This paper aims to identify and quantitatively evaluate various critical mechanisms associated with the processes of desiccation shrinkage and cracking in drying silty soils. A previously developed 1D bundle-of-tubes model is refined to simulate the various stages of drying shrinkage in 2D, using the actual pore size distribution based on Mercury Intrusion Porosimetry (MIP) data. Experimental evidence at a meso-scale has shown that the air entry phenomenon may occur in two possible scenarios: air incursion at the external surface and formation of vapor nucleus in the interior. Further transition of solid-water structural configuration into funicular and pendular states from initially capillary state is simulated.