In geotechnical engineering, there is a significant potential of using image analysis technique to study cracking soils by quantifying the characteristics of the crack network. In the current work, the image analysis process was used to obtain comprehensive information about the cracking mechanism and shrinkage during drying. Artificial soil samples investigated in the lab via desiccation tests under different boundary and environment conditions. Soil specimens with smooth and rough bottom contact surfaces were allowed to desiccate under opened and closed environments with specific pressure and temperature conditions. Digital photos were regularly taken during the tests then processed with image j software to characterize the crack patterns. The investigated effects were expressed in terms of crack intensity factor, CIF, and total crack intensity factor, (CIF)tot. The friction of the bottom contact surface, the environment, and the exposition to a saturated salt solution affect cracks formation and affect the cracking mechanism and shrinkage during drying. Smooth and rough boundaries showed significant differences at the end. For rough bottom contact surface, the difference between the values of suction under the opened environment and the closed one may have a small or insignificant effect on (CIF)tot, also the pattern of the cracks did not differ that much. CIF increases with an increase in the friction of the bottom contact surface. Also, samples dried under the open environment exhibit higher CIF and (CIF)tot than those under a closed environment. However, (CIF)tot decreases with an increase in the friction of the bottom surface. For the rough boundary condition under the open environment, the samples exposed to a salt solution had lower CIF and (CIF)tot in comparison with the other one not exposed. Since the orthogonal intersections are more dominant than others, it could be observed that the tensile stresses have a significant effect on desiccation cracks under the investigated conditions.