The role of elastic mismatch in determining critical conditions for indentation fracture in brittle coatings on substrates of unlike modulus was investigated. A model transparent trilayer system, consisting of a glass coating layer bonded to a thick substrate of different glass or polymer by a thin layer of epoxy adhesive, facilitated in situ observations of crack initiation and propagation. A tungsten carbide sphere was used to load the layer system. Abrasion flaws were introduced into the top and bottom glass coating surfaces to control the flaw populations and to predetermine the origins of fracture: cone cracks occurred at abraded top surfaces, radial cracks at abraded bottom surfaces. Analytical relations for the critical loads are presented for each crack system in terms of elastic modulus mismatch, indenter and coating dimensions, and material fracture parameters. Implications concerning materials selection for resistance to crack initiation are considered.