Navigating the ever changing world of FOSS can be confusing for developers, entrepreneurs and decision makers. This presentation is about making sense out of the complexity of FOSS, its long-term evolution and identifying the new challenges brought to open source communities as it reaches industry maturity. It can be useful to understand the four models that have been brought to us by FOSS’ 30+ year history: the community model, the enterprise model, the collaborative innovation model and the capitalistic model. As FOSS becomes mainstream and broaden its scope, new challenges emerge. The presentation will discuss six of them: the first concerns free riders, the second is uncontrolled re-use, the third one is SaaS, the fourth challenge is verticalisation, the fifth is from opportunistic foundations and the sixth, last but not least is AI.