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I am using a VPN -> Virtual Machine -> OpenVPN -> Tor -> Hide.me (proxy in url)

Exactly how anonymous am I?

closed as unclear what you're asking by techraf, S.L. Barth, Dog eat cat world, Anders, Dmitry Grigoryev Sep 30 '16 at 8:27

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    You are exactly somewhatly anonymous. – techraf Sep 30 '16 at 3:29
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    You are exactly 6969 anonymous – Jedi Sep 30 '16 at 4:50
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    Interesting question is, are your More, or less Anonymous then if you were just using Tor? I suspect less, since now their are more links in the chain to be compromised. – Lyndon White Sep 30 '16 at 7:26
  • A starting point for checking might be to run panopticlick.eff.org and check how unique your fingerprint is. – Lyndon White Sep 30 '16 at 7:28
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It depends on what you are doing. If you're running BitTorrent from your laptop, you aren't anonymous at all, for instance, since it publishes your IP. If you log into your email, or your Facebook, again, you've de-anonymized yourself.

Any application layer traffic, which identifies you, negates all your other protections.

If you are using a vulnerable web browser and visit a site which takes advantage of the vulnerability, now you're de-anonymized and possibly compromised!

Is your Virtual Machine running on shared hardware? Do you trust whoever is hosting it for you?

A very high level player could also be watching the traffic pattern into your OpenVPN host and out of Tor to determine the source of the Tor traffic is your OpenVPN host. They can then drill further either by hacking or, more likely, just subpoenaing the hosting provider. Did you pay the hosting provider in an anonymous fashion? Hope so.

My point is that if some org is powerful enough and wants to enough, and you aren't both brilliant and lucky, you can be de-anonymized.

  • +1 for "[...]and you aren't both brilliant and lucky, you can be de-anonymized." – Lembik Sep 30 '16 at 8:23
  • If applications like bittorrent can leak your IP depends on your VPN configuration. Personally I'm using a VM based setup where such leaks shouldn't happen. – CodesInChaos Sep 30 '16 at 8:29

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