The embedment behavior of dowels in timber structures, as an essential parameter in the design of connections, is the subject of this thesis. There are numerous advantages using timber structures, including sustainability, energy efficiency, and aesthetic appeal. The mechanical performance of connections in timber structures can be affected by environmental variables, such as moisture content. Thus, in the thesis the embedment behavior of dowels in timber, including the embedment strength and elastic and plastic stiffness at various moisture levels was investigated. In addition to different moisture contents, the effects coming along with changing the moisture content, like swelling and shrinkage, in combination with the assembly history were studied. The study investigated the effects of moisture content variations on the embedment behavior of dowels in timber loaded perpendicular to the grain at relative humidity levels of 38%, 65%, and 85% at a temperature of 20◦C. The study also explored the impact of assembly history of the steel dowels on the embedment behavior. The expression ”assembly history” refers the effects of drilling and assembling steel dowels at different times, i.e. if drilling the timber occurs before changing the moisture content or after changing the moisture content.  Full-hole embedment tests were conducted in five different series to cover all three levels of moisture content while taking the assembly history into account. In total, 100 embedment experiments were carried out, with 50 samples of spruce and 50 samples of birch being assessed perpendicular to the grain. In addition, 20 solid timber specimens were exposed to cyclic loading to evaluate the embedment behavior under these conditions. To evaluate the stress on the timber around the dowel, finite-element simulations, using linear-elastic material behavior in combination with volumetric changes due to moisture variation were conducted. Corresponding to the assembly history in the experiments, the situations of moisture variation in presence and absence of the steel dowel for the swelling and shrinkage case were investigated. The experimental results showed that while the elastic and plastic embedment stiffness can be impacted by moisture content only in low MC situations, it can potentially affect embedment strength in both dry and wet conditions. Additionally, the assembly history influences only the plastic stiffness in a low MC condition. Results from cyclic loading have shown no significant difference to embedment strength and stiffness gained from monotonic loading. According to numerical simulations, the tensile normal stress in the direction perpendicular to the load direction is higher than the tension strength for the shrinkage case with the dowel present. This might be explained by using a simple linear elastic material model in the FEM simulation, which causes an overestimation in the stiffness properties. In conclusion, this thesis offers new perspectives and a deeper knowledge of how moisture content, assembly history, and cyclic loading perpendicular to the grain affect the embedment behavior of dowels in timber connections.