The enthesis is the anatomical interface between the soft and hard tissues where tendons or ligaments connect into bone, the stress distribution under shear and tension loads in these areas is defined by complex transitions in collagen fiber architecture, mineral content, and stiffness. There are numerous experimental studies that detail mineral phase gradients and mesoscale mineralized spherules, however, there is limited study into their integration into scaffold design. Aiming to address this gap, this study focuses on the development of accurate models of scaffolds that replicate key functional characteristics of native enthesis function by incorporating multiscale structural features. This study makes use of the CAD software to generate scaffold geometries in order to incorporate site-specific features such as collagen fiber bundle orientation and spatial mineralization patterns. Using Finite Element Analysis (FEA) these models are then subjected to simulate physiological loading scenarios and assess mechanical behavior across the scaffold, including stiffness gradients, stress distribution, and potential failure zones. This research aims to establish a robust design framework and foundation for developing enthesis-mimicking scaffolds by integrating structural hierarch into the scaffold model and validating its mechanical performance. The goal is the development of biomaterials that support seamless tissue integration, aiding improved mechanical resilience and clinical outcomes in tissue engineering and regenerative medicine.