On August 15, 2018 GitHub was deployed to production running Rails 5.2. This was a historic event; for years GitHub had been behind Rails and dependent on a custom fork of Rails 2.3. This talk will visit GitHub's past, including our tumultuous relationship with the Rails framework, and the grueling effort it took to get our application on the latest version. You’ll learn what mistakes to avoid and the reasons why such a difficult upgrade was worth it. We’ll explore what tracking master means for the future and establish that GitHub and Rails are in it together for the long haul.