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Learn about the challenges and strategies of modernizing legacy software systems through this conference talk from EclipseCon 2023, where David Matějček of Omnifish OU shares insights from the Eclipse GlassFish project's transformation journey. Explore how a new team of committers and contributors approached the daunting task of updating long-unchanged code, addressing critical questions about backward compatibility, risk management, and the necessity of radical changes. Discover practical approaches to revitalizing established software projects while balancing technical debt, compatibility requirements, and modernization needs in this 38-minute presentation that uses GlassFish's evolution through various corporate stewardships as a compelling case study.