Cutter suction dredgers (CSD) are highly vulnerable to large wave loading due to their stiff, spud-based mooring. Many mitigations targeted at reducing the resulting stresses on the spud and other critical operating components have been proposed in recent years, most notably by adding a level of flexibility to the connection between the pontoon and the spud for rotational motions. Investigating the merits of the implementation of a flexible spud keeper however are hindered by the lack of accurate, CSD-specific models that are able to simulate real waves in the working area, as well as the multibody system of a CSD and its complex interactions with the sea floor. In this thesis, an ANSYS AQWA model is developed to conduct an operability analysis of a CSD in operation in offshore, coastal conditions. Three modelling objectives were established to provide a complete analysis of the effect of increased flexibility in a spud keeper: adding non-linear wave effects, improvement of the soil boundary conditions, and building a dynamic multibody system of a CSD in ANSYS AQWA. A wave model is developed that expands upon standard Linear Wave Theory (LWT) through the use of Stokes 2nd Order Wave Theory (S2). S2 was found to be valid for a larger range of water depths and wave parameters than other wave theories, mainly in shallow, coastal conditions, which is the main operating area of a CSD. These non-linearities cannot be implemented into a frequency domain (FD) model, therefore a time domain (TD) model is required. A combination of S2 waves in a JONSWAP spectrum is used to simulate the motion and force response in TD, as well as second-order forces from the interaction of wave groups with the CSD. The model output is then used as a means of verification of these assumptions and to show the effect of the wave shapes on the spud bending stress. An altered spud model is proposed for shallow, wide spuds, using a rotational spring system instead of the commonly used clamped model. For the use-case of a CSD it shows a spud's tendency for rigid motion below the mudline, while also providing an upper operational limit for soil failure around the spud. The model output showed this upper limit to likely not be a important operational limit, but it can be used to investigate spud rotation below the mudline. Mooring effects from the cutter are absent in older models, but are added in the form of spring elements to better approach reality. Finally, a number of CSDs with different levels of flexibility are tested for four operational limits. The model shows a clear shift in motion resonance towards lower frequencies when the stiffness is decreased, while operability analysis in TD presents a significant increase in operability when a CSD is free to move in pitch. This completely flexible connection provides a major reduction in spud bending stress, but is governed by the acceleration limit of the pontoon. Other reduced stiffness designs are shown to only provide limited benefits to the operability.