This paper describes an embedded modeling methodology for identifying gear meshing stiffness from measured gear angular displacement or transmission error. An embedded model integrating a physical based model of the gearbox and a parametric representation, in the form of truncated Fourier series, of meshing stiffness is established. A solution method is then used to find the meshing stiffness that minimizes the discrepancy between model output and the measured output. Furthermore, an algorithm is also developed to estimate the size of tooth crack from identified meshing stiffness. Both simulation and experimental studies were conducted to evaluate if identified tooth meshing stiffness can reveal a tooth crack more effectively, and if the crack size can be estimated with an adequate level of accuracy. [Work supported by ONR under the Multidisciplinary Research Program of the University Research Initiative.]