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Windows 7 Virtual XP CISCO VPN

Posted on 2011-04-18
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Last Modified: 2012-05-11
I have a machine that i currently have running in virtual XP mode as we are not ready to deploy Windows 7 yet. We also are still running NT 4 for our domain (yes that's right NT 4, no need for jokes i've heard them all).

This user is often remote, and needs to access the virtual machine with XP through the Cisco Anyconnect VPN. I fire up windows 7, connect to VPN, then launch my virtual machine. My problem is that the XP virtual machine doesn't seem to be picking up the VPN connection from Windows 7. The virtual machine won't let me login because it keeps saying the domain isn't available.

I have played with the adapter settings in the VM. First i tried setting only the first adapter to NAT with no success. Then i tried setting the first adapter to NAT and the second adapter to just regular wireless.

It would seem the traffic is not passing correctly from Windows 7 VPN connection to the VM. Any ideas? Is this more so the fault of the Cisco VPN or is the network adapter config i am attempting wrong?

thanks,
-jess
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Question by:RobertetInc
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by:John Hurst
ID: 35420292
I don't know if XP mode offers bridged networking; I use VMware. I could not get VPN to work through NAT. That was some time back and may have been because of the VPN application at the time (Juniper Netscreen from SafeNet). Bridged mode is more straightforward, so try that if you can. .. Thinkpads_User
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Svet Paperov earned 1000 total points
ID: 35420535
I don’t think it is possible to use a VPN initiated interface as a network interface for Virtual PC. The reason is that the VPN traffic travels encrypted and is decrypted only on layer 3 with IPsec VPN or layer 4 of OSI model in case of SSL VPN as for Cisco AnyConnect.

On the other hand the communication from Virtual PC and the physical network adapter is done on layer 2.

Let say, you bring up the VPN before firing up the virtual machine. In that case the Cisco AnyConnect VPN Client adapter would be available in the list for the VM and you could select it but your virtual machine will not be able to establish a communication channel because the device on the remote site (your Cisco device) will expect encrypted traffic and will discard all packets from the VM as errors.  

I think that your only option is to install the VPN on the virtual machine and to use Start-before-logon feature - not available with Cisco AnyConnect Essential license, but available with IPsec client for Windows XP. I have never done this but I think it is possible and I will try it someday. I’ve done something similar: configured Windows 7 in Apple OS virtual machine to bring up a VPN so I don’t see why it cannot be possible within a Virtual PC virtual machine.
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