Frank Lanitz <fr...@frank.uvena.de> wrote:
> Is there a way of using a squid proxy in transparent way [...] for SSL.
> If I'm entering the proxy directly into
> e.g. Firefox it's working -- but don't got it running via transparent mode.

As you'll know, it's pretty straightforward to set up a transparent
proxy for (unencrypted) HTTP traffic. However, creating one for HTTPS/SSL
traffic is far harder.

The simplistic answer is that you can't do this. The reason here is
that the web browser won't issue a proxy CONNECT request unless it knows
there's a proxy involved. And because you've got a transparent setup it
doesn't know. So it tries to go directly to the target website. But you're
intercepting the traffic and routing it via squid, so it can't get there -
or else you're going to be providing an incorrect certificate.

There are a number of options you've got at this point.

1. Prevent all SSL-based web browsing. (Probably unrealistic.)

2. Create a Certificate Authority and install your CA certificate on all
users' web browers. Hijack tcp/443 SSL traffic as before but spoof the
appropriate certificate dynamically (sign it with your own CA). Decrypt
the traffic, route it via squid or whatever, re-encrypt it and send it
on to the target host. (Probable privacy concerns with this option.)

3. Abandon the transparent approach. Block all tcp/80 and tcp/443 access
except via your proxy. Provide a wpad configuration file that people will
find by enabling "auto configure", and have this instruct web browsers
to use your proxy. (Recommended solution.)

3a. As for #3 but also continue to hijack tcp/80 and tcp/443, pointing
them to a static page that explains how to enable automatic configuration.

If you really want/need to force all traffic via your proxy I'd recommend
you seriously consider option 3/3a.

Chris


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