In the US today, gun violence takes the lives of nearly 3,000 youth annually, leaving a footprint of trauma in thousands of schools and affecting tens of thousands of the victims’ friends and classmates, about whom very little research has been undertaken. During my two years of ethnographic research in an all-boys, all-Black Philadelphia high school, three students died in separate violent incidents. The dissertation shows the interactional and institutional mechanisms through which the grief that follows gun violence tangibly impacts Black adolescent boys’ school engagement, relationships with peers and teachers, and ideas about their own futures – as well as the consequences of our society’s too-frequent neglect of Black boys’ emotional lives. Specifically, the dissertation offers a three-stage theory of institutional and personal grief within the school: The easy hard, hard hard, and hidden hard stages highlight a progression over time in how friends experience and express their grief and how school policies, practices, and individual teachers’ behaviors support and constraint students’ recovery. Drawing on ethnographic and social media observation, in-depth interviews with students and adults, and students’ school records, I show, on the one hand, the efforts of administrators and teachers to care for and support grieving students and, on the other hand, the structural challenges they face dealing with boys’ emotions in educational spaces designed to maintain order and respond to the perceived “crisis” of Black boys’ education. The research uncovers layers of conflict between institutional mourning practices, leveraged to collectively recognize shared loss and then renormalize academic routines and classroom life, and students’ unresolved (and frequently concealed) grief. Using the framework of racialized and gendered emotion work, I analyze the particularities of Black boys’ individual and peer group grieving rituals, and assess the costs to their emotional and educational trajectories. My attention to boys’ regular social media posts, in particular, reveals how the medium functions as a key vehicle for social solidarity and public emotional expression when it is silenced in school or stigmatized by stubborn norms of racialized masculinity. The dissertation concludes with recommendations for how schools might help students productively translate their grief into grievance.