Resolved: OpenVPN

Jesus. It’s only the second week of school and I’ve already pulled my first all-nighter. This time, however, it was not for school. I was determined to get my OpenVPN server properly setup so that I could finally browse the web securely from the dorms. I only expected this to take a few minutes, but I ended up spending over 7 hours of research, troubleshooting, and configuration changes.

This post will contain a slew of information about smoothwall, zerina, openvpn, and iptables. I’m mostly just going to throw all of my findings here without much of any logical flow.

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Smoothwall Update

A few weeks ago, I finally got around to downloading and installing 4 updates to my smoothwall box. Unlike Ubuntu upgrades, this process was farily painless except for one thing: my Zerina OpenVPN ‘plugin’ broke.

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Smooth Wall

I’ve wanted to setup a serious linux-based firewall for my home network for some time now, and I finally got around to it yesterday.

There are TON of linux router distros out there, but instead of spending 8 hours picking & choosing, comparing & contrasting, nitpicking & debating, I asked someone else ;). Two buddies of mine have a similar setup at their homes: one uses Smooth Wall; one uses IPCop. I arbitrarily chose Smooth Wall (after actually setting it up, though, I think IPCop would have been a better choice–c’est la vie.

The installation is supposed to be quite painless, and it was–for the most part. The documentation and install process was intuitive and easy to follow, but it didn’t work OOTB. I probably only had so much difficulty because of hardware issues (fried NICs?) which is by no means Smooth Wall’s fault. Nevertheless, it took ~5 hours of bang-your-head-against-the-table troubleshooting ’till I could finally unhook the monitor & keyboard, shove it in a corner, and get some sleep.

I was also disappointed with two things that didn’t work as I had expected OOTB:

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