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Summary Animals' teeth have evolved to provide food procurement, mastication, and protection. These functions, directly linked to survival of many living animal species, require superior hardness and abrasion resistance in the animal's dentition system. Such resistance typically emerges from damage tolerance and sharpness preservation during the organism’s life span. An example is the sea urchin tooth, which through gradients in mechanical properties together with exploitation of microstructural features achieves such functionality. Using contact mechanics, dimensional analysis, and a novel in situ scanning electron microscopy experimental methodology, conditions for tooth deformation and wear, via a self-sharpening mechanism consisting in plate chipping, were imaged and quantified. Nonlinear finite-element modeling of the self-sharpening mechanism provided insight into the synergy between constituent material properties and tooth microstructural elements. The findings reported here should inspire the design of novel tools used in machining operations, e.g., cutting and grinding, as well as in mining and tunnel boring.