Open source software plays a critical role in the infrastructure of most modern organizations. Yet despite this fact, the health and long term viability of most open source projects are fraught with risk and uncertainty. Establishing sustainable business models to support open source is a non-trivial problem. A few companies have demonstrated that it is possible to build a successful business around open source software, however far more open source maintainers are suffering from fatigue and burnout. In this session we are going to explore the challenges and opportunities related to open source sustainability, including a candid and unbiased view into the mechanics of these fragile ecosystems.