSTS file is configured.
On the Windows 8 fresh load the Command prompt returns the IP Address from the HOSTS file, but IE just goes no where.  I have attached the screen shot of the errors I have, but this should not be a DNS issue since DNS should not be checked if the record is found in the HOSTS file.  Well at least that is they way IE used to work.
RDGatewayError.PNG
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becraigCommented:
This sounds like a proxy override in the browser.

Please check the connection settings in the browser and uncheck any proxy / autocheck boxes you see selected restart the browser and try again.
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YeoLyleAuthor Commented:
That is a good thought.  I do have a proxy, but removing it was one of the first things I tried.  Even attempted to restart IE after removing it, still no go.  I even scoured the advance settings in IE and Site settings.  I even went as far as resetting IE back to the Defaults which removes the proxy settings and many more, but still no joy.  This happens on both my home network and even if I am on a public network not protected by a firewall.  The odd part is that if I am internal to the network, I can use an Internal IP address in the Hosts file without a problem.

Your idea made me think, so I then went through the services to see if by chance there was something in there, and stopped any services that even resembled Connection, DNS, or Proxy services.  Again I still was unable to browse the page.

Part of me thinks if I put the test system active in DNS, that it will work, but it doesn't give me the warm fuzzy feelings when things don't work as you expect.

Thanks
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becraigCommented:
ok So here is a silly question, is there a device between the internet and your RD server ?

It seems as you indicate DNS resolves perfectly and once you are inside you can route to the server by internal ip.

It sounds as though traffic is not routing to that box on the public side.

Can you provide a little more info on the network architecture ?
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YeoLyleAuthor Commented:
Doubt that it is the Firewalls, since the Windows 7 box that was upgraded to Windows 8 works fine, as well as any number of Windows 7 systems.  It is Just the fresh loaded Windows 8 is giving me fits.

Thanks.
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becraigCommented:
Ok I just re-read your original post (Sometimes in the discussion you miss things)

Do this from the fresh box:
1. run tracert to the domain name and see if it resolves to the correct (test server)
2. try installing fiddler - www.fiddlertool.com on the win8 box to see what route it takes when you call it in the browser.

Let me know how both things go for you.
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YeoLyleAuthor Commented:
Wow do I feel silly.  I had a Dyslexic moment.  I looked at the IP Address multiple times, but today noticed I had the 2nd digit in the IP address incorrect.  

Thanks for your help, but in the end it ended up being user error.
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