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I have a Windows 2008R2 server, I'll call this 'dedserver' for clarity, that has hyperv on it. It runs another Windows 2008R2 server with IIS on it, I'll call this 'vpsserver'.

Both have a dedicated public ip address:
(faked addresses for security reasons)
dedserver: 64.64.64.64  
vpsserver: 64.64.64.65

Both are accessible from the internet. I'm actually on the dedserver now typing this. I can access the vpsserver via hyper-v manager and I can goto a computer in the office and home and access the website.

When I attempt to access the website from the dedserver, which resides on the vpsserver, I am getting a timeout.

I rebooted both machines just to make sure. I did a ipconfig /flushdns, no luck.

I then did a tracert thewebsite.com:

C:\Users\someone>tracert www.thewebsite.com

Tracing route to techguy.ws [64.64.64.65]
over a maximum of 30 hops:

  1  PLATINUM [64.64.64.64]  reports: Destination host unreachable.

Trace complete.

It shows it is going through the dedserver to access the vpsserver, which makes sense.

What am I missing? Why can I not access the vpsserver's website from the dedserver?

I would like to use this for testing and it's really causing me to have a bad week :P

Any help would be greatly appreciated!

  • please note, these are not the true ips or urls. – JohnDoe Sep 13 '13 at 19:53
  • The site on the VPS, can you access it from outside of the VPS at all? (You said you can go to a office/home computer and access the site - thats on the same net as the Ded/VPS?) If not, I would look at Firewall on the VPS (test by telnet <VPS.IP> 80 to see if you can connect to port 80)... Otherwise if the only one not able to access the VPS site is the Dedicated, sounds like a Network/Routing issue between Ded/VPS – Brock Hensley Sep 13 '13 at 21:23
  • I was thinking it was the network setup also, I think I screwed up something. Any suggestions where I look? The network adapters seem like they are correctly setup. What tells them to be able to see each other? – JohnDoe Sep 13 '13 at 21:54
  • What type of Network did you create in Hyper-V? I'd recommend External. Basically you should search for Host/Guest communication in Hyper-V andrewconnell.com/… google.com/… – Brock Hensley Sep 13 '13 at 22:06
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Test to see if you can access the site on the VPS from outside of the VPS at all (i.e. from the Host machine or another computer on your network).

You can test if you can connect to IIS at all (i.e. testing whether the Network communication and Firewall is working as expected) by using telnet:

telnet 10.2.3.4 80 where 10.2.3.4 is the IP of the VPS. (If it goes to a blank screen after the command that means it is connecting).

Otherwise if the only one not able to access the VPS site is the Dedicated, sounds like a Network/Routing issue between Ded/VPS

What type of Network did you create in Hyper-V?

I'd recommend External network if you want the VM to act like a normal node on your network and be accessible from anywhere on your network.

Basically you should search for Host/Guest communication in Hyper-V, here is a good link:

http://www.andrewconnell.com/allowing-a-host-machine-to-talk-to-guest-vms-in-hyper-v

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