The sources of elastic anisotropy in organic-rich shale and their relative contribution therein remain poorly understood in the rock-physics literature. Given the importance of organic-rich shale as source rocks and unconventional reservoirs, it is imperative that a thorough understanding of shale rock physics is developed. We made a first attempt at establishing cause-and-effect relationships between geochemical parameters and microstructure/rock physics as organic-rich shales thermally mature. To minimize auxiliary effects, e.g., mineralogical variations among samples, we studied the induced evolution of three pairs of vertical and horizontal shale plugs through dry pyrolysis experiments in lieu of traditional samples from a range of in situ thermal maturities. The sensitivity of P-wave velocity to pressure showed a significant increase post-pyrolysis indicating the development of considerable soft porosity, e.g., microcracks. Time-lapse, high-resolution backscattered electron-scanning electron microscope images complemented this analysis through the identification of extensive microcracking within and proximally to kerogen bodies. As a result of the extensive microcracking, the P-wave velocity anisotropy, as defined by the Thomsen parameter epsilon, increased by up to 0.60 at low confining pressures. Additionally, the degree of microcracking was shown to increase as a function of the hydrocarbon generative potential of each shale. At 50 MPa confining pressure, P-wave anisotropy values increased by 0.29–0.35 over those measured at the baseline — i.e., the immature window. The increase in anisotropy at high confining pressure may indicate a source of anisotropy in addition to microcracking — potentially clay mineralogical transformation or the development of intrinsic anisotropy in the organic matter through aromatization. Furthermore, the evolution of acoustic properties and microstructure upon further pyrolysis to the dry-gas window was shown to be negligible.