At incident.io, the goal to achieve a five-minute deploy time became increasingly challenging as the codebase and test suite expanded, initially resulting in deployment times exceeding 11 minutes. To address these delays, the team transitioned their CI/CD pipeline to Buildkite, allowing them to run their own high-powered servers and implement effective caching strategies for both Go and TypeScript codebases. This shift significantly reduced test times, with production deploys decreasing by 27% and hotfix deploys achieving the target of under five minutes. However, the transition faced challenges such as managing server resources, optimizing disk I/O, addressing flaky tests, and resolving cache issues. Despite these obstacles, the improvements align with the company’s core value of increasing pace and enable faster delivery of new features to customers, though the quest for consistently achieving the five-minute deploy target for regular releases continues.