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Learn from StackHPC's extensive experience managing OpenStack cloud upgrades across global deployments in this 29-minute conference talk. Discover how a small engineering team efficiently handles numerous upgrades annually through strategic automation and tooling. Explore Ark, StackHPC's centralized software repository that snapshots artifacts including Kolla container images, host OS images, and software packages to maintain tested and repeatable environments. Understand the integration of Kubernetes resources as CI runners within OpenStack clouds using Magnum and Actions Runner Controller (ARC) for GitHub repositories, creating flexible automated testing environments. Gain insights from four years of development experience, including painful lessons learned and strategic vision for future improvements in OpenStack upgrade processes.