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Here at work we have an Squid proxy setup, and every employee has an user and a password. This works great most of the time, but at the IT department is a problem because lots of software can't be updated throught a proxy.

I've thought of setting up an iptables redirection in one of the servers, so when we need to update some problematic software in a machine, we can just point its gateway to that server and let the redirection do the work.

But I don't know how to do it. To redirect to a local squid is fairly easy, but how do I redirect to a remote squid that needs user and password?

Important: we'll use my user and password for every request, so asking for the authentication is not the problem, but how to pass it, being always the same, to the proxy.

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If I correctly understand, that you need some server to act as gateway for updated machine, but all requests should go thought your proxy, you need to set up Transparent proxy on that server. This transparent proxy will use your existing proxy with some user/password. Squid can do this: howto

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But the question is, how do you pass the user and password to the proxy? – Saiyine Sep 19 '11 at 16:51
cache_peer config directive. You need something like cache_peer 3128 0 no-query default login=<user>:<password> Note: icp port 0 and no-query option are important. – Selivanov Pavel Sep 20 '11 at 16:43

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