In this study, the dynamic cracking processes in porcine cortical bone were visualized in real-time using the high-speed synchrotron X-ray phase-contrast imaging (PCI) technique in three osteon orientations:​ in-plane transverse, out-of-plane transverse and in-plane longitudinal. The dynamic flexural loading applied on the pre-notched bone specimens was introduced by a modified Kolsky compression bar. High-speed X-ray images of the entire loading events were documented with a high-speed camera. Three-dimensional X-ray micro-computed tomography was conducted to examine the intact microstructures and obtain the basic material properties of the bone material used for mechanical characterizations. The onset location, where crack initiated, and the subsequent direction, along which the incipient crack propagated, were measured quantitatively using the high-speed X-ray images and the latter was found dependent on the osteon direction significantly. The crack propagation velocities were dependent on crack extension over the entire crack path significantly for all the three directions while the initial velocity for in-plane longitudinal direction was lower than the other two directions. Straight-through crack paths were observed for in-plane longitudinal specimens while the cracks were deflected and twisted in the in-plane transverse direction. For out-of-plane transverse direction, the cracks follow paths with tortuosity fall in between the other two directions, showing a mixed mode of fractures of the former two extreme cases. The toughening mechanisms, visualized by the high-speed X-ray images, and the corresponding fracture toughness, evaluated in terms of fracture initiation toughness and crack growth resistance curve (R-curve), were also found significantly different among the three osteon directions, suggesting an overall transition from brittle to ductile-like fracture behaviors at the dynamic displacement rate (5.4 m/s) as the osteon orientation varies from in-plane longitudinal to out-of-plane transverse, and to in-plane transverse eventually.