I finally got a chance to open up my Christmas present to myself a few months late. I was excited all the same because it was a Raspberry Pi 400.

This is an incredible form factor for the raspberry Pi. It’s an all in one unit that fits into a keyboard. The keyboard is the computer. Just incredible.

Once you plug in power, the mouse and an HDMI monitor you have a working Linux computer running Raspbian. What to do next? Install Tailscale of course !!

Tailscale is a mesh VPN and allows you to link up all your devices in a private network no matter where they are. I’ve blogged about it here. So far I’ve linked up macOS, iOS, windows, Linux centos as well as Synology and QNAP NAS so now let’s add a raspberry Pi.

First things first let’s update the raspberry Pi because it’s been sitting in its box for a while. I didn’t have much luck with the add / remove software gui app (maybe because it was still getting on wifi) but after getting on the network I fired up apt to update all the things.

sudo apt list --upgradeable

Using apt you can get a list of what is upgradeable. This was my first step the gui app didn’t list any software that had updates. A few months in a box and there should be a lot of updates. This is Linux we are talking about.

 sudo apt update

Then it is just a matter of upgrading everything.

The next step is to install Tailscale. Read the instructions for Raspberry Pi on the Tailscale website. Before installing Tailscale we have to install other needed components and we have to tell Linux where to find the software. Similar to my adventures with CentOS Linux and yum you have to tell Raspbian Linux what to do with apt.

First we fetch the signing key and tell it where the repo is. Note: Always be mindful when using curl to download and install items or scripts.

   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

Just a few more steps now. Install the needed https components. Check with apt for updates then we can finally install Tailscale.

sudo apt-get install apt-transport-https
sudo apt-get update
sudo apt-get install tailscale

The next step is to authorize Tailscale which is usually done with a login to our account we created the Tailscale network with. But this time I wanted to try a pregenerated keys from the Tailscale admin panel.

sudo tailscale up --authkey tskey-gh37374737292a4847382

Now to test the new secure Tailscale mesh VPN set up I wanted to login to my MunkiReport web server.

Using the Tailscale cli to list all devices on my private network I found the IP.

tailscale status

Find the ip of the server or device from the status list and connect.

Next I outputted the raspberry Pi cli history to a file and sent it to my iPhone where I edited this blog post with the WordPress app.

history > raspberry-history.txt

tailscale file cp raspberry-history.txt iPhone:

I am looking forward to working on many fun projects with my raspberry Pi. After Tailscale is on there then it is easy to connect from my iPhone or from anywhere Tailscale is installed.

In the example below I used ssh shellfish app on my iPhone to connect.

Tailscale has great documentation and despite this I had a small misstep when I went to look at the install instructions. It defaulted to Ubuntu or misdetected my raspbian linux so I wondered for a second why it wasn’t working. I soon realized I’d copy pasted the wrong thing. Checked the drop down install menu for the raspberry Pi instructions and voila happy times.