Headless Pi Configuration with Multi-Wifi Remote Access

Andrew Bolster

Senior R&D Manager (Data Science) at Synopsys Software Integrity Group and Treasurer @ Bsides Belfast and NI OpenGovernment Network

Raspberry Pi’s are great, but often have a lot of baggage associated with them, and I keep forgetting all the clever things you can do to get them up and running without having a sea of cables attached…


Raspberry Pi that can be sshd into from anywhere in the world* without poking any firewall rules or anything other than power connected to it, that works in a range of WiFi access points.

*(Requires access to an external domain or static IP server)


  • Raspberry Pi with Wifi (Either onboard or dongle)
  • Externally accessible sshable server
  • (Micro) SD Card reader and SD Card (>=8GB)
  • Another machine to do all the magic with
  • You to be sitting in a WiFi area that you know the key for…


OS Image

  1. Install Etcher (Or similar, see here for other options)
  2. Download Rasbian Lite from here
  3. Use Etcher (or whatever) to burn the downloaded image to the SD card
  4. Once verified, eject, unplug, and replug the SD card into the machine.

Boot Fiddling

Enable SSH

When you plug the card back in, you should see a boot volume appear in your Finder/Explorer/File Manager, in it, create an empty file called ssh. e.g.

touch /Volumes/boot/ssh

Pre-Configure Wifi

Then in your favourite text editor, create another file in the same directory called wpa_supplicant.conf that looks something like this, populated with the ssid and psk keys for your relevant networks.

country=GB #Or your ISO 3166 country code  
# https://en.wikipedia.org/wiki/List_of_ISO_3166_country_codes

ctrl_interface=DIR=/var/run/wpa_supplicant GROUP=netdev




If you have a ‘weird’ password with quotes or unescaped symbols, you can use wpa_passphrase MY_SSID to generate the relevant pre-encrypted psk’s that are acceptable by wpa_supplicant.conf, and you should be able to run this either on the pi directly later, any other pi, or any other linux-based wifi enabled machine… You can probably to it in a VM too but I haven’t tested that… Source

Squeaky Bum Time

At this point, eject and unplug the SD card from the machine, and plug it into the (unpowered) Pi, and then the moment of truth; power it on…

At this point I recommend waiting at least 5 minutes, get a coffee or a ClubMate

While you’re waiting, take some time to review the Power/Startup section of the Pi Troubleshooting Guide, just in case…

First Login

Easy Mode; mDNS

If you’re lucky and have a nice router on your wifi network, you might be able to log in to your device using the default password raspberry using the below

ssh pi@raspberrypi


Hard Mode; Port Scan

Using a network scanner like nmap, scan for IP’s that have the SSH port (22) open, and try a few. YMMV.

On basic networks this should be as simple as:

sudo nmap -sS -p 22 

But you may also want to check out the Fing android network scanner which is great at identifying Raspberry Pi’s based on their Vendor MAC Address

Once you’ve identified the IP address of the Pi, you can connect to it like:

ssh pi@<IP-ADDRESS>

Good Housekeeping

Now that we’re in, there are a few steps that we should do just for good housekeeping;

  1. Update the Pi with sudo apt-get update; sudo apt-get upgrade -y
  2. Using sudo raspi-config, perform the following actions
    1. Change the pi user password to something custom
    2. Network Options > Set the Hostname to something memorable (We’ll be referring to this in future as PI_HOST)
    3. Advanced Options > Update
  3. Reboot with sudo reboot
  4. Log back in with either ssh pi@PIHOST, or your previously found IP address (or return to the “Port Scan” section if that doesn’t work)
  5. Run ssh-keygen (without specifying a passphrase)
  6. Print out and note the contents of the public key generated using cat ~/.ssh/id_rsa.pub

Prepping autossh

We’ll be using the autossh program to, well, automate ssh. This will be able to provide us with a “Reverse SSH Tunnel” to get into the Pi via an internet-accessible server, that we’ll be calling JUMPBOX


Log into the JUMPBOX, and create a new nologin user

All the commands in this section should be executed on JUMPBOX as the root user (or add appropriate sudos)

useradd -m -s /sbin/nologin --disabled-password autotunnel
su - autotunnel -s /bin/bash

You’ll be asked for a passphrase here, don’t enter one, as this ensures we’ll be able to securely setup the tunnel without manually entering passwords

Then we’ll construct an authorized_keys file (note the Americanisation!) in the .ssh directory so our pi will be able to log into this account automatically.

mkdir ~/.ssh
vim ~/.ssh/authorized_keys

In this file, add the contents of the cat ~/.ssh/id_rsa.pub call that we performed on the Pi, and save it (with <ESC>:wq, incase you forgot…)

We need to make sure these files have the correct permissions, so…

chmod 700 ~/.ssh
chmod 600 ~/.ssh/authorized_keys


Autossh isn’t installed by default

sudo apt-get install autossh -y

Similar to the setup of the autotunnel user on the JUMPBOX, we do the same on the PI_HOST

sudo useradd -m -s /sbin/nologin --disabled-password autotunnel
sudo su - autotunnel -s /bin/bash
ssh-copy-id JUMPBOX

At this point you’ll be asked to confirm things like accepting the SSH key of the JUMPBOX server, but you won’t actually get a login shell and will be kicked off; this is because we setup the autotunnel@jumpbox user with /sbin/nologin, so it’s fine.

Now, using CTL + D to “escape” from the autotunnel user back to the pi user

Finally, sudo -sh into the root user and execute the following to create a auto-starting services file

cat > /etc/systemd/system/autossh-JUMPBOX.service << EOF

Description=Keep a tunnel to 'JUMPBOX' open 

ExecStart=/usr/bin/autossh -f -M 0 -N -i /home/autotunnel/.ssh/id_rsa -o ServerAliveInterval=30 -o ServerAliveCountMax=3 -o UserKnownHostsFile=/dev/null -o StrictHostKeyChecking=false autotunnel@JUMPBOX -R 2222:
ExecStop=/usr/bin/pkill -9 -u autotunnel


systemctl enable autossh-JUMPBOX.service
systemctl daemon-reload

And then wait a while and hope for the best!

Persistent Connections

All-in-one command to test your JUMPBOX/PI_HOST connection;

ssh -J user@JUMPBOX pi@localhost -p 2222

Once you’re happy that this is fairly stable, you can set up a ‘shortcut’ to this host in your local ~/.ssh/config file with something like this

        HostName localhost
        Port 2222
        ProxyJump user@JUMPBOX
        User pi

Then you can excute the following to set up passwordless pasthrough connection

ssh-copy-id PI_HOST


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