The gearbox is widely applied as the mechanical transmission system of intelligent manufacturing systems, such as machine tools and robotics. The harsh working environments make the gear surface prone to wear. The progression of surface wear can bring severe failures to the gear tooth, including gear tooth root crack, surface spalling of gear tooth, and tooth breaking, all of which could damage the whole transmission system. Hence, it is essential to monitor and evaluate the gear surface wear propagation. The gear wear has been proven highly relevant with the vibration second-order cyclostationary (CS2) characteristics. Therefore, this paper develops a novel cyclostationarity-based framework to monitor and evaluate gear wear propagation. More specifically, the squared envelope (SE) of the residual signal, removing deterministic components, is utilized to identify the gear wear distribution and its propagation trends, validated using the measured gear surface morphology. Moreover, a new CS2-based indicator is proposed to assess the severity of gear surface wear, achieving a high correlation with measured surface roughness: [Formula: see text] is more than 0.9. The developed cyclostationarity-based framework can comprehensively evaluate the degradation status of the gear system caused by surface wear, significantly benefiting the health management of the gear transmission system, which is of great practical value for the health management of intelligent manufacturing systems. A series of endurance tests are conducted to verify the effectiveness and superiority of the developed framework for gear wear monitoring compared with the conventional indicators.