Situated within the intersections of stereotomy (the art of cutting solids), the evolution of machine tools and structural design principles; this research investigates contemporary digital stereotomic practice, both its historical context and current contribution to the Architectural discipline. This dissertation develops modular prototypes of subtractive fabrication methods with a focus on utilising variations of osteomorphic blocks (based on Abeille’s vault) for interlocking joint systems. Interlocking assemblies in the construction industry have gained acceptance for their versatility and reduced labour costs in comparison to traditional brick and mortar methods. The ease of assembly and disassembly make using these mortar-less interlocking blocks for arched and vaulted spaces appropriate. Past methods of stereotomic practice and emerging multi-axis robotic fabrication techniques are investigated in relation to case studies of specific structural conditions. These include a novel approach towards robotic fabrication of wave jointed blocks, columns and arches, followed by beam and cantilever structures. Examining the machine generation of specific geometries of wave block modules forms a base to establish criteria for testing material outcomes. This thesis aims to highlight the value of ‘crafting’ through robotic technologies. The structural prototyping workflows, quantitative test results of failure mechanisms and contribution to historical knowledge of this thesis, can extend to the wider manufacturing industries and heritage conservation departments. Here, the implementation of the design and production workflows of interlocking self-supporting assemblies can be used to adapt past methods of traditional stone carving and assembly techniques. Further extending to the construction of spaces in extreme climates and unstable conditions where flexibility of structures is beneficial. Allowing humanity to progress further and explore new environments and habitats.