Description. Tailscale is easy and works great when you have client applications set up on your devices, however, there are times when you want to reach other devices that. Tailscale helps you connect your devices together. For that to be possible, Tailscale needs to run on your device. Tailscale works seamlessly with Linux, Windows, macOS, Raspberry Pi, Android, Synology, and more. Download Tailscale and log in on the device. Download Tailscale. Step 3: Add another machine to your network.