This book contributes to the emerging field of men’s health studies, delving into how men incorporate, adapt, negotiate, or reject health care practices to perform masculinities in social interactions. By moving beyond the simplistic association between men, masculinity and the adoption of ‘risky’ or ‘unhealthy’ practices, this book draws from recent critical perspectives on the study of men’s health, seeking to challenge and problematize the relationship between masculinities and health. The text presents original empirical findings derived from qualitative and digital research examining the different ways in which men (re)negotiate their masculinities after the onset of a chronic illness, focusing on diabetes as a strategic case study. Living with a chronic illness implies that those gender practices that are usually taken for granted suddenly become unachievable and impose a reconfiguration of the masculine self, as well as a negotiation of the very meaning of masculinity. The volume aims to critically examine this interactive process of (re)negotiation, while also reflecting on men, masculinities and their health on a more general level. This book serves as a valuable resource for students and scholars in social sciences working on the intersection of gender and health, as well as for health professionals seeking a deeper understanding of the connection between men, gender and health.