How To Install Pi-Hole on FreeNAS

I’ve been playing around a lot with my FreeNAS installation since assembling it last year as my “Pandemic Project” (which, of course, would become the first of many), and I’m constantly looking for new things to implement. Advertising has been a thorn in my side since the early days of the internet, so it seemed only logical that I should see what all the fuss with Pi-Hole was about!

Pi-Hole is most readily installed on a Raspberry Pi, but I’m trying to consolidate as much of my infrastructure as possible, so I thought I might have a go getting it working on the server. Unfortunately, FreeNAS is based on BSD while Pi-Hole is written for Linux (so there’s no plugin available), so we’ll have to install it on a virtual machine.

Installing Ubuntu Server on a Virtual Machine

The first thing we’ll need, of course, is the installation media. There’s a flavor of Pi-Hole written specifically for Ubuntu, so that seems to be the logical choice! My recommendation is to install the most compact version available, and the netboot installer image allows you to pick Ubuntu Server with minimal options. It’s a little difficult to find the correct download, so just grab the URL below:

Of course, if Bionic Beaver is outdated, just change the /bionic directory to the current version!

Back in FreeNAS, go to the Virtual Machines menu and add a new Linux VM. Give it a name that you’ll remember (“pihole” is a solid choice) and set the virtual CPU count to 1 and the memory size to 512MiB. On the Disks page, create a new AHCI disk and set its Zvol location to /data/pihole and size to 4GiB. When you get to the options for installation media, select “Upload an installer image file” and choose the mini.iso file you downloaded earlier. Once all your settings are configured, you can boot the virtual machine and install Ubuntu. The VNC option opens a virtual terminal that will allow you to connect to and interact with the virtual machine through the installation process.

If you are prompted for DNS servers, use Google’s ( and as a default for now.

When the install completes, Ubuntu will prompt you to remove installation media and reboot. Once you are disconnected from the VNC, stop the virtual machine and remove the installation media by deleting the CDROM from the “Devices” list under the virtual machine options.

Setting up Pi-Hole

Restart the virtual machine and connect to the VNC. Log into Ubuntu and invoke the following commands:

sudo apt update
sudo apt upgrade
sudo apt install net-tools
sudo apt install wget

The first thing we need to do is set up a static IP address for the virtual machine. Use ifconfig to find the local IP address.

In this example, the device is called ‘enp0s4’.

We will now need to change the settings for this device by editing the netplan config. Invoke the following command:
sudo nano /etc/netplan/01-netcfg.yaml

You will need to change edit the file so that it look like the image below. Pay special attention to the number of spaces for each indentation.

Once this is complete, reboot the VM.

After rebooting and logging back into Ubuntu, install Pi-Hole using the automatic installation script, just like you normally would.

wget -O

sudo bash

Before you log into

Once the script finishes, you can access the web UI by navigating to [PIHOLEIPADDRESS]/admin. Make sure to change your password!

The last thing you’ll need to do is set up your router’s DHCP settings, but that’s best explained by Pi-Hole’s own documentation.

Using Pi-Hole For Whole-Network Ad Blocking

Internet advertising was once a fairly benign minor annoyance that spiraled into the oft-lampooned dark world of pop-ups on top of pop-ups. In these early years, simple ad-blocking plugins for popular browsers like Netscape Navigator (and its successor, Mozilla Firefox) were enough to keep these nuisances at bay, but as advertising technology got more sophisticated, Web 2.0 became more commercialized, and surveillance capitalism became the business model du jour, ad-blockers have moved from convenience to absolute necessity while simultaneously become more difficult to implement at the browser level.

Most commercial websites now can detect ad-blocker software and refuse to serve content in response. In these cases, it becomes necessary to allow some level of ad servicing–usually through whitelisting specific sites–but this also comes at the extended (and immeasurable) cost of privacy. Advertising networks track users’ movements across the internet and serve consistent ads based on that user’s specific browsing history. In this Brave New World, a user’s very identity is a commodity that must be exchanged in order to participate in society. One must sell their soul in an asymmetrical exchange to merely experience the world outside while the buyer resells the soul indefinitely and reaps exponential profits.

Pi-Hole is an application that adjusts the balance of power back into the hands of the user by allowing ads to be served, but intercepting and dumping them into a “black hole” before being displayed. Additionally, Pi-Hole blocks trackers from “phoning home” by directing their calls into the same virtual black hole, thus allowing the user to retain control over their identity. The result is a cleaner, safer, and more pleasant user experience with faster page load times and less noise in the browsing experience. Granted, Pi-Hole does have a few flaws that are more difficult to work around (such as Google’s first-party tracking), but by-and-large, the application is well-worth the few minutes that it takes to set up.

In my current network arrangement, I have Pi-Hole installed on a Raspberry Pi Zero W plugged into a 5V wall wart and connected to the WiFi. It’s not the fastest arrangement, of course, but it has a very low power consumption and serves my needs at the moment. I have also tried using Pi-Hole installed on an Ubuntu virtual machine in my FreeNAS server, but I noticed that it resulted in a noticeable increase in system resources (and noise, considering the case sits behind my sofa) so I migrated to the Pi. If you have the hardware to spare, I would probably recommend a Pi3B+ or better as the right nexus of speed and power consumption.

Installation on the Pi is fairly straightforward, following the directions of the Pi-Hole website. The most difficult part seems to be arranging the DNS settings on your router (which isn’t altogether difficult, but it doesn’t enjoy the virtue of an automatic installation script). I will put together a setup guide for the FreeNAS instance in a future number, for those who may be inclined (or whenever I upgrade my server and stuff it in an air-conditioned closet).

Pi-Hole is not a silver bullet to stop advertising and privacy-invading browser trackers wholesale, but I do recommend it as another tool in the ever-growing arsenal that users can employ to reclaim some of their own power on the internet. I’m still playing around with the idea of obfuscation, and seeing if it is even worth considering (it probably isn’t, but it may just be for fun), and I have been implementing other changes that have made my life–both online and especially off–better and less stressful than it used to be.

Subway: “We Cut Prices Too!” (circa 1992)

Oh, this takes me back! Once upon a time, you could get a pretty decent sub at Subway for a pretty decent price. Now, you have to ask for the toppings like 5 times in order to get 3 little slivers of onion, bell pepper, or olive. Things went downhill fast when they changed the way they cut the bread.

I still say Blimpie was the superior fast food sandwich, though.

TBS Tonight: “Submarine X-1” (circa 1989)

Has anyone actually seen this film? I should add it to my Friday night flix list…

Sugar: “Sweet, Pure, and Natural” (circa 1988)

I can’t even begin with this.

WXIA-TV Atlanta 11 Alive News EXTRA: “Superstitions” (circa 1988)

Only Atlanta’s finest new source would DARE to go so far in-depth on the important subjects of our time: ARE YOU SUPERSTITIOUS?

Surevue Contact Lenses (circa 1993)

I dunno about y’all, but I’ve been wearing the same pair of contacts for 3 years now. Maybe I should switch to Surevue?

Introducing the Hershey Symphony Bar (circa 1989)

Say what you will about the lower quality of most American chocolates, I still enjoy a “fancy” Hershey bar from time to time!

Ad Council: “Take Pride In America: Clint Eastwood” (circa 1989)

Remember when Eastwood was a “bleeding heart liberal” who cared about the environment?

Target: “Right on the money” (circa 1989)

We never shopped at Target because it was too expensive.

Adventitious Geekery and other distractions created or curated by Matthew "Atari" Eargle