This paper reports on experiences of creating resilience-empowering simulation-gaming exercises concerning disruptions in the payment system. The aim of the exercises was to utilize gaming-simulation as a training environment where teams of practitioners can learn to develop in-depth understanding of systemic interaction (i.e., cascading effects of disruptions) and learn how to develop collaborative resilience across many different critical infrastructures. Interaction between different stakeholders in the payment system, such as business owners, banks, municipality crisis managers are considered as the foundation for building collaborative resilience. Designing the exercises in such a way that they encourage and support such interactions are therefore seen as a primary design goal. This paper describes lessons learned from the process of conducting the 17 exercises in terms of creating a well-balance simulation and an immersive experience.