Tailscale: The Best Free App Most Mac Power Users Aren’t Using

Someone asked me to name the best free app available to Mac users in 2026. I didn’t hesitate before choosing Tailscale.

Tailscale is a VPN, but not in the usual sense. It’s a private, encrypted, identity-based network where your devices recognize each other no matter where they are. It uses WireGuard technology and is often described as a mesh network. The terminology isn’t important. This isn’t the kind of VPN that simply masks your home IP address or anonymizes web traffic.

Tailscale lets you treat a collection of devices in different geographic locations as if they were all in the same building, plugged into the same network and connected to the same switch. In practice, you can link computers in your home, at your office, while staying in a hotel, and even machines belonging to family members. It works across platforms, and all traffic is end-to-end encrypted. You don’t mess with opening ports or exposing your home network to the internet. You don’t have to learn AWS, firewalls, or how to configure TLS certificates. The computers associated with your free Tailscale account are referred to as your Tailnet.

You don’t have to feel like you’re studying for your CCNA whenever you use software that relies on networking. If some of the details sound confusing, that’s fine. Tailscale doesn’t require you to understand subnets, routing, or DNS to be useful. You install it, sign in, and your devices can see each other.

If that sounds confusing, don’t worry. You don’t need to fully understand it to take advantage of the power of this free tool. You just need to learn how to use the Tailscale app, which isn’t overwhelming at all. You don’t have to understand subnets or routing.

One of the most useful features of Tailscale is the concept of an exit node. An exit node is a computer you control that has internet access. When you need to access the internet in a private and protected way from another computer, you can toggle a single switch in Tailscale to route your network traffic through that remote machine, no matter where you are.

I recently vacationed in Central America and relied on hotel Wi-Fi. I didn’t need to enable—or even install—a conventional VPN on my laptop. I simply chose a computer in my home, 2,000 miles away, as my exit node and used it as my gateway to the internet.

If you have a VPN subscription to a service like Nord or Mullvad that’s limited to a small number of devices, you can sometimes work around that limitation by using one of your machines as an exit node. You can even access that exit node from your phone, whether you’re on a cellular network or Wi-Fi. Once connected, all of your traffic appears to the receiving services as if it’s coming from your home computer.

I use a private tracker to download what are commonly referred to as Linux ISOs. That tracker only works when it sees my computer as being connected from the IP address assigned to my home router. If I’m traveling and need access, I just connect through the Tailscale exit node on my self-hosted server and everything works as expected.

There’s also an Apple TV app for Tailscale. I gave my brother, who lives on the opposite side of the country, access to my Tailnet so he can watch regional sports like NCAA basketball that are only broadcast locally.

Tailscale isn’t a replacement for every kind of VPN. It won’t automatically anonymize all your traffic the way a commercial VPN service does, and it doesn’t make unsafe devices magically secure. You still need good passwords, disk encryption, and basic common sense.

What it does exceptionally well is remove friction. It gives your devices a private, encrypted way to find each other without turning you into an amateur network engineer.

Using an iPhone or iPad with an SSH client, I can connect to my home-based Macs and Linux boxes to run scripts, reboot machines, restart services, and transfer files.

Because I can use macOS Screen Sharing, I can also easily access Macs belonging to family members for whom I provide technical support. When I need to remote into their machines, there’s nothing to set up. They don’t have to find or report their IP address to me. I can see everything I need in the Tailscale app.

Another use case for power users is remote backups using rsync. This is especially useful if you follow the 3-2-1 backup model: three copies of your data, on at least two different types of media, in at least two different geographic locations. You can set up a headless Mac or Linux box at a friend’s or relative’s house and sync your important documents and media with a simple script. As far as your computer is concerned, that remote system might as well be sitting right beside it.

A free Tailscale account allows you to add up to 100 devices and assign management access to three users. If you’re setting up computers for family members or friends who aren’t technically proficient, you don’t have to give up one of those seats. You install Tailscale using your account, and they rarely—if ever—have to do anything other than turn their computer on. From there, you can use tools like Keyboard Maestro, Hazel, and other automation utilities to get real work done.

Tailscale is good, solid technology packaged in easy-to-use apps. It still requires sensible password management, like any other tool. You’ll still want a conventional VPN if you need to anonymize traffic from at least one device. But Tailscale removes barriers that once made these kinds of setups the exclusive domain of network engineers—and it does so quietly, reliably, and for free.