Chipping caused by micrometric particles poses a threat to the structural integrity of modern dental prosthetic materials. It can degrade their fracture strength and cause wear of both artificial crowns and antagonist teeth. Here, surface chipping of the main types of commercial ceramic-based dental materials at the microcontact/particle level is investigated by means of indentation tests. Conical tips of different sizes (radii 20 and 200 μm) under axial and sliding loading are employed to simulate individual microcontacts. Both decreasing particle size and adding a lateral contact force decrease the chipping load below typical bite forces. Specific damage mechanisms are identified as predominantly brittle fracture in ceramics with small, equiaxed crystals, with significant quasiplastic damage in ceramics containing large, elongated crystals and composites. Critical loads for the occurrence of chipping are quantified (lowest values in equiaxed glass-ceramics; greatest in zirconia) and analyzed within the framework of fracture mechanics. The brittleness index (BI) is proposed as a simple indicator of the resistance to chipping of dental materials-the lower the BI, the greater the resistance. Special attention is paid to the effect of the materials' microstructure, which can result in transformation toughening (as in zirconia) or quasi-plastic behavior (as in lithium disilicate), both highly beneficial to increasing the chipping resistance. Finally, practical implications for the selection of current dental materials as well as for the development of novel materials with improved durability are discussed.