The aim of the experimental study presented herein is the assessment and quantification of the behavior of individual dowels in multi-dowel connections loaded by a bending moment. For this purpose, doubleshear, steel-to-timber connections with nine steel dowels arranged in different patterns and with different dowel diameters were tested in 4-point bending. In order to achieve a ductile behavior with up to 7° relative rotation, the connections were partly reinforced with self-tapping screws. The reinforcement did not influence the global load-deformation behavior, neither for dowel diameters of 12 mm nor for 20 mm, as long as cracking was not decisive. The deformation of the individual dowels was studied by means of a non-contact deformation measurement system. Thus, the crushing deformation, i.e. the deformation at the steel plate, and the bending deformation of the dowels could be quantified. In case of 12 mm dowels, the bending deformation was larger than the crushing deformation, while it was smaller in case of 20 mm dowels. Moreover, dowels loaded parallel to the grain showed larger bending deformations than dowels loaded perpendicular to the grain. This indicates that the loading of the individual dowels in the connection differs, depending on their location.