This chapter provides a context for understanding the gender harms associated with young men’s online engagements. It canvases key contemporary debates about these harms that have led to renewed scrutiny on boys, men and masculinity and produced a sense of urgency around addressing what seems to have become a ubiquitous term in discussions of young men’s online behaviours, ‘toxic’ masculinity. The chapter situates this scrutiny and urgency within a broader context of volatile and polarising gender politics where there exists simultaneously, a strong focus on redressing misogyny, sexism and other forms of gender-based violence and a strong backlash that cast men and boys as the real victims of gender discrimination. Amid these politics, the chapter argues for the significance of research that better understands the nuances and complexities of young men’s online worlds, the imperative of listening to their voices, and the importance of recognising the criticality and agency of their online engagements. The chapter explores young men’s positive and negative engagements online and describes the qualitative study upon which the book is based. It concludes with an overview of each of the subsequent chapters.