This chapter reviews recent experimental findings applying non-linear dynamical techniques, termed non-linear elastic wave spectroscopy (NEWS), to infer progressive mechanical damage in human bone, in vitro. Standard measures of bone mechanical properties are compared where possible, including the quasi-statically derived stiffness and hysteresis. The goal is to explore whether or not the methods can ultimately be applied in vivo, for applications such as diagnosing and monitoring the progression of osteoporosis, as well as bone healing. It is shown that the NEWS methods are extremely sensitive to progressive damage, far more so than the other methods applied. The results are promising, and current discussion involves how to conduct similar experiments in vivo.