I haven't tried this and am wondering if it is possible to obfuscate my location further by using a VPN on my Win10 install and then opening a VM such as Ubuntu or Win7 and then run a VPN in that. I'd use the same provider but different locations. Thanks

  • This is a question I'd be very interested in knowing how to do. My school provides a free VPN, but then there are things that I do not want associated with my school account. Nothing illegal, but all the same, there are things you don't search at work either, regardless of legality and even if they are not specifically forbidden. So I'd like to then VPN to my home machine and be able to do everything that I do at home. – JFA Aug 18 '15 at 13:09

If they already know who you are (if you pay them they do) then there is really no point, is there?

To an outside observer your VPN traffic is unintelligible either way.

  • I would agree, but question is it technologically possible? – Todd Aug 17 '15 at 23:18
  • Definitely. Back in 2004, I remember, I used to run a VM with Win/XP for my USB cable modem, which connected to the Internet, and shared that connection out to my Hackintosh host, that shared that out to my Ubuntu workstation, that connected to an OpenVPN at my workplace, from where I used the PPTP VPN for on-site management consoles, in some forgotten part of the world. – godDLL Aug 17 '15 at 23:32
  • Old skool nice. Btw what were you doing in 04 with a VPN? – Todd Aug 17 '15 at 23:34
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    Workplace requirements. Not leaking any company secrets, I suppose. – godDLL Aug 17 '15 at 23:35
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    @godDLL hypothetically – JFA Aug 18 '15 at 13:05

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