Upgrading Rails can go from easy-to-hard quickly. If you've struggled to upgrade to a new version of Rails, you're not alone. And yet, with useful deprecation warnings and extensive beta periods, Rails has never made it easier to upgrade. So what makes it hard? By looking at the past ten years of Rails upgrades at Clio (and other notable apps), let's see what we can learn. Gain insight into the tradeoffs between different timelines and approaches and learn practical ways to keep your app up-to-date.