In recent years, timber has emerged as a sustainable alternative material in structural engineering. However, due to its orthotropic nature, the mechanical properties of timber vary significantly concerning its grain direction, presenting challenges in its application, particularly in bolted connections perpendicular to the grain, as it causes the joints to fracture prematurely and causes damage to the bolted timber frame when subjected to tensile strain. This paper presents an experimental study on the effects of such loading configurations on timber connections in order to have a comprehensive understanding of the failure mechanisms, as it becomes essential to assess the real capacity of brittle failure modes in timber connections. This paper investigates experimental data from timber connections loaded perpendicular to the grain, taking into account differences in loaded edge distance. Using image-based data, the study penetrates the strain field of bolted timber connections, revealing insights unreachable by conventional laboratory measurements alone. Through image-based analysis, crucial parameters such as crack initiation load and fracture patterns at failure load are evaluated, enhancing the understanding of timber connection behavior. This study also explains the image-based analytic approach to strain field measurement in various cross-sections of timber connections.