Art historians have long viewed southern Italy, especially the Salento region in Apulia, as a Byzantine artistic province even centuries after Byzantine rule ended there in c. 1070. The Orthodox monastery of Santa Maria di Cerrate, near Lecce, is widely considered to possess some of the region’s “most Byzantine” paintings (twelfth to fourteenth centuries). Yet a close examination of these frescoes reveals significant iconographic and stylistic differences from alleged Byzantine norms. A historiographic synopsis and review of problematic definitions of “Byzantine” art are followed in this article by a critique of reductionist labels. Embracing the concept of vagueness offers an alternative way to think about Cerrate and similar borderline cases—not in terms of fixed categories (“Byzantine” or “Western”), but as points on an art-historical continuum that is enriched by acknowledging complexity.