This project explores the intersection of craft and digital fabrication through a human-computer collaboration system for sculpting. Following traditional carving techniques we developed the FreeD: a handheld digital milling device, which is tracked and controlled with reference to a virtual 3D model. The FreeD allows unskilled makers to produce complex carving tasks, as well as personalizing and modifying the digital 3D models while physically carving. The control software offers guidance according to static virtual models or dynamic ones, which may be altered directly or parametrically. In addition, the FreeD is also able to semi-autonomously move and carve. This creates synergetic cooperation between human and machine that ensures accuracy in recreation of the model while preserving the expressiveness of manual carving.