Since its inception, the Xen Orchestra project which uses AGPLv3, always had a philosophy to listen and engage the community. User feedback shaped our initial concept, which first targeted system administrators. Eventually, our users drove us to support cloud-scale deployments supporting up to 2000 VM's. Retaining simplicity in usage and installation, while evolving Xen Orchestra to cloud scale posed many challenges. This led us to build many new features such ACLs, self-service, live charts, config drive management, and more, forced us to constantly evolve our architecture. First we will show how user needs changed our architecture, and how we implemented challenging problems such as user permissions, ACLs, Containers in a virtualized infrastructure and self service. We will conclude with a short demo, what is next and a lessons learned.