Current approaches to understanding shame are rooted in controversial and even radically contrasting assumptions about shame and its relevance for social interaction and individual well-being. Classical and medieval sources themselves embrace surprisingly various notions about the workings of shame. While the Aristotelian tradition prevails in late antique and medieval philosophical psychology, it is also possible to discern a parallel tradition of shame that adapts and exploits Latin Stoic and eclectic material. This article surveys this largely unexplored Latin tradition (Cicero and Ambrose) and its treatment in later moral-philosophical and pastoral debates (Gregory the Great, Richard of St. Victor, Thomas Aquinas, Albert the Great, and William Peraldus). Late antique and medieval Christian authors regard a positive responsiveness to shame as a constructive habit signaling the ability to live a socially harmonious life. The discussion demonstrates the inherent moral value of shame (and other self-reflexive emotions) and the constitutive role of shame for moral agency.