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I use Squid on my Ubuntu box at home to give me "proxy like" tunnel access back home wherever my laptop goes. The machine is on the DMZ of the network.

Currently, I have to do this:

sudo ssh -L 3128: user@homeip

then my browser is using the proxy localhost:3128

It works, but I have to authenticate twice (sudo then ssh) on the local machine before I get access. Also, If I sleep with an active connection, it will fail to reconnect on wake and I have to kill the process.

All to much of a hassle.

Bottom line here. What I want to do is setup Squid so that I can put externalIP:3128 in my browsers proxy settings and go. Just go.

How do I configure Squid to do this?

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Or, at the very least, is there a way to make the SSH connection successfully reconnect on wake without me having to worry about it? I would be fine with that. – Tyler Molamphy Mar 15 '11 at 20:04
You shouldn't need to use sudo to use SSH. You could run gSTM, or autossh on your linux box to initiate your connections. gSTM is a GUI, and could be automatically started on login. Autossh is a daemon. Anyway, this is not a question about professional system administration, so it is off-topic for serverfault. – Zoredache Mar 15 '11 at 20:59

You can configure squid as transparent proxy:

http_port 8080 transparent name=self_proxy

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