Why? Manufacturers are making great form factors that are very portable, sleek, with great battery life, and it runs Linux!I will talk about what led me to using a Chromebook as my main laptop and how I’ve customized it for my daily workflow. I’ve used a Chromebook for the OSCP lab and HacktheBox and will show how I access these labs and get everything working so that I’m just as productive as I would be with any system running Linux. I will also show the solutions for the issues that you will come across if you do this. I’ll go over how I’ve installed Ubuntu alongside Chrome OS and how I use it without having to switch between Chrome OS and a Linux GUI, but can still run GUI Linux software when needed in Chrome OS. Using Crouton I’ve found a setup that works best and discovered what doesn’t work. I’ll go over both and show tips for managing your Crouton install and how best to work with the limited amount of internal space on most Chromebooks. I’ll also go over my recommended methods for tool installation to a Crouton install and the workflow that I use for pentesting and CTF challenges. I’ll introduce command line tools and settings to improve your workflow which will be important on the Chromebook, but can also be applied to pentesting from any Linux command line. I’ll introduce some Tmux configuration options such as setting up logging for evidence collection. Tmux and Vim also go great together so I’ll show my Vim tips and integrations. Then a demo from my Chromebook of setting up a VPN connection to a lab and a quick exploit walkthrough of a CTF VM using what I’ve shown.