SSH Into Raspberry Pi with Tailscale VPN

In today's interconnected world, accessing devices remotely has become essential for many tech enthusiasts and professionals. Whether you're a hobbyist working on projects at home or an IT professional managing multiple devices, having secure remote access is crucial. One tool that stands out for this purpose is Tailscale.

Tailscale is a mesh VPN service that simplifies the process of creating a secure network between your devices. With Tailscale, you can easily access your Raspberry Pi from anywhere in the world, just as if you were on the same local network. In this tutorial, we'll walk you through setting up a Raspberry Pi with Tailscale to SSH into it from an external network. We'll cover the installation process on both the Raspberry Pi and a Mac, show you how to authenticate your devices, and demonstrate how to establish an SSH connection. Note that the steps for Windows users are similar.

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Step 1: Setting Up Tailscale on the Raspberry Pi

Update Your Raspberry Pi: Begin by updating your Raspberry Pi to ensure all packages are up to date. Open the terminal and run:

sudo apt update
sudo apt upgrade -y

Install Tailscale: Next, install Tailscale. First, add the Tailscale repository to your Pi:

curl -fsSL https://pkgs.tailscale.com/stable/raspbian/buster.gpg | sudo apt-key add -
curl -fsSL https://pkgs.tailscale.com/stable/raspbian/buster.list | sudo tee /etc/apt/sources.list.d/tailscale.list

Update the package list and install Tailscale:

sudo apt update
sudo apt install tailscale

Start Tailscale: Once installed, start the Tailscale service

sudo tailscale up

Follow the prompts to authenticate your Raspberry Pi with your Tailscale account. This will involve logging into your Tailscale account via a web browser and authorizing the device.

Step 2: Setting Up Tailscale on Your Mac

• Download Tailscale: Visit the Tailscale website and download the Mac version of Tailscale.
• Install Tailscale: Open the downloaded file and follow the installation instructions.
• Authenticate Your Mac: Open Tailscale from the Applications folder and sign in with your Tailscale account. This will add your Mac to your Tailscale network.

Step 3: Connecting to the Raspberry Pi via SSH

Find Your Raspberry Pi's Tailscale IP: On your Raspberry Pi, run:

tailscale ip -4

This command will output your Raspberry Pi's Tailscale IP address (e.g., 100.x.x.x).

SSH into Your Raspberry Pi: On your Mac, open the terminal and use the following command to SSH into your Raspberry Pi:

ssh pi@<tailscale-ip>

Replace <tailscale-ip> with the IP address you obtained in the previous step. For example:

ssh pi@100.64.0.1

If this is your first time connecting, you may be prompted to add the host to your list of known hosts. Type yes and press Enter.

Note for Windows Users: The steps for setting up Tailscale on a Windows machine are similar to those on a Mac. Download the Tailscale installer from the Tailscale website, install it, and sign in with your Tailscale account. Then, use an SSH client like PuTTY or the Windows Terminal to SSH into your Raspberry Pi using its Tailscale IP.

Conclusion

With Tailscale, setting up secure remote access to your Raspberry Pi is straightforward and efficient. By following the steps outlined in this tutorial, you can easily manage your Raspberry Pi from anywhere, ensuring your projects and systems are always within reach. Whether you're using a Mac or Windows, Tailscale's seamless integration makes remote SSH access a breeze. Happy hacking.