Steel-wood-steel connection is widely seen in many applications, such as timber structures. The stiffness of steel-wood-steel connection loaded parallel to grain for softwoods originated from Malaysia was investigated in this study. Numerical models have been developed in ABAQUS to study the stiffness connection. Softwoods of Damar Minyak and Podo have been selected in this analysis. The comprehensive study focused on the effect of bolt configurations on stiffness. Numerical analysis is carried out and the developed model has been validated with the previous study. Further investigations have been made by using the validated model. From this model, numerical analysis of the stiffness values have been made for various bolt configurations, including bolt diameter, end distance, bolt spacing, number of rows and bolts and edge distance. The result shows that the stiffness of bolted timber connections for softwood depends on the bolt diameter, number of rows and bolts, end distance and edge distance. Based on the result, stiffness increased as the diameter of the bolt, end distance, number of rows and bolts and edge distance increased. It is also discovered that the stiffness equation in Eurocode 5 (EC5) is inadequate as the equation only considered parameters which are wood density and bolt diameter. Other connection parameters such as geometry are not considered in the EC5 equation.