The use of advanced and widely available commercial finite element computer programs in design of anchored retaining structures confront designers with several challenges that may, if not properly accounted for, lead to poor and even unsafe design. The paper addresses this issue and proposes a strategy for numerical modelling of retaining structures in medium stiff to stiff soils. The proposed strategy is verified on three case histories and a good agreement is achieved between calculated and measured displacements of the retaining structures. Measures the designers could take to ensure the structural safety, particularly with regard to its brittleness, are also proposed.