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Okay, so I've been looking around at the benefits of using tor to access you vpn and vice versa. Here's what I've come up with:

VPN -> Tor

Pros:

  • Hides Tor usages from isp
  • Hides your activities from VPN logs (They only see that you're using tor)

Cons:

  • If VPN does log, it's no better than using tor via ISP
  • If VPN connection drops, and you are not using a kill switch, ISP will see tor usage

Tor -> VPN

Pros:

  • More anonymous to VPN in case they keep logs
  • Protects you from compromised Tor nodes

Cons:

  • Show's ISP that you are using tor
  • Can't access .onion sites

So, I was thinking that if you were to invest in two separate VPN accounts using bitcoin and some means to prevent tracing of payment you could then chain VPN to tor -> VPN -> Tor. Wouldn't this remove all cons?

If you looked at their privacy policy, checked all legal documents, and made absolutely sure that they keep absolutely 0 logs of data, Wouldn't this chain be optimal? The first VPN prevents your ISP from seeing that you are using tor, then tor encrypt your data to the second VPN, and finally the second vpn sends it's data to tor again so that we can access .onion sites.

Also, would it still be unwise to connect to social media sites and things of that sort? If so, why?

EDIT: I was thinking more about it and I suppose that if you had a VPN who you were sure kept absolutely zero logs then you could simply use tor to access .onion sites, but wouldn't that be the only point?

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  • I think VPN-->TOR-->VPN-->TOR-->Destination is same as VPN--->TOR-->Dest. or VPN-->TOR-->VPN-->TOR-->VPN--->TOR-->Dest. Am I missing something? In either way you can hide the fact of using Tor from your ISP and also access the .onion sites
    – ρss
    Jun 19, 2015 at 12:54
  • Your question sounds interesting but can you describe your thinking more? For example in both VPN->Tor and Tor->VPN you say it's more anonymous from hiding logs.
    – Celeritas
    Dec 2, 2015 at 7:11

1 Answer 1

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You better use VPN -> Tor, because you have actually no cons you've listed:

  • If VPN does log, it's no better than using tor via ISP It is better, because VPNs are not censoring network access like ISPs: you can always find a VPN provider that will allow Tor usage, willingly or not - bridges with pluggable transports like obfs4 are very good for that. And both VPN and your ISP will have a log/protocol of your connections unmappable to your actions.
  • If VPN connection drops, and you are not using a kill switch, ISP will see tor usage nope, you use a proper firewall config and ifup/ifdown scripts to not-to-leak a single byte from tor except through a tunnel interface. It's a piece of cake task: you're running Tor under an unprivileged user and allowing this user to use your tunnel interface only. In case of ifdown event you set DisableNetwork 1 and Tor "sleeps" until you will re-enable it in ifup event handler.
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