While the progressive collapse mechanisms of concrete and steel buildings have been widely researched, limited studies have been carried out on mass timber buildings. Experimental testing under given loading scenarios of the entire system or a representative large part of it, may be required to extend the knowledge and improve design rules. However, due to the limited laboratory space and budget restrictions, fullscale tests are rare and may not always be possible. In steel and concrete, tests are frequently performed on scaled down systems. Since timber is an inhomogeneous material, interpreting experimental results on scaled down timber structures may not always be straightforward. Knowing that connectors play a vital role in the performance and robustness of timber buildings, analysing the scale effect on the behaviour of connectors would therefore provide a solid understanding of how experimental results from scaled systems should be interpreted. Furthermore, current Australian and international design codes in timber structures recommend a linear elastic approach for designing beam-to-column timber connections. In the event of an unexpected loading or losing a main load-carrying element such as a column, connections may experience large deformations resulting from disproportionate shear and bending actions. Under such a scenario, the structure may undergo nonlinear plastic deformations. The connector’s capability in obtaining large rotations is a critical factor in the robustness of the structure with regards to a potential progressive collapse. In this context, the current study is aiming to (i) experimentally and numerically investigate the scaling effects in three types of beam-to-column timber connections used in mass timber buildings, (ii) to investigate the behaviour of connections subjected to shear and bending moment, (iii) introduce a connection that can undergo large rotations in a progressive collapse event, and numerically investigate the proposed connections’ response to combined shear and bending actions.