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Re: Privoxy usage?

> I may be doing a horrible job of explaining the problem.

No, you're doing fine.  I'm just going to explain it differently.

> IP over IP works.
> UDP over UDP works if your UDP protocol supports it.
> TCP over TCP fails. The timeout rules cannot stack properly.

You missed the two important cases ;-)

  TCP over IP works (duh)
  TCP over UDP works

This last case is why things like OpenVPN can do their job.

TCP over TCP is extremely inefficient; it will cause spurious
retransmissions, seriously impair the throughput you get and congest
the tor network.

(This does not apply to tunnelling over ssh, since ssh tunnels the
higher-layer data stream rather than the TCP packets.)