A milling depth compensation system for milling rock determines a target position of a machine, an initial position of the work surface, and a target pose of the machine based on the target position of the machine and the initial position of the work surface. An actual pose of the machine is determined and differences between the actual pose and the target pose are used to determine a dynamic milling path of a milling tool. The dynamic milling path includes movement of the milling tool along a first path, a second path, and a third path. Command signals are generated to move the milling tool along the dynamic milling path.