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Windows 7: IIS not working across subnets

11 Mar 2014   #1

Windows 7
IIS not working across subnets

Hello and thank you for your time. Here is my situation. I recently got help with setting up multiple subnets on my hyper-v host server. The thread located here Configuring Static Routes Everything has been working great! Until I started testing some IIS applications.

Hyper-V Windows Server 2012 -

Guest VM - Windows Server 2008 R2 -

Guest VM - Windows Server 2008 R2 -

Guest VM - Windows 7 client -

Using the Windows 7 test client mentioned above, I can successfully access the IIS site running on When I try to access the same IIS site on, I receive the authentication prompt, but receive a HTTP 400 Bad Request error.

I've used programs like Fiddler to watch the traffic from client to server. I really cannot figure this one out. Normally I would think it must be something in IIS for the site I'm trying to access. If that were the case, I should get the same error when I'm accessing the IIS site on It's not until I try to cross subnets, that I encounter issues.

I'm wondering if I need some additional routing internally?

An interesting test that I did was to use my personal desktop. This desktop is a Windows 8.1 machine, not joined to the domain I have. It is in the same subnet as the hyper-v server and hyper-v guests on the subnet. The desktop utilizes the same gateway, but completely different DNS server. The DNS server utilized by my desktop is my ISP's DNS.

So, my the desktop I goto and it loads fine. I then goto and it loads fine.


I wonder if this means that the routing and remote access services on the hyper-v host, which just routes LAN traffic, needs some additional help?

My System SpecsSystem Spec
13 Mar 2014   #2

Windows 7

Bumping up. Anyone have any thoughts on this? If I had to guess it would seem like maybe I need to add something to routing and remote access.... I just can't figure out what.
My System SpecsSystem Spec

 IIS not working across subnets

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