<p>The cobble–boulder strata, characterized by poor grading, high strength, and strong abrasiveness, pose significant challenges to shield machine (SM) working, where rapid abrasive wear and fracture damage of cutters become critical bottlenecks for safe and efficient tunneling. However, existing studies on such strata have not differentiated the underlying mechanisms between damage phenomena and abrasive wear, hindering the understanding and mitigation of cutter failure. Through laboratory tests and field measurements, this study analyzes the abrasion and damage characteristics of SM cutters in cobble–boulder strata, establishing distribution patterns for abrasion rates and damage probabilities across cutter types. Microscopic imaging and analysis of failed cutter surfaces revealed distinct failure mechanisms: deformation-induced wear and brittle phase detachment dominated in the base material and wear-resistant coatings, while carbide inserts exhibited combined effects of frictional abrasion, brittle fracture, and fatigue fracture. By integrating failure mechanisms with cutterhead design principles, targeted structural improvements of cutter base materials, wear-resistant coatings, and carbide inserts enhanced abrasion and damage resistance, enabling extended tunneling distances in cobble–boulder strata.</p>