Finite element models tend to overestimate the actual elastic response of structural timber connections. The paper shows how such overprediction relates to the modelling of the contact between fasteners and timber. The use of a control parameter called stiffness contact is proposed. After an experimental campaign, a method to determine it, based only on the geometry of a rectangular contact area, is proposed. The modeling adequacy is demonstrated by applying it to dowel embedment and moment resistant wood joint tests. The obtained results show good agreement with the experimental test series.