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I've been running into cloudflare issues quite a bit when browsing with Tor and it seems to be becoming more and more of an issue. Sometimes I get captchas, sometimes I don't, but regardless it's becoming quite a headache just to try to casually browse semi anonymously. I don't particularly trust proxies and VPNs are as good as their privacy policies I guess but I figure that if I am trying to keep myself private and not so much data traveling back and forth (I do not log into sites etc or do other serious stuff with the Tor Browser Bundle (TBB), I save that for TAILS).

So, this is a two parter:

  1. Would running Tor -> Proxy help hide the fact that I am using tor from cloudflare? (It seems to me it would but I wanted to check)
  2. How does/can one setup the TBB to route Tor traffic through a proxy? I of course found the option "this computer needs to use a proxy to access the internet" and the Preferences -> Proxy Settings but (and forgive me, I do not really understand this stuff) it sounded to me like those would give me a Proxy -> Tor setup which would still give me the cloudflare problem.
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You may choose to do Tor to VPN meaning Tor exit node connect to VPN and from there to your selected site. This way as you mentioned, the destination site will have difficulty figuring out you are using Tor. However the VPN service can easily figure out you are using Tor, but this may not be a concern in your case. For maximum anonymity use a free VPN service. This would eliminate the money trail to you. And yes, Cloudflare disturbance will reduce substantially this way. To figure out how to do this read the following question and answer and if you need more help get a professional assistance. Me -> Tor -> Vpn [How?]

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It still exits through the exit node, so VPN would not help. The web service you are accessing 'sees' you as the exit node IP, regardless if you run VPN on your end.

  • So there is no way to chain them up so that first the connection goes through the tor node and then exits through the proxy? (perhaps an addon or something? I have found a few external chaining programs such as proxifier [alternativeto.net/software/proxifier/] and proxychains [alternativeto.net/software/proxychains/] but so far nothing about how to do it within FF/TBB) – user2520176 Sep 19 '14 at 8:36
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    not so, what you are speaking of is user -> VPN -> Tor and the OP is speaking of user -> Tor -> VPN which is not so easy to do but in the end the VPN to communicates directly to the website. tails.boum.org/blueprint/vpn_support – mchid Oct 20 '14 at 16:15

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