How to Install Tailscale on Multiple Devices (Quick Reference)

Tailscale Setup – Detailed Summary

Set up Tailscale to create a private, encrypted network that connects all devices securely, no matter the location. Tailscale is a zero-config mesh VPN built on WireGuard. It lets computers and phones talk to each other as if they were on the same local network, without opening ports or dealing with complicated traditional VPN setups.

Why Tailscale Is Useful

  • Devices stay connected automatically, even after reboots.
  • Can SSH into the desktop from the laptop or phone from anywhere.
  • Securely transfer files between devices using Taildrop or SFTP.
  • Nothing is exposed to the public internet.
  • Works across Linux, Windows, macOS, iOS, and Android.
  • The free personal plan is more than enough for personal use.

What Was Accomplished

  1. Installed Tailscale on a Debian desktop.
  2. Installed and connected a second Debian laptop.
  3. Enabled Tailscale SSH on both machines for easy remote login.
  4. Disabled key expiry so the devices stay logged in permanently.
  5. Turned on MagicDNS so machines can be reached by simple names instead of IP addresses.
  6. Added an iPhone 12 Pro Max to the same network.
  7. Confirmed that all three devices can now see and communicate with each other over private Tailscale IPs.

Now any of these devices can be securely reached from the others—whether at home, at work, or while traveling.

How Tailscale Was Installed on Multiple Devices

On Linux (Debian machines)

Bash

curl -fsSL https://tailscale.com/install.sh | sh
sudo tailscale up

On iPhone Installed the official Tailscale app from the App Store, logged in with the same account, and allowed the VPN configuration.

Used the same login account on every device so they all joined the same private network automatically.

Optional steps also completed:

  • Enabled Tailscale SSH with sudo tailscale set –ssh
  • Disabled key expiry in the admin console
  • Turned on MagicDNS