This article is an attempt to demonstrate the transformations which took place in Lesser Poland in the late 13th century. The Krakow–Sandomierz Prince Boleslaw the Chaste knew very well that changes were both necessary and instrumental in creating new opportunities. The Prince tried to get the Krakow bishopric and the Krakow capitule involved in the rhythm of these transformations. Thanks to the support of the Krakow Church, he managed to modernise and accelerate changes in all of the Krakow-Sandomierz Principality. Mutual collaboration allowed the strengthening of both the bishopric and the capitule through via the acquisition of extensive privileges and the economic development of their estates. It also enabled the application of new models of goods distribution. Thanks to the model collaboration between the Krakow Church and the monarch, long-term and oftentimes costly conflicts, similar to ones observed in neighboring principalities, could be avoided.