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I'm facing some connectivity issues with accessing Tails along with IP vanish software. This is what I'm doing

  1. Used IP vanish and selected a different server location
  2. Installed Oracle Virtual Box and installed Tails OS. It simply says that TOR is unable to connect due to some proxy settings

Now I'm doing this because I believe using IP vanish along with Tails would offer a better security from being traced back

Any solutions?

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The checklist is:

  • pluggable transports: obfs3, obfs4, meek
  • pre-seeding first on a working conection
  • using no entry guards

post your logs, so I'll be able to help you further

UPDATE: So thats "what is this, what it's for and how exactly can it help in your case": Grade-zero: a very valuable addition to your question will be a tor run log, so it will be more clear technically in details what's happening.

First, it seems that a direct Tor protocol seems to be blocked and/or messed up by a network connection you're using(IPVanish, I presume. But there can be a MitM before/between your VPN). So the "medicine" here is a thing, "that changes a Tor protocol from it's original way to look like something else". That's the exact definition and puropse of a pluggable transport. There are many of them, you can see a semi-full list on an official website page about them. The ones I've mentioned are the most working ones: ObFS is a synonym/alias for "obfuscation" word, so there are some versions/generations of it, and I do recommend you not to start from the latest one - obfs4 - but start from more common obfs3. If it still will not work - try Meek, that tries to mimic HTTPS in general. And also an endpoints for connecting to Tor network(=Guards/EntryGuards) can be banned on by-ip basis, so that's why I do recommend you to seed at working connection first - to obtain an offline copy of the most actual state of the network, so some entries won't be banned. And even if they are - you can not to use them as a first hop, and try to pick any relay to be an entry point.

  • Alexey, I really appreciate the comments but I'm kinda new here so could you please explain in detail? Thank you – Chandra Shekhar May 15 '16 at 14:28
  • @ChandraShekhar you're welcome! Take a look at my update and feel free to ask further questions if you need more info - I'd like to help! And - please - post your torrc config and running log. It will help me a lot to help you – Alexey Vesnin May 15 '16 at 19:22

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