Install Tailscale over SSH on Linux

Published: January 10, 2026

If you have a Raspberry Pi or other Linux machine on your local network and want secure, easy remote access from anywhere, Tailscale is an excellent option. Tailscale creates a private mesh network (WireGuard-based) that allows you to access your devices without port forwarding or complex firewall rules. In this guide, I’ll show you how to install Tailscale over SSH on Raspberry Pi OS (though these instructions work on most Debian-based Linux distributions).

This guide assumes you’ve already SSH’d into your remote machine on your local network and are ready to set up Tailscale for easier remote access.

Run all these commands on your Linux/remote machine:

Install Tailscale:

The official Tailscale installation script handles everything for you — it detects your OS, adds the repository, and installs the package:

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

Start Tailscale and authenticate:

This command brings up the Tailscale connection and provides a URL for authentication:

sudo tailscale up

After running sudo tailscale up, you’ll see output like this in your terminal:

To authenticate, visit:

    https://login.tailscale.com/a/xxxxxxxxxxxx

Important: Since you’re connected via SSH, copy this URL and open it in a browser on your current PC (not on the remote machine). This lets you authenticate using your Tailscale account from your local browser. Sign in with your Tailscale account (or create one if you haven’t already). Once authenticated, the remote device will be added to your Tailscale network.

Check Tailscale status:

After authentication completes, verify that Tailscale is running and connected:

tailscale status

You should see output showing your device and its Tailscale IP address (typically in the 100.x.x.x range). This confirms the machine is now part of your private Tailscale network.

That’s it! Your Raspberry Pi (or Linux machine) is now accessible via Tailscale from anywhere you have internet access. You can SSH into it using its Tailscale IP or hostname, access web services, or use it as part of your secure mesh network. Tailscale handles NAT traversal, encryption, and key management automatically, so you can focus on using your devices rather than managing network configuration.

Tailscale Documentation: https://tailscale.com/kb/start

Onward and upward!