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Two longstanding goals in subsurface science are to induce fractures with a desired geometry to adaptively control the interstitial geometry of existing fractures in response to changing subsurface conditions. Many energy and water-related engineering applications that use induced fractures to withdraw and inject fluids from subsurface reservoirs occur in some sedimentary rock. Sedimentary rock such as shales often exhibit anisotropic mechanical properties because of bedding, layering and mineral texture. These structural and textural features also affect fracture formation and in turn the resulting fracture geometry. Understanding the interplay between the microscopic mineral fabric and structure and how it effects fracture geometry is important for the prediction of the geometry of induced fractures and to the determination of the most ideal conditions for maximizing energy production and minimizing leaks from sequestration sites in the subsurface. This Ph.D. thesis research focuses on the formation and geometry of fractures in anisotropic rock and the identification of geophysical signatures of fracture formation using additively manufactured gypsum rock analogs. Specifically, the work is grouped into three topics: (1) material controls on fracture geometry, toughness and roughness in additively manufactured rocks; (2) acoustic emissions (AE) during fracture formation in anisotropic additively manufactured rocks; and (3) determination of the effect of fluid-filled oriented voids in fractures on compressional to shear wave conversions. For topic (1), unconfined compressive strength (UCS), Brazilian and 3-point bending (3PB) tests under pure and mixed mode mechanical tests were performed on cast and 3D printed gypsum samples that were characterized using 3D Xray microscopy, Xray Diffraction and SEM to examine the micro-structure of the samples. Research on topic 1 discovered microstructural controls on fracture surface roughness and the failure behavior of anisotropic rock and that the failure mode (tensile, mixed mode I and II, mixed mode I and III) affects the fracture propagation path and the surface roughness which is controls to the flow paths through a fracture. The results suggest that detailed mineralogical studies of mineral texture/fabric in laboratory or core samples is important to unravel failure strength, surface roughness, and how fractures propagate in layered geological media. For topic (2), UCS tests were performed with concurrent measurements of acoustic emissions (AE) on cylindrical specimens: cast gypsum (CG) samples, and 3D printed (3DP) samples with five different orientations of bassanite layer and gypsum texture relative to the loading direction. Mechanical properties and induced fracture surface information were compared with the collected the AE signals to study if there is a way to tell the differences between the induced fracture surfaces with the AE signals patterns together with loading data. Examination of the AE signal amplitude from post-peak loading revealed that more ductile behavior was associated with more AE events that occurred over a longer period of time, and the resultant fracture surfaces were rougher than for narrow time distributions of events. For topic (3), a detail study of fracture void orientation was performed using ultrasonic compressional, P, and shear, S, waves to determine how energy is partitioned when P-to-S or S-to-P conversions occur for waves normally incident on an air-filled or fluid-filled fracture. In this study, experiments and computer simulations were performed to demonstrate the link among cross-coupling stiffness, micro-crack orientation and energy partitioning into P, S, and P-S/S-P wave. The cross-coupling stiffness was created by 3D printing samples with linear arrays of micro-cracks oriented at $0^o$, $\pm15^o$, $\pm30^o$, $\pm45^o$, $\pm60^o$, $\pm75^o$, and $90^o$. For $45^o$ orientation, measurements were made on air-filled and fluid-filled (silicon oil). For the air-filled fractures, the observed energy partitioning matched the simulated behavior obtained from discontinuous Galerkin simulations. Information on local fracture geometry is contained in the far-field waves. When filled with a viscous fluid, the P- and S- waves amplitude exhibited slight increases and decreases, respectively. The P-to-S converted mode amplitude decreased 30\% with an increase in fluid viscosity from 1–300kcSt. This suggests that P-S converted mode provides a potential method to remotely probe changes in fluid viscosity in fractures. The work from the 3 research topics demonstrated that micro-scale structure impacts macroscale behavior and signals used for monitoring the condition of a rock. Additively manufactured samples enabled the exploration and determination of (1) the impact of mineral fabric orientation in layered media on failure load, fracture propagation path, and fracture surface roughness, (2) the sensitivity of P-to-S conversions to fluid viscosity, and (3) how oriented voids within a fracture effect energy partitioning. These research findings advances our current understanding of role microscopic properties and structure on the generation, propagation and geometry of induced fractures in anisotropic rock, and help to identify the best imaging modalities to use to identify the seismic signatures of the viscosity of fluids in fractures with oriented voids. These contributions will help unravel the complex behavior often observed in natural rock that is structurally and compositionally complex with features and heterogeneity.