Back in 2016, the speaker deployed an ASP.NET monolith app to IIS on Windows. It worked but it was clunky in every sense of the word. Over the years, the app was freed from Windows (thanks to .NET Core), containerized to run consistently in different environments (thanks to Docker) and decomposed into a set of loosely-coupled, event-driven, microservices (thanks to Knative and Cloud Run). The end result is a simpler and portable serverless architecture, easier and cheaper to run and maintain. In this talk, we'll go through the modernization journey, explore the decision points and deep dive into the final architecture.