<p>Periodic roof collapse, blasting vibrations, and excavation disturbances subject anchored rock masses to cyclic dynamic loads, leading to progressive damage and an increased risk of dynamic disasters such as rockbursts. In this study, the dynamic mechanical responses of anchored rock-like samples were investigated on the basis of a self-developed rockbolt impact testing system. The stress wave propagation, prestress loss, and slippage of the anchored rock-like samples were systematically analyzed. The results showed that the failure of the interfacial anchoring system occurs through progressive debonding that begins at the outer end and moves towards the inner end. The number of impacts endured by the anchored rock-like samples decreases with increasing incident energy and increases with increasing initial prestress when the initial prestress disappears or when the rockbolt–grout interface fails. The slippage of the rockbolt increases exponentially with increasing number of impacts. These findings offer theoretical insights and practical guidance for the design and maintenance of prestressed rockbolt support systems in deep underground engineering, aiding in the mitigation of dynamic failure risks under cyclic loading conditions.</p>