After months of preparation, GitHub successfully upgraded its production environment to Ruby 2.7, addressing over 11,000 deprecation warnings and replacing unmaintained gems to ensure a deprecation-free codebase. This upgrade was significant due to changes in keyword argument behavior introduced by the Ruby Core team, which required extensive coordination across 40 teams and numerous gem updates. The transition was facilitated by a dual-boot setup allowing backwards compatibility with Ruby 2.6, enabling smoother integration of changes. The upgrade resulted in a notable improvement in performance, including faster application boot times and reduced object allocations, enhancing overall system efficiency. GitHub's meticulous deployment process, which involved gradual traffic increases and comprehensive testing, ensured minimal user impact and no downtime. This effort not only reinforces application health and stability but also supports ongoing contributions to the open-source community, with GitHub emphasizing the critical importance of staying current with software updates to maintain a robust and resilient application infrastructure.