Microcracks have been associated with age-related bone tissue fragility and fractures. The objective of this study was to develop a simple osteonal cortical bone model and apply linear elastic fracture mechanics theory to understand the micromechanics of the fracture process in osteonal cortical bone and its dependence on material properties. The linear fracture mechanics of our composite model of conical bone, consisting of an osteon and interstitial bone tissue, was characterized in terms of a stress intensity factor (SIF) near the tip of a microcrack. The interaction between a microcrack and an osteon was studied for different types of osteons and various spacing between the crack and the osteon. The results of the analysis indicate that the fracture mechanics of osteonal cortical bone is dominated by the modulus ratio between the osteon and interstitial bone tissue: A soft osteon promotes microcrack propagation toward the osteon (and cement line) while a stiff one repels the microcrack from the osteon (and cement line). These findings suggest that newly formed, low-stiffness osteons may toughen cortical bone tissue by promoting crack propagation toward osteons. A relatively accurate empirical formula also was obtained to provide an easy estimation of the influence of osteons on the stress intensity factor.