OpenVPN + Squid3 with Transparent Proxying on Debian Wheezy HowTo

Posted by npn on Oct 5, 2014 5:53 PM EDT
IODigitalSec; By Adam Palmer
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A step by step HOWTO covering Squid3 transparent proxying on an OpenVPN server. Also covers PKI setup for OpenVPN.

Before my last extended period travelling and using public networks, I decided to set up a new low spec virtual machine on one of my hosted servers. I trust my datacenter and their uplinks more than I trust the free WiFi and public networks I travel through, and so while all my internet traffic is being routed over an encrypted tunnel to my dedicated server, I’m a lot happier.

I threw Squid3 into the mix, as it caches common assets and the sites I visit. This speeds up my web access and page load time.

OpenVPN can be configured more simply with a ‘static key’ configuration, however I’ve chosen to go down the PKI route for future growth.

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