A combined experimental/analytical work is carried out to elucidate the fracture resistance of a thin, hard coating bonded to a semi-infinite substrate due to indentation by a cylindrical surface. The bending of the coating under the softer substrate induces concentrated tensile stress regions at the lower and upper surfaces of the coating, from which cracks may ensue. The evolution of such damage in a model transparent system (glass/polycarbonate) is viewed in situ from below and from the side of the specimen. The critical load needed to initiate a crack on the lower coating surface generally increase proportionally to the coatings thickness, d. An interesting departure from this trend occurs for thin coatings, where the fracture load, although marred by a large scatter, increases somewhat with decreasing d. The fracture data for the upper coating surface are limited to relatively thick coatings due to the recurrence of premature failure from the coating edges. The behavior in this range is similar to that for the lower surface crack, albeit with an order of magnitude greater fracture resistance. A fracture mechanics analysis in conjunction with FEM is performed to elucidate the stress intensity factors responsible for crack propagation. A crack normal to the coating surface is assumed to emanate either from the lower or upper surface of the coating. A major feature of the solution is the occurrence of a bending-induced compression stress field over a region ahead of the crack tip. This effect, which become more dominant as the ratio between the contact length and the coating thickness is increased, tends to delay the onset of crack propagation, especially for the lower surface crack. Consequently, in applications associated with large indenters, thin and/or tough coatings and stiff substrates, cracking from the upper coating surface may precede that from the lower surface. An interesting feature of this crack shielding mechanism is that when the coating surface contains a distribution of flaws rather than a single crack, small flaws in this population may be more detrimental than large ones. Incorporation of these aspects into the analysis leads to a good correlation with the test results. In the special case of line loading, which constitutes a lower bound for the critical loads, a closed-form, approximate solution for the stress intensity factors or the critical loads are obtained. Plane-strain indentation, although less common than spherical indentation, allows for characterizing the fracture resistance of opaque films through observation from the specimen edge. This approach is not easily implemented to thin films (i.e., less than about a hundred microns), however.