The engineering design of dowel type steel-to-timber connections is comprehensive and shall also include the surrounding timber matrix, as required by the principles specified in Eurocode 5. As one part of a hierarchically structured research program, the loading and failure modes of multi-dowel connections has been investigated, including both the elastic as well as the cracked domain of the load history. Depending on the presence of local reinforcement, in order to prevent premature brittle failure and to insure local ductile dowel behavior, the global response became more or less ductile. The monitoring of surface deformations of the timber by means of a contact free displacement measurement system (DIC) supported the identification of stepwise changing structural systems. This data constitutes a valuable basement for the completion resp. improvement of the present design procedures with respect to consistency and effectiveness.