Gradual Typing in Ruby - A Three Year Retrospective by Ufuk Kayserilioglu, Alexandre Terrasa We began adopting gradual typing on Shopify's giant monolith almost 3 years ago. Today, we are running the monolith with great type coverage and even see some internal teams commit to stricter typing in their components. The road to get here was not easy, though. We had to work with our developers to solve the right problems at the right levels of abstraction to ensure the adoption was healthy. This talk will go over some of the challenges and some of our wins along the way. It will also help you decide if gradual typing might work for your codebase and your team, as well.