The paper deals with dynamic analysis of automatic ship steering gear systems utilising complex controls that function according to the principle of proportional, integral and derivation regulators. The analysis involves a system dynamic simulation modelling methodology as one of the most suitable and effective means of dynamic modelling of complex non- linear, natural, organisational and technical systems. The paper discusses system dynamics simulation models being used in qualitative (mental-verbal, structural) and quantitative (mathematical and computer) simulation models on ships equipped with trailing steering systems and PID regulator. Authors suggest using the presented models for designing and constructing new steering systems, for diagnosing existing constructions and for education in Universities.