How to loopback a Windows VM VPN connection to an Ubuntu host?

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Asked By CuriousCactus42 On

Hey everyone! I hope this isn't too silly of a question. I've spent the last couple of days searching for answers and trying to figure it out using ChatGPT, but I'm stuck on a tricky issue here. Our department primarily uses Ubuntu, but we need access to certain resources that only work through a Windows VPN.

The plan is to set up a Windows VM where I can install the VPN, which would create a new connection (the VPN tunnel). After that, I need to find a way to loop back this Windows connection to my Ubuntu system so that all traffic can flow through the VPN. Sounds easy, right? The problem is I can't seem to get the Ubuntu machine to recognize the connection from the VM.

I've got a deadline coming up this week, and I'm really anxious about it, so any help would be greatly appreciated! Here's my setup:
- Host: Ubuntu 20.04
- VM: Windows 11
- VM Software: VirtualBox 7.1.8
- Connection: Standard LAN with one NIC. Any tips or solutions would be amazing! Thanks in advance!

1 Answer

Answered By TechGuru99 On

It sounds like you’re trying to configure a routing setup with your VM acting like a router for your host. Without more details on what exactly happens when you say 'Ubuntu refuses to recognize the connection from the VM,' it’s hard to pinpoint the issue.

However, here are a few things to check:
1. Make sure you’re bridging the VM's network adapter with the host's network. This way, both the Ubuntu host and Windows VM can communicate smoothly.
2. If you're using NAT, that could complicate things; a bridged connection would be better for your needs.
3. For the return traffic, you'll want to set up static routing on your Ubuntu machine so that it knows to send the traffic destined for the VPN's subnet back through the Windows VM. This way, the packets can find their way back to where they originated.

Hopefully, this helps to set things up!

UbuntuUser87 -

Thanks for the insights! Just to clarify, when you mention 'static routing,' are you saying that I need to add a specific route that points to the Windows VM IP for traffic going to the VPN subnet? That makes sense!

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