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Hear me out. Your typical remote device model for an organization it to VPN onto their network. However, what if you want to work from somewhere outside if your normal homespace, such as working permanantly remote for long periods of time in another country. IS it possible to set up a second VPN (obviously one I'd set up myself) to create the appearance that I am in the geographic area of my real home and place of work, and while on this VPN, simultaneously get on my works VPN as well?
I won't go into the moral issues with what you're trying to accomplish.
From a technical standpoint, yes, you can layer VPN tunnels. I do this at home. My router is always connected to a VPN service that rotates everyday. When I need to connect to my office network, I pull up the VPN client on my laptop, and connect to the office VPN. My computer (and the VPN client on my computer) is not aware of the fact that the router is funneling traffic through another VPN behind the scenes.
If someone were to look through the logs of the office VPN, they would see my connections appearing from a different location each day.
Can you? Yes. It's a fairly common function (for redundancy and obfuscation reasons).
That said - whether it's actually meeting your requirements is a different story.
For example - if you're remoting into your work with a work laptop and if they have the right management agents installed - having multiple layers of VPN may still not hide where you are. Since that agent is on the laptop, it can still phone home with other info that can give your location.
It also seems like a complicated solution to a problem that may not even be a problem...
I don't understand how you're going to VPN from VPN because the point of VPN is to provide a secure tunnel from you to your destination and only to your destination. Depends how your VPN is configured, if it then allows access to public internet after it reaches your destination, you can access the secondary VPN otherwise you cannot. Also, in this case you may connect to VPN gateway closes to the destination device which may deter your QOS.
Just know that those downloadable VPN clients from your home internet is not true to VPN. You don't even know if your traffic is behind a proxy server unless you know the technology and configuration being used on server side.
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