The experimental investigation of extreme wave/structure interaction scenarios puts high demands on wave generation and calculation. This paper presents different approaches for modelling non-linear wave propagation. Results of numerical simulations from two different numerical wave tanks are compared to models tests. A further approach uses analytical wave models which are combined with empirical terms to allow a fast and precise prediction of non-linear wave propagation for day-to-day use. All approaches can be used either separately or in combination — depending on their particular purpose. As an application, different special wave scenarios — both academic and realistic — are generated and validated by measurements. The advantages and disadvantages of the presented methods are discussed in detail with regard to their appropriate use for investigations of extreme structure behaviour.