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It's well known that VPN clients might leak their true IP, due to applications like Skype or WebRTC clients or who knows. Moreover, services like Google keep complaining that I connected from an "unknown device" and they lock even simplest services (e.g., IMAP) until manual confirmation, just because I appear to have switched to an overseas IP.

So, I'm thinking of a different setting: for private/sensitive activities, I'll use a Linux system on top of VirtualBox, which has a VPN client on it. The Linux box will have the bare minimum, won't use my regular accounts, won't use rubbish browsers like Chrome, etc. For all the rest, which is not critical and I don't mind much if they track me and send me ads based on what I browsed on Amazon, I'll keep using the host, without VPN and with more basic protection against spies (e.g., firewall, anti-spyware/malware software, using Linux and not crappy Windows).

Question is: will this setting decrease the security of that VM/VPN client? I mean, compared to a physical machine connecting the wifi or the home router directly? Is there some danger that they track the host, e.g., by inspecting TCP/IP data? Can they do other tricks to associate the VPN connection to the host, or some other device in the same home network (e.g., smartphones/tablets, which of course aren't on the VPN either)?

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It is very hard to say whether or not using a VM is more secure. As you are referring to technicalities, please take a look at this page written by the maintainers of Tails (a well known Linux distribution for anonymity via TOR). These warnings apply to every VM, not only Tails.

On one hand utilizing compartmentalization can add security, however this added layer also means an extra attack vector. If you are sloppy with running patches, might have downloaded some software from weird places, having your little brother using your PC as well, etc, these things might make you vulnerable, using a VM or not. And even worse, it might have you end up with not one but two compromised systems.

If you think you can be a good 'host' for your VM, go for it as I think the risks are low (now that I made you aware of those). If you require even more security, then you probably better of using a dedicated computer for these events.

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  • Makes sense, thanks, although I'm trying to compare the two situations (with or without the host in between) keeping all the rest the same, to assess possible additional risks. Both systems would be pretty sure anyway, since I'm a software developer with some experience as server admin.
    – zakmck
    Commented Feb 4, 2018 at 20:53
  • Well, since you are in control of the host, the risk of a host compromising a VM should be minimal. The other way around shouldn't be possible, as this shouldn't be possible by design. But as sometimes bugs pop up, like Meltdown, that could cause VMs getting out of their sandbox. Not sure if this is much of your worry when just browsing websites and expecting a bit more privacy routing your connection through a VPN.
    – user258572
    Commented Feb 4, 2018 at 21:56
  • Thanks again. My main concern is about leakage of my true IP, mainly because I've been reading about collaborations between ISPs and third-party sharks (e.g., protonmail.com/blog/private-browsing-history).
    – zakmck
    Commented Feb 4, 2018 at 23:33
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    If you use a competent and trustworthy VPN provider, you should be safe. Disable WebRTC in your browser and you are good to go. Even connected via VPN tracking still can happen; always use a new private window for every site you visit, and (auto) remove cookies and history. Especially on those sites where you log on with an account that can identify you.
    – user258572
    Commented Feb 5, 2018 at 19:24

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