By Dan Moren

April 30, 2018 8:13 PM PT

Applications Folder: Tunnelblick

It may have been well over a decade since I was last employed as a technology professional, but one of the ways I like to keep my hand in is by running my own Linux server, which I host over at Linode. (Full disclosure: Linode does regularly sponsor my podcast Clockwise, but we don’t get any special deals beyond what we offer to all listeners of the show.)

I enjoy the challenge of trying to navigate the arcane command line and install and configure various services that I think might be handy to have access to. One of the first attempts I made was setting up a VPN server, which I installed with the help of one of Linode’s handy guides. But once I got over the hurdle of setting it all up, I ran into an issue closer to home: macOS’s built-in VPN client doesn’t support the server that I’d used, OpenVPN.

Fortunately, there’s an alternative in the form of the free open-source VPN client Tunnelblick, which is designed for use with OpenVPN. Like the Mac’s built-in VPN features, Tunnelblic presents as a menu bar icon where you can connect or disconnect from your VPN.

While it may not be the most user friendly software (in particular, there’s a conflict with High Sierra that requires an annoying workaround, once you get Tunnelblick up and running, it works as smoothly as the Mac’s own VPN client, and it has a few extra features that in some cases make it preferable. For one, it lets you quickly check your external IP in the menu bar, to ensure that traffic is going through your encrypted connection. To do that with macOS’s built-in VPN client, you generally need to visit a website or use another utility.

Look, attractive Tunnelblick isn’t. And it has its own shortcomings—for example, I notice that it only seems to check for updates on a restart, and I don’t restart my Macs very often, so I’m perennially a version or two behind. Plus, when configurations go awry, it can take a bit of tweaking to get things working again. But it gets the job done, and it mostly does so without getting in the way. Setting up your own VPN server requires more than a little bit of know-how, and it’s not for the faint of heart. But having gotten that far, I’m at least glad that it wasn’t all for nothing.

[Dan Moren is the East Coast Bureau Chief of Six Colors. You can find him on Twitter at @dmoren or reach him by email at dan@sixcolors.com. His latest novel, The Nova Incident, comes out in July and is available to pre-order now, so do it!]