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OpenVPN + Squid3 Transparent Proxying on Debian Wheezy HowTo

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Web Webster
Web Webster
Oct 6, 2014

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.

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Web Webster

Web Webster

Web Webster has more than 20 years of writing and editorial experience in the tech sector. He’s written and edited news, demand generation, user-focused, and thought leadership content for business software solutions, consumer tech, and Linux Today, he edits and writes for a portfolio of tech industry news and analysis websites including webopedia.com, and DatabaseJournal.com.

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