The present study investigates the interplay between artistic production, social relationships and the urban fabric in Bologna between the late fifteenth and early sixteenth centuries. In doing so, the analysis focuses on the architectural patronage of a select group of Bolognese families, interrogating how the form, materiality, aesthetic, function and location of their artistic commissions affected and were influenced by social, political and familial ties. Starting with the case study of the Felicini family, the investigation first explores the architectural patronage of the household and later analyses how their patronage interacted with that of other members of the Bolognese urban elite. In order to map such interactions, the study examines in depth the refashioning of the Augustinian church of Santa Maria della Misericordia (c. 1480- 1530) and the Franciscan Observant complex of Santissima Annunziata (c. 1470-1510), two of the main foci of patronage for the Bolognese civic elite. Through a wealth of hitherto unused archival documentation, the dissertation aims at demonstrating the existence of a dynamic network of exchanges based on family relationships and social bonds that was largely independent from the Bentivoglio court, and which greatly determined the urban development of Balogna throughout the late Quattrocento and early Cinquecento.