The thesis reports the outcomes of a comprehensive study on how bolted timber connections with Laminated Veneer Lumber (LVL) respond to loading that is perpendicular to the grain. It investigates the topic in three main sections: understanding the stress-strain characteristic of LVL, checking how much splitting failure occurs in unreinforced bolted joints, and improving the splitting resistance by inserting self-tapping screws. In the first phase, AS/NZS 4063.1-2010 tensile tests were conducted on LVL samples of two lengths using a three-point bending set-up. The load, deflection, stress, strain, and failures of the samples were measured and analyzed to evaluate their mechanical performance. Digital Image Correlation (DIC) identified key deformation stages-elastic, fracture, and softening. The bilinear model was used and proven to match the relationship between stress and strain under perpendicular tension. The second phase focused on the splitting behavior of unreinforced bolted joints. Full-scale tests changed the distance between the loaded edge and the connection, the width of the connection and the placement of bolts. When the relative edge distance (he/h) surpassed 0.6, it was found that the main mode of resistance splitting involved ductile failure. With more connections added, the capacity grew less significantly. The findings were checked against DIN 1052, Van der Put, Ballerini, and the Australian standard. Even though the majority of models agreed with experiments for a single-bolt connection, the Australian model had a significant difference. Results from the models fell short when there were more than four bolts. Use of tensile strength parameters made the revised DIN 1052 model more precise. In phase three, STS reinforcement was added to improve connection behavior. Various tests were performed that changed the screw diameter, the depth it was embedded, and where it was placed. STS reinforcement enhanced both strength and ductility by shifting failure modes from brittle to ductile. According to the withdrawal tests, the diameter and depth of the screw were critical. According to the DIC analysis, strain decreased, and the time for cracks to grow was delayed after using the STS. Based on the data and on SEM and regression statistics, resisting STS withdrawal was considered the main factor. After completing the study, it is recommended to incorporate STS rules into design codes to strengthen and secure timber connections.