Craniomaxillofacial trauma is an important focus in bone regeneration research due to its relative complexity and importance compared to the larger bones in the body, and due to the high rates of incidence in both military and civilian personnel in battlefield scenarios. This thesis builds off previous work in 3D bio-printing and the development of a modular scaffolding system for craniomaxillofacial regeneration and presents a computational shape fitting model for use with these technologies in a clinical setting. Presented is an evolutionary model which initializes then optimizes a shape fit configuration for a given shape. Testing on simple shapes, a rat skull, and a human mandible sample demonstrates that the model can generate an accurate, stable shape fit configuration in <2 seconds with >95% connectivity for a variety of shapes with differing sizes and complexities and can be adapted to fit any desired physical block size for the shape fit configuration. This model demonstrates proof of concept for the automated configuration of our modular scaffolding system, which is an important step in future clinical application of this technology.