Timber is becoming an increasingly popular construction material particularly due to its great environmental properties. Just alone around Linnaeus University in Växjö city, dozens of multistory buildings in timber have risen. As the demand for more timber construction is becoming popular, the understanding of timber design must evolve at the same pace. One of the most important parts of timber construction are the connections that hold everything together. One variable that is used to design connections is the embedment behavior. This thesis examined how the embedment behavior of a steel dowel in wood is influenced by moisture content, assembly history, and artificial cracks. In this case the assembly history refers to if the drilling and insertion of the steel dowel was done before or after drying or wetting the specimen. The idea behind the artificial crack was to achieve something similar to a real crack where the crack was created with a precision saw to separate the fibers parallel to the grain. The embedment behavior was studied by means of embedment strength, elastic- and plastic embedment stiffness. In total, 140 embedment experiments were conducted to study the embedment behavior of the dowel in wood. All embedment experiments were carried out parallel to the fiber direction using two species of wood, spruce and birch. Each experimental series had its own attributes to allow a comparison of how the embedment behavior is influenced by moisture content, assembly history, and artificial cracks. The data from the experiments was then used as input to create computer models where the beam on foundation modeling approach was used in conjunction with the finite element computer program Abaqus. A timber-steel-timber connection was modeled to study the influence of the side timber member thickness on the overall strength. The results of the experiments showed that the moisture content and the assembly history can potentially affect the embedment strength and the elastic, and the plastic embedment stiffness. The series that studied the influence of artificial cracks showed that mostly the embedment strength and elastic embedment stiffness are affected by artificial cracks. The numerical simulations indicated that the moisture profile from the experimental data had less influence on the strength for thicker timber side members than it did on thinner. In general, this thesis provides new insights and a better understanding of how the embedment behavior is influenced by moisture content, assembly history, and artificial cracks.