Managing complex systems requires addressing a number of unique characteristics to ensure their successful operation. One of the greatest challenges in asset management is understanding and dealing with unexpected events and the unknown.Unexpected deviations from normal operating conditions raise significant concerns regarding the reduction of safety and reliability. Despite the remarkable industrial transformation of recent decades—characterized by an unprecedented convergence of digital, physical, and biological technologies—approaches for achieving comparable improvements in safety and reliability have not evolved at the same pace. As a result, organizations still face major challenges in managing the growing complexity of modern systems.Complex assets require new approaches capable of coping with unpredictable events and disorder. Consequently, it is essential to incorporate, already during the design phase, methods and techniques that enable systems not only to withstand stress (Kriete, 2013), but also to become stronger without the need to predict every possible circumstance. Following the ideas proposed by Taleb (2012), reliability professionals increasingly require antifragile approaches that enable systems to embrace disruption, uncertainty, and the unknown.The aim of this seminar is to discuss the current state of the art and ongoing developments in managing unexpected events in complex systems—such as critical infrastructures and energy production systems. The seminar will present emerging techniques and methodologies while critically examining their strengths, limitations, and uncertainties in order to improve the reliability and resilience of complex assets.