This article presents the results of an experimental research carried to investigate the mechanics of cracking of soil layers under drying conditions. The tests were conducted under controlled laboratory conditions and in an environmental chamber with circular and rectangular specimens to investigate the effect of the boundary conditions (size, shape, and aspect ratio of the specimens and containers) on the process of initiation and propagation of cracks and on the final crack pattern at the end of desiccation. The tests in the environmental chamber were conducted with imposed temperature and relative humidity and provided new insight into the mechanics of the formation of cracks in a drying soil, and they showed that cracks can initiate either at the top, bottom, or at both surfaces of the drying specimen. The results also reveal how the crack patterns are controlled by the existing mechanical and hydraulic boundary conditions. The cracks seem to form sequentially in patterns that can be explained by three key factors: stresses higher than the tensile strength, the direction of the generated stresses, and the stress redistribution in the vicinity or inside the newly formed domain. In order to substantiate the sequential nature of the crack pattern formation, experimental evidences showing the existence of a cracking sequence during the laboratory desiccation experiments are presented and analyzed.