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Platform teams often struggle with a set of interrelated issues: systems that seem unsustainable to operate or that aren’t meeting the current needs, the desire to fix this problem through brand new technology, and the cost of executing on these big migrations from one system to another. In this talk we’ll walk through these questions: how to decide when to rewrite vs when to evolve, how to plan and execute the work, and keeping your stakeholders and customers happy during this process.