Contemporary systems of systems are often challenged by unexpected disruptive events, which are frequently difficult to predict. Antifragile systems can withstand and benefit from outlier events, whereas fragile and robust systems cannot. However, while engineering robust systems has been the subject of research in the past, designing systems that are expected to cope with severe disruptions, and survive or even thrive in a context of volatility and uncertainty opens the stage to several challenges. In this talk, while discussing the challenges that must be addressed to attain the systematic development of antifragile systems of systems, we support the vision that an effective application of the antifragility principle requires a clear understanding of the implications of its adoption and its relationships with other approaches sharing a similar objective.