The CTO at work pointed me to this application: Tunnelblick. It’s seriously badass. Why? Because you don’t have to know jackshit about how VPN works to get it up and running. The complete setup took me less than five minutes, and it works brilliantly.
Before you begin, you need these files: ca.crt (the Certification Authority certificate), <yourname>.crt (your certificate), <yourname>.key (your key), and possibly ta.key (Transport Layer Security Authorization key if your VPN server requires it). Ask your network admin for these files, or generate them yourself using OpenVPN.
Download the DMG, mount, launch, install. Run the app from your Applications folder. The first time, it will complain that it could not find a valid profile. Click the “Continue” button which will prompt the program to create a sample configuration file to which you will make some simple changes.
Copy the aforementioned files to your ~/Library/openvpn/ directory, which was created upon installation. Edit the configuration file (~/Library/openvpn/openvpn.conf) to specify your VPN server at line 42 (remote my-server-1 1194), the locations of your keys at lines 88-90, and—if necessary—uncomment line 107 to use the tls-auth key.
Save the file and click the Tunnelblick icon in your title bar, then click “Connect”. Blickity-BLAM! VPN, bitches.