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Explore the complex decision-making process behind software rewrites through a real-world case study in this 54-minute conference talk from NDC Melbourne 2025. Learn when rewrites can actually be justified despite conventional wisdom warning against them, as the speaker shares her team's experience maintaining and eventually rewriting an academic C++ service despite having no C++ expertise. Discover practical strategies for choosing appropriate technology stacks for rewrites, understand how junior developers can step into leadership roles when domain knowledge becomes crucial, and gain insights into translating academic code into production-ready software. Examine the circumstances that make rewrites viable, including technical debt assessment, team capabilities, and business requirements, while exploring the challenges of bridging the gap between academic research code and commercial software development.