This study investigates the effects of collagen network quality on the fracture behavior of bovine cortical bone, specifically dynamic fracture initiation toughness. Two collagentargeted treatments are investigated, degradation through heat treatment or manipulation via ribosylation incubation, to mimic the effects of prolonged type 2 diabetes. A single loading rate consistent with conditions representative of a fall event is paired with a three-point bend impact experiment utilizing a custom-built drop tower with high-speed imaging and an orthotropic linear elastic fracture mechanics approach to determine mixedmode stress intensity factors and dynamic fracture initiation toughness. This study’s findings i ndicate n o s tatistically s ignificant effects of co llagen cross-linking quality on the fracture toughness of bovine cortical bone under fall event representative conditions. However, trends between cross-link degradation and decreases in fracture toughness were observed. The ribosylation treatment successfully replicated the amount of altered collagen cross-links associated with the effects of 30 years of prolonged type 2 diabetes. However, the fracture characteristics exhibited by the ribosylation treatment group were not significant. Thus, these collagen-targeted treatments may not represent the compounding microstructural effects accrued over a patient’s lifetime. The conclusions reached are that further investigation into the microstructural changes that occur alongside collagen alterations overtime is needed to characterize the observed increased fracture risk associated with type 2 diabetes. Limitations of this study include the inability to draw findings and conclusions explicitly relevant to human bone, even though bovine cortical bone has been accepted as a model material for improving the understanding of fracture and failure processes. This study contributes to the scientific community’s understanding of the role collagen cross-linking has on fracture strength and subsequent resistance to fracture present in cortical bone, with the intent that this work can be furthered by applying the presented methodologies to diabetic human bone.