[tor-talk] Tor to VPN to Internet = Bad. Why?

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> Recently, I'd come across some chatter that suggested that connecting to
> a VPN via TOR was not a good idea and, rather, the better idea was to connect
> to a VPN that then used Tor.  I've not found any articles on the net that
> really discuss this issue.  My concern stems from more of a curiosity due
> to an encrypted private web proxy I used to run for foreign activists.  While
> the proxy would have appeared entirely benign to anyone in their regime,
> a number used Tor to connect to it. My larger question is, if there is a
> security concern for using Tor to connect to a VPN which then connects to
> the internet, would the same concerns apply to people who use Tor to connect
> to an encrypted web proxy?  Thanks in advance for any replies.

It has been discussed a few times in different places on the internet including the tor-talk mailing list. I done my best and wrote an article, which hopefully covers all aspects, all pros and cons of all combinations.

https://trac.torproject.org/projects/tor/wiki/doc/TorPlusVPN

Please read and leave feedback. If there are open questions, ask again.

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