Moment connections in glulam members are desirable over simple connections to increase load-carrying capacity and reduce deflections for the same gulam cross section. However, moment connections in glulam members often result in a large tension-compression couple. To achieve high tension capacity, a large number of fasteners acting in dowel shear are often utilized. Brittle failure modes such as block shear and group tear-out can dominate such connections. This study evaluates the structural performance of high capacity glulam moment and tension connection in two configurations based on the results of physical testing. Calculation-based results and physical load test results are compared. The results from this study show that block shear capacity estimations as adopted in design standards may be unconservative for high capacity moment or tension connection. A potential modification through perpendicular-to-grain reinforcing screws to help mitigate the block shear failure is presented.