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Hi I am wondering if chaining 2 different VPNs from 2 different VPN providers through a Virtual Machine needs any extra routing settings or any extra settings in general.. I have searched and I've seen that if you choose to chain VPNs with VM all you need to do is run VPN1 on your host OS then boot your VM OS and run VPN2 from there and then u have the 2 VPNs chained..Is it really that simple? And if it is that simple what are some problems that may occur? I'm a newbie and I am really struggling to find an answer!

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Yes it should be that simple. Traffic on the virtual machine should in theory redirect through the inner VPN, which should in turn redirect traffic to the outer VPN, and finally out to the internet. However, all of this is highly dependent on both how you configure the VPNs and how you configure the virtual machine.

You need to first ensure that your settings on the virtual machine prevent internet traffic from circumventing your inner VPN and going directly through your outer VPN.

Then, depending on what you're trying to do, you need to configure both of your VPNs to be as restrictive or non-restrictive as you'd like. I can only assume based on the premise of this question, that you would want as much security as possible, in which case you will probably want to prevent ip leaks and disable DNS leakage and change other settings of that nature.

It's also probably a good idea to ensure that your VPNs are using UDP rather than TCP, because if they are both using TCP, then you can get a very nasty effect known as TCP Meltdown, that might make your connection horribly slow. There is an informative Computerphile video on TCP Meltdown here if you're interested.

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