Sanity check: Virtual Machine, VPN on the host or the guest?

[bonbon77 0]

I would like some advice on how to setup my VPN. My host is a live CD (Ubuntu) and my guest is also an Ubuntu VM. The only thing I use the host for is to connect to the internet via a captive portal via public WIFI and then boot my VM and I do all of my internet activity in the VM. Nothing is done on the host other than establishing a wifi connection via the captive portal of the public wifi.

 

My options are to run the VPN on the host or guest.

A few specific questions:

 

 

1. What would be the pros/cons of running the VPN on the host vs. the guest in the above scenario?

2. From the perspective of the public wifi router, would there be any difference in what it would “see” if the VPN was on the host vs. the guest? If my browser connects to a “Google” IP, would the router see the Air VPN IP instead of the Google IP in both cases (host vs. guest VPN)?

3. If the public wifi blocks VPN connections so that a VPN connection can only be established by using an SSL/SSH tunnel, would that make a difference regarding running the VPN in the host/guest?

4. Assuming I need to connect with a SSL/SSH tunnel to the VPN, if I also then wanted to use TOR browser in the guest, would it matter if the VPN was established in the host vs. the guest?

5. This probably goes back to question #1, but are there any security implications in running the VPN in the guest vs. the host (DNS leaks, IPV6 issues, dropped connections, etc…)

Thank you!

[Monotremata 22]

Running it on the host should be fine. A virtual machine just takes its network connection from the hosts connected network adapter anyways. Its gonna use the same traffic path as the host is using. Better to let the host handle the network performance hit of the VPN, then making your virtual machine do even more work than its already doing with the system its trying to emulate..

[bonbon77 0]

My preference would be to run Eddie on the guest. Since the host is a live CD and it doesn't currently have Eddie installed, it would be a bit of a pain to have to respin the live CD to install it and then every time I need to update Eddie. However, it is more secure to run Eddie on the host then I would do so.