SREcon19 Asia/Pacific

Ever burned out or even quit your job after an arduous migration? Keeping up to date with operating systems versions, runtimes like Docker or JDK, and new instance types are a significant source of toil. The complexity increases when we consider several hundred microservices across tens of thousands of machines. At Pinterest, we've had multiple migrations that have gone on YEARS beyond their original schedule, hurting developer productivity and morale. In this talk, we analyze the reasons behind these failures, share our learnings, and demonstrate our pipeline for automating upgrade validation and deployment.