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I would like to chain a couple, say 6 or 7, VPNs together to create a sort of "super" encrypted lane on the internet. I'm not too concerned about speeds, all I want is privacy and anonymity.

I've read online about adding a Tor exit node to the equation for an even better level of privacy. Is this a safe option to increase my VPN chain?

I'm going to use this "super" VPN Chain mostly on public WiFi so does this rule out any attacker might get ahold of my data? Some sites I use on a daily basis don't have an SSL layer and there are also some sites that have me worried about their level of security.

  • 2
    what speaks against standard TOR usage? – SEJPM Apr 11 '15 at 20:20
  • I'd prefer to go with the VPN route because Tor is just incredibly slow. – Martijn Apr 11 '15 at 20:21
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    In your question you say you're "not too concerned" about speeds... – ǝɲǝɲbρɯͽ Apr 11 '15 at 20:22
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    TOR will be faster than 6-7 vpn chained as you've only got 3 hops. – SEJPM Apr 11 '15 at 20:24
  • @ǝɲǝɲbρɯͽ Sorry for being unclear. I meant, speed is not high on the priority list but I don't want to start living in the dial-up times. :) – Martijn Apr 11 '15 at 20:32
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It depends on what you're trying to defend against.

If you're trying to prevent a site operator from identifying who you as a user are, multiple VPNs won't gain you anything. The operator will see the traffic as coming from the endpoint of the final VPN regardless of how many there are in the chain. You're still vulnerable to being identified through other means (eg. if you sign up with a username you use elsewhere). This is essentially the same level of anonymity you'd get through TOR, but it costs more (and presumably has better performance).

If you're trying to keep a government from tracking you down, multiple VPNs again won't gain you anything. The government just needs to identify the last one in the chain, and then ask who's paying for it. Here, TOR is better, since there's no financial link to you.

If you're dealing with an adversary who can monitor packet movements on the Internet, but can't monitor financial transactions or serve subpoenas (I can't think of any), chained VPNs will increase your anonymity by increasing the number of traffic flows they need to monitor. But this is a very rare case, if it exists at all.

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    Several VPN providers offer payment systems intended to provide anonymity, like bitcoins for example. Associate such payment system, with a one-time free email account opened and accessed through a VPN, then it would become harder to link this VPN account to anyone (even-though TOR would remain easiest to use and more secure due to the dynamic chaining). – WhiteWinterWolf Apr 12 '15 at 7:18
  • Tor (not TOR) is also useful because it does not expose your networking stack to TCP/IP fingerprinting. – forest Dec 19 '17 at 4:07
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Not really. Your question is about security and privacy of your data in transit, but you don't trust the endpoints. You can secure the route all you want, but it's difficult to force all applications to use it, especially those that compromise you from the other end of the VPN.

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