The evolution of the elastic properties of organic-rich shale as a function of thermal maturity remains poorly constrained. This understanding is pivotal to the characterization of source rocks and unconventional reservoirs. To better constrain the evolution of the elastic properties and microstructure of organic-rich shale, we have studied the acoustic velocities and elastic anisotropy of samples from two microstructurally different organic-rich shales before and after pyrolysis-induced thermal maturation. To more physically imitate in situ thermal maturation, we performed the pyrolysis experiments on intact core plugs under applied reservoir-magnitude confining pressures. Iterative characterization of the elastic properties of a clay-rich, laminar Barnett Shale sample documents the development of subparallel to bedding cracks by an increase in velocity sensitivity to pressure perpendicular to the bedding. These cracks, however, are not visible through time-lapse scanning electron microscope imaging, indicating either submicrometer crack apertures or predominant development within the core of the sample. At elevated confining pressures, in the absence of pore pressure, these induced cracks close, at which point, the sample is acoustically indistinguishable from the prepyrolysis sample. Conversely, a micritic Green River sample does not exhibit the formation of aligned compliant features. Rather, the sample exhibits a largely directionally independent decrease in velocity as load-bearing, pore-filling kerogen is removed from the sample. Due to the weak alignment of minerals, there is comparatively little intrinsic anisotropy; further, due to the relatively directionally independent evolution of velocity, the evolution of the anisotropy as a function of thermal maturity is not indicative of aligned compliant features. Our results have indicated that horizons of greater thermal maturity may be acoustically detectable in situ through increases in the elastic anisotropy of laminar shales or decreases in the acoustic velocities of nonlaminar shales, micritic rocks, or siltstones.