Masonry is one of the oldest building materials. In addition, it is widespread all over the world. Masonry building can be subjected to various loading, including earthquakes, floods, winds, or soil settlements. On the other hand, climate change leads to dryer summer and wetter winter which, consequently, leads to more pronounced soil settlements. The response of masonry structures to soil settlements is still not completely understood, which threaten these constructions that hold both an economical (functional) and cultural value. In particular, the global stiffness of masonry structures when subjected to settlements requires further investigations. The present work aims at calibrating a numerical discrete element model on existing settlement experiments. It discusses the pros, the cons, and the methodology to follow for a discrete element modelling of such systems.