The cortical bone is a hierarchical composite material that, at the microscale, is segmented in an interstitial matrix, cement line, osteons, and Haversian canals. The cracking of the structure at this scale directly influences the macro behavior, and, in this context, the cement line has a protagonist role. In this sense, this work aims to simulate the crack initiation and propagation processes via cortical bone microstructure modeling with a two-dimensional mesh fragmentation technique that captures the mechanical relevance of its constituents. In this approach, high aspect ratio elements are inserted between the regular constant strain triangle finite elements to define potential crack paths a priori. The crack behavior is described using a composed damage model with two scalar damage variables, which is integrated by an implicit-explicit (Impl-Ex) scheme to avoid convergence problems usually found in numerical simulations involving multiple cracks. The approach’s capability of modeling the failure process in cortical bone microstructure is investigated by simulating four conceptual problems and one example based on a digital image of an experimental test. The results obtained in terms of crack pattern and failure mechanisms agree with those described in the literature, demonstrating that the numerical tool is promising to simulate the complex failure mechanisms in cortical bone, considering the properties of its distinct phases.