On the Chinese Loess Plateau (CLP), crack-induced sliding in paleosols triggers retrogressive slope collapse, compromising the long-term stability of loess slopes. Establishing a quantitative relationship between crack depth and slide size is key to elucidating the progressive evolution of crack-induced sliding in paleosols; however, research on this topic is scarce. In this study, a model test was conducted on a paleosol slope subjected to five drying–rainfall cycles. Three-dimensional (3D) laser scanning technology was employed to accurately quantify the variations in crack depth and slide size, and water content sensors were embedded to monitor the preferential flow changes induced by these cracks. Results reveal that crack depth plays a pivotal role in initiating and controlling the propagation of crack-induced sliding in paleosols by influencing the preferential flow capacity through cracks. In the slide initiation stage, a critical crack depth capable of triggering sliding by inducing a sufficiently significant preferential flow and large saturation zones was identified. The depth at which sliding occurs can be expressed as a variable dependent on crack depth based on the single triggering effect of cracking on sliding. Once a crack-induced slide is initiated, the combined action of prior sliding events and current crack propagation accelerates the subsequent sliding in terms of increased size and varying spatial locations by influencing the preferential flow capacity and sliding force values. A comprehensive empirical formula was established to characterize the depth of crack-induced slides, considering the dominant influence of crack depth and slope gradient on sliding development at this stage of slide evolution. Our findings emphasize the pivotal role of crack depth in triggering progressive crack-induced sliding in paleosols, thereby providing valuable insights for soil conservation in paleosol areas on loess slopes on the CLP.