Kickstarter
Kickstarter upgraded its main Rails application to Rails 5, alongside payments app Rosie, to support site security and performance while moving a nine-year-old legacy codebase forward. The team planned a three-month project, upgraded Ruby 2.2.5 to 2.4.x, classified release-note changes, resolved dependency conflicts, used Rails’ upgrade script, and moved through twelve documented steps. Work included merging Rails 4.2-compatible fixes, repairing nearly 4,000 CI test failures from a roughly 70 percent coverage baseline, removing deprecations, smoke-testing major flows, backporting more than thirty pull requests, and preparing reviewers and deployment contingencies. The upgrade met its timeline without rollbacks or major downtime, although untested bugs increased Zendesk tickets and exposed issues involving ActionController::Parameters, tracking events, and mobile applications. A retrospective emphasized planning, documentation, cross-team communication, and broader native-team participation for future upgrades.