ISSA Kentuckiana | Pi Hole Workshop
About this Event
Build-a-Pi-Hole: A Hands-On Raspberry Pi and Linux Workshop
Join Kentucky ISSA for a hands-on workshop where you'll build a fully functional Pi-hole DNS sinkhole using a Raspberry Pi while learning the engineering principles behind modern Linux systems.
This is much more than a Pi-hole installation. Throughout the workshop you'll assemble a Raspberry Pi, install Raspberry Pi OS, configure a headless Linux server using cloud-init, remotely administer the system over SSH, learn Linux command-line fundamentals, understand DNS, and deploy your completed Pi-hole to your home network.
Rather than simply following installation instructions, you'll learn why each step is performed and how the underlying technologies work. Topics include Infrastructure as Code, cloud-init, YAML, mDNS, UART recovery, Linux networking, NetworkManager, DNS, DHCP reservations, and Pi-hole automation.
By the end of the workshop you'll leave with a working Raspberry Pi running Pi-hole, along with the knowledge to maintain it, troubleshoot it, and deploy it on your own network.
No prior Linux experience is required. The workshop assumes only basic computer skills and is designed for both beginners and experienced cybersecurity professionals.
What You'll Learn
Attendees will learn how to:
- Assemble a Raspberry Pi 4
- Install Raspberry Pi OS Lite
- Configure Linux using cloud-init
- Manage a headless Linux server using SSH
- Understand the Linux filesystem and command line
- Understand DNS and DNS sinkholes
- Install and configure Pi-hole
- Automate Pi-hole maintenance
What's Included
Each attendee will receive:
- Raspberry Pi 4 kit with microSD card
- Raspberry Pi OS image
- Workshop configuration files
- Lab guide
Laptop Requirements
Attendees must bring their own laptop.
Supported operating systems:
- Windows 11 (recommended)
- macOS (recent version)
- Linux desktop distributions
Administrator privileges are required for software installation. "Locked-down" company laptops are not recommended. A Chromebook is not recommended because several required tools are unavailable or difficult to install.
Before You Arrive
Please complete the following before arriving.
1. Bring a Laptop
Bring a fully charged laptop with Wi-Fi capability.
A power outlet will be available, but a fully charged battery is recommended.
2. Install Raspberry Pi Imager
Download and install Raspberry Pi Imager: https://www.raspberrypi.com/software/
3. Install PuTTY (Windows)
Windows users should install PuTTY: https://www.chiark.greenend.org.uk/~sgtatham/putty/latest.html
macOS and Linux users may use their built-in SSH client instead.
4. (Optional) Install Nmap
Installing Nmap before the workshop is recommended: https://nmap.org/download.html
5. Bring an SD Card Reader (or USB adaptor)
Many laptops no longer include a built-in SD card reader. If your laptop does not have one, please bring a USB SD card reader.
We will have a limited number of USB-A SD card readers available during the workshop. If your laptop only has USB-C ports (the small oval connector), be sure to bring a USB-C to USB-A adapter so you can use the available card readers.6. Verify You Can Connect to Wi-Fi
Your laptop should be able to connect to a standard Wi-Fi network.
During the Workshop
We'll provide:
- Raspberry Pi hardware
- Workshop operating system image
- Workshop configuration files
- Local file server
- Local Wi-Fi network
- Lab exercises
Who Should Attend?
No previous Raspberry Pi or Linux experience is required. This workshop is appropriate for:
- Home users
- IT professionals
- Cybersecurity practitioners
- Students
- Linux beginners
- Raspberry Pi enthusiasts
- Anyone interested in learning how modern Linux systems are provisioned and managed
Where:
JCPS Center for Professional Learning - 3903 Atkinson Square Dr, Louisville, KY 40218
When:
Saturday, September 12th, 2026
8:30 AM - 4:30 PM
Cost:
Normally $1,500.00
Special ISSA Kentuckiana Subsidized Price $250.00
ISSA Kentuckiana Chapter Members $150! ($100 off w/ use of member discount code!)
Info on ISSA Kentuckiana Chapter membership benefits available here: https://www.issa-kentuckiana.org/membership
Costs are subsidized by the ISSA Kentuckiana Chapter to make high quality training available for everyone!
Refunds not available for this event.
CPEs
Attendees will recieve 6 CPE Credits for this event
Important: This workshop will require you to bring a laptop. You will also need to install some software and do some pre-event setup. Detailed installation and configuration instructions will be emailed to registered attendees closer to the event. Please watch your inbox and complete the setup before the workshop to ensure you can fully participate in the hands-on exercises.
Who:
Jeremy Druin
Certified Security Penetration Tester & Cloud Security Architect
Google PCSE|OSCP|GPCS|GCLD|GXPN-GOLD|GPEN-GOLD|GWAPT-GOLD|GCIH-GOLD|GMOB|GSEC|GISF|Sec+
Jeremy is the Distinguished Cybersecurity Architect for the largest multi-national transportation logistics company in the world. Jeremy is also the owner of Ellipsis Information Security and teaches courses for Ellipsis and SANS Institute. As a Director of Education for the Kentucky ISSA chapter, Jeremy presents on application security, penetration testing and defense along with operating the "webpwnized" YouTube video channel. Additionally, Jeremy develops the open-source OWASP Mutillidae II training environment. Jeremy has a Bachelor of Science in Computer Science from Indiana University, a Graduate Certificate in Cybersecurity and Master of Computer Science and Engineering from the University of Louisville and is a GIAC-certified Web, API, Mobile and Network Security Penetration Tester, and Cloud Security Architect.
Agenda
🕑: 08:30 AM - 09:00 AM
Registration & Setup
🕑: 09:00 AM - 12:00 PM
Pi-Hole Workshop
🕑: 12:00 PM - 01:00 PM
Lunch & Sponsor Info
🕑: 01:00 PM - 04:30 PM
Pi-Hole Workshop
Where is it happening?
Event Location & Nearby Stays:
USD 250.00
