We present TimberTool (TTool v2.1.1), a software designed for woodworking tasks assisted by augmented reality (AR), emphasizing its essential function of the real-time localization of a tool head’s poses within camera frames. The localization process, a fundamental aspect of AR-assisted tool operations, enables informed integration with contextual tracking, facilitating the computation of meaningful feedback for guiding users during tasks on the target object. In the context of timber construction, where object pose tracking has been predominantly explored in additive processes, TTool addresses a noticeable gap by focusing on subtractive tasks with manual tools. The proposed methodology utilizes a machine learning (ML) classifier to detect tool heads, offering users the capability to input a global pose and utilizing an automatic pose refiner for final pose detection and model alignment. Notably, TTool boasts adaptability through a customizable platform tailored to specific tool sets, and its open accessibility encourages widespread utilization. To assess the effectiveness of TTool in AR-assisted woodworking, we conducted a preliminary experimental campaign using a set of tools commonly employed in timber carpentry. The findings suggest that TTool can effectively contribute to AR-assisted woodworking tasks by detecting the six-degrees-of-freedom (6DoF) pose of tool heads to a satisfactory level, with a millimetric positional error of 3.9 ± 1 mm with possible large room for improvement and 1.19 ± 0.6° for what concerns the angular accuracy.