This experience report is about rearchitecture from a monolith to cloud-native practices. We cover moving stepwise from single tenancy to multitenancy, scaling up to scaling out, fixed resources to optimized variable costs, periodic upgrades to zero-downtime updates, single backlog to continual experimentation, linear to progressive deployment with a controlled blast radius, long release cycles to continual testing, opacity to observability, and pre-release security reports to continuous security practices.

Dylan Smith was a Microsoft MVP (ALM) and DevOps consultant for many years before joining Microsoft to lead the DevOps Customer Advisory Team. Now he works with Microsoft’s largest customers to help them accelerate their DevOps journey.

Sam Guckenheimer is the Product Owner for the Microsoft Visual Team Services and Team Foundation Server. In this capacity, he acts as the chief customer advocate, responsible for strategy of the next releases of these products, focusing on DevOps, Agile and Application LifeCycle Management.

Sam edits the website, DevOps at Microsoft. He is a regular speaker and has keynoted at many conferences including DevOps Enterprise Summit and Agile. He is the author of four books, most recently Journey to Cloud Cadence, Visual Studio Team Foundation Server 2012: Adopting Agile Software Practices: From Backlog to Continuous Feedback. Prior to joining Microsoft in 2003, Sam was Director of Product Line Strategy at Rational Software Corporation, now the Rational Division of IBM. Sam lives in the Seattle area with his wife and three children in a sustainable house they built that has been described in articles in Metropolitan Home and Houzz.