Cant get traffic to flow through manual route in Windows to VM, and on through VPN

2

Have done some reading around but not found a solution that works yet.

Basically, I have an old computer that has a configured VPN Connection. I now have a new computer and wanted to access that same VPN - I cannot get it reconfigured natively on the new computer. So, I converted the old computer into a Virtual Machine which is running in VMWare Workstation Pro.

I can connect that VM up to the VPN and browse the intranet behind it. My next step is I want to do some routing to pass-through traffic destined for that network, through to the VM and then onto the VPN Network.

The layout is as follows

  • Local LAN - 192.168.1.x
  • VPN Network Destination - 10.46.x.x
  • New Computer (Windows 10 Pro) - 192.168.1.244
  • Virtual Machine on Bridged Mode (Windows 8.1 Pro) - 192.168.1.199.

I tried to instead use a Host Only adapter between the Guest and Host OS's as to avoid a loop. The Addresses there for the new computer is 192.168.233.1 and the VM is 192.168.233.128. I can ping from the VM to the New Computer over that interface so there is connectivity - however I cannot ping from Outside to the VM, which I believe is some security policy enforced in the VM to not respond to pings.

I added the following route using ROUTE ADD successfully

route add 10.46.0.0 mask 255.0.0.0 192.168.233.128 IF 18 - where Interface 18 matches up with the VMWare Network Card that is connected to that host only network.

When I connect the VPN, I can do everything inside the VM that I want to. When I try to ping or traceroute from outside the VM, everything just times out.

Any ideas?

Cameron Stubber

Posted 2016-02-18T08:00:10.307

Reputation: 21

You do have routing enabled on your VM, do you? And why couldn't you configure the VPN on your new PC? – Lenniey – 2016-02-18T08:08:40.093

Long story short is that our IT Department, whenever they touch something it breaks. This is my second reinstall on this new computer already because they corrupted it the first time. I have a connection that works if I can avoid having them interfere with it. And did I miss an obvious setting in VMWare about routing? – Cameron Stubber – 2016-02-18T08:40:13.373

Should I perhaps have done something in terms of making a virtual network segment in the VMWare Infrastructure? – Cameron Stubber – 2016-02-18T08:52:23.917

You have to at least enable IP forwarding / routing in your VM to forward the packets from your Win10 machine. I can't delve into detail right now because I don't have the time atm, sorry. Have a look at this registry key: HKLM\SYSTEM\CurrentControlSet\Services\Tcpip\Parameters\IPEnableRouter. I don't know if this suffices in Win 8.1, I just want to point you in the (hopefully) right direction. – Lenniey – 2016-02-18T09:01:53.360

Thanks Lenniey appreciate the advice at least :) WIll take a look there – Cameron Stubber – 2016-02-18T09:09:59.343

Did you achieve anything yet? – Lenniey – 2016-02-23T07:24:00.180

Hi Lenniey, No unfortunately not yet.

Work has been a bit busy so for the time being I have been just living with using the VM for VPN Stuff. I really only need it for company intranet and to push/pull code from other teams so it is livable, but not ideal. I will likely revisit it in the next week or so but I may house the VM on my physical server which has a few network cards anyway, might make life a bit easier to do routing on that box.

I did find that IPEnableRouter registry setting but dont really know what it did. – Cameron Stubber – 2016-02-27T15:31:32.900

No answers