An ordinary electric drill was integrated into a context-aware augmented reality (AR) framework to assist in timber-drilling tasks. This study is a preliminary evaluation to detail technical challenges, potential bottlenecks, and accuracy of the proposed object- and tool-aware AR-assisted fabrication systems. In the designed workflow, computer vision tools and sensors are used to implement an inside-out tracking technique for retrofitted drills based on a reverse engineering approach. The approach allows workers to perform complex drilling angle operations according to computer-processed feedback instead of drawing, marking, or jigs. First, the developed methodology was presented, and its various devices and functioning phases were detailed. Second, this first proof of concept was evaluated by experimentally scanning produced drillings and comparing the discrepancies with their respective three-dimensional execution models. This study outlined improvements in the proposed tool-aware fabrication process and clarified the potential role of augmented carpentry in the digital fabrication landscape.