This paper describes the mechanical behavior of artificially cemented sands with strong, intermediate, and weak bond strengths, using experimentation and 3D discrete element method (DEM) simulation. The focus is on the features of bond breakage and the associated influences on the stress–strain responses. Under triaxial shearing, the acoustic emission rate captured in the experiment and the bond breakage rate recorded in the simulations show resemblance to the stress–strain response, especially for strongly and intermediately cemented samples, where a strain softening response is observed. The simulations further reveal the shear band formation coincides with the development of bond breakage locations due to the local weakness caused by the bond breakages. Strain softening and volumetric dilation are observed inside the shear band, while the region outside the shear band undergoes elastic unloading. The weakly cemented sample exhibits a strain hardening response instead; bond breakages and the associated local weaknesses are always randomly formed such that no persistent shear band is observed. Note that in the DEM simulation, the flexible membrane boundary is established by a network of bonded membrane particles; the membrane particle network is further partitioned into finite triangular elements. The associated algorithm can accurately distribute the applied confining pressure onto the membrane particles and determine the sample volume.