A detailed understanding of the failure characteristics of infilled jointed rock is a key concern in underground engineering and is critical to the design, construction and maintenance of relevant projects. In this paper, uniaxial compression tests were performed to investigate the effect of the joint arrangement (different rock bridge angles) on the strength and crack propagation of red sandstone containing a set of preexisting infilled flaws of the same sizes and angles, while the crack fracturing process was observed by AE and strain monitoring. When the angle between the rock bridge and loading stress was less than 24°, the rock mass failure form was tensile failure with some localized shear failure occurring in the rock bridge damaged by crack penetration, leading to an overall decrease in the carrying capacity. The turning points of the strain and AE signal were clearly observed to be caused by the initiation and propagation of cracks, and the energy consumed by the initiation of shear cracks was greater than that of tensile cracks. The study was further conducted using the fracture mechanics numerical code FRACOD to investigate the crack propagation law and failure mechanism under different loading stress conditions. Simulation results from three 2D similar models showed that the percentage of open fractures decreased, but slipping increased; in addition, the total length of the fractures was greatly reduced with increasing confining stress. These results are important and valuable for understanding the crack mechanism of rock engineering in deep underground mining excavations.