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Re: Tunneling https (with proxy chaining)

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On Wed, Mar 2, 2011 at 11:02 PM, Amos Jeffries <squid3@xxxxxxxxxxxxx> wrote:
> On Wed, 2 Mar 2011 17:50:20 +0100, Leonardo wrote:
>>
>> Hi all,
>>
>> I have successfully set up a bridge on my Debian 5.0.5 with Squid
>> 3.1.7 to tunnel http traffic.
>
> ? these two concepts do not overlap.
>
> Do you have a bridge server with intercepting proxy on it?
>  OR a regular forward proxy doing tunneling?


Sorry, forgot to specify.  It's a transparent (=intercepting) proxy on
a bridge server, built as described in
http://freshmeat.net/articles/configuring-a-transparent-proxywebcache-in-a-bridge-using-squid-and-ebtables
.  (The article refers to an older version of Squid; I adapted
squid.conf for my newer version.)


>
>>  Through proxy chaining, my Squid
>> connects to another non-Squid proxy.
>> Would it be possible to do the same with https, or there are security
>> issues related to Squid acting as a MITM?
>
> With HTTP tunneling this is not a problem. Set "nonheirarchichal_direct off"
> in squid.conf. The tunnel will be diverted through the peer same as it goes
> through the local Squid.
>
> With bridging+intercept this is not possible.
>
> MITM would be a bridge+intercept. So no, not possible with HTTPS.
>
> We are slowly building squid towards an architecture where non-HTTP traffic
> is not broken in intercept mode. But this is going to take a lot more work
> and time to achieve.
>
> Amos


That's too bad, but thanks a lot anyway for your answer.  I look
forward for this new coming-not-so-soon feature.

L.



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