Tailscale is a pioneering approach to VPN technology with full support for macOS and iOS.

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There is a concept of building from first principles that can create some pretty incredible products. For example, one technology that I have long considered more complex than it should be is VPN. VPNs have taken center stage with telecommuting and employees who need access to company resources wherever they are. I recently came across a product that works great on macOS that takes this first-principle approach to how VPN connections work, and it’s called Tailscale.

About Apple@Work: Bradley Chambers managed the corporate IT network from 2009 to 2021. Through his experience deploying and managing firewalls, switches, MDM, enterprise-grade Wi-Fi, hundreds of Macs and hundreds of iPads, Bradley highlights how Apple IT managers deploy Apple devices, build networks to support them, and train users, stories from the IT management trenches, and ways Apple can improve its products for IT departments.

Setting up a VPN is clunky at best. Different firewalls require different settings, and sometimes it can be difficult to connect the right devices to the right servers depending on the subnet, IP scheme, etc. By implementing Tailscale, you can easily connect to a different network using a stable IP address for each. device (server, laptop, etc.). These addresses remain the same no matter where the nodes move in the physical world where the devices are located. Each device receives an IP address in the 100.X range, and it is assigned based on the device and Tailscale login.

Using Tailscale with macOS

I have a fairly simple use case for Tailscale for personal use. I want to remotely access my Umbrel server (find out how to create one in my previous tutorial) as well as my Plex server. Umbrel has a Tailscale app in the App Store, so installation was painless. Now I can access it from anywhere. It runs on my Umbrel server and Plex server, so when I want to connect to those servers directly, I just turn on Tailscale on my Mac and can connect to those devices.

What problem does it solve in the enterprise?

Tailscale is built on top of WireGuard. WireGuard is a fast, encrypted network protocol that offers a number of performance advantages over regular VPNs. Tailscale complements WireGuard by adding automatic mesh configuration, single sign-on support, two-factor authentication, NAT traversal, and centralized access control lists (ACLs).

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Let’s say you have employees spread across the country (or the world) and you want to give them secure access to secure company resources, such as internal servers, via a VPN, while still allowing public internet traffic to work locally. TailScale works this way out of the box. It acts as an overlay network and routes traffic only between devices running Tailscale, but does not affect traffic that is not destined for the Tailscale device. With this default setting, you can leave Tailscale running on macOS or iOS all the time without sending all your traffic through them.

To sum it up, Tailscale is an affordable VPN that requires no configuration, installs on any device in seconds, handles firewall rules for you, and works from anywhere. While my use case is 100% personal, you can see the benefits it can bring to businesses all over the world. Tailscale is truly a VPN for the world of remote work. This is one of those rare solutions that “just works”. Pricing starts free for a single user with 20 devices, while paid plans start at $5/month (billed annually). So, if you’re struggling to roll out VPN access to your entire company in a way that doesn’t overwhelm your team with troubleshooting, give Tailscale a try. Its VPN is so simple that I’m not sure Apple or Google could make it any easier. It works great on macOS, iPhone and iPad.

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