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Explore the challenges and strategies involved in upgrading a large-scale application to Ruby 2.7 in this informative conference talk. Dive into GitHub's experience of addressing over 11,000 deprecation warnings, contributing patches to multiple gems, and upgrading numerous dependencies. Learn about the custom monkey patch developed for capturing warnings, the approach to dividing work among teams, and key factors for a successful upgrade. Understand the importance of staying current with Ruby versions and discover the notable performance improvements in Ruby 2.7. Gain valuable insights from Eileen Uchitelle, a Staff Software Engineer at GitHub and Rails Core team member, as she shares her expertise in scalability, performance, and open source contribution.