This project investigates various factors which influence the behaviour of a timber roof structure designed by Smith & Wallwork Engineers. The first part of the project focused on material of sweet chestnut, where Digital Image Correlation (DIC) was employed to obtain values for the shear modulus. DIC was able to implement the shear field test method prescribed in BS EN 408:2010, along with two new methods developed based on additional information available through DIC. These methods were accurate, fast to implement, and potentially more robust than the shear field test method. A method to estimate the true value of the Timoshenko shear coefficient was also developed. The second section of the project involved physical testing of portions of the roof structure to investigate the behaviour of screw-reinforced and unreinforced timber loaded perpendicular to grain. Together with finite element modelling, it was noticed that a key aspect of the connection's behaviour was the axial force transfer between overlapping screws via shear in the timber, and the resulting relative displacement between the screws. A simple spring model was developed to characterise the compression stiffness of the roof which can now be used in reverse to calculate the forces due to moisture expansion or contraction.