In the late 1420s, Abbot Gomezio di Giovanni initiated a major building campaign to reform the Benedictine monastery of the Florentine Badia. Designed to provide its community with an orderly space in which to pursue the Benedictine Observance, the compound rises around the so-called Orange Cloister, long considered to be an early work of Bernardo Rossellino. A reevaluation of the archival record demonstrates that Rossellino was one of many who contributed to the project, which was a collaborative effort codirected by master mason Antonio di Domenico della Parte and master stonecutter Giovanni d’Antonio da Maiano. In addition to issues of authorship, this article investigates why the building looks the way it does, how it was built, and how it served the abbot’s reform program. Answers to these questions allow us to develop our appreciation of Benedictine life and architectural practice in Early Renaissance Florence.