Open source software is now ubiquitous, recognized across industries as a fundamental component to infrastructure, as well as a critical factor for driving innovation. Over the past twenty years, the OSI has worked to promote and protect open source software, development, and communities, championing software freedom in society through education, collaboration, and infrastructure, stewarding the Open Source Definition (OSD), and preventing abuse of the ideals and ethos inherent to the open source movement. The “open source” label was created at a strategy session held at the start of February 1998 in Mountain View, California. That same month, now almost twenty years ago, the OSI was founded as a general educational and advocacy organization to raise awareness and adoption for the application of free software in an open development process. Some of the largest forces in business today — consumer-facing companies like Google and Facebook, business-facing companies like Salesforce and SUSE, companies outside the tech industry such as BMW, Capital One, and Zalando, even first-gen tech corporations like Microsoft and IBM — all increasingly depend on open source software. Governments too, including the European Union, France, India, the United Kingdom, the United States, and many others have discovered the benefits of open source software and development models. Successful collaborative development of software and infrastructure used by these organizations is enabled by the safe space created when they use their IP in new ways... to ensure an environment for co-creation where the four essential freedoms of software are guaranteed. As open source adoption has expanded, we have seen changes in the assumptions surrounding licensing, governance and development of open source projects. We will document that evolution and look ahead to see what trends and pressures face the global free and open source software movement as it expands beyond ICT to wireless, distributed devices and beyond.