Free and Open Source Software “won”–it successfully democratized access to code and technology—but the industry changed. Cloud computing has created an always online, software-defined world orchestrated around running software-as-a-service. This reintroduced practical limits to software freedom as hyperscalers create proprietary differentiation through secretive operation and management software. In practice, we have become dependent on proprietary services built on a FOSS foundation. This proprietary capture threatens to undermine the very ability to create Free and Open Source Software. This presentation explores suggestions (such as the Operate First initiative) for how FOSS can, and must, evolve to face these challenges and democratize the cloud. Free and Open Source Software has successfully democratized access to code and technology. FOSS has become the common, universal base for software development. However, despite “winning” the industry, FOSS largely stops with 'software at rest' (the runtimes, toolchains, and code components used when running your environment and building your applications). Upstream projects can take these software components and run them, but putting them into production at scale is mostly protected as proprietary knowledge by the companies offering cloud services on top of FOSS. FOSS enabled the evolution of computing through cloud and microservices, as well as the increasing ubiquity of software control in the physical world. With this widespread adoption the challenges to FOSS have changed: the software industry has remade development into the aggregation of black-box services running on infrastructure controlled by a third party. It has, in essence, re-created the problem of the mainframe. To survive, FOSS must evolve through open sourcing operations. Operate First is one way to do that.