In late Spring 2014, the nonprofit organization Creative Time commissioned artist Kara Walker to create her first large-scale public installation. Hosted in the industrial relics of the leg- endary Domino Sugar Factory in Brooklyn, Walker’s A Subtlety, or the Marvelous Sugar Baby was as controversial as it was revered. The powerful presence of the installation, coupled with its immersion in historical consciousness, makes A Subtlety rich in educational value. This article engages in a comparative reading of A Subtlety in the light of female writers and thinkers from the Caribbean, but also incorporates some of the generative questions Walker’s installation has pro- voked my students to ask. I especially engage questions on how to unravel the mixed metaphors that make A Subtlety the artistic embodiment of the textured experience of the African diaspora, with its complex history, cultural hybridity and transnational ramifications. While Walker’s instal- lation seems to sustain its many layers of meanings through both form and content, the (mostly white, US-born) students in my class have responded to it in a range of critical ways that pointed especially to their emotional and critical response toward female Blackness, and reflections about the artist’s responsibility toward her intention. The article reflects on the inherent possibilities for teaching A Subtlety and other forms of what I consider “vulnerable art,” which at its best helps to channel our collective and personal discomfort in effective, healing ways.